Myrrh & Related Commiphora - Cropwatch
Myrrh & Related Commiphora - Cropwatch
Myrrh & Related Commiphora - Cropwatch
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www.cropwatch.org<br />
THE FIRST TRULY INDEPENDENT WATCHDOG FOR THOSE<br />
WORKING WITH NATURAL AROMATIC MATERIALS<br />
E: info@cropwatch.org T: ++44 (0)7771 872 521<br />
<strong>Cropwatch</strong>’s Bibliography of <strong>Myrrh</strong>: <strong>Commiphora</strong> myrrha (Nees)<br />
Engl., & other related <strong>Commiphora</strong> spp.<br />
Compiled by <strong>Cropwatch</strong> v1.01 Jan 2010.<br />
[to be progressively extended].<br />
<strong>Cropwatch</strong> Introduction: The <strong>Commiphora</strong> genus contains up to 200 species of<br />
often thorny shrubs or small- to medium-sized dioecious trees with a peeling,<br />
papery bark distributed across Africa & the Arabian peninsula, with four species<br />
also found in India. <strong>Myrrh</strong> itself is the air-dried gum oleoresin principally obtained<br />
from the schizogenous gum-oleoresin cavities in the stem or branches of the<br />
small tree <strong>Commiphora</strong> myrrha (Nees) Engl. or C. myrrha (Nees) Engl. var.<br />
molmol (Fam. Burseraceae) and other <strong>Commiphora</strong> spp. such as C. abyssinica -<br />
(Berg.) Engl., C. schimperi (Berg.) Engl. These shrubs grow in sandy and rocky<br />
areas in Somalia, Sudan, Ethiopia, S. Arabia (Saudi Arabia, Yemen) and Kenya.<br />
Still other species yielding types of myrrh include C. africana (A. Rich) Engl., C.<br />
mukul (Hook ex Stocks) Engl. and C. guidottii (Chiov. ex Guidottii) which yields<br />
‘scented myrrh’.<br />
General reference: Gillett, J.B. (1973). “<strong>Commiphora</strong> Jacq. (Burseraceae) - Englerian species<br />
which disappear.” Kew Bull. 28(1), 25-28.<br />
Contents<br />
<strong>Commiphora</strong> africana (A. Rich) Engl.<br />
<strong>Commiphora</strong> caudata (Wight & Arn.) Engl.<br />
<strong>Commiphora</strong> confusa Vollesen.<br />
<strong>Commiphora</strong> erythraea (Ehrenb.) Engl.<br />
<strong>Commiphora</strong> guidottii Chiov. ex Guidottii.<br />
<strong>Commiphora</strong> holtziana<br />
<strong>Commiphora</strong> incisa Chiov..<br />
<strong>Commiphora</strong> kataf (Forssk.) Engl.<br />
<strong>Commiphora</strong> kua (R.Br. ex Royle) Vollesen.<br />
<strong>Commiphora</strong> madagascariensis Jacq.<br />
<strong>Commiphora</strong> merkeri Engl.<br />
<strong>Commiphora</strong> molmol Engl. ex Tschirch. syn. C. myrrha<br />
<strong>Commiphora</strong> mukul Hook ex Stocks.<br />
<strong>Commiphora</strong> myrrha (Nees) Engl. - Chemistry &<br />
Composition<br />
<strong>Commiphora</strong> myrrha (Nees) Engl. - Properties.<br />
1
<strong>Commiphora</strong> opobalsamum L.<br />
<strong>Commiphora</strong> pseudopaoli JB Gillet<br />
<strong>Commiphora</strong> schimperi (Berg.) Engl.<br />
<strong>Commiphora</strong> sphaerocarpa Chiov. Chiovenda.<br />
<strong>Commiphora</strong> tenuis. K. Vollesen<br />
<strong>Commiphora</strong> wightii Arnott.<br />
<strong>Commiphora</strong> africana (A. Rich) Engl.<br />
syn <strong>Commiphora</strong> pilosa Engl.<br />
<strong>Cropwatch</strong> comments: Source of “myrrh-like resin” (Gachathi 1997)<br />
Ayedoun M.A. (1998) "Aromatic plants of Tropical West Africa. VI. alpha-<br />
Oxobisabolene as main constituent of the leaf essential oil of <strong>Commiphora</strong><br />
africana (A. Rich.) Engl. from Benin." Journal of Essential Oil Research 10(1),<br />
105-107. Abstract. The leaf oil of <strong>Commiphora</strong> africana has been analyzed by<br />
GC, GC/MS coupling and 13C-NMR spectroscopy. The two major compounds<br />
identified in the oil were alpha-oxobisabolene (60%) and gamma-bisabolene<br />
(10%).<br />
Banso A. & Mann A. (2006) "Antimicrobial alkaloid fraction from <strong>Commiphora</strong><br />
africana (A. Rich)." J of Pharmacy & Bioresources 3(2), 98-102. Abstract. An<br />
alkaloid fraction was isolated from <strong>Commiphora</strong> africana (<strong>Myrrh</strong>) and assayed<br />
against Escherichia coli, Bacillus subtilis, Staphylococcus aureus, Pseudomonas<br />
aeruginosa and Streptococcus pyogenes using the agar diffusion method. The<br />
fraction exhibited antimicrobial activities against all the test microorganisms<br />
Bacillus subtilis was the most susceptible to the alkaloids followed by<br />
Staphylococcus aureus, Escherichia coli, Streptococcus pyogenes and<br />
Pseudomonas aeruginosa respectively. The minimum inhibitory concentration<br />
ranged between 3.5mg/ml and 4.5mg/ml while the minimum bactericidal<br />
concentration ranged between 4.0mg/ml and 5.0mg/ml. The alkaloids fraction<br />
from <strong>Commiphora</strong> africana could be a potential source of chemotherapeutic<br />
agents.<br />
Choudhury M.K., Johnson E.C. & Agbaji A.S. (2006) "l investigation of the bark of<br />
<strong>Commiphora</strong> africana (Burseraceae)." Indian Journal of Pharmaceutical<br />
Sciences. 62(4), 311-2. Abstract. The methanolic extract of bark of the plant<br />
<strong>Commiphora</strong> africana (family:Burseraceae) gave a homogeneous product<br />
through chromatographic separation which after crystallization from methanol<br />
furnished needles (mp. 142-143 degree), characterized as dimethylterephthalate<br />
(benzene-1, 4-dicarboxylic acid dimethylester), C(10) H(10) O(4) (M+194) on the<br />
basis of spectral analysis (UV, IR, NMR, Mass) and comparison with the<br />
synthetic dimethylester prepared from terephthalic acid.<br />
Gachathi F. N. (1997) “Recent advances on classification and status of main<br />
gum-producing species in the Family Burseraceae” available at<br />
http://www.fao.org/documents/show_cdr.aspurl_file=/docrep/X0098e/X0098e01.<br />
htm<br />
2
Gbolade A.A. & Adeyemi A.A. (2008) "Anthelmintic activities of three medicinal<br />
plants from Nigeria." Fitoterapia 79(3), 223-5. Abstract. Aqueous extracts of the<br />
leaf, stem bark and root bark from Canna bidentata, Spondias mombin and<br />
<strong>Commiphora</strong> africana were examined for anthelmintic activity against earthworm.<br />
All the extracts demonstrated a concentration-dependent activity at tested<br />
concentrations of 10-80 mg/ml. Higher activities were observed at the higher<br />
concentrations, 40-80 mg/ml for all the plant extracts. C. bidentata with a<br />
paralysis time of 3-5 min and death time of 5-18 min at these concentrations for<br />
the stem bark, and S. mombin which exhibited comparatively higher efficacy (34-<br />
44 min paralysis time and 105 min death time for the leaf) at lower<br />
concentrations of 10-20 mg/ml were adjudged the outstanding anthelmintics of<br />
plant origin accordingly.<br />
Ma J., Jones S.H. & Hecht S.N. (2005) “A dihydroflavonol glucoside from<br />
<strong>Commiphora</strong> africana that mediates DNA strand scission” Journal of Natural<br />
Products 68(1),115-117. Abstract. A crude CH 2 Cl 2 −MeOH extract prepared from<br />
<strong>Commiphora</strong> africana was found to mediate Cu2+-dependent relaxation of<br />
supercoiled plasmid DNA. Bioassay-guided fractionation of this extract was<br />
carried out and was monitored by the use of an in vitro DNA strand scission<br />
assay. The dihydroflavonol glucoside phellamurin (1) was identified as the active<br />
principle responsible for the DNA cleavage activity of the crude extract.<br />
<strong>Commiphora</strong> caudata (Wight & Arn.) Engl.<br />
Chandrasekar K., Rajan V., Raj C.D. Gowrishankar N.L. (2009) "Antiulcerogenic<br />
activity of <strong>Commiphora</strong> caudata bark extract against ethanol-induced gastric<br />
ulcer in rats." Journal of Pharmacy Research 2(4), 701-703. Abstract. The<br />
ethanolic extract of <strong>Commiphora</strong> caudata bark extract was evaluated for their<br />
cytoprotective activity against ethanol-induced gastric lesions in rats. Four groups<br />
of male Sprague Dawley rats each consist of 6 animals. Group I animals were<br />
pretreated with phosphate buffer saline 5 ml/kg, p.o. as a control, whereas Group<br />
II and Group III rats were pretreated with 200 mg/kg, p.o. and 400 mg/kg p.o. of<br />
<strong>Commiphora</strong> caudata bark extracts respectively. Group IV rats were pretreated<br />
with cimetidine 50 mg/kg p.o. as reference. After 30 minutes, all animals were<br />
administered orally with 1 ml of absolute ethanol. After 15 minutes, all rats were<br />
sacrificed. Macroscopically, oral administration of absolute ethanol to rats<br />
pretreated with PBS significantly produced extensive hemorrhagic lesions of<br />
gastric mucosa, whereas animals pretreated with 200 mg/kg and 400 mg/kg<br />
ethanolic extract or cimetidine significantly reduced the formation of gastric<br />
lesions, when compared to control group. These results strongly document the<br />
beneficial cytoprotective effects of plant extract against ethanol-induced gastric<br />
ulcer in rats.<br />
Latha S., Selvamani P., Pal T.K.., Gupta J.K. & Ghosh L.H. (2009) “Antibacterial<br />
Activity of <strong>Commiphora</strong> caudata and <strong>Commiphora</strong> berryi Leaves” Indian Drugs<br />
40(10), 696-698.<br />
3
Latha S., Selvamani P., Pal T.K.., Gupta J.K. & Ghosh L.H. (2006)<br />
"macognostical studies on leaves of <strong>Commiphora</strong> caudata (Wight et Arn) Engl."<br />
Ancient Science of Life 26(1/2), 19-25<br />
Kannan C. (2009) "ulcerogenic activity of <strong>Commiphora</strong> caudata bark extract<br />
against ethanol-induced gastric ulcer in rats." Journal of Pharmacy Research<br />
2(4). Abstract. The ethanolic extract of <strong>Commiphora</strong> caudata bark extract was<br />
evaluated for their cytoprotective activity against ethanol-induced gastric lesions<br />
in rats. Four groups of male Sprague Dawley rats each consist of 6 animals.<br />
Group I animals were pretreated with phosphate buffer saline 5 ml/kg, p.o. as a<br />
control, whereas Group II and Group III rats were pretreated with 200 mg/kg, p.o.<br />
and 400 mg/kg p.o. of <strong>Commiphora</strong> caudata bark extracts respectively. Group IV<br />
rats were pretreated with cimetidine 50 mg/kg p.o. as reference. After 30<br />
minutes, all animals were administered orally with 1 ml of absolute ethanol. After<br />
15 minutes, all rats were sacrificed. Macroscopically, oral administration of<br />
absolute ethanol to rats pretreated with PBS significantly produced extensive<br />
hemorrhagic lesions of gastric mucosa, whereas animals pretreated with 200<br />
mg/kg and 400 mg/kg ethanolic extract or cimetidine significantly reduced the<br />
formation of gastric lesions, when compared to control group. These results<br />
strongly document the beneficial cytoprotective effects of plant extract against<br />
ethanol-induced gastric ulcer in rats.<br />
Nanthakumar R., Stephen Ambrose S., Sriram E., Babu G., Chitra K. and Uma<br />
maheswara Reddy C. (2009) "Effect of bark extract and gum exudate of<br />
<strong>Commiphora</strong> caudata on aspirin induced ulcer in rats." Pharmacognosy<br />
Research 11(6), 375-380. Abstract. <strong>Commiphora</strong> caudata is used in Indian folk<br />
medicine as an antiulcerogenic agent. Despite of its promising use, there has<br />
been no scientific report present regarding its antiulcer activity. Therefore, this<br />
study was designed to evaluate the antiulcer activity of bark extract and gum<br />
exudate of <strong>Commiphora</strong> caudata on aspirin induced ulcer in rats. Acute toxicity<br />
study was performed and 200 mg/kg was selected as an effective dose. Four<br />
groups of Albino Swiss rats were included in this study. Aspirin suspended in 0.5<br />
% carboxymethyl cellulose (CMC) was given orally to group 1 rats as a negative<br />
control group. Group 2 and group 3 animals received methanolic extract and gum<br />
exudate of <strong>Commiphora</strong> caudata respectively. Sucralfate was given orally to<br />
group 4 animals as a positive control. The methanolic extract of <strong>Commiphora</strong><br />
caudata has been found to reduce total acidity as much as by sucralfate.<br />
However, it has not changed the fluid secretion. The gum preparation not only<br />
reduced the total acidity but also considerably reduce the gastric fluid secretion.<br />
In case of ulcer score sucralfate, methanolic extract and the gum have produced<br />
the low ulcer score compared to aspirin. Increased gastric mucosal protective<br />
mechanism by bark extract and gum exudate is probably due to the presence of<br />
some active principles present in the plant. However, further investigations are<br />
required to elucidate their exact mechanism of anti-ulcer activity.<br />
4
Sivakumar T., Kannan K., Kannappan N. & Kathiresan K. (2009)<br />
"Antiinflammatory activity of <strong>Commiphora</strong> caudata [Wight and Arn]." Asian<br />
Journal of Chemistry 21(5),4130-4132.<br />
<strong>Commiphora</strong> confusa Vollesen.<br />
<strong>Cropwatch</strong> comments: Source of “myrrh-like resin” (Gachathi 1997).<br />
Dekebo A., Dagne E., Curry P., Gautun O.R. & Aasen A.J. (2002) "Dammarane<br />
triterpenes from the resins of <strong>Commiphora</strong> confusa." Bulletin of the Chemical<br />
Society of Ethiopia 16(1),81-86(6). Abstract. The resin of <strong>Commiphora</strong> confusa<br />
afforded two new dammarane triterpenes, (3R,20S)-3,20-dihydroxydammar-24-<br />
ene and (3R,20S)-3-acetoxy-20-hydroxydammar-24-ene along with the known<br />
triterpenes, cabraleadiol 3-acetate and -amyrin.<br />
Manguro L.O., Ugi I. & Lemmen P. (2003) "Dammarane triterpenes of<br />
<strong>Commiphora</strong> confusa resin.” Chem Pharm Bull 51, 483–486. Abstract.<br />
Fractionation of a steam distilled residue of <strong>Commiphora</strong> confusa resin has<br />
yielded four novel dammarane triterpenes characterised as (20S)-3beta-acetoxy-<br />
12beta,16beta-trihydroxydammar-24-ene,<br />
(20S)-12beta,16betatrihydroxydammar-24-ene-3beta-O-beta-glucopyranoside,<br />
(20S)-3beta-acetoxy-<br />
12beta,16beta,25-tetrahydroxydammar-23-ene, and (20S)-<br />
3beta,12beta,16beta,25-pentahydroxydammar-23-ene. The known compounds<br />
beta-amyrin, 3beta-amyrinacetate, 2-methoxyfuranodienone, 2-<br />
acetoxyfuranodienone, (20R)-3beta-acetoxy-16beta-dihydroxydammar-24-ene,<br />
(20R)-3beta,16beta-trihydroxydammar-24-ene, 3beta-acetoxy-16betahydroxydammar-24-ene,<br />
3beta-hydroxydammar-24-ene, 3beta-acetoxydammar-<br />
24-ene, and beta-sistosterol were also isolated from the same extract. The<br />
structures of the compounds were determined using spectroscopic, physical, and<br />
chemical methods.<br />
Gachathi F. N. (1997) “Recent advances on classification and status of main<br />
gum-producing species in the Family Burseraceae” available at<br />
http://www.fao.org/documents/show_cdr.aspurl_file=/docrep/X0098e/X0098e01.<br />
htm<br />
<strong>Commiphora</strong> erythraea (Ehrenb.) Engl. var glabrescrens Engl.<br />
Opoponax.<br />
<strong>Cropwatch</strong> comments: Source of opoponax.<br />
Carroll J.F., Maradufu A. & Warthen Jr. J.D. (1989) "An extract of <strong>Commiphora</strong><br />
erythraea: a repellent and toxicant against ticks." Entomol. Exp. Appl. 53, 111-<br />
116. Abstract. A hexane extract of the gum of an African plant, <strong>Commiphora</strong><br />
erythraea Engler (Burseraceae), has larvicidal and repellent activity against the<br />
lone star tick, Amblyomma americanum (L.) and the American dog tick,<br />
Dermacentor variabilis (Say). Adult deer ticks, Ixodes dammini Spielman,<br />
Clifford, Piesman and Corwin, were also repelled by the extract. Concentrations<br />
of 0.02 mg/cm 2 of the extract impregnated onto filter paper killed 96.15 (+<br />
3.56)% of A. americanum larvae exposed to it for 24 h. A concentration of 0.16<br />
5
mg/cm 2 was needed to kill 80.3% of D. variabilis larvae. The extract was less<br />
effective as a larvicide against A. americanum and D. variabilis than permethrin.<br />
Less than 15.5% of A. americanum larvae and adults and D. variabilis and L<br />
dammini adults entered and remained for 2 or 3 min on areas of cloth strips<br />
treated with the extract at the rate of 0.2 mg/cm 2. However, 73.3 to 83.3% of the<br />
ticks tested entered and remained in areas treated with hexane. Permethrin was<br />
about 1 or 2 orders of magnitude more effective against A. americanum larvae as<br />
a repellent than the extract.<br />
Lawrence B.M. (1983). “Opoponax oil <strong>Commiphora</strong> erythraea var. glabrescens”<br />
Perfum. & Flav. 8, 27-28.<br />
Lawrence B.M. (2004) Progress in Essential Oils: Opoponax & Other<br />
<strong>Commiphora</strong> spp. Perf. & Flav. 29(7), 88-101.<br />
Marcotullio M.C., Santi C., Mwankie G.N.O.-M. & Curini M. (2009) "Chemical<br />
Composition of the essential oil of <strong>Commiphora</strong> erythraea." Natural Product<br />
Communications 4(12),1751-1754.<br />
Maradufu A. (1982) “Furanosesquiterpenoids of <strong>Commiphora</strong> erythraea and C.<br />
myrrh.” Phytochemistry 21, 677–680.<br />
Wenninger J.A. & Yates R.L. (1969) J. Assocn. of Anal. Chem. 52, 1155 through<br />
Khalid S.A. (1983) “Chemistry of the Burseraceae” Ann. Proc. Phytochem. Soc.<br />
Europe 22, 281-299.<br />
<strong>Commiphora</strong> guidottii Chiov. ex Guidottii.<br />
Scented <strong>Myrrh</strong>. Bissabol. Habak Hadi.<br />
Ali A.Y. & Bowen I.D. (2005) "Antifeedant and molluscicidal activity of scented<br />
myrrh applied as a spray." IOBC WPRS Bulletin 28(6),9-14.<br />
Andersson M., Bergendorff O., Shan R.D., Zygmunt P. & Sterner O. (1997)<br />
Planta Med 63, 251–254. Abstract. Minor components with smooth muscle<br />
relaxing properties from scented myrrh (<strong>Commiphora</strong> guidottii).<br />
Claeson P., Andersson R. & Samuelsson G. (1991). T-cadinol: a<br />
pharmacologically active constituent of scented myrrh: introductory<br />
pharmacological characterization and high field 1H- and 13C-NMR data. Planta<br />
Med. 57, 352-6.<br />
Craveiro A., Corsano S., Proietti G. & Strappaghetti G. (1983) “Constituents of<br />
essential oil of <strong>Commiphora</strong> guidottii.” Planta Med 48, 97–98. Abstract. From the<br />
essential oil of <strong>Commiphora</strong> guidotti seven sesquiterpene hydrocarbons and a<br />
furanosesquiterpenoid, furanodiene, were isolated.<br />
Thulin M. & Claeson P. (1991) "The botanical origin of Scented <strong>Myrrh</strong> (Bissabol<br />
or Habak Hadi)." Economic Botany 45(4), 487-494. Abstract. It is concluded that<br />
the botanical origin of scented myrrh (bissabol or habak hadi), a major article for<br />
export from Somalia since ancient times, is <strong>Commiphora</strong> guidottii (Burseraceae)<br />
6
and not C. erythraea as generally has been presumed. The reasons for the<br />
previous confusion are discussed, and an updated synonymy and distribution<br />
map for C. guidottii are given.<br />
<strong>Commiphora</strong> holtziana ssp. holtziana<br />
syn. <strong>Commiphora</strong> caerurea<br />
Gum haggar.<br />
<strong>Cropwatch</strong> comments: Source of opoponax.<br />
Birkett M.A., Al Bassi S., Kröber T., Chamberlain K., Hooper A.M., Guerin P.M.,<br />
Pettersson J., Pickett J.A., Slade R. & Wadhams L.J. (2008) "Antiectoparasitic<br />
activity of the gum resin, gum haggar, from the East African plant, <strong>Commiphora</strong><br />
holtziana." Phytochemistry 69(8), 1710-1715. Abstract. The mechanism of ixodid<br />
tick (Acari: Ixodidae) repellency by gum haggar, a resin produced by<br />
<strong>Commiphora</strong> holtziana (Burseraceae), was investigated by evaluating activity<br />
against the cattle tick, Boophilus microplus. In an arena bioassay, a hexane<br />
extract of the resin of C. holtziana exhibited a repellent effect lasting up to 5 h.<br />
The hydrocarbon fraction of the resin extract was shown to account for the<br />
repellent activity, and was analysed by coupled gas chromatography–mass<br />
spectrometry (GC–MS). Major sesquiterpene hydrocarbons were tentatively<br />
identified as germacrene-D, δ-elemene and β-bourbonene. The identity and<br />
stereochemistry of the former compound was confirmed as the (+)-isomer by<br />
peak enhancement using enantioselective GC, whereas the latter 2 compounds,<br />
which are most likely degradation products of germacrene-type precursors, were<br />
identified through isolation by preparative gas chromatography followed by<br />
microprobe-NMR spectroscopy. GC comparison of gum haggar with another<br />
resin, C. myrrha, which was inactive in the tick bioassay, showed that the latter<br />
contained much lower levels of these hydrocarbons. To assess the suitability of<br />
the gum haggar resin as a general acarine repellent, further tests were made on<br />
a major acarine pest of European and US animal husbandry systems, the red<br />
poultry mite, Dermanyssus gallinae (Acari: Dermanyssidae). Gum haggar extract,<br />
and the isolated hydrocarbon fraction, showed strong repellent effects in an<br />
olfactometer assay, and again gum myrrh showed no effect. These findings<br />
provide a scientific basis for the observed anti-tick properties of gum haggar, and<br />
demonstrate the potential for its development as a general acarine repellent for<br />
use in animal husbandry systems.<br />
Cavanagh I.S., Cole M.D., Cavanagh J.S., Gibbons S., Gray A.I., Provan G.J &<br />
Waterman P.G. (1992) "A novel sesquiterpene, 1,2-epoxyfurano-10(15)-<br />
germacren-6-one, from the resin of <strong>Commiphora</strong> holtziana Engl." Flav. & Frag. J.<br />
8(1),39-41. Abstract. Three known and one novel furanogermacrenes have been<br />
isolated from the resinous exudate of <strong>Commiphora</strong> holtziana Engl. The structures<br />
of the known compounds were determined by comparison of 1H- and 13C-NMR<br />
spectra with those already published. The structure of the novel compound was<br />
determined as 1,2-epoxyfurano-10(15)-germacren-6-one (IV), using<br />
spectroscopic techniques. Some previous 13C-NMR assignments for the known<br />
compounds were corrected or clarified.<br />
7
Manguro L.O.A., Opiyo S.A., Herdtweck E. & Lemmen P. (2009) "Triterpenes of<br />
<strong>Commiphora</strong> holtziana oleo-gum resin." Canadian Journal of Chemistry<br />
87(8),1173-1179. Abstract. Chemical analysis of the acetone extract of<br />
<strong>Commiphora</strong> holtziana gum resin has led to the isolation of triterpenes<br />
characterized as methyl 3-oxo-1α,19α,28-trihydroxyurs-12-en-24-oate (1), methyl<br />
3β-acetyl-2α,11α,19α,28-tetrahydroxyurs-12-en-24-oate (2), methyl 3β,11αdiacetyl-1α,2α,28-trihydroxyurs-12-ene-24-oate<br />
(3), and 3β,28-diacetyl-1α,2α,25-<br />
trihydroxydammar-23-ene (4). The known compounds isolated from the same<br />
extract included cabraleadiol monoacetate (5), mansumbinol (6), 3β-acetylamyrin<br />
(7), 3α-acetylboswellic acid (8), 2-methoxy-8,12-epoxygermacra-1(10),7,11-trien-<br />
6-one (9), 2-methoxy-5-acetylfuranogermacra-1(10),7,11-trien-6-one (10),<br />
furadienone (11), 2-methoxy-5-acetyl-4-furanogermacra-1(10)Z-en-6-one (12), α-<br />
amyrin (13), sistosterol (14) and stigmasterol 3-O-acetate (15). Structural<br />
elucidation was carried out using spectroscopic and physical methods as well as<br />
by comparison with the literature data.<br />
Provan G. J., Gray A. I. & Waterman P. G. (1987) “Monoterpene-rich Resins from<br />
some Kenyan Burseraceae” Flav. Frag. J. , 2, 115-118. Abstract. Volatile oils<br />
obtained by the steam distillation of resins from Boswellia neglecta, <strong>Commiphora</strong><br />
africana, C. campestris and C. ogadensis have been examined by capillary GC<br />
and GC-MS. In each case the oils were found to be entirely monoterpenoid in<br />
constitution. All four oils were generally characterized by large amounts of -<br />
pinene. Other constituents that were important markers of individual species<br />
included -thujene (B. neglecta, C. africana), sabinene (C. campestris), myrcene<br />
and car-3-ene (C. ogadensis) and p-cymene (B. neglecta, C. africana).<br />
<strong>Cropwatch</strong> comments: According to Provan et al. (1987)The main constituents<br />
of the oil of <strong>Commiphora</strong> holtiziana are 1 (10),2-methoxy-8,12-epoxygermacra-<br />
1(10, 7, 11-trien-6-one, 5-acetoxy-2-methoxy-8,12-epoxygermacra-1(10),7,11-<br />
trien-6-one, 3-methoxy-8,12-epoxygermacra-1,7,10(15),11-tetraen-6-one, elemol,<br />
furanodiene, furanodienone, isofuranogermacrene, curzerenone, lindestrene,<br />
furanoeudesma-1,3-diene, furanoeudesma-1,4-diene-6-one, 1(10)Z, 4Zfuranodiene-6-one,<br />
2-methoxy-furanodiene, 2-acetoxyfuranodiene, 4,5-<br />
dihydrofuranodiene-6-one.<br />
<strong>Commiphora</strong> incisa Chiov..<br />
syn. C. candidula Sprague.<br />
<strong>Cropwatch</strong> comments: Source of “myrrh-like resin” (Gachathi 1997). Local use<br />
as masticatory gum.<br />
Duwiejua M., Zeitlin I.J., Waterman P.G., Chapman J., Mhango G.J. & Provan<br />
G.J. (1993) "Anti-inflammatory activity of resins from some species of the plant<br />
family Burseraceae." Planta Med. 59(1),12-6. Abstract. The anti-inflammatory<br />
activities of extracts from the resins of four species of the plant family<br />
Burseraceae, Boswellia dalzielli, Boswellia carteri (gum olibanum), <strong>Commiphora</strong><br />
mukul, and <strong>Commiphora</strong> incisa, were studied. The aqueous extracts of the resins<br />
of B. dalzielli, C. incisa, and C. mukul significantly inhibited both the maximal<br />
edema response and the total edema response during 6 h of carrageenan-<br />
8
induced rat paw edema. The octanordammarane triterpenes, mansumbinone and<br />
mansumbinoic acid, isolated from the resin of C. incisa, were separated and<br />
tested. Administered prophylactically, mansumbinone proved to be more than 20<br />
times less potent than indomethacin and prednisolone in inhibiting carrageenaninduced<br />
rat paw edema. However, the molar potency of mansumbinoic acid was<br />
within one order of magnitude of those of indomethacin and prednisolone. The<br />
anti-inflammatory action of the acid on the carrageenan-induced edema was<br />
dose-related between 1.3 x 10(-5) and 2.5 x 10(-4) mol kg-1 when given before<br />
the inflammatory stimulus. The acid was able to reverse an established<br />
carrageenan-induced inflammatory response when administered 2 h after<br />
induction. Daily administration of mansumbinoic acid at a single dose level (1.5 x<br />
10(-4) mol kg-1) significantly reduced joint swelling in adjuvant arthritis in rats.<br />
The results indicated that this compound is worthy of further investigation as an<br />
anti-inflammatory drug.<br />
Gachathi F. N. (1997) “Recent advances on classification and status of main<br />
gum-producing species in the Family Burseraceae” available at<br />
http://www.fao.org/documents/show_cdr.aspurl_file=/docrep/X0098e/X0098e01.<br />
htm<br />
Provan G.J. & Waterman P.G. (1988) "Major triterpenes from the resins of<br />
<strong>Commiphora</strong> incisa and C. kua and their potential chemotaxonomic significance."<br />
Phytochemistry 27(12),3841-3843. Abstract. The resin obtained from<br />
<strong>Commiphora</strong> incisa has yielded two novel triterpenes which have been identified<br />
as 1α-acetoxy-9,19-cyclolanost-24-en-3β-ol and 29-norlanost-8,24-dien-<br />
1α,2α,3β-triol. No trace could be found of the octanordammaranes previously<br />
reported for this species and it now appears that these originate from the closely<br />
related C. kua.<br />
Provan G.J. & Waterman P.G. (1985)"Piropolygamain: a new lignan from<br />
<strong>Commiphora</strong> incisa." Planta Medica 51(3), 271-272. Abstract. The resin<br />
produced by <strong>Commiphora</strong> incisa has yielded two epimeric aryltetralin lignans<br />
which have been identified as the known polygamain (1 R, 2 R, 3 R) and its novel<br />
C-2 epimer to which the trivial name picropolygamain (1 R, 2 S, 3 R) has been<br />
assigned.<br />
Provan G.J. & Waterman P.G. (1986) “The mansumbinanes:<br />
Octanordammaranes from the resin of <strong>Commiphora</strong> incisa." Phytochemistry<br />
25(4), 917-922. Abstact. The resin of <strong>Commiphora</strong> incisa (Burseraceae) has<br />
yielded three C22 compounds derived by loss of the C-17 side chain from a<br />
dammarane triterpene. They have been ident̀ified by spectral analysis and<br />
chemical modification as 4α,4β,8β,10β,14α-pentamethyl-5α-gon-16-en-3-one<br />
(mansumbinone), the corresponding 3-hydroxy compound (mansumbinol) and<br />
the derivative 3,4-seco-mansumbinoic acid in which the A-ring has opened<br />
between C-3 and C-4. A fourth compound was characterized as 16(S),20(R)-<br />
dihydroxydammar-24-en-3-one, a possible precursor of the mansumbinanes<br />
<strong>Commiphora</strong> kataf (Forssk.) Engl.<br />
9
African Opoponax.<br />
<strong>Cropwatch</strong> comments: Source of opoponax.<br />
ANLAP data-base http://www.ics.trieste.it/EssentialOils/EssentialOil.aspxID=19<br />
<strong>Cropwatch</strong> comments: This reports the following components confirmed by GC-<br />
MS and NMR in a Kenyan steam distillled essential oil of C. kataf: camphene<br />
(0.8%), γ-elemene (2.4%), β-elemene (14.4%), germacrene-D (15.5%), elmol<br />
(4.6%), furanogermacra-1, 10(15)-diene-6-one (16.7%).<br />
Baser K.H.C., Demirci B., Dekebo A. & Dagne E. (2003) “Essential oils of some<br />
Boswellia spp, <strong>Myrrh</strong> and Opoponax” Fl. & Frag. J. 18, 153-6. <strong>Cropwatch</strong><br />
comments: Baser et al. indicate the presence of the following components in C.<br />
kataf oil: germacrene D, germacrene B, furanosesquiterpene and (1E)-8,12-<br />
epoxygermacra-1,7,10,11-tetraen-6-one.<br />
<strong>Commiphora</strong> kua (R.Br. ex Royle) Vollesen.<br />
Kenya, Ethiopia, Somalia & Yemen<br />
Awadh Ali N.A., Wurster M., Lindequist N.A.U. & Wessjohann L. (2008)<br />
"Essential oil composition from oleogum resin of Soqotraen <strong>Commiphora</strong> kua."<br />
Rec. Nat. Prod. 2:3 (2008), 70-75. Abstract. The major constituents of the<br />
essential oil obtained by hydrodistillation from the oleogum resin of <strong>Commiphora</strong><br />
kua Vollesen were identified by GC-MS. Sixteen constituents were detected from<br />
the essential oil, which constituted about (90.5%) of the total amount. Major<br />
constituents of the oil were α- cadinol (33.0%), γ-cadinene (22.5%), δ-cadinene<br />
(17.0%), isocaryophyllene (3.7%), allo-aromadendrene (2.8%), α-muurolene<br />
(2.7%), and α-humulene (2.4%). The Oil of <strong>Commiphora</strong> kua showed moderate<br />
antifungal activity against Cladosporium cucumerinum.<br />
Battu, G.R., Zeitlin, I.J. & Gray, A.I. (2000). "Anti-inflammatory activity of<br />
adjuvant-induced arthritis in rats of octanordammarane triterpenes from resin<br />
extracts of <strong>Commiphora</strong> kua." Br. J. Pharmacol. 133, 199.<br />
Battu, G.R., Zeitlin, I.J. and Gray, A.I. (2000). “Investigation of anti-inflammatory<br />
actions of molecules from Kenyan <strong>Myrrh</strong>, <strong>Commiphora</strong> kua.” J. Pharm.<br />
Pharmacol. 52, 309.<br />
Battu, G.R., Zeitlin, I.J. & Gray, A.I. (2000). Anti-inflammatory activity of<br />
myeloperoxidase inhibitory molecules isolated from resin extracts of <strong>Commiphora</strong><br />
kua. Br. J. Pharmacol. 131, 187p.<br />
Battu G.R., Zeitlin I.J., Gray A.I & Watermann P.G. (1999). “Inhibitory actions on<br />
rat myeloperoxidase of molecules isolated from antinflammatory extracts of<br />
<strong>Commiphora</strong> kua. “ Brit J. Pharmacol. 128, 274 Suppl. S.<br />
Dekebo A., Dagne E., Hansen L.K., Gautun O.R. & Aasen A.J. (2002) "Two<br />
octanordammarane triterpenes from <strong>Commiphora</strong> kua." Phytochemistry 58(4),<br />
399-403. Abstract. The resin of <strong>Commiphora</strong> kua yielded two new<br />
octanordammarane triterpenes namely 15α-hydroxymansumbinone and 28-<br />
acetoxy-15α-hydroxymansumbinone, along with the four known compounds,<br />
10
mansumbinone, mansumbinol, (16S, 20R)-dihydroxydammar-24-en-3-one and T-<br />
cadinol. These structures were elucidated by spectroscopic techniques, including<br />
1D and 2D NMR spectroscopy, and X-ray analysis.<br />
Manguro L.O.A., Ugi I. & Lemmen P. (2003) "Further bisabolenes and<br />
dammarane triterpenes of <strong>Commiphora</strong> kua resin." Chem Pharm Bull. 51(5), 479-<br />
482. Abstract. From the resins of <strong>Commiphora</strong> kua a novel bisabolene; 6-<br />
hydroxy-2-methyl-5-(5'-hydroxy-1'(R),5'-dimethylhex-3'-enyl)-phenol together with<br />
two new dammarane triterpenes, 3.BETA.,16.BETA.,20(S),25-<br />
tetrahydroxydammar-23-ene and 3.BETA.-acetoxy-16.BETA.,20(S),25-<br />
trihydroxydammar-23-ene, have been isolated. In addition, being reported are<br />
known compounds identified as 2-methyl-5-(4'(S)-hydroxy-1'(R),5'-dimethylhex-<br />
5'-enyl)-phenol, 2-acetoxyfuranodienone, 2-methoxyfuranodienone,<br />
3.BETA.,16.BETA.,20(R)-trihydroxydammar-24-ene and its acetate derivative,<br />
3.BETA.-acetoxy-16.BETA.,20(R)-dihydroxydammar-24-ene, and .BETA.-amyrin<br />
and its acetate derivative. 2-Methyl-5-(4'(S)-hydroxy-1'(R),5'-dimethylhex-5'-enyl)-<br />
phenol displayed fungicidal activity against Cladosporium cucumernum on TLC<br />
assay.<br />
Manguro L.O., Mukonyi K.M. & Githiomi J.K. (1996) "Bisabolenes and<br />
furanosesquiterpenoids of Kenyan <strong>Commiphora</strong> kua resin." Planta Med. 62(1),<br />
84-5. Abstract The isolation and structure determination of a new bisabolene, 2-<br />
methyl-5-(5'-hydroxy-1',5'-dimethyl-3'-hexenyl)phenol, together with known<br />
bisabolene, xanthorrhizol and furanosesquiterpenoids, 2- O-acetyl-8,12-<br />
epoxygermacra-1(10),4,7,11-tetraene and 2- O-methyl-8,12-epoxygermacra-<br />
1(10),4,7,11-tetraene, from gum exudate of <strong>Commiphora</strong> kua are reported.<br />
<strong>Commiphora</strong> madagascariensis Jacq.<br />
syn. <strong>Commiphora</strong> abyssinica (Berg.) Engl.<br />
syn. <strong>Commiphora</strong> habessinica (Berg) Engl.<br />
<strong>Cropwatch</strong> comments: Source of “myrrh-like resin” (Gachathi 1997)<br />
Gachathi F. N. (1997) “Recent Advances on Classification and Status of Main<br />
Gum-Producing Species in the Family Burseraceae” available at<br />
http://www.fao.org/documents/show_cdr.aspurl_file=/docrep/X0098e/X0098e01.<br />
htm<br />
<strong>Commiphora</strong> merkeri Engl.<br />
Zebrabark <strong>Myrrh</strong><br />
Fourie T.G. & Snyckers F.O. (1989) “A pentacyclic triterpene with anti-<br />
Inflammatory and analgesic activity from the roots of <strong>Commiphora</strong> merkeri.” J.<br />
Nat Prod 52, 1129–1131.<br />
<strong>Commiphora</strong> molmol Engl. ex Tschirch.<br />
syn <strong>Commiphora</strong> myrrha var molmol<br />
True myrrh. Molmol (N.E. Kenya).<br />
11
Al Faraj S. (2005) "Antagonism of the anticoagulant effect of warfarin caused by<br />
the use of <strong>Commiphora</strong> molmol as a herbal medication: a case report." Annals of<br />
Tropical Medicine and Parasitology 99(2). 219-220.<br />
Ashry K.M., El-Sayed Y.S., Khamiss R.M., El-Ashmawy I.M. (2009) "Oxidative<br />
stress and immunotoxic effects of lead and their amelioration with myrrh<br />
(<strong>Commiphora</strong> molmol) emulsion." Food Chem Toxicol. 2009 Oct 8. Abstract. The<br />
possible role of <strong>Commiphora</strong> molmol emulsion (CME) in protecting against lead<br />
(PbAc)-induced hepatotoxicity, oxidative stress and immunotoxicity in rabbits was<br />
assessed. Six groups of animals were used: groups I (control) and II (PbAc) were<br />
not supplemented with CME. Groups III (CME50) and IV (CME50+PbAc) were<br />
administered with CME in a dose rate of 50mg/kgbwt, while groups V (CME100)<br />
and VI (CME100+PbAc) were received 100mgCME/kg bwt daily p.o for<br />
successive 14weeks. Groups II, IV and VI were given 80mg PbAc/kg bwt/day<br />
orally for 6weeks starting from the 9th week. At the 12th week, animals were<br />
subjected to immunization by a single dose of sheep RBCs. The PbAc-group<br />
showed 220% increase in hepatic malondialdehyde levels, while glutathione,<br />
glutathione S-transferase and glutathione peroxidase levels decreased. Leadacetate<br />
induced hypoproteinemia and hypoalbuminemia, and increased<br />
aminotransferases activity. It reduced the values of lymphocyte transformation<br />
test, phagocytic activity, phagocytic index and antibody titer against sheep<br />
SRBCs. Interestingly, pretreatment with CME attenuated these adverse effects in<br />
a dose-dependent protection. CME, therefore, is a potent antioxidant, and can<br />
protect against PbAc-induced hepatic oxidative damage and immunotoxicity by<br />
reducing lipid peroxidation and enhancing the antioxidant and immune defense<br />
mechanisms.<br />
Haffor A.S. "Effect of myrrh (<strong>Commiphora</strong> molmol) on leukocyte levels before and<br />
during healing from gastric ulcer or skin injury." J Immunotoxicol. 2009 Dec 8.<br />
Abstract. <strong>Myrrh</strong> (<strong>Commiphora</strong> molmol) has been widely used as an antiinflammatory<br />
and wound healing commercial product. As white blood cell<br />
(WBC)/leukocyte counts have been used as an indicator by clinicians to monitor<br />
progress of healing in patients, the purpose of this study was to examine effects<br />
of myrrh supplementation on blood WBC numbers before an injury and during<br />
healing. Male rats (7-8-wk-of-age) were randomly assigned to four groups. Group<br />
1 (SIM) served as "skin injury treated + myrrh treatment (500 mg/kg/day)," Group<br />
2 (SI) as "skin injury alone", Group 3 (GUM) as "gastric ulcer treated + myrrh<br />
treatment", and Group 4 (GU) as gastric ulcer only. <strong>Myrrh</strong> treatments (via<br />
drinking water) began 4 wk before induction of injury and continued for a 2 wk<br />
period post-injury. Baseline values for each WBC type were recorded before start<br />
of the myrrh treatments. Counts were performed again on Day 1 of the 5th wk (1-<br />
2 hr before injury) and post-injury on Days 4 and 7 of the 5th wk, and a final time<br />
on Day 4 of the 6th wk. Results showed that levels of all WBC types were<br />
significantly (P < 0.05) elevated before either injury in myrrh-treated rats (Groups<br />
1 and 3) as compared with levels in rats in Groups 2 and 4. At all timepoints,<br />
there were neither significant differences between the values seen with rats in<br />
Groups 1 and 3, nor between those in Groups 2 and 4. Treatment with myrrh<br />
12
also induced an initial increase in WBC levels that persisted through the postinjury<br />
healing period. Levels of most cell types only increased in the Group 2 and<br />
4 rats once the injury was induced, but then declined over the healing period.<br />
Since myrrh enhanced WBC levels before injury, we conclude that myrrh likely<br />
contains substances that could induce an apparent antigen-driven response. As<br />
the myrrh also helped maintain elevated WBC levels throughout the healing<br />
period, this implied it was also able to induce maturation/differentiation/activation<br />
of both myeloid and lymphoid cell types during the effector phase of the immune<br />
responses involved in wound healing.<br />
Massoud A. M., Kutkat M. A., Abdel-Shafy S., El-Khateeb R. M., Labib I.M.<br />
(2005) "Acaricidal efficacy of myrrh (<strong>Commiphora</strong> molmol) on the fowl tick Argas<br />
persicus (Acari: Argasidae). J Egyptian Soc of Parasitology 35(2),667-686.<br />
Rahman M.M.. Garvey M., Piddock L.J. & Gibbons S. (2008) "Antibacterial<br />
terpenes from the oleo-resin of <strong>Commiphora</strong> molmol (Engl.)." Phytotherapy<br />
Research 22(10),1356-1360. Abstract. Two octanordammaranes,<br />
mansumbinone (1) and 3,4-seco-mansumbinoic acid (2), and two<br />
sesquiterpenes, beta-elemene (3) and T-cadinol (4) have been isolated from the<br />
oleo-resin of <strong>Commiphora</strong> molmol (Engl.). The structures of these compounds<br />
were established unambiguously by a series of 1D and 2D-NMR analyses. We<br />
have also unambiguously assigned all (1)H and (13)C NMR resonances for 2<br />
and revised its (13)C data. The crude extract of the oleo-resin of C. molmol<br />
displayed potentiation of ciprofloxacin and tetracycline against S. aureus, several<br />
Salmonella enterica serovar Typhimurium strains and two K. pneumoniae strains.<br />
The antibacterial activity of terpenes 1-4 was determined against a number of<br />
Staphylococcus aureus strains: SA1199B, ATCC25923, XU212, RN4220 and<br />
EMRSA15 and minimum inhibitory concentration (MIC) values were found to be<br />
in the range of 4-256 microg/ml. The highest activity was observed by the seco-<br />
A-ring octanordammarane 2 with an MIC of 4 microg/ml against SA1199B, a<br />
multidrug-resistant strain which over-expresses the NorA efflux transporter, the<br />
major characterized antibiotic pump in this species. This activity compared<br />
favorably to the antibiotic norfloxacin with an MIC of 32 microg/ml. Compound 2<br />
also displayed weak potentiation of ciprofloxacin and tetracycline activity against<br />
strains of Salmonella enterica serovar Typhimurium SL1344 and L10.<br />
Tonkal A.M.D. & Morsy T.A. (2008) "An update review on <strong>Commiphora</strong> molmol<br />
and related species." Egyptian Society of Parasitology 18(3),763-796. Abstract.<br />
The origins of myrrh and frankincense are traced to the Arabian Peninsula.<br />
According to Herodotus (5th century BC): "Arabia is the only country which<br />
produces frankincense, myrrh, cassia, and cinnamon.., the trees bearing the<br />
frankincense are guarded by winged serpents of small size and various colors."<br />
Diodorus Siculus wrote, in the second half of the first century BC, that "all of<br />
Arabia exudes a most delicate fragrance; even the seamen passing by Arabia<br />
can smell the strong fragrance that gives health and vigor." He also mentioned<br />
gold mines so pure that no smelting was necessary. The Magi, carrying myrrh,<br />
frankincense, and gold, came from the East: Arabia. The frankincense trade<br />
13
oute, with transport by donkeys and later by camel caravans, reached<br />
Jerusalem and Egypt from the Dhofar region of what is today Oman, through<br />
Yemen, turning north to follow the Red Sea coast. It is likely that the same or<br />
similar species of the resin-bearing plants grew across the Red Sea in the area<br />
that is now Somalia and Ethiopia, while the collection of the gum resins was<br />
initiated in Arabia. <strong>Myrrh</strong> contributed much in the human welfare.<br />
Schistosomiasis was known in ancient Egypt since remote times. Haematuria<br />
with urinary bladder disturbances was mentioned in four Papyrus papers dated<br />
back to 1950-1900 BC, and Schistosoma ova was detected in a cirrhotic liver of a<br />
mummy from 1200 BC (Ruffer, 1910). Also, Fasciola eggs were detected in a<br />
mummy (Looss, 1896). Fascioliasis infected over 17 million people worldwide<br />
causing marked morbidity and mortality (Haseeb et al., 2002). Schistosomiasis<br />
affected over 200 million people in 74 countries and territories worldwide (WHO,<br />
1999) causing several chronic complications. Both were incriminated to<br />
predispose or accompanied human hepatitis and predisposed to HCV (Wahib et<br />
al., 2006). Most zoonotic helminthes induced immune response (Nutman, 2001)<br />
characterized by producing of type 2 cytokines, Ig G1, IgG2, IgE antibodies and<br />
eosinophil and mast cell activation (Hoffman et al., 2002). Treatment of<br />
fascioliasis required high or drug multiple doses with side effect (Farid et al.,<br />
1990). In schistosomiasis, praziquantel (PZQ) in use for > 20 years was faced<br />
with low efficacy (Leishout et al., 1998), or with increased resistance (Coles et<br />
al., 1986; Watt et al., 1988; Herrera et al., 1994; Ismail et al., 1994; 1999; Tonelli<br />
et al., 1995; Stelma et al., 1995; Fallon et al., 1997; Bennett et al., 1997; Boisier<br />
et al., 1998; Periera et al., 1998; Kusel and Hagan, 1999; Liang et al., 2000; King<br />
et al., 2000; N'Goran et al., 2003; Raso et al., 2004), potentiality of<br />
carcinogenicity, genotoxicity (Rosenkranz et al., 1995), mutagenicity (Montero et<br />
al., 1993), big dose lethality and enhanced clastogenicity of environmental<br />
pollutants (Anwar, 1994). On the other hand, Nomicos (2007) in USA reported<br />
that since antiquity, the genus <strong>Commiphora</strong> is composed of more than 200<br />
species, and exploited as a natural drug to treat pain, skin infections,<br />
inflammatory conditions, diarrhea, and periodontal diseases. He added that in<br />
more recent history, products derived from C. myrrha and various other species<br />
of <strong>Commiphora</strong> are becoming recognized to possess significant antiseptic,<br />
anesthetic, and antitumor properties. Traditional practice and evidence-based<br />
research have supported that these properties are directly attributable to<br />
terpenoids (especially furanoses-quiterpenes), the active compounds present in<br />
myrrh essential oil. Very recently, current studies have focused on applying<br />
clinical trial methodologies to validate its use as an antineoplastic, an<br />
antiparasitic agent, and as an adjunct in healing wounds. Weeks and Simpson<br />
(2007) in USA presented the molecular phylogeny of <strong>Commiphora</strong>, a<br />
predominantly tropical African, arid-adapted tree genus to test the monophyly of<br />
its taxonomic sections and to identify clades to help direct future study of this<br />
species-rich and geographically widespread taxon. The multiple fossil<br />
calibrations of <strong>Commiphora</strong> phylogeny proved that it is sister to Vietnamese<br />
Bursera tonkinensis and that its crown group radiation corresponds with the<br />
onset of the Miocene. Auffray (2007) in France studied the impact of two types of<br />
14
antioxidant on sebum squalene peroxidation by UV irradiation. The first type was<br />
free radical scavenger (Butyl hydroxyl toluene and an olive extract rich in<br />
hydroxytyrosol). The second type was the essential oil of C. myrrha, a singlet<br />
oxygen quencher. These properties were confirmed using the 2,2-diphenyl-1-<br />
picrylhydrazyl test for anti-radical capacity and 1,3-diphenylisobenzofuran test for<br />
the capacity to quench singlet oxygen. Also, the author extended an ex vivo<br />
method to classify the efficacy of cosmetics to protect squalene by collecting<br />
sebum in vivo and irradiating it in a controlled way. The squalene<br />
monohydroperoxide formation was monitored by high performance liquid<br />
chromatography. This method compared the efficiency of 3 antioxidants at 0.6%<br />
in a cosmetic formulation to protect squalene from photo oxidation. The data<br />
showed that essential oil of C. myrrha gave the best protection against squalene<br />
peroxidation, and that squalene peroxidation during solar exposure was mainly<br />
because of singlet oxygen and not due to free radical attack, and that sun care<br />
cosmetics should make use not only of free radical scavengers but also of singlet<br />
oxygen quenchers. This study aimed to review more than 70 out of hundreds<br />
papers (Pub-med-indexed for Medline) on the medical importance and safety of<br />
<strong>Commiphora</strong> molmol and other <strong>Commiphora</strong> species.<br />
<strong>Commiphora</strong> mukul Hook ex Stocks.<br />
Guggal or Guggul<br />
<strong>Cropwatch</strong> comments: Common adulterant of myrrh.<br />
Amjad A.M. & Mashooda H. (1967) “Chemical investigation of <strong>Commiphora</strong><br />
mukul.” Pakistan J Sci Ind Res 10, 21–23.<br />
Arora R.B., Kapoor V., Gupta S.K. & Sharma R.C. (1971) “Isolation of a<br />
crystalline steroidal compound from <strong>Commiphora</strong> mukul & its anti-inflammatory<br />
activity.” Indian J Exp Biol 9, 403–404.<br />
Arora R.B., Taneja V., Sharma R.C. & Gupta S.K. (1972) “Anti-inflammatory<br />
studies on a crystalline steroid isolated from <strong>Commiphora</strong> mukul.” Indian J Med<br />
Res 60, 929–931.<br />
Saeed M.A & Sabir A. W. (2004) "Antibacterial activities of some constituents<br />
from oleo-gum-resin of <strong>Commiphora</strong> mukul." Fitoterapia 75(2), 204-208. Abstract.<br />
The essential oil, chloroform extract and seven sesquiterpenoids compounds<br />
newly isolated from the oleo-gum-resin of <strong>Commiphora</strong> mukul showed a wide<br />
range of inhibiting activity against both Gram (+) and Gram (-) bacteria.<br />
Bajaj A.G. & Sukh D.S. (1982) “Chemistry of Ayurvedic crude drugs-V: Guggulu<br />
(resin from <strong>Commiphora</strong> mukul) -5 some new steroidal components and,<br />
stereochemistry of guggulsterol-I at C-20 and C-22.” Tetrahedron 38, 2949–<br />
2954.<br />
Bhati A. (1950) “Essential oil from the resin of <strong>Commiphora</strong> mukul.” J Indian<br />
Chem Soc. 27, 436–440.<br />
15
Bose S. & Gupta C. (1964) “Structure of <strong>Commiphora</strong> mukul gum: Part I – Nature<br />
of sugars present & the structure of the aldobiouronic acid.” Indian J Chem 2,<br />
57–60.<br />
Bose S, & Gupta C. (1964) “Structure of <strong>Commiphora</strong> mukul gum: Part III –<br />
Methylation & periodate oxidation studies.” Indian J Chem 4, 87–89.<br />
Bose S, Gupta C. (1964) “Structure of <strong>Commiphora</strong> mukul gum: Part II –<br />
Structure of the degraded gum.” Indian J Chem 2, 156–158.<br />
Cornick C.L., Strongitharm B.H., Sassano G., Rawlins C., Mayes A.E., Joseph<br />
A.N., O'Dowd J., Stocker C., Wargent E., Cawthorne M.A., Brown A.L., Arch J.R..<br />
(2009) "Identification of a novel agonist of peroxisome proliferator-activated<br />
receptors alpha and gamma that may contribute to the anti-diabetic activity of<br />
guggulipid in Lep(ob)/Lep(ob) mice." J Nutr Biochem. 20(10), 806-15. Abstract.<br />
The ethyl acetate extract of the gum of the guggul tree, <strong>Commiphora</strong> mukul<br />
(guggulipid), is marketed for the treatment of dyslipidaemia and obesity. We have<br />
found that it protects Lep(ob)/Lep(ob) mice from diabetes and have investigated<br />
possible molecular mechanisms for its metabolic effects, in particular those due<br />
to a newly identified component, commipheric acid. Both guggulipid<br />
(EC(50)=0.82 microg/ml) and commipheric acid (EC(50)=0.26 microg/ml)<br />
activated human peroxisome proliferator-activated receptor alpha (PPARalpha)<br />
in COS-7 cells transiently transfected with the receptor and a reporter gene<br />
construct. Similarly, both guggulipid (EC(50)=2.3 microg/ml) and commipheric<br />
acid (EC(50)=0.3 microg/ml) activated PPARgamma and both promoted the<br />
differentiation of 3T3 L1 preadipocytes to adipocytes. Guggulipid (EC(50)=0.66<br />
microg/ml), but not commipheric acid, activated liver X receptor alpha<br />
(LXRalpha). E- and Z-guggulsterones, which are largely responsible for<br />
guggulipid's hypocholesterolaemic effect, had no effects in these assays.<br />
Guggulipid (20 g/kg diet) improved glucose tolerance in female Lep(ob)/Lep(ob)<br />
mice. Pure commipheric acid, given orally (960 mg/kg body weight, once daily),<br />
increased liver weight but did not affect body weight or glucose tolerance.<br />
However, the ethyl ester of commipheric acid (150 mg/kg, twice daily) lowered<br />
fasting blood glucose and plasma insulin, and plasma triglycerides without<br />
affecting food intake or body weight. These results raise the possibility that<br />
guggulipid has anti-diabetic activity due partly to commipheric acid's<br />
PPARalpha/gamma agonism, but the systemic bioavailability of orally dosed,<br />
pure commipheric acid appears poor. Another component may contribute to<br />
guggulipid's anti-diabetic and hypocholesterolaemic activity by stimulating<br />
LXRalpha.<br />
Francis J.A., Raja S. N. & Nair M.G. (2004) "Bioactive terpenoids and<br />
guggulusteroids from <strong>Commiphora</strong> mukul gum resin of potential anti-<br />
Inflammatory Interest." Chemistry and Biodiversity 1(11), 1842-1853.<br />
Kakrani H.K. (1981) “Flavonoids from the flowers of <strong>Commiphora</strong> mukul. “<br />
Fitoterapia 52, 221–223.<br />
16
Kakrani H.K. (1982) Physicochemical examination of seed oil from <strong>Commiphora</strong><br />
mukul Hook ex Stocks.” Indian Drugs 19, 339–341.<br />
Kumar V. & Dev S. (1987) “Chemistry of Ayurvedic crude drugs-VII: Guggulu<br />
(resin from <strong>Commiphora</strong> mukul). 6. Absolute stereochemistry of guggultetrols.”<br />
Tetrahedron 43, 5933–5948.<br />
Mesrob B., Nesbitt C., Misra R. & Pandey R.C. (1998) High-performance liquid<br />
chromatographic method for fingerprinting and quantitative determination of E-<br />
and Z-guggulsterones in <strong>Commiphora</strong> mukul resin and its products. J.<br />
Chromatogr B 720, 189–196.<br />
Nohr LA, Rasmussen LB, Straand J (2008) "Resin from the mukul myrrh tree,<br />
guggul, can it be used for treating hypercholesterolemia A randomized,<br />
controlled study." Complement Ther Med. 17(1),16-22. Abstract.<br />
BACKGROUND: Guggul, herbal extract from resin of the <strong>Commiphora</strong> mukul<br />
tree, is widely used in Asia as a cholesterol-lowering agent based on Indian<br />
Ayurvedic medicine. Its popularity for this use is increasing in the US and<br />
Western Europe. Guggulsterones, the presumed bioactive compounds of guggul,<br />
may antagonise two nuclear hormone receptors involved in cholesterol<br />
metabolism, which is a possible explanation for hypolipidemic effects of these<br />
extracts. However, publications of efficacy data on the use of guggul extracts in<br />
Western populations are scarce. OBJECTIVE: To study the efficacy of a guggulbased<br />
formulation (short: guggul) on blood lipids in healthy adults with<br />
moderately increased cholesterol. METHODS: Double-blind, randomised,<br />
placebo controlled trial in Norwegian general practice. 43 women and men, age<br />
27-70, with moderately increased cholesterol, randomised to use 2160mg guggul<br />
(4 capsules) daily, or placebo for 12 weeks. OUTCOME MEASURES: Mean<br />
change in total cholesterol, low-density lipoprotein cholesterol (LDL-C),<br />
triglycerides, high-density lipoprotein cholesterol (HDL-C) and total<br />
cholesterol/HDL-C ratio compared with baseline. Lipids were analysed at<br />
baseline, and at 6 and 12 weeks. In addition, unexpected events and adverse<br />
effects were recorded. RESULTS: Two dropouts, one withdrawal, and incomplete<br />
lab results for six persons left 34 participants to accomplish the trial (18-guggul,<br />
16-placebo) with complete lab test data. After 12 weeks, mean levels of total<br />
cholesterol and HDL-C in the active group were significantly reduced compared<br />
with the placebo group. However, the mean levels of LDL-C, triglycerides, and<br />
total cholesterol/HDL-C ratio between the two groups did not change<br />
significantly. Ten guggul users (vs. four in the placebo group) reported side<br />
effects: mild gastrointestinal discomfort (n=7), possible thyroid problems (n=2),<br />
and generalized skin rash (n=1). The latter resulted in withdrawal from trial.<br />
CONCLUSIONS: Even if total cholesterol and HDL-C were significantly reduced,<br />
the clinical magnitude of this remains obscure. More and larger studies are<br />
needed to establish effects and safety of guggul-based formulations in the<br />
treatment for hypercholesterolemia.<br />
Ojha S.K., Nandave M., Arora S., Mehra R.D., Joshi S., Narang R. & Arya D.S.<br />
(2008) "Effect of <strong>Commiphora</strong> mukul extract on cardiac dysfunction and<br />
17
ventricular function in isoproterenol-induced myocardial infarction." Indian J Exp<br />
Biol. 46(9), 646-52. Abstract. In present study, hydroalcoholic extract of C. mukul<br />
significantly improved the cardiac function and prevented myocardial ischemic<br />
impairment manifested in the form of increased heart rate, decreased arterial<br />
pressure, increased left ventricular end diastolic pressure, and altered myocardial<br />
contractility indices. C. mukul treatment additionally also produced a significant<br />
increase in lactate dehydrogenase levels and prevented decline of protein<br />
content in heart. C. mukul preserved the structural integrity of myocardium.<br />
Reduced leakage of myocyte enzyme lactate dehydrogenase and maintenance<br />
of structural integrity of myocardium along with favorable modulation of cardiac<br />
function and improved cardiac performance indicate the salvage of myocardium<br />
with C. mukul treatment. Guggulsterones which are considered to be responsible<br />
for most of the therapeutic properties of C. mukul may underlie the observed<br />
cardioprotective effect of C. mukul against cardiac dysfunction in isoproterenolinduced<br />
ischemic rats.<br />
Patil V.D., Nayak U.R., Dev S. (1972) “Chemistry of Ayurvedic crude drugs-I:<br />
Guggulu (resin from <strong>Commiphora</strong> mukul) -1: Steroidal constituents.” Tetrahedron<br />
28, 2341–2352.<br />
Patil V.D., Nayak U.R., Dev S. (1973) “Chemistry of Ayurvedic crude drugs-II:<br />
Guggulu (resin from <strong>Commiphora</strong> mukul) -2: Diterpenoid constituents.”<br />
Tetrahedron 29, 341–348.<br />
.<br />
Patil V.D., Nayak U.R, Dev S. (1973) “Chemistry of Ayurvedic crude drugs-III:<br />
Guggulu (resin from <strong>Commiphora</strong> mukul) - 3 long-chain aliphatic tetrols, a new<br />
class of naturally occurring lipids.” Tetrahedron 29, 1595–1598.<br />
Prasad R.S. & Dev S. (1976) “Chemistry of Ayurvedic crude drugs-IV: Guggulu<br />
(resin from <strong>Commiphora</strong> mukul - 4 absolute stereochemistry of mukulol.”<br />
Tetrahedron 32, 1437–1441.<br />
Purushothaman K.K. & Chandrasekharan S. (1976) “Gugulsterols from<br />
<strong>Commiphora</strong> mukul (Burseraceae).” Indian J Chem, Sect B 14B, 802–804.<br />
Rücker G. (1972) "Über monocyclische Diterpene aus dem indischen Guggul-<br />
Harz (<strong>Commiphora</strong> mukul).“ Arch. Pharm. (Weinheim) 305, 486–493.<br />
Wang X., Greilberger J., Ledinski G., Kager G., Paigen B. & Juergen G. (2004).<br />
"The hypolipidemic natural product <strong>Commiphora</strong> mukul and its<br />
componentguggulsterone inhibit oxidative modification of LDL.” Atherosclerosis.<br />
172, 239-46.<br />
<strong>Commiphora</strong> myrrha (Nees) Engl. - Chemistry & Composition<br />
True <strong>Myrrh</strong> or Somalian <strong>Myrrh</strong><br />
Ahmed F., Ali M. & Singh O. (2006) "New compounds from <strong>Commiphora</strong> myrrha<br />
(Nees) Engl." Pharmazie 61(8),728-731.<br />
18
El-Ashry E.S., Rashed N., Salama O.M. & Saleh A. (2003) "Components,<br />
therapeutic value and uses of myrrh." Pharmazie 58(3), 163-8. Abstract.<br />
Occurrence, constituents and medicinal use of myrrh, obtained from the stem of<br />
different <strong>Commiphora</strong> species are reviewed. The constituents of the volatile oil,<br />
the resin and the gum are outlined in detail. <strong>Myrrh</strong> has considerable antimicrobial<br />
activity and is medicinally used in a variety of diseases.<br />
Baser K.H.C, Demirci B, Dekebo A, Dagne E. (2003) “Essential oils of some<br />
Boswellia spp., myrrh and opopanax.” Flavour Fragrance J 18, 153–156.<br />
Brieskorn C.H. & Noble P. (1983) “Two furanoeudesmanes from the essential oil<br />
of myrrh.” Phytochemistry 22, 187–189.<br />
Brieskorn C.H, & Noble P. (1983) "Furanosesquiterpenes from the essential oil of<br />
myrrh." Phytochemistry 22, 1207–1211.<br />
Brieskorn C.H. & Noble P. (1982) "Inhaltsstoffe des etherischen Öls der <strong>Myrrh</strong>e.<br />
II: Sesquiterpene und Furanosesquiterpene.” Planta Med 44, 87–90.<br />
Brieskorn C.H. & Noble P. (1980) “Drei neue furanogermacrene aus myrrhe.”<br />
Tetrahedron Lett 21, 1511–1514.<br />
Hanuš L.O., Rosenthal D., Ezanka T., Dembitsky V. M. & Moussaief A.(2008)<br />
"Fast and easy GC/MS identification of myrrh resins." Pharmaceutical Chemistry<br />
Journal c/c of Khimitko-Farmatsevticheskii Zhurnal 42(12),719-720. Abstract.<br />
Extracts prepared from <strong>Commiphora</strong> molmol resins were analyzed by GC-MS.<br />
Twenty-two terpenoid compounds were identified in the hexane extract of the<br />
resin. Among them, 2-acetoxyfuranodiene (9.80%), furanoeudesma-1,3-diene<br />
(8.97%), isofuranogermacrene (6.71%), epicurzerenone (3.64%), 2-<br />
methoxyfuranodiene (2.97%), and lindestrene (2.74%) were the main<br />
compounds from the first myrrh resin (Tamar Ltd.), and furanoeudesma-1,3-<br />
diene (20.59%), isofuranogermacrene (17.94%), 2-acetoxyfuranodiene (8.80%),<br />
2-methoxyfuranodiene (7.33%), and lindestrene (6.24%) from the second myrrh<br />
resin (Pamir Ltd)..<br />
Hanus L.O., Řezanka T., Dembitsky V.M. & Moussaieff A. (2005) "<strong>Myrrh</strong> –<br />
<strong>Commiphora</strong> chemistry" Biomed. Papers 149(1), 3–28. Abstract. <strong>Myrrh</strong> and<br />
opopanax has been used throughout history in incense and as a perfume. Since<br />
Bible times it has been used for the treatment of wounds. The first attempts to<br />
identify content compounds were almost 100 years ago. In this review we<br />
discuss the present state of knowledge in the chemistry of substances of<br />
<strong>Commiphora</strong> spp.<br />
[Available at http://biomed.papers.upol.cz/pdfs/bio/2005/01/01.pdf]<br />
Kimura I., Yoshikawa M., Kobayashi S., Sugihara Y., Suzuki M., Oominami H.,<br />
Murakami T., Matsuda H/ & Doiphode VV. (2001) “New triterpenes, myrrhanol A<br />
and myrrhanone A, from guggulgum resins, and their potent anti-inflammatory<br />
effect on adjuvantinduced air-pouch granuloma of mice. Bioorg Med Chem Lett<br />
11, 985–989.<br />
19
Ma X., Yu X., Zheng Z. & Mao J. (1992) “Investigation of volatile composition in<br />
frankincense and myrrh using analytical supercritical fluid extraction technique.”<br />
Yaowu Fenxi Zazhi 12, 83–86.<br />
Maradufua A. & Warthen Jr. J.D. (1998) "Furanosesquiterpenoids from<br />
<strong>Commiphora</strong> myrrh oil." Plant Science 57(2), 181-184. Abstract. Highperformance<br />
liquid chromatography has made possible the separation of<br />
furanosesquiterpenoids in <strong>Commiphora</strong> myrrh oil. Combined application of NMR,<br />
UV, and MS techniques have revealed that oil from C. myrrh gum resins contains<br />
isofuranogermacrene (1), lindestrene (2), furanoeudesma-1,3-diene (3), and<br />
furanodiene (4).<br />
Marongiu B., Piras A., Porcedda S. & Scorciapino A. (2005) "Chemical<br />
Composition of the essential oil and supercritical CO2 extract of <strong>Commiphora</strong><br />
myrrha (Nees) Engl. and of Acorus calamus L." Journal of Agricultural and Food<br />
Chemistry 53(20), 7939-7943. Abstract. Volatile concentrates from the oleo-gum<br />
resin of <strong>Commiphora</strong> myrrha (Nees) Engl. and from the rhizomes of Acorus<br />
calamus were isolated by supercritical extraction with carbon dioxide. The volatile<br />
oil of myrrh was obtained at 9.0 MPa and 50 °C and at a CO2 flow of 1.5 kg/h.<br />
Acorus calamus was extracted at 9.0 MPa and 45 °C and at a CO2 flow of 1.6<br />
kg/h. In both cases, an oil devoid of cuticular waxes was obtained with a single<br />
depressurization stage. The SFE myrrh oil had a yield, Y, of 3.2%. Its main<br />
components, identified and quantified by GC/MS, were furanoeudesma-1,3-<br />
diene, 34.9%; lindestrene, 12.9%; curzerene, 8.5%; and germacrone, 5.8%. The<br />
essential oils from the same starting material by hydrodistillation, HD, (Y = 2.8%)<br />
and by steam distillation, SD, (Y = 0.4%) were quite similar to the SFE extract.<br />
The main components of the SFE oil of A. calamus (Y = 3.5%) were acorenone,<br />
13.4%; iso-acorone, 11.6%; (Z)-sesquilavandulol, 11.0%; dehydroxy<br />
isocalamendiol, 7.7%; and β-asarone, 5.5%. The comparison with hydrodistilled<br />
(Y = 1.8%) and steam distilled (Y = 1.0%) oils revealed large differences in the<br />
content of iso-acorone and crypto-acorone.<br />
Monti D., Manitto P., Tagliapietra S., Dada G. & Speranza G. (1986) “The<br />
absolute stereochemistry of two furanogermacranes of myrrh as determined by<br />
the circular dichroism exciton chirality method.” Gazz Chim Ital 116, 303–306.<br />
Morteza-Semnani K, Saeedi M. (2003) “Constituents of the essential oil of<br />
<strong>Commiphora</strong> myrrha (Nees) Engl. var. molmol.” J Essent Oil Res 15, 50–51.<br />
Shen T. Wan W.Z., Wang X.N., Yuan H.Q., Ji M. & Lou H.X. (2009) "A<br />
triterpenoid and sesquiterpenoids from the resinous exudates of <strong>Commiphora</strong><br />
myrrha." Helevitica Chimica Acta 92(4),645-652.<br />
El-Sherbini G.T., El Gozamy B.R., Abdel-Hady N.M. & Morsy T.A. (2009)<br />
"Efficacy of two plant extracts against vaginal trichomoniasis." J Egypt Soc<br />
Parasitol. 39(1),47-58. Abstract. Trichomoniasis vaginalis is now an important<br />
worldwide health problem. Metronidazole has so far been used in treatment, but<br />
the metronidazole-resistant strains and unpleasant adverse effects have been<br />
20
developed. Treatment of patients with metronidazole refractory vaginal<br />
trichomoniasis constitutes a major therapeutic challenge and treatment options<br />
are extremely limited. In the present study, 33 metronidazole-resistant T.<br />
vaginalis females were treated with a combined course of metronidazole and<br />
tinidazole. Those still resistant to the combined treatment were given<br />
<strong>Commiphora</strong> molmol (<strong>Myrrh</strong>) as two capsules for six to eight successive days on<br />
an empty stomach two hours before breakfast. Also, natural plant extract purified<br />
from (Roman) was in-vitro investigated for its efficacy against T. vaginalis on<br />
fresh Diamond media. The anti-trichomoniasis vaginalis activity of both P.<br />
granatum (in-vitro) and C. molmol (in-vivo) extracts gave promising results.<br />
Wiendl R.M., Müller B.M. & Franz G. (1995) “Proteoglycans from the gum<br />
exudate of myrrh.” Carbohyd Polym 28, 217–226.<br />
Wiendl R.M. & Franz G. (1994) “<strong>Myrrh</strong>. New chemistry of an old plant drug.”<br />
Dtsch Apoth Ztg 134, 27–29, 31–32.<br />
Wilson R.A. & Mookherjee B.D. (1983) “Characterization of aroma donating<br />
components of myrrh.” Proceedings of 9th International Congress of Essential<br />
Oils, Singapore, 13–17 March, paper no. 400, pp. 1– 10, Book 4. Singapore:<br />
Essential Oils Association of Singapore.<br />
Yang G.-C., Li Z.-L., Li W. & Hua H.-M. (2008) The structure of a<br />
franosesquiterpenoid extracted from myrrh elucidated by NMR Spectroscopy."<br />
Chinese J of Magnetic Resonance 25(4), 548-553.<br />
Yu X, Ma X, Ding X. (1993) “GC/ITD study of major constituents of the extracts of<br />
myrrh and Curcuma zedoaria.” Fenxi Ceshi Xuebao 12, 8–13.<br />
Zhu N., Sheng S., Sang S., Rosen R.T. & Ho C-T. (2003) “Isolation and<br />
characterization of several aromatic sesquiterpenes from <strong>Commiphora</strong> myrrha.”<br />
Flavour Fragrance J. 18, 282–285.<br />
Zhu N., Kikuzaki H., Sheng S., Sang S., Rafi M.M., Wang M., Nakatani N.,<br />
DiPaola R.S., Rosen R.T, & Ho C.-T. (2001) "Furanosesquiterpenoids of<br />
<strong>Commiphora</strong> myrrha." Abstract. An investigation on the gum exudates of<br />
<strong>Commiphora</strong> myrrha has led to the isolation of six sesquiterpenoids. On the basis<br />
of spectroscopic data interpretation, they were determined as two new<br />
furanosesquiterpenoids, rel-1S,2S-epoxy-4R-furanogermacr-10(15)-en-6-one (1)<br />
and rel-2R-methyl-5S-acetoxy-4R-furanogermacr-1(10)Z-en-6-one (2), and four<br />
known furanosesquiterpenoids, rel-3R-methoxy-4S-furanogermacra-1E,10(15)-<br />
dien-6-one (3), rel-2R-methoxy-4R-furanogermacr-1(10)E-en-6-one (4),<br />
furanogermacra-1(10)Z,4Z-dien-6-one, and curzerenone [6,7-dihydro-5βisopropenyl-3,6β-dimethyl-6-vinylbenzofuran-4(5H)-one].<br />
This is the first report of<br />
the relative stereochemistry for the known compounds 3 and 4. Compound 1<br />
exhibited weak cytotoxic activity against a MCF-7 breast tumor cell line in a<br />
clonogenic assay, while the other five compounds were inactive in this assay.<br />
<strong>Commiphora</strong> myrrha (Nees) Engl. – Properties.<br />
21
True <strong>Myrrh</strong> or Somalian <strong>Myrrh</strong>.<br />
Abdul-Ghani RA, Loutfy N, Hassan A. (2009) "<strong>Myrrh</strong> and trematodoses in Egypt:<br />
an overview of safety, efficacy and effectiveness profiles. Parasitol Int. 58(3),<br />
210-4. Abstract. <strong>Myrrh</strong> is an herbal product that has been used since ancient<br />
ages for traditional medication and other purposes. The revolution of myrrh as an<br />
antiparasitic agent in Egypt began in the 1990s through scientific evidence-based<br />
research. The human trematode infections in Egypt were the main focus of<br />
research with stories of success and disagreement, at times. The present paper<br />
reviewed the antiparasitary activity of myrrh with stress on its possible mode of<br />
action, its safety, efficacy and effectiveness on trematode infections in<br />
experimental studies and clinical trials in Egypt as well as its molluscicidal effects<br />
on the intermediate hosts of trematodes.<br />
Bone, K. (2006) "<strong>Myrrh</strong>: A significant development in the treatment of parasites."<br />
Townsend Letter for Doctors and Patients 276, 46-54.<br />
Dolara P., Corte B., Ghelardini C., Pugliese A.M., Cerbai E., Menichetti S., Lo<br />
Nostro A. (2000) “Local anaesthetic, antibacterial and antifungal properties of<br />
sesquiterpenes from myrrh. Planta Med 66, 356–358. Abstract. We extracted,<br />
purified and characterized 8 sesquiterpene fractions from Commyphora molmol.<br />
In particular, we focused our attention on a mixture of furanodiene-6-one and<br />
methoxyfuranoguaia-9-ene-8-one, which showed antibacterial and antifungal<br />
activity against standard pathogenic strains of Escherichia coli, Staphylococcus<br />
aureus, Pseudomonas aeruginosa and Candida albicans, with minimum<br />
inhibitory concentrations ranging from 0.18 to 2.8 micrograms/ml. These<br />
compounds also had local anaesthetic activity, blocking the inward sodium<br />
current of excitable mammalian membranes.<br />
Dolara P., Luceri C., Ghelardini C., Monserrat C., Aiolli S., Luceri F., Lodovici M.,<br />
Menichetti S. & Romanelli M.N. (1996) "Analgesic effects of myrrh." Nature<br />
379(6560), 29.<br />
Lemenih M. & Teketay D. (2003) "Frankincense and myrrh resources of Ethiopia:<br />
II. Medicinal and industrial uses." SINET: Ethiopian Journal of Science 26(2),<br />
161-172(12). Abstract. Oleo-gum resins such as frankincense and myrrh are<br />
some of the economically and culturally valuable products obtained from trees<br />
and shrubs of the genera Boswellia and <strong>Commiphora</strong>, respectively. They are<br />
important natural plant products used in several industries that include<br />
pharmacology, food, flavour, liqueur and beverage, cosmetics, perfumery and<br />
others. Moreover, frankincense and myrrh have several local applications in<br />
medicinal, hygienic, and insecticide areas that could be developed through<br />
research. They are widely used in traditional medicines of several countries for<br />
treatments of a wide variety of ailments from embalming to cancer, leprosy,<br />
bronchitis, diarrhea, dysentery, typhoid, mouth ulcers, inflammatory complaints,<br />
viral hepatitis, female disorders, infections/wounds, coughs, tumour, and others.<br />
Although Ethiopia is one of the few countries that are endowed with large<br />
frankincense and myrrh resources, little proper exploitation of these resources<br />
22
has been made so far. In this paper a review is presented on pharmacological<br />
and industrial applications of these valuable resources. The information is<br />
expected to prompt the enormous economic opportunity that these resources<br />
could provide both at national and local levels. Concurrently, this opportunity, if<br />
properly exploited, will contribute significantly towards the conservation and<br />
management of the vegetation resources that yield frankincense and myrrh as<br />
well as their ecosystems.<br />
Lv L., Yan G.-Y., Zhao Y.-L., He X.-J., Jiang X., Zhuo Y.-Q., Wang Y.-L. Wang L.<br />
& Cen X.-B. (2009) "Investigation of the dermal sensitizing potential of traditional<br />
medical extracts in local lymph node assays." Experimental Biology and Medicine<br />
234, 306-313. Abstract. "Traditional medical extracts are commonly used as<br />
complex mixtures, which may contain naturally occurring contact sensitizers. In<br />
this investigation, the mice local lymph node assay (LLNA) was performed to<br />
evaluate the dermal sensitization potential of <strong>Myrrh</strong>, Borneolum, Olibanum,<br />
Moschus and Cassia Bark, which are widely used in topical traditional<br />
medication. In the radioactive LLNA, the stimulation index (SI) values were<br />
calculated for each medical extract. <strong>Myrrh</strong>, Borneolum, Olibanum and Moschus<br />
induced dose-dependent cell proliferation and SI was more than 3. Cassia Bark<br />
showed no positive response over the range of test concentrations. In the flow<br />
cytometry analysis, the total number of CD3+, CD4+, and CD8+ cells in local<br />
lymph nodes was increased in Moschus-, Olibanum-, <strong>Myrrh</strong>- and Borneolumtreated<br />
mice. The ratio of the B220+/CD3+ (B/T cell ratio) and the percentage of<br />
I-Ak+ cells that was also positive for the CD69 marker (I-Ak+/ CD69+) were<br />
increased in the Moschus-, Olibanum- and <strong>Myrrh</strong>-treated mice. However, no<br />
ofbvious change was observed in Borneolum-treated mice. Cassia Bark did not<br />
induce changes in the lymphocyte subpopulations. These results indicate that<br />
Moschus, Olibanum and <strong>Myrrh</strong> can be regarded as sensitizers, and Borneolum<br />
regarded as an irritant. Cassia Bark is neither a sensitizer nor an irritant. The<br />
combination of radioactive and flow cytometric LLNA can be used for the<br />
prediction of sensitizing potential of medical extracts which lead to allergic<br />
contact dermatitis in humans. "<br />
Massoud A.M., El Ebiary F.H. & Abd El Salam N.F. (2004). "Effect of myrrh<br />
extract on the liver of normal and bilharzially infected mice. An ultrastructural<br />
study." J Egypt Soc Parasitol. 34, 1-21.<br />
Massoud A.M., Labib I.M. & Rady M (2001). "Biochemical changes of Culex<br />
pipiens larvae treated with oil and oleo-resin extracts of <strong>Myrrh</strong> <strong>Commiphora</strong><br />
molmol." J Egypt Soc Parasitol. 31, 517-29.<br />
Mayer J.G. (2008) “[Gold, frankincense and myrrh]” Dtsch Med Wochenschr.<br />
133 (51-52):2665-8.<br />
Mincione E. & Lavarone C. (1972) “ Terpeni dalla Commifera mirra Arabica. Nota<br />
I.” Chim Ind (Milan) 54, 424–425.<br />
23
Nomicos E.Y. (2007) "<strong>Myrrh</strong>: medical marvel or myth of the Magi" Holist Nurs<br />
Pract. 21(6), 308-23. Abstract. Since antiquity, the genus <strong>Commiphora</strong> is<br />
composed of more than 200 species, and has been exploited as a natural drug to<br />
treat pain, skin infections, inflammatory conditions, diarrhea, and periodontal<br />
diseases. In more recent history, products derived from <strong>Commiphora</strong> myrrha and<br />
various other species of <strong>Commiphora</strong> are becoming recognized to possess<br />
significant antiseptic, anesthetic, and antitumor properties. Traditional practice<br />
and evidence-based research have supported that these properties are directly<br />
attributable to terpenoids (especially furanosesquiterpenes), the active<br />
compounds present in myrrh essential oil. More recently, current studies have<br />
focused on applying clinical trial methodologies to validate its use as an<br />
antineoplastic, an antiparasitic agent, and as an adjunct in healing wounds.<br />
Pank F. (2009) "Incense and myrrh - incense between mysticism and medicine."<br />
Zeitschrift fur Arznet und Gewurzpflanzen 14(4), 145-145.<br />
Racine P. & Auffray B. (2005) "Quenching of singlet molecular oxygen by<br />
<strong>Commiphora</strong> myrrha extracts and menthofuran." Fitoterapia 76(3-4), 316-23.<br />
Abstract. The quenching activity against singlet oxygen, an actor of lipid<br />
peroxidation and DNA degradation, of the essential oil and resinoid of<br />
<strong>Commiphora</strong> myrrha from Somalia has been studied and compared to DL-alphatocopherol<br />
using 1,3-diphenylisobenzofuran (DPBF) as a probe. To insure that<br />
the furan ring was the site of the reaction, experiments were conducted with<br />
menthofuran. The essential oil and menthofuran show a higher activity than DLalpha-tocopherol,<br />
suggesting their potential usefulness to neutralise this<br />
deleterious form of molecular oxygen.<br />
Saeed M.A. & Sabir A.W. (2004) “Irritant potential of some constituents from<br />
oleo-gum-resin of <strong>Commiphora</strong> myrrha.” Fitoterapia 75(1), 81-4.<br />
Shen T. & Lou HX. (2008) "Bioactive constituents of myrrh and frankincense, two<br />
simultaneously prescribed gum resins in Chinese traditional medicine." Chem<br />
Biodivers. 5(4), 540-53.<br />
Su SL, Duan JA, Tang YP, Zhang X, Yu L, Jiang FR, Zhou W, Luo D, Ding AW<br />
(2009) "Isolation and biological activities of neomyrrhaol and other terpenes from<br />
the resin of <strong>Commiphora</strong> myrrha". Planta Med. 75(4), 351-5. Abstract. A new<br />
cycloartane-type triterpene named cycloartane-1alpha,2alpha,3beta,25-tetraol<br />
(neomyrrhaol) (1), along with four known terpenes, sandaracopimaric acid (2),<br />
abietic acid (3), 2-methoxy-5-acetoxyfruranogermacr-1(10)-en-6-one (4), and<br />
dehydroabietic acid (5) have been isolated from the resin of COMMIPHORA<br />
MYRRHA. Their structures were elucidated by means of 1D, 2 D NMR and HRmass<br />
spectroscopy. Compounds 2-5 are known compounds but not previously<br />
isolated from the resin of C. Myrrrha. Compounds 4 and 5 exhibited significant<br />
aromatase inhibiting activity with IC50 values at 0.2 microM and 0.3 microM,<br />
respectively. As shown in the MTT assay, 2, 3, 4, and 5 had inhibitory effects on<br />
HUVEC growth with IC50 values of 0.122 microM (2), 0.125 microM (3), 0.069<br />
microM (5). Compounds 1-5 did not inhibit contraction of the isolated uterine and<br />
24
did not protect HUVEC from damage induced by H2O2 at the tested<br />
concentration.<br />
Tipton D.A., Lyle B., Babich H. & Dabbous M.Kh. (2003) "In vitro cytotoxic and<br />
anti-inflammatory effects of myrrh oil on human gingival fibroblasts and epithelial<br />
cells." Toxicol In Vitro. 17(3), 301-10.<br />
Tucker A.O. (1986) “Frankincense and <strong>Myrrh</strong>.” Econ Bot 40, 425–433. Abstract.<br />
While frankincense and myrrh have been harvested from a multitude of species,<br />
certain species have predominated in history. Boswellia carteri and B. frereana<br />
are the main sources of frankincense today, while B. papyrifera was the principal<br />
source of antiquity and B. sacra was the principal species of classical times.<br />
<strong>Commiphora</strong> myrrha is the chief source of myrrh today, but C. erythraea was the<br />
principal source of ancient and classical times. Each of these oleo-gum-resins<br />
has a characteristic odor that is predominately due to a mixture of complex<br />
sesquiterpenes.<br />
<strong>Commiphora</strong> opobalsamum L.<br />
syn. <strong>Commiphora</strong> gileadensis (L.) C. Chr.<br />
Balm of Gilead or Mecca Balsam.<br />
<strong>Cropwatch</strong> comments: Do not confuse with Cedronella canariensis syn.<br />
Cedronella triphylla, (Canary Balm) native to the Canary Islands and of marketed<br />
by European plant nurseries as Balm of Gilead, or with exudates or extracts of<br />
poplar buds (Populus balsamifera Moench). which are also offered as Balm of<br />
Gilead (but also sold as Tacamahac or Gum Tacamahac, a term previously<br />
applied to the fragrant resin from Bursera gummifera L.).<br />
Abbas F. A., Al-massarany S. M., Khan S., Al-howiriny T.A., Mossa J. S. &<br />
Abourashed E.A. (2007) "Phytochemical and biological studies on Saudi<br />
<strong>Commiphora</strong> opobalsamum L." Natural Product Research 21(5).383-391,<br />
Abdul-Ghani A.S. & Amin R. (1997) “Effect of aqueous extract of <strong>Commiphora</strong><br />
opobalsamum on blood pressure and heart rate in rats.” J Ethnopharmacol 57,<br />
219–222. Abstract. The cardiovascular effects of aqueous extracts from the<br />
branches of <strong>Commiphora</strong> opobalsamum tree were investigated. The intravenous<br />
administration of 4 mg/kg of the aqueous extract depressed systemic arterial<br />
blood pressure by 20% (P
(80% ethanol, 0.2 M NaOH and 25% NaCl), hypothermic restraint stress, pyloric<br />
ligation (Shay) and indomethacin. Balessan, 250 and 500 mg/kg administered<br />
orally (intraperitoneally in Shay rat model) showed a dose-dependent ulcer<br />
protective effects in all the above ulcer models. Besides, the extract offered<br />
protection against ethanol-induced depletion of stomach wall mucus and<br />
reduction in nonprotein sulfhydryl (NP-SH) concentration. Ethanol treatment also<br />
caused histopathological lesions of the stomach wall. Pretreatment with Balessan<br />
extract provided a complete protection of gastric mucosa through supporting both<br />
the offensive and defensive factors. Balessan extract was also showed a large<br />
margin of safety without any apparent adverse effects in rats.<br />
Al-Howiriny T.A., Al-Sohaibani M.O., Al-Said M.S., Al-Yahya M.A., El-Tahir K.H.<br />
& Rafatullah S. (2004). "Hepatoprotective properties of <strong>Commiphora</strong><br />
opobalsamum ("Balessan"), a traditional medicinal plant of Saudi Arabia."<br />
Drug.Exp Clin Res 30, 213-20.<br />
Al-Massarany S.M., Abbas F.A., Demirci B., Baser K.H.C., Khan S.I., Al-Rehaily<br />
A.J., Mossa J.S. & Abourashed E.A. (2007) "Chemical composition and biological<br />
evaluation of the essential oil of <strong>Commiphora</strong> opobalsamum L." Journal of Herbs<br />
Spices and Medicinal Plants 13(4),111-122. Abstract. The chemical composition<br />
of three essential oil samples (stored aerial parts, fresh aerial parts, and fresh<br />
flowering tops) of <strong>Commiphora</strong> opobalsamum L., obtained by hydrodistillation,<br />
was determined using GC-MS analysis. The identified constituents represented<br />
69.5 to 84.4 percent of the total chemical compounds of the three samples. The<br />
major components were -cadinol in the stored aerial parts, -calacorene in the<br />
fresh aerial parts, and terpinen-4-ol in the fresh flowering tops. The essential oil<br />
from the fresh aerial parts exhibited antimicrobial activity against Bacillus subtilis,<br />
Staphylococcus aureus, Candida glabrata, C. krusei, Cryptococcus neoformans,<br />
and Mycobacterium intracellulare. The same oil sample was non-selectively<br />
cytotoxic to four tumor cell lines: SK-MEL, KB, BT549 and SK-OV3. Weak<br />
antioxidant activity of the oil from the fresh aerial sample was demonstrated in a<br />
DPPH free-radical scavenging assay.<br />
Chaudhary & Al Jowaid (1999) Vegetation of the Kingdom of Saudi Arabia pub.<br />
Ministry of Agric. & Water, Kingdom of Saudi Arabia 1999. <strong>Cropwatch</strong> comments:<br />
Authors say of C. giladensis ““more valuable than frankincense.”<br />
Shen T., Yuan H.-Q.,Wan W-Z. , Wang X.-L., Wang X.-N., Ji M. & Lou H.-X.<br />
(2008) "Cycloartane-Type triterpenoids from the resinous exudates of<br />
<strong>Commiphora</strong> opobalsamum." J. Nat. Prod., 71(1), 81–86. Abstract. Eight new<br />
cycloartane-type triterpenoids, cycloartan-24-ene-1α,2α,3α-triol (1), 3βacetoxycycloartan-24-ene-1α,2α-diol<br />
(2), 1α-acetoxycycloartan-24-ene-2α,3β-diol<br />
(3), 3β-isovaleroyloxycycloartan-24-ene-1α,2α-diol (4), cycloartan-24-ene-1α,3βdiol<br />
(5), cycloartan-23E-ene-1α,2α,3β,25-tetrol (6), and an epimeric mixture of<br />
24R,25-epoxycycloartane-1α,2α,3β-triol (7) and 24S,25-epoxycycloartane-<br />
1α,2α,3β-triol (8), together with one known compound, cycloartan-24-ene-<br />
1α,2α,3β-triol (9), were isolated from the resinous exudates of <strong>Commiphora</strong><br />
opobalsamum. Their structures were established on the basis of mass<br />
26
spectrometry and multidimensional NMR spectroscopy. The cytotoxicity of<br />
compounds 1–9 was evaluated against the PC3 and DU145 human prostate<br />
tumor cell lines. All of the compounds except 1 and 5 exhibited moderate<br />
cytotoxicity against PC3 or DU145 cells with IC50 values ranging from 10.1 to<br />
37.2 µM.<br />
Shen T., Wan W.-Z., Wang X.-N., Sun L.-M., Yuan H.-Q., Wang X.-L., Ji M., &<br />
Lou H.-X. (2008) "Sesquiterpenoids from the resinous exudates of <strong>Commiphora</strong><br />
opobalsamum (Burseraceae)." Helvetica Chimica Acta 91(5), 881-887.<br />
Shen T., Wan W., Yuan H., Kong F., Guo H., Fan P. & Lou H. (2007) "Secondary<br />
metabolites from <strong>Commiphora</strong> opobalsamum and their antiproliferative effect on<br />
human prostate cancer cells." Phytochemistry 68(9),1331-1337. Abstract. A<br />
cycloartane-type triterpenoid (1), an aliphatic alcohol glycoside (2), an<br />
eudesmane-type sesquiterpenoid (3), and a guaiane-type sesquiterpenoid (4)<br />
were isolated from the resinous exudates of <strong>Commiphora</strong> opobalsamum along<br />
with six known sesquiterpenoids (5–10). Their structures were established by<br />
extensive analysis of their 1D and 2D NMR spectroscopic data and chemical<br />
methods. The isolated compounds 1–3 and 5–9 were tested against human<br />
prostate cancer cell PC 3 and LNCaP. Among them, 1 and 2 showed moderate<br />
antiproliferative effects on human prostate cancer cell lines with IC50 values<br />
ranging from 5.7 to 23.6 µM; they were also able to inhibit the expression of<br />
androgen receptor (AR) in LNCaP cells. The six sesquiterpenoids were inactive<br />
in the bioassays.<br />
<strong>Commiphora</strong> pseudopaoli JB Gillet<br />
syn. <strong>Commiphora</strong> paolii Chiov.<br />
<strong>Cropwatch</strong> comments: Source of opoponax (Gachathi 1997).<br />
Gachathi F. N. (1997) “Recent advances on classification and status of main<br />
gum-producing species in the Family Burseraceae” available at<br />
http://www.fao.org/documents/show_cdr.aspurl_file=/docrep/X0098e/X0098e01.<br />
htm<br />
<strong>Commiphora</strong> schimperi (Berg.) Engl.<br />
syn. <strong>Commiphora</strong> buraensis.<br />
<strong>Cropwatch</strong> comments: Source of “myrrh-like resin” (Gachathi 1997); Frequent<br />
adulterant of gum myrrh - Dekebo et al. (2002).<br />
Dekebo A., Dagne E. & Sterner O. (2002) “Furanosesquiterpenes from<br />
<strong>Commiphora</strong> sphaerocarpa and related adulterants of true myrrh.” Fitoterapia –<br />
Milano 73(1), 48-55.<br />
Gachathi F. N. (1997) “Recent advances on classification and status of main<br />
gum-producing species in the Family Burseraceae” available at<br />
http://www.fao.org/documents/show_cdr.aspurl_file=/docrep/X0098e/X0098e01.<br />
htm<br />
27
Paraskeva M.P., van Vuuren S.F., van Zyl R.L., Davids H. & Viljoen A.M. (2008)<br />
"The in vitro biological activity of selected South African <strong>Commiphora</strong> species." J<br />
Ethnopharmacol. 119(3),673-9. Abstract. Ten South African <strong>Commiphora</strong><br />
(Burseraceae) species were investigated to validate their use in traditional<br />
healing rites. The leaf and stem extracts of each species were analysed for the<br />
anti-oxidant (ABTS and DPPH assays), antimicrobial (MIC and death kinetic<br />
assays), anti-inflammatory (5-LOX assay), anticancer (SRB assay) properties, as<br />
well as the cytotoxic effects (tetrazolium-based assay). The best anti-oxidant<br />
activity (ABTS assay) was observed for the stem extracts of <strong>Commiphora</strong><br />
tenuipetiolata IC(50)=5.10 microg/ml), <strong>Commiphora</strong> neglecta (IC(50)=7.28<br />
microg/ml) and <strong>Commiphora</strong> mollis (IC(50)=8.82 microg/ml). Extracts generally<br />
exhibited poor anti-oxidant activity in the DPPH assay, with the exception of<br />
<strong>Commiphora</strong> schimperi (stem), <strong>Commiphora</strong> neglecta (stem), <strong>Commiphora</strong><br />
tenuipetiolata (stem and leaf), and <strong>Commiphora</strong> edulis (stem), with IC(50) values<br />
ranging between 7.31 and 10.81 microg/ml. The stem extracts exhibited<br />
moderate to good 5-LOX inhibitory activity with <strong>Commiphora</strong> pyracanthoides<br />
(stem) displaying the greatest inhibitory effect (IC(50)=27.86+/-4.45 microg/ml).<br />
For the antimicrobial (MIC) assay, a greater selectivity was exhibited by the<br />
extracts against the Gram-positive bacteria (0.01-8.00 mg/ml) and the yeasts<br />
(0.25-8.00 mg/ml) than against the Gram-negative bacteria (1.00-8.00 mg/ml).<br />
Using death kinetic studies (time-kill studies), the rate at which <strong>Commiphora</strong><br />
marlothii (stem) kills Staphylococcus aureus over a 24h period was determined.<br />
Mostly, a concentration-dependent antibacterial activity was observed beginning<br />
after ca. 30 min. All concentrations exhibited antibacterial activity, with complete<br />
bactericidal effect achieved by the 24(th) hour. The most active <strong>Commiphora</strong><br />
species against the HT-29 cells (SRB anticancer assay) were <strong>Commiphora</strong><br />
glandulosa (leaf and stem) and <strong>Commiphora</strong> marlothii (leaf). The MCF-7 cells<br />
(SRB anticancer assay) exhibited the highest sensitivity to indigenous<br />
<strong>Commiphora</strong> species, with <strong>Commiphora</strong> edulis (leaf and stem), <strong>Commiphora</strong><br />
glandulosa (leaf and stem), <strong>Commiphora</strong> marlothii (leaf), <strong>Commiphora</strong><br />
pyracanthoides (leaf and stem), <strong>Commiphora</strong> schimperi (stem), and <strong>Commiphora</strong><br />
viminea (stem) all possessing a percentage inhibition greater than 80% at 100<br />
microg/ml. <strong>Commiphora</strong> glandulosa (leaf and stem) and <strong>Commiphora</strong><br />
pyracanthoides (leaf and stem) were the two most active species against the SF-<br />
268 cells (SRB anticancer assay), with IC(50) values ranging between 68.55+/-<br />
2.01 and 71.45+/-1.24 microg/ml. The majority of the <strong>Commiphora</strong> extracts were<br />
largely non-cytotoxic against Graham human kidney epithelial cells when<br />
investigated in the MTT assay.<br />
<strong>Commiphora</strong> sphaerocarpa Chiov. Chiovenda.<br />
Dekebo A., Dagne E. & Sterner O. (2002) "Furanosesquiterpenes from<br />
<strong>Commiphora</strong> sphaerocarpa and related adulterants of true myrrh." Fitoterapia<br />
73(1),48-55. Abstract. A new furanosesquiterpene, (1E)-8,12-epoxygermacra-<br />
1,7,10,11-tetraen-6-one (3), was isolated from the resin of <strong>Commiphora</strong><br />
sphaerocarpa together with the known compounds curzerenone (1),<br />
furanodienone (2), (1E)-3-methoxy-8,12-epoxygermacra-1,7,10,11-tetraen-6-one<br />
28
(4), (1(10)E,2R*,4R*)-2-methoxy-8,12-epoxygermacra-(10),7,11-trien-6-one (5),<br />
and dihydropyrocurzerenone (6). Hydrodistillates of the resins of C.<br />
sphaerocarpa, C. holtziana, C. kataf and C. myrrha were analysed. The<br />
identifications were aided by NMR, GC and GC-MS.<br />
Dekebo A., Dagne E., Hansen L.K. Gautun O.R. & Aasen A.J. (2000) "Crystal<br />
structures of two furanosesquiterpenes from <strong>Commiphora</strong> sphaerocarpa"<br />
Tetrahedron Letters 41(50), 9875-9878. Abstract. The relative stereochemistry of<br />
a furanosesquiterpene, reported previously from myrrh, but isolated here from<br />
<strong>Commiphora</strong> sphaerocarpa is determined for the first time as (1(10)E,2R*,4R*)-2-<br />
methoxy-8,12-epoxygermacra-1(10),7,11-trien-6-one. Likewise the<br />
stereochemistry of furanodienone was established by NMR and X-ray<br />
crystallography as (1(10)E,4E)-8,12-epoxygermacra-1(10),4,7,11-tetraen-6-one<br />
<strong>Commiphora</strong> tenuis K. Vollesen.<br />
Asres K., Tei A., Moges G., Sporer F. & Wink M. (1998). "Terpenoids<br />
composition of the wound – induced bark exudate of <strong>Commiphora</strong> tenuis from<br />
Ethiopia.” Planta Med. 64, 437-475. Abstract. The bark of <strong>Commiphora</strong> tenuis<br />
Vollensen exudes a translucent, free-flowing odoriferous liquid upon wounding<br />
which was analysed by capillary GLC and GLC-MS. 42 mono- and<br />
sesquiterpenes were detected and 37 identified. The main components of the<br />
monoterpenoid fraction were alpha-pinene (60.8%), beta-pinene (8.8%),<br />
sabinene (6.3%), alpha-thujene (8.9%), limonene (5.5%), 3-carene (3.7%), betamyrcene<br />
(1.8%), and beta-elemene (1.1%) constituting 97% of the oil. Identified<br />
sesquiterpenoid components constituted approximately 1.6% of the oil. Oleanolic<br />
acid acetate was isolated and identified as the main triterpene from the resin by<br />
1H- and 13C-NMR. Three other triterpenes of the olean-12-ene group were also<br />
detected using GC-MS. The essential oil exhibited antibacterial activities against<br />
Staphylococcus aureus. Proteus mirabilis and E. coli with MIC between 0.5 and<br />
1%.<br />
<strong>Commiphora</strong> wightii Arnott.<br />
syn. <strong>Commiphora</strong>. mukul (Hook ex Stocks)<br />
Guggal or Indian Bdellium<br />
Bai S. & Jain M. (2008) "1H and 13C assignments of five cembrenes from<br />
guggul." Magn Reson Chem. 46(8), 791-3. Abstract. Chemical shift assignments<br />
of (1)H and (13)C of five cembrene compounds isolated from the hexane extract<br />
of guggul, the resin of <strong>Commiphora</strong> mukul, are reported. Using (1)H, (13)C, and<br />
2D NMR methods their structures were determined as cembrene (1-isopropyl-<br />
4,8,12-trimethyl-cyclotetradeca-2,4,7,11-tetraene), cembrene A (1-isopropenyl-<br />
4,8,12-trimethyl-cyclotetradeca-4,8,12-triene), cembrenol (1-isopropyl-4,8,12-<br />
trimethyl-cyclotetradeca-3,7,11-trienol), mukulol (1-isopropyl-4,8,12-trimethylcyclotetradeca-3,7,11-trienol),<br />
and verticillol (4,8,12,15,15-pentamethylbicyclo[9.3.1]pentadeca-3,7-dien-12-ol).<br />
29
Bhatt J.R., Nair M.N.B. & Ram H.Y.M. (1989) "Enhancement of oleo-gum resin<br />
production in <strong>Commiphora</strong> wightii by improved tapping technique." Current<br />
Science 58(7), 349-357.<br />
Coulter J. (1987) Market study for frankincense and myrrh from Somalia<br />
(unpubl). Study undertaken for the European Association for Cooperation.<br />
Chatham, UK: Natural Resources Institute.<br />
Fatope M.O. et al. (2003) "Muscanone: a 3-O-(1", 8", 14"-<br />
trimethylhexadecanyl)naringenin from <strong>Commiphora</strong> wightii." Phytochemistry<br />
62(8),1251-1255. Abstract. A new antifungal flavanone, muscanone (1), was<br />
isolated along with known naringenin (2) from <strong>Commiphora</strong> wightii (Arn.)<br />
Bhandari (Burseraceae) by directing the fractionation of an EtOH extract of the<br />
air-dried trunk of C. wightii with microbial sensitivity assay. The structures of 1<br />
and 2 were determined from EIMS, HREIMS, DEPT, 1H–1H COSY, HSQC and<br />
HMBC spectral data. Muscanone (1) was identified as 3-O-(1″, 8″,14″-<br />
trimethylhexadecanyl)naringenin and was found to be active against Candida<br />
albicans. The isolation, structure elucidation, NMR spectral assignments, and<br />
bioactivities of 1 and 2 are reported.<br />
Haque I, Bandopadhyay R, Mukhopadhyay K.(2010) “Population genetic<br />
structure of the endangered and endemic medicinal plant <strong>Commiphora</strong> wightii.”<br />
Mol Biol Rep. 37(2), 847-54 Abstract. <strong>Commiphora</strong> wightii is a medicinally<br />
important endangered species endemic to the Thar Desert of Rajasthan, India<br />
and adjoining areas of Pakistan. The populations of this species are declining<br />
sharply because of its extensive use as a natural herb. Random amplified<br />
polymorphic DNA analysis was conducted to find the genetic variation among 7<br />
populations of C. wightii. Of the 100 random primers screened, 44 primers<br />
yielded 220 loci. Statistical analysis indicated low genetic diversity (H (pop) =<br />
0.0958; I = 0.1498; mean polymorphic loci = 14.28%), and high genetic<br />
differentiation among the populations (G (ST) = 0.3990; AMOVA Phi (ST) of<br />
0.3390; Bayesian theta ((II)) = 0.3002). The low genetic diversity may be due to<br />
geographic isolation and restricted gene flow (N (m) = 0.7533) between the<br />
fragmented populations. Unsustainable utilization of the plant has fragmented the<br />
population continuum which served the purpose of genetic exchange between<br />
populations. Mantel's test was performed which revealed a highly significant<br />
positive correlation between genetic and geographic distance (r (2) = 0.614, P =<br />
0.023) among the populations studied. Low variation can also be attributed to<br />
poor seed setting and the slow growth pattern of the species, which is also an<br />
apomict. In UPGMA dendrogram the <strong>Commiphora</strong> wightii samples were divided<br />
into two major and one minor cluster. These findings can serve as a guide to<br />
preserving the genetic resources of this medicinal plant species.<br />
Meselhy M.R. (2003) "Inhibition of LPS-induced NO production by the oleogum<br />
resin of <strong>Commiphora</strong> wightii and its constituents." Phytochemistry 62(2), 213-218<br />
Abstract. Three new (1–3) and five known compounds (4–8) were isolated from<br />
the oleogum resin of <strong>Commiphora</strong> wightii (Arnott.) Bhanol. Their structures were<br />
elucidated by spectroscopic and chemical methods. The MeOH extract and the<br />
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EtOAc-sol. fraction were found to demonstrate significant inhibition of NO<br />
formation in lipopolysaccharide (LPS)-activated murine macrophages J774.1 in<br />
vitro (IC50 values of 16.4 and 12.8 µg/ml, respectively). When compared with<br />
curcumin (IC50 value of 12.3 µM), Z- and E-Guggulsterones (4 and 5,<br />
respectively) were the most potent inhibitors of NO production (IC50 values of<br />
1.1 and 3.3 µM, respectively), followed by myrrhanol A (7) and myrrhanone A (8)<br />
(IC50 values of 21.1 and 42.3 µM, respectively). Guggulsterone-M (1) and its<br />
didehydro derivative (2) were weak inhibitors, while guggulsterols I (6) and Y (3)<br />
were inactive (IC50 >500 µM).<br />
Raut A.A., Sunder S., Sarkar S., Pandita N.S. & Vaidya A.D. (2008) "Preliminary<br />
study on crystal dissolution activity of Rotula aquatica, <strong>Commiphora</strong> wightii and<br />
Boerhaavia diffusa extracts." Fitotherapia 79(7-8), 544-7. Abstract. Several<br />
Ayurvedic plants are known to have activity against diverse urinary crystals. The<br />
traditional knowledge of Ayurveda, collective clinical experience in arthritis and<br />
the earlier experimental studies on urinary crystals led to the selection of three<br />
plants, viz. Rotula aquatica, <strong>Commiphora</strong> wightii Bhandari syn. C.mukul. and<br />
Boerhaavia diffusa for screening anticrystal activity against basic calcium<br />
phosphate (BCP), calcium pyrophosphate (CPPD) and monosodium urate<br />
monohydrate (MSUM). The effects of each plant were assayed on microcrystals<br />
in 24-well microplates in vitro. Our results show that the aqueous extracts of only<br />
R. aquatica and C. wightii have shown crystal dissolving activity against MSUM.<br />
Salavert M, Amarger S, Le Bouedec MC, Roger H, Souteyrand P, D'incan M.<br />
(2007) "Allergic contact dermatitis to guggul in a slimming cream." Contact<br />
Dermatitis. 56(5), 286-7.<br />
Satyavati G.V. (1991) Guggulipid: A promising hypolipidaemic agent from gum<br />
guggul (<strong>Commiphora</strong> wightii). Economic and Medicinal Plant Research, 5. Plants<br />
and Traditional Medicine, 47–82.<br />
Satyavati G.V. (1988) "Gum guggul (<strong>Commiphora</strong> mukul)-the success story of an<br />
ancient insight leading to a modern discovery." Indian J Med Res. 87,327-35.<br />
Shishodia S, Harikumar K.B., Dass S, Ramawat K.G., Aggarwal B.B.. (2008)<br />
"The guggul for chronic diseases: ancient medicine, modern targets." Anticancer<br />
Res. 28(6A),3647-64. Abstract. Identfication of active principles and their<br />
molecular targets from traditional medicine is an enormous opportunity for<br />
modern drug development. Gum resin from <strong>Commiphora</strong> wightii (syn C. mukul)<br />
has been used for centuries in Ayurveda to treat internal tumors, obesity, liver<br />
disorders, malignant sores and ulcers, urinary complaints, intestinal worms,<br />
leucoderma (vitiligo), sinuses, edema and sudden paralytic seizures.<br />
Guggulsterone has been identified as one of the major active components of this<br />
gum resin. This steroid has been shown to bind to the farnesoid X receptor and<br />
modulate expression of proteins with antiapoptotic (IAP1, XIAP, Bfl-1/A1, Bcl-2,<br />
cFLIP, survivin), cell survival, cell proliferation (cyclin D1, c-Myc), angiogenic,<br />
and metastatic (MMP-9, COX-2, VEGF) activities in tumor cells. Guggulsterone<br />
mediates gene expression through regulation of various transcription factors,<br />
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including NF-kappaB, STAT-3 and C/EBPalpha, and various steroid receptors<br />
such as androgen receptor and glucocorticoid receptors. Modulation of gene<br />
expression by guggulsterone leads to inhibition of cell proliferation, induction of<br />
apoptosis, suppression of invasion and abrogation of angiogenesis. Evidence<br />
has been presented to suggest that guggulsterone can suppress tumor initiation,<br />
promotion and metastasis. This review describes the identification of molecular<br />
targets of guggulsterone, cellular responses to guggulsterone, and animal<br />
studies and clinical trials of guggulsterone in cancer and other diseases.<br />
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