nts
Pla
Medic
in
Aromat
i
c
&
al
ISSN: 2167-0412
Medicinal & Aromatic Plants
Fahmy et al., Med Aromat Plants 2015, 4:5
DOI: 10.4172/2167-0412.1000218
Review Article
Research
Article
OpenAccess
Access
Open
Genus Terminalia: A phytochemical and Biological Review
Fahmy NM, Al-Sayed E and Singab AN*
Department of Pharmacognosy, Faculty of Pharmacy, Ain-Shams University, Cairo, 11566, Egypt
Abstract
Context: Terminalia is the second largest genus of family Combretaceae. The plants of this genus were used in
traditional folk medicine worldwide.
Objectives: This review is a comprehensive literature survey of different Terminalia species regarding their
biological activities and their isolated phytochemicals. The aim of this review is to attract the attention to unexplored
potential of natural products obtained from Terminalia species, thereby contributing to the development of new
therapeutic alternatives that may improve the health of people suffering from various health problems.
Materials and methods: All the available information on genus Terminalia was compiled from electronic databases
such as Medline, Google Scholar, PubMed, ScienceDirect, SCOPUS, Chemical Abstract Search and Springer Link.
Results: Phytochemical research has led to the isolation of different classes of compounds including, tannins,
flavonoids, phenolic acids, triterpenes, triterpenoidal glycosides, lignan and lignan derivatives. Crude extracts and
isolated components of different Terminalia species showed a wide spectrum of biological activities.
Conclusion: phytochemical studies on genus Terminalia have revealed a variety of chemical constituents.
Numerous biological activities have validated the use of this genus in treatment of various diseases in traditional
medicine. Further studies are needed to explore the bioactive compounds responsible for the pharmacological effects
and their mechanism of action.
Keywords: Terminalia; Tannins;
Combretaceae; Traditional medicine
Flavonoids;
Terpenoids;
Abbreviations:A549: Human lung epithelial cancer; AChE:
Acetylcholinesterase; ACP: Acid phosphatase; ALP: Alkaline phosphatase;
ALT: Alanine aminotransferase; AST: Aspartate aminotransferase; Bw:
Body weight ; COLO-205: Human colon cancer ; COX-2: Cyclooxygenase-2
enzyme; DPPH•: 2;2-diphenyl-1-picrylhydrazyl radical; DU-145: Human
prostate cancer; FRAP: Ferric reducing ability of plasma; GSH: Glutathione;
HbA1c: Glycated hemoglobin; HCT-15: Human colorectal cancer; HL-60:
Human promyelocytic leukemia ; IMR: Ischemic mitral regurgitation;
iNOS: inducible nitric oxide synthase ; K562: Human immortalised
myelogenous leukemia; MBC: Minimum bactericidal concentration;
MDA-MB-231:M.D.anderson-metastatic breast cancer; MIC: Minimum
inhibitory concentration; ORAC: Oxygen radical absorbance capacity;
PPARα / PPARγ: Peroxisome proliferator-activated receptor alpha/ gamma
; STZ: Streptozotocin; T: Terminalia
Introduction
The genus Terminalia is the second largest genus of the Combretaceae
after Combretum, with about 200 species. These plants are distributed
in tropical regions of the world with the greatest genetic diversity
in Southeast Asia [1]. Genus Terminalia gets its name from Latin
terminus, since the leaves appear at the tips of the shoots [2]. Terminalia
species range from shrubs to large deciduous forest trees. Mostly they
are very large trees reaching in height up to 75 m tall [3]. Members
of the genus Terminalia are widely used in traditional medicine in
several continents in the world for the treatment of numerous diseases
including, abdominal disorders, bacterial infections, colds, sore throats,
conjunctivitis, diarrhea, dysentery, fever, gastric ulcers, headaches,
heart diseases, hookworm, hypertension, jaundice, leprosy, nosebleed,
edema, pneumonia and skin diseases [4]. The fruits of both T. bellerica
and T. chebula are important components of triphala, a popular
Ayurvedic formulation that possess numerous activities in the Indian
traditional medicine [5]. T. chebula fruit possess an extraordinary
power of healing and is called the “King of Medicine” in Tibet as it’s
used for the treatment of various diseases [6,7]. The Bark of T. arjuna
are used as cardioprotective and anti-hyperlipidemic in folklore
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
medicine [8]. In Africa, T. mollis is used to treat diarrhea, gonorrhea,
malaria, and in HIV treatment, while T. brachystemma is used for the
treatment of shistosomiasis and gastrointestinal disorders [9]. The
diverse phytochemical constituents and various biological activities
attracted us to perform a comprehensive literature survey of different
Terminalia species regarding their phytochemical constituents, their
ability to exert biological activities and the evidence-based information
regarding the phytochemistry and biological activities of this genus.
The present review is divided into two main sections, the first include
a phytochemical review of various chemical constituents and their
occurrence within the Terminalia species, the second comprises the
numerous biological studies conducted for different species of the
genus Terminalia.
Phytochemical Studies
Phytochemical studies performed on different Terminalia
species have demonstrated the occurrence of several classes of active
constituents, such as tannins, pentacyclic triterpenes and their glycoside
derivatives, flavonoids and other phenolic compounds [10].
Literature survey has revealed that genus Terminalia is a rich
source of tannins and pseudotannins, including gallic acid and its
simple gallate esters, chebulic and non-chebulic ellagitannins, ellagic
acid derivatives and ellagic acid glycosides (Table 1 and Figure 1).
*Corresponding author: Singab AN, Department of Pharmacognosy, Faculty
of Pharmacy, Ain Shams University, 11566, Cairo, Egypt. Tel: +20224051120;
Fax: +20224051107; E-mail: dean@pharma.asu.edu.eg
Received October 17, 2015; Accepted November 23, 2015; Published November
26, 2015
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A
phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants 4:
218. doi:10.4172/2167-0412.1000218
Copyright: © 2015 Fahmy NM, et al. This is an open-access article distributed
under the terms of the Creative Commons Attribution License, which permits
unrestricted use, distribution, and reproduction in any medium, provided the
original author and source are credited.
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 2 of 21
No.
A.
1
Compound
Species
Part used (Type of extract)
Reference (s)
T. chebula
T. bellerica
T. horrida
T. muelleri
T. nigrovenulosa
T. arjuna
T. superba
T. macroptera
T. mollis
T. catappa
T. oblongata
T. pallida
T. stenostachya
T. myriocarpa
Leaves (H2O), fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Leaves, fruits, bark (MeOH)
Bark (EtOAc)
Leaves (EtOH), fruits, bark
Stem bark (CH2Cl2: MeOH)
Leaves
Leaves (MeOH)
Leaves (H2O)
Leaves
Fruits (EtOH)
Leaves
Leaves
[27, 82]
[27]
[27]
[28, 50]
[52]
[83, 84]
[18]
[54]
[9]
[85]
[86]
[87]
[49]
[88]
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Stem bark (CH2Cl2: MeOH)
Leaves
[27]
[27]
[27]
[18]
[88]
Gallic acid and simple gallate esters
Gallic acid
2
Methyl gallate
T. chebula
T. bellerica
T. horrida
T. superba
T. myriocarpa
3
Ethyl gallate
T. arjuna
T. chebula
T. myriocarpa
Arial parts (MeOH)
Leaves
Leaves
[64]
[59]
[88]
4
1,6-di-O-galloyl-β-ᴅ-Glc
T. chebula
T. bellerica
T. horrida
Leaves (H2O), fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27, 82]
[27]
[27]
5
3,4,6-tri-O-galloyl-β-ᴅ-Glc
T. chebula
T. bellerica
T. horrida
Leaves (H2O), fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27, 82]
[27]
[27]
6
1,3,4,6-tetra-O-galloyl-β-ᴅ-Glc
T. chebula
T. bellerica
T. horrida
Leaves (H2O), fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27, 82]
[5, 27]
[27]
7
2,3,4,6-tetra-O-galloyl-β-ᴅ-Glc
T. arjuna
Leaves (EtOH)
[83]
Leaves (H2O), fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Leaves (EtOH)
[27, 82]
[27]
[27]
[83]
8
1,2,3,4,6-penta-O-galloyl-β-ᴅ-Glc
T. chebula
T. bellerica
T. horrida
T. arjuna
9
3,4,5-tri-O-galloyl-shikimic acid
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
Fruits (MeOH, EtOH)
Fruits (MeOH)
Fruits (MeOH)
[27, 33]
[27]
[27]
B.
Chebulic acid and chebulic ellagitannins
10
Chebulic acid
T. chebula
T. bellerica
T. horrida
11
Neo-chebulic acid
T. chebula
Fruits (EtOH)
[33]
T. chebula
T. bellerica
T. horrida
T. brachystemma
T. mollis
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Leaves (MeOH)
Leaves (MeOH)
[12, 27]
[27]
[27]
[9]
[9]
T. bellerica
T. chebula
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[12, 27]
[27]
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27, 60]
[27]
[27]
Methyl neochebulinate
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
Chebulagic acid
(1-O-galloyl-2,4-O-chebuloyl-3,6-OHHDP-β-ᴅ-Glc)
T. chebula
T. bellerica
T. horrida
T. catappa
Fruits (MeOH), seeds
Fruits (MeOH)
Fruits (MeOH)
Leaves (H2O)
[27, 89]
[5, 27]
[27]
[34]
12
13
14
Chebulanin
(1-O-galloyl-2,4-O-chebuloyl-β-ᴅ-Glc)
Chebulinic acid
(1,3,6-tri-O-galloyl-2,4-O-chebuloyl-βᴅ-Glc)
Methyl neo-chebulanin
15
16
17
Methyl neochebulagate
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
18
1,6-di-O-galloyl-2,4-O-chebuloyl-β-ᴅ-Glc
(or 1,3-)
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
C.
Non-chebulic ellagitannins
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 3 of 21
19
Tellimagrandin(I)
(2,3-di-O-galloyl-4,6-O-HHDP-α/β-ᴅ-Glc)
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
20
Corilagin
(1-O-galloyl-3,6-O-HHDP-β-ᴅ-Glc)
T. chebula
T. bellerica
T. horrida
T. catappa
Fruits (MeOH, EtOH)
Fruits (MeOH)
Fruits (MeOH)
Leaves (H2O)
[27, 90]
[27]
[27]
[34]
21
Tercatain
(1,4-di-O-galloyl-3,6-O-HHDP-β-ᴅ-Glc)
T. catappa
Leaves (Acetone)
[91]
22
Arjunin
(3-O-galloyl-4,6-O-gallagyl-α/β-ᴅ-Glc)
23
24
Punicalin
(4,6-O-gallagyl-α/β-ᴅ-Glc)
Punicalagin
(2,3-O-HHDP-4,6-O-gallagyl-α/β-ᴅ-Glc)
25
2,3:4,6-bis-O-HHDP-1-O-galloyl-β-ᴅ-Glc
26
Tergallagin
27
28
29
T. arjuna
Leaves (EtOH)
[83]
T. bellerica
T. chebula
T. horrida
T. arjuna
T. catappa
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Leaves (EtOH)
Leaves (Acetone)
[27]
[27]
[27]
[83]
[91]
T. chebula
T. bellerica
T. horrida
T. oblongata
T. brachystemma
T. macroptera
T. catappa
T. arjuna
T. myriocarpa
Leaves (H2O), fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Leaves (H2O)
Leaves (Acetone)
Roots (EtOH)
Leaves (Acetone, H2O)
Bark
Leaves
[27, 90]
[27]
[27]
[92]
[9]
[55]
[61, 91]
[93]
[88]
T. arjuna
Leaves (EtOH)
[83]
T. catappa
Leaves (Acetone)
[91]
Terflavin (A)
(4-O-flavogallonyl-6-O-galloyl-2,3-OHHDP-α/β-ᴅ-Glc)
T. chebula
T. catappa
T. macroptera
Fruits (H2O)
Leaves (Acetone)
Stem bark (EtOAc)
[90]
[91]
[94]
Terflavin (B)
(4-O-flavogallonyl-6-O-galloyl-α/β-ᴅ-Glc)
T. chebula
T. bellerica
T. horrida
T. catappa
T. macroptera
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Leaves (Acetone)
Stem Bark (EtOAc)
[27]
[27]
[27]
[91]
[94]
T. chebula
T. catappa
T. arjuna
Fruits (H2O)
Leaves (Acetone)
Bark
[90]
[91]
[93]
T. calamansanai
Leaves
[93]
T. chebula
T. macroptera
T. arjuna
Fruits (H2O)
Roots (EtOH)
Bark
[90, 95]
[55]
[93]
Terflavin (C)
(4-O-flavogallonyl -2,3-O-HHDP-α/βᴅ-Glc)
30
Calamansanin
(4-O-flavogallonyl-6-O-galloyl-2,3-OHHDP-α-ᴅ-Glc)
31
Terchebulin
32
Isoterchebulin
T. macroptera
Stem bark (EtOAc)
[94]
33
4,6-O-isoterchebuloyl-α/β-ᴅ-Glc
T. macroptera
Stem bark (EtOAc)
[94]
T. chebula
T. arjuna
Fruits (H2O)
Bark (Acetone)
[90]
[48]
34
Casurarinin
35
Casuariin
T. arjuna
Bark
[96]
36
Castalagin
T. arjuna
Leaves
[93]
T. chebula
T. bellerica
T. horrida
T. muelleri
T. arjuna
T. superba
T. macroptera
T. pallida
T. paniculata
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Bark, fruits (MeOH)
Leaves (EtOH), fruits
Stem bark (CH2Cl2: MeOH)
Leaves
Fruits (EtOH)
Heartwood (alc.)
[27]
[27]
[27]
[28]
[83, 84]
[18]
[54]
[87]
[97]
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
T. chebula
T. bellerica
T. horrida
T. superba
T. paniculata
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Stem bark (CH2Cl2: MeOH)
Heart wood (alc.)
[27]
[27]
[27]
[18]
[97]
T. catappa
Fruits, Leaves (EtOH)
[98]
D.
Ellagic acid and ellagic acid derivatives
37
Ellagic acid
38
3-O-methyl ellagic acid
39
3,3’-di-O-methyl ellagic acid
40
3,4,4’-tri-O-methyl ellagic acid
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 4 of 21
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
Flavogallonic acid
T. chebula
T. bellerica
T. horrida
T. myriocarpa
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Leaves
[27]
[27]
[27]
[88]
43
Methylflavogallonate
T. chebula
T. bellerica
T. horrida
T. myriocarpa
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Leaves
[27]
[27]
[27]
[88]
44
3,4,3’-O-trimethyl flavellagic acid
T. paniculata
Heartwood (alc)
[97]
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
41
3,4,8,9,10-Pentahydroxydibenzo[b,d]
pyran-6-one
42
45
E.
Gallagic acid.
Ellagic acid glycosides
46
3’-O-methyl-4-O-(β-ᴅ-xylopyranosyl)
ellagic acid
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
47
3,3’-di-O-methyl-4-O-(β-ᴅ-xylopyranosyl)
ellagic acid
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
48
3’-O-methyl-4-O-(n”-O-galloyl-β-ᴅxylopyranosyl) ellagic acid (n = 2, 3,
or 4)
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
3,3’-di-O-methyl-4-O-(n”-O-galloyl-βᴅ-xylopyranosyl) ellagic acid. (n = 2, 3,
or 4)
T. chebula
T. bellerica
T. horrida
T. superba
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Stem bark (CH2Cl2: MeOH)
[27]
[27]
[27]
[18]
49
50
4’-O-galloyl-3,3’-di-O-methyl-4-O-(β-ᴅxylopyranosyl) ellagic acid
T. superba
Stem bark (MeOH)
[56]
51
3’,4-di-O-methyl-3-O-(β-ᴅ-xylopyranosyl)
ellagic acid
T. superba
Stem bark (MeOH)
[56]
52
3’-O-methyl-4-O-(α-L- rhamnopyranosyl)
ellagic acid
T. arjuna
T. mollis
Bark (MeOH)
Stem bark (MeOH)
[99]
[9]
53
4-O-(4”-O-galloyl-α-L-rhamnopyranosyl)
ellagic acid
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
54
4-O-(3”,4”-di-O-galloyl-α-Lrhamnopyranosyl) ellagic acid
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
55
3’-O-methyl-4-O-(3”,4”-di-O-galloyl-α-Lrhamnopyranosyl) ellagic acid
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
56
3,3’-di-O-methyl-4-O-(β-Dglucopyranosyl-(1→4)-β-Dglucopyranosyl-(1→2)-α-Larabinopyranosyl) ellagic acid
T. alata
Roots
[58]
Table 1: Tannins and pseudotannins and their occurrence within Terminalia species.
Phenolic acids (Table 2 and Figure 2), flavonoids (Table 3 and Figure
3), triterpenes and triterpenoidal glycosides (Table 4 and Figure 4) are
also present in high amounts in various Terminalia species, few lignan
and lignan derivatives have been isolated from genus Terminalia (Table
5 and Figure 5).
Biological Studies
Screening of available literature on genus Terminalia revealed
numerous biological activities in various in vivo and in vitro models.
Biological activities included anti-diabetic, anti-hyperlipidemic,
antioxidant, anti-bacterial, anti-fungal, anti-viral, anti-inflammatory,
anti-cancer, anti-ulcer, anti-parasitic, hepatoprotective and
cardioprotective activities.
Anti-diabetic activity
T. chebula showed a strong anti-diabetic activity, compounds isolated
from the fruits, such as corilagin and ellagic acid acted as α-glucosidase
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
inhibitors [11]. Additionally, chebulanin, chebulagic acid and chebulinic
acid possessed a potent intestinal maltase inhibitory activity, with IC50
values of 690 μM, 97 μM and 36 μM, respectively [12]. In another study,
T. chebula fruits and seeds exhibited a dose-dependent reduction in blood
glucose in STZ-induced diabetic rats [13]. Furthermore, ellagitannins
and gallotannins isolated from T. bellerica and T. chebula fruit extracts
enhanced the PPARα and/or PPARγ signaling [5]. The aqueous extract of
T. paniculata bark reduced the elevated blood glucose, HbA1c, creatinine,
urea, ALT, AST levels and reversed the abnormal status of endogenous
antioxidants and the lipid profile levels towards their normal levels in
STZ-induced diabetic rats in comparison with the untreated diabetic
rats [14]. Nampoothiri [15] reported that the methanolic extract of T.
bellerica fruits exhibited a potent α-amylase and α-glucosidase inhibitory
activities. Moreover, the anti-diabetic activity of T. bellerica fruit extract
is attributed to its gallic acid content, as it induced a dose-dependent
reduction in blood glucose level with a simultaneous increase in plasma
insulin (62.92%), C-peptide (79.74%), total protein (42.41%) and albumin
(51.52%) in STZ-induced diabetic rats when compared to the untreated
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 5 of 21
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 6 of 21
Figure 1: Chemical structures of tannins and pseudotannins isolated from different Terminalia species.
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 7 of 21
No.
Compound
Species
Part used (Type of extract)
57
Caffeic acid
T. chebula
Leaves
[90]
58
Ferulic acid
T. chebula
T. catappa
Leaves
Fruits, leaves (EtOH)
[90]
[98]
59
Vanillic acid
T. chebula
T. catappa
Leaves
Fruits, leaves (EtOH)
[90]
[98]
60
Coumaric acid
T. chebula
T. catappa
Leaves, fruits
Leaves (H2O)
[90]
[85]
61
p-hydroxybenzoic acid
T. catappa
Leaves (H2O)
[85]
3,4-dihydroxybenzoic acid
T. nigrovenulosa
T. catappa
Bark
Leaves (H2O)
[75]
[85]
62
Reference (s)
Table 2: Phenolic acids and their occurrence within Terminalia species.
Figure 2: Chemical structures of phenolic acids isolated from different Terminalia species.
No.
A.
Compound
Species
Part used (Type of extract)
Reference (s)
Quercetin
T. arjuna
T. muelleri
T. macroptera
T. bellerica
T. chebula
Fruits (MeOH)
Bark, fruits, leaves (MeOH)
Leaves
Bark, fruits, leaves (MeOH)
Leaves
[28]
[28]
[54]
[28]
[100]
[101]
Flavonols
63
64
Kaempferol
T.arjuna
Bark
65
Kaempferol 3-O-rutinoside
T. myriocarpa
Leaves
[88]
66
Rutin
(Quercetin-3-O-rutinoside)
T. chebula
T. myriocarpa
Leaves
Leaves
[100]
[88]
Luteolin
T. arjuna
T. chebula
Arial parts (MeOH)
Fruits
[64]
[59]
68
Apigenin
T. arjuna
Leaves (MeOH)
[102]
69
Arjunolone
(6,4’-dihydroxy-7-O-methylflavones)
T. arjuna
Stem bark
[103, 104]
70
Baicalein
(5,6,7-trihydroxy-flavones)
T. arjuna
Stem bark
[103, 104]
71
Orientin
T. mollis
T. catappa
T. myriocarpa
Leaves (Acetone)
Leaves
Leaves
[9]
[105]
[88]
72
Isoorientin
T. brachystemma
T. catappa
T. macroptera.
T. myriocarpa
Leaves (Acetone)
Leaves
Leaves
Leaves
[9]
[105]
[54]
[88]
T. arjuna
T. catappa
T. myriocarpa
Leaves (MeOH)
Leaves
Leaves
[102]
[105]
[88]
B.
67
Flavones
Vitexin
73
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 8 of 21
74
Isovitexin
T. arjuna
T. brachystemma
T. catappa
T. myriocarpa
Leaves (MeOH)
Leaves (Acetone)
Leaves
Leaves
[102]
[9]
[105]
[88]
75
2”-O-galloylvitexin
T. mollis
T. catappa
Leaves (MeOH)
Leaves
[9]
[105]
76
2”-O-galloylisovitexin
T. catappa
Leaves
[105]
77
Arjunone
(5,7,2’,4’-tetra-O-mrthyl-flavones)
T. arjuna
Fruits (EtOH)
[106]
C.
Flavans
78
7,3’-dihydroxy-4’-O-methyl-flavan
T. argentea
Bark (EtOH)
[107]
79
7,4’-dihydroxy-3’-O-methyl-flavan
T. argentea
Bark (EtOH)
[107]
80
7-hydroxy-3’,4’-methylenedioxyflavan
T. bellerica
Fruits
[108]
D.
Flavanones
81
8-methyl-5,7,2’,4’-tetra-O-methylflavanone
T. alata
Roots (EtOH)
[109]
82
5,7,2’-tri-O-methyl-flavanone
4’-O-α-L-rhamnopyranosyl-(1→4)β-ᴅ-glucopyranoside
T. alata
Roots
[58]
E.
Flavan-3-ol
83
Catachin
T. arjuna
T. mollis
T. brachystemma
Leaves, stem bark
Stem bark (MeOH)
Leaves (Acetone)
[84]
[9]
[9]
84
Gallocatechin
T. arjuna
T. catappa
T. mollis
Stem bark
Bark
Stem bark (MeOH)
[84]
[93]
[9]
85
Epicatechin
T. arjuna
T. catappa
T. mollis
Stem bark
Bark
Stem bark (MeOH)
[84]
[93]
[9]
86
3-O-galloyl-epicatechin
T. catappa
Bark
[93]
Epigallocatechin
T. arjuna
T. catappa
T. mollis
Stem bark
Bark
Stem bark (MeOH)
[84]
[93]
[9]
3-O-galloyl-epigallocatechin
T. catappa
Bark
[93]
2-O-β-ᴅ-glucosyloxy-4,6,2’,4’tetramethoxychalchone
T. alata
Roots (EtOH)
[109]
T. arjuna
Bark
[101]
T. arjuna
Bark (MeOH)
[110]
87
88
F.
89
G.
90
H.
91
Chalcones
Anthocyanidins
Pelargonidin
Leucoanthocyanidins
Leucocyanidin
Table 3. Flavonoids and their occurrence within Terminalia species.
diabetic rats [16]. The ethanolic leaf extracts of T. arjuna, T. catappa, T.
bellerica and T. chebula had a potent α-glucosidase inhibition activity
[17]. Gallic acid and methyl gallate isolated from T. superba stem bark
showed a significant α-glucosidase inhibitory activity [18]. Additionally,
the methanolic and the aqueous extracts of T. catappa fruits exhibited
significant anti-hyperglycemic activities and showed an improvement
in body weight and lipid profile as well as regeneration of β-cells of the
pancreas [19]. Also, T. pallida fruit extract showed a significant antidiabetic activity in alloxan-induced diabetic rats at a dose of 0.50 g/kg
bw [20].
Anti-hyperlipidemic activity
The oral administration of gallic acid isolated from T. bellerica
fruit at a dose of 20 mg/kg bw significantly reduced the serum total
cholesterol, triglyceride and LDL-cholesterol levels [21]. Moreover, T.
chebula fruits possessed anti-hyperlipidemic activity against cholesterolinduced hypercholesterolemia and atherosclerosis in rabbits [22]. In
addition, the ethanolic extract of T. arjuna tree bark reduced the serum
total cholesterol, LDL, VLDL, triglycerides and raised HDL levels in
diet-induced hyperlipidemic rabbits [23]. Also, it was shown that T.
bellerica, T. chebula and T.arjuna had anti-hyperlipidemic activities T.
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
arjuna the most potent one caused an inhibition of rabbit atheroma
after oral administration in hyperlipidemic rabbits [24].
Antioxidant activity
Most Terminalia species were reported to possess an antioxidant
activity. The antioxidant activity of the T. arjuna bark was studied and
the results of DPPH• assay, superoxide radical scavenging activity and
lipid peroxidation assay were comparable with the standard antioxidant
ascorbic acid [25]. T. chebula fruit extract possessed a potent
antioxidant activity and can be used as a radio-protector as it protected
from γ-irradiation-induced oxidative stress in rats by the reduction of
radiation-induced cellular DNA damage [26].
The antioxidant activities of the methanolic fruit extract of T.
bellerica and its isolated compounds was examined using DPPH•,
oxygen radical absorbance capacity (ORAC) and ferric reducing ability
of plasma (FRAP) in vitro assays. Chebulic ellagitannins showed the
highest antioxidant activity [27]. Moreover, the high antioxidant
activity of the aqueous methanolic extracts of the leaves, bark and fruits
of T. arjuna, T. bellerica, T. chebula and T. muelleri were attributed to
their high phenolic contents (72.00-167.20 mg/g) [28].
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 9 of 21
Figure 3: Chemical structures of flavonoids isolated from different Terminalia species.
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 10 of 21
No. Compound
A.
Species
Part used (Type of extract)
Reference (s)
Triterpenes
92
Ursolic acid
T. brachystemma
T. catappa
Leaves (n-hexane)
Leaves (EtOH)
[9]
[42]
93
2α-hydroxyursolic acid
T. chebula
T. mollis
Leaves (Acetone)
Stem bark (n-hexane)
[111]
[9]
94
2α,3β,23-trihydroxyurs-12-en-28-oic acid
T. catappa
Leaves (EtOH)
[42]
95
Asiatic acid
T. brassii
T. complanata
Wood (Et2O)
Wood (Et2O)
[112]
[112]
96
Oleanolic acid
T. arjuna
T. superba
Root bark
Stem bark (CH2Cl2: MeOH)
[84]
[18]
97
Methyl oleonate
T.arjuna
Fruits
[106]
98
Arjunic acid
T. arjuna
T. macroptera
Fruits, roots, stem bark
Bark
[84, 113],
[114]
99
Arjunolic acid
(2α,3β,23-trihydroxyolean-12-en-28-oic aid)
T. arjuna
T. brassii
T. complanata
Bark (pet. ether)
Wood (Et2O)
Wood (Et2O)
[32]
[112]
[112]
100 23-O-galloyl-arjunolic acid
T. macroptera
Stem bark (EtOAc)
[114]
Arjungenin
101
(2α,3β,19α,23-tetrahydroxyolean-12-ene-28-oic acid)
T. arjuna
T. bellerica
T. macroptera
Bark (EtOH)
Stem bark (MeOH)
Bark
[113]
[115]
[114]
102
Tomentosic acid
(2α,3β,19β,23-tetrahydroxyolean-12-ene-28-oic acid)
T. arjuna
T. tomentosa (T.
alata)
Stem bark
Heart wood
[84]
[116]
103
Sericic acid
(2α,3β,19α,24-tetrahydroxy-olean-12-en-28-oic acid)
T. sericea
T. macroptera
Roots
Stem bark
[117]
[114]
104
Belleric acid
(2α,3β,23,24-tetrahydroxy-olean-12-en-28-oic acid)
T. bellerica
Stem bark (MeOH)
[115]
105
Bellericagenin A
(2α,3β,7α,23-tetrahydroxyolean-12-en-28-oic acid)
T. bellerica
Stem bark
[118]
Bellericagenin B
106
(2α,3β,19α,23,24-pentahydroxyolean-12-en-28-oic acid)
T. bellerica
Stem bark
[118]
Terminolic acid
107
(2α,3β,6β,23-tetrahydroxyolean-12-en-28-oic acid)
T. macroptera
T. glaucesence
T. catappa
T. laxiflora
T. avicennioides
Stem bark
Heartwood (Et2O)
Heartwood (Et2O)
Heartwood (Et2O)
Heartwood (Et2O)
[114]
[119]
[119]
[119]
[119]
T. chebula
Leaves (Acetone)
[111]
108
Maslinic acid
(2α,3β-dihydroxyolean-12-en-28-oic acid)
109 3-acetylmaslinic acid
T. alata
Root bark
[120]
110 2α-hydroxymicromeric acid
T, chebula
Leaves (Acetone)
[111]
111
Terminic acid
(3β,13β-dihydroxylup-20-en-28-oic acid)
T. arjuna
Root bark (n-hexane)
[121]
112 Friedelin
T. arjuna
T. glaucescens
T. mollis
T. alata
Fruits
Stem bark
Stem bark (n-hexane)
Roots
[106]
[122]
[9]
[58]
113 β-sitosterol
T. chebula
T. superba
T. bellerica
T. glaucescens
T. phanerophlebia T.
sambesiaca
T. arjuna
Stem bark
Stem bark ( CH2Cl2: MeOH)
Fruits
Stem bark
Leaves (EtOH)
Leaves
Stem bark, fruits
[123]
[18]
[124]
[122]
[36].
[125]
[84]
114 β-sitosterone
T. phanerophlebia
Leaves (EtOH)
[36]
115 Stigmasterol
T. superba
T. glaucescens
T. arjuna
Stem bark (CH2Cl2: MeOH)
Stem bark
Leaves (MeOH)
[18]
[122]
[102]
116 Stigma-4-ene-3,6-dione
T. phanerophlebia
Leaves (EtOH)
[36]
117 Terminalin A
T. glaucescens
Stem bark
[122]
118 2α,3β-dihydroxyurs-12,18-dien-28-oic acid-28-O-β-ᴅ-glucopyranoside
T. arjuna
Bark (MeOH)
[99]
119 2α,3β,23 trihydroxyurs-12,18-dien-28-oic acid-28-O-β-ᴅ-glucopyranoside
T. arjuna
Bark (MeOH)
[99]
120 2α,3β,23 trihydroxyurs-12,19-dien-28-oic acid-28-O-β-ᴅ-glucopyranoside
T. arjuna
Bark (MeOH)
[99]
Quadranoside VIII
121
(2α,3β,23-trihydroxyurs-12,19-dien-28-oic acid-28-O-β-ᴅ-glucopyranoside)
T. arjuna
Bark (MeOH)
[99]
Kajiichigoside F1
122
(2α,3β,19α-trihydroxyurs-12-en-28-oic acid-28-β-ᴅ-glucopyranoside)
T. arjuna
Bark (MeOH)
[99]
B.
Triterpenoidal glycosides
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 11 of 21
T. argentea
T. arjuna
Bark (EtOH)
Stem, root bark (EtOH)
T. arjuna
Root bark (EtOAC, MeOH)
125 2α,3β,19α-trihydroxyolean-12-en-28-oic acid-methylester-3-O-rutinoside
T. alata
Roots (EtOH)
[109]
2α,3β,19α-trihydroxyolean-12-en-28-oic acid-3-O-β-ᴅ-galactopyranosyl- (1→3)-β-ᴅ126
glucopyranoside
T. alata
Roots
[127]
T. alata
Roots
[58]
T. arjuna
Stem bark
[110]
123
Arjunetin
(2α,3β,19α-trihydroxyolean-12-en-28-oic acid-28-β-ᴅ-glucopyranoside)
Arjunosides (I)
(3-O-β-ᴅ-galactoside of arjunic acid)
Arjunosides (II)
(3-O-β-ᴅ-glucosyl-2-deoxy-α-L-rhamnoside of arjunic acid)
124
Arjunosides (III)
(28-β-ᴅ-glucuronopyranoside of arjunic acid)
Arjunosides (IV)
(3-O-α-L-rhamnoside of arjunic acid)
127
2α,3β,19β,23-tetrahydroxyolean-12-en-28-oic acid 3-O-β-ᴅ-galactopyranosyl-(1→3)β-ᴅ-glucopyranoside-28-O-β-ᴅ-glucopyranoside
Arjunolitin
128 (2α,3β-23-trihydroxyolean-12-en-28-oic acid-3-O-β-ᴅ-glucopyranosyl-28-O-β-ᴅglucopyranoside)
129 Tormentic acid-β-ᴅ-glucopyranoside
[107]
[113, 126]
[84, 126]
T. argentea
Bark (EtOH)
[107]
130
Chebuloside (I)
(2α,3β,23-trihydroxyolean-12-en-28-oic acid-28-O-β-ᴅ-galactopyranoside)
T. chebula
Stem bark (MeOH)
[123]
131
Chebuloside (II)
(2α,3β,6β,23-tetrahydroxyolean-12-en-28-oic acid-28-O-β- glucopyranoside)
T. chebula
Stem bark (MeOH)
[123]
Stem bark (MeOH)
[114]
132 23-galloylarjunolic acid-28-O-β-ᴅ-glucopyranoside
Arjunglucoside (I)
133
(2α,3β,19α,23-tetrahydroxyolean-12-en-28-oic acid-28-O-β-ᴅ-glucopyranoside)
T. macroptera
T. bellerica
T. chebula
T. tropophylla
T. macroptera
T. arjuna
Fruits, Stem bark
Stem bark (MeOH)
Roots (EtOH)
Bark
Stem bark
[115]
[123]
[128]
[114]
[126, 129]
134
Arjunglucoside (II)
(2α,3β,23-trihydroxyolean- 12-en-28-oic acid-28-O-β-ᴅ-glucopyranoside)
T. arjuna
Stem bark
[129]
135
Terminoside (A)
(1α,3β,22β-trihydroxyolean-12-en-28-oic acid-3-O-β-ᴅ-glucopyranoside)
T. arjuna
Bark (EtOH)
[130]
Termiarjunoside (I)
136
(1α,3β,9α,22α-tetrahydroxyolean-12-en-28-oic acid-3-O-β-ᴅ-glucopyranoside)
T. arjuna
Bark (EtOH)
[131]
T. arjuna
Bark (EtOH)
[131]
T. sericea
T. tropophylla
T. macroptera
T. ivorensis
Roots
Roots (EtOH)
Stem bark
Bark
[117]
[128]
[114]
[65]
Bark
[65]
Bark
[65]
T. ivorensis
Bark
[65]
137
138
139
140
Termiarjunoside (II)
(3α,5α,25-trihydroxyolean-12-en-23,28-dioic acid-3-O-α -ᴅ-glucopyranoside)
Sericoside
(2α,3β,19α,24-tetrahydroxy-olean-12-en-28-oic acid -28-O-β- ᴅ-glucopyranoside)
Ivorenoside (A)
(Dimer of 18,19-seco-2α,3β,19,19,24-pentahydroxyolean-12-en-28-oic acid-28-O-βT. ivorensis
ᴅ-glucopyranoside and 2α,3β,19α,24-tetrahydroxyolean-12-en-28-oic acid-28-O-β-ᴅglucopyranoside)
Ivorenoside (B)
(Dimer of 18,19-seco-24-carboxyl-2α,3β,19,19-tetrahydroxyolean-12-en-28-oic acidT. ivorensis
28-O-β-ᴅ-glucopyranoside and 2α,3β,19α,24-tetrahydroxyolean-12-en-28-oic acid-28O-β-ᴅ-glucopyranoside)
Ivorenoside (C)
141 (2α,3β,19β,24-tetrahydroxyolean-11-oxo-olean-12-en-28-oic acid-28-O-β-ᴅglucopyranoside)
142
Bellericoside
(2α,3β,23,24-tetrahydroxyolean-12-en-28-oic acid-28-O-β-ᴅ-glucopyranoside)
T. chebula
T. bellerica
Stem bark (MeOH)
Stem bark (MeOH)
[123]
[115]
143
Bellericaside (A)
(2α,3β,7α,23-tetrahydroxyolean-12-en-28-oic acid-28-O-β-ᴅ-glucopyranoside)
T. bellerica
Stem bark
[118]
Bellericaside (B)
T. bellerica
144
(2α,3β,19α,23,24-pentahydroxyolean-12-en-28-oic acid-28-O-β-ᴅ-galactopyranoside)
Stem bark
[118]
145 2α,19α-dihydroxy-3-oxo-olean-12-en-28-oic acid-28-O-β-ᴅ-glucopyranoside
T.arjuna
Roots
[101]
T. stulhamanii
Stem bark (CH2Cl2)
[132]
1α,3β,23-trihydroxy-olean-12-en-29-oic acid-23-O-α-L-(4-acetylrhamnopyranosyl)-29T. stulhamanii
α-rhamnopyranoside
Stem bark (CH2Cl2)
[132]
146
147
1α,3β,23-trihydroxy-olean-12-en-29-oic acid-23-O-α-L-4-acetylrhamnopyranoside
148 16,17-dihydroneridienone-3-O-β-ᴅ-glucopyranosyl-(1→6)-O-β-ᴅ-galactopyranoside
T.arjuna
Roots
[133]
Daucosterol
149
(β-sitosterol-3-O-β-ᴅ-glucopyranoside)
T. catappa
T. arjuna
T. bellerica
Fruits, leaves (EtOH)
Leaves (MeOH)
Fruits (MeOH)
[98]
[102]
[5]
Table 4. Triterpenes and triterpenoidal glycosides and their occurrence within Terminalia species.
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 12 of 21
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 13 of 21
Figure 4A: Chemical structures of triterpenes isolated from different Terminalia species.
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 14 of 21
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 15 of 21
Figure 4B: Chemical structures of triterpenoidal glycosides isolated from different Terminalia species.
Hepato and nephro-protective activities
T. muelleri polyphenolic-rich fraction possessed hepato
and nephro-protective activities in CCl4-induced hepato- and
nephrotoxicities in mice [29]. The ethanolic bark extract of T.
paniculata possessed hepatoprotective activity and reduced the elevated
serum biochemical parameters and lipid peroxides in paracetamolinduced liver damage in rats [30]. Also, oral administration of T.
arjuna fruit extract inhibited the hepatic damage and oxidative stress
in cadmium-induced hepatotoxicity in rats [31]. In addition, Manna
demonstrated the protective role of arjunolic acid, isolated from the
bark of T. arjuna, against sodium arsenite-induced oxidative stress in
mouse hepatocytes [32]. In vitro treatment of hepatocytes with chebulic
acid and neochebulic acid, isolated from T. chebula ethanolic fruit
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
extract, significantly reduced the tert-butyl hydroperoxide-induced
cell cytotoxicity, reactive oxygen species level, and increased the
hepatic GSH [33]. Corilagin, isolated from T. catappa protected against
galactosamine and lipopolysaccharide-induced hepatotoxicity in rats
at a dose of 1 mg/kg by decreasing the oxidative stress and apoptosis
[34]. Also, pre-treatment with T. bellerica leaf extract in CCl4-induced
hepato- and nephrotoxicities, exhibited a dose-dependent recovery in
all the biochemical parameters, while gallic acid from its extract had a
more pronounced effect at a dose of 200 mg/kg [35].
Anti-inflammatory activity
The ethanolic extract of T. phanerophlebia stem as well as its isolated
compound β-sitosterol selectively inhibited cyclooxygenase enzyme
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 16 of 21
No.
Compound
Species
Part used (Type of extract)
Reference (s)
150
Isoguaiacin
T. argentea
Bark (EtOH)
[107]
151
Termilignan
T. bellerica
Fruits
[108]
152
Thannilignan
T. bellerica
Fruits
[108]
153
Anolignan (B)
T. bellerica
T. sericea
Fruits
Roots (EtOAc)
[108]
[40]
154
4’-hydroxy-4-methoxy-7,7’-epoxylignan
T. superba
Stem bark (CH2Cl2: MeOH)
[18]
155
4,4’-dimethoxy-7,7’-epoxylignan
T. superba
Stem bark (CH2Cl3: MeOH)
[18]
Table 5. Lignan and lignan derivatives and their occurrence within Terminalia species.
Figure 5: Chemical structures of lignans isolated from different Terminalia species.
(COX-2) [36]. The aqueous extract of T. paniculata bark significantly
reduced the edema volume in carrageenan-induced rat paw edema
[37]. Furthermore, the extract at a dose of 400 mg/kg also reduced
the carrageenan-induced leukocyte migration and myeloperoxidase
activity in air pouch exudates and exhibited anti-rheumatic and
analgesic activities at a dose of 200 mg/kg. T. ferdinandiana fruit had
a unique anti-inflammatory activities in lipopolysaccharide-activated
murine macrophages, by inhibiting the expression of COX-2 and
inducible nitric oxide synthase (iNOS), as well as by inhibiting the
production of prostaglandin E2 [38].
Chebulagic acid from T. chebula seeds, significantly suppressed
the onset and progression of collagen-induced arthritis in mice [39].
Moreover, anolignan B isolated from the ethyl acetate root extract of
T. sericea possessed an inhibitory activity against both COX-1 and
COX-2 enzymes [40]. Punicalagin at a dose of 10 mg/kg and punicalin
at a dose of 5 mg/kg isolated from the leaves of T. catappa possessed
an anti-inflammatory activity against carrageenan-induced hind paw
edema in rats [41]. Ursolic acid and 2α,3β,23-trihydroxyurs-12-en-28oic acid isolated from T. catappa leaf ethanolic extract were responsible
for its anti-inflammatory activity, as it caused a significant reduction
(over 50%) of the edema induced in mice ear at 0.30 mg/ear dose [42].
Gastroprotective activity
Chebulinic acid isolated from T. chebula fruit showed a gastro
protective effect against ulcers induced by cold restraint (62.90%
gastro protection), aspirin (55.30%), alcohol (80.67%) and pyloric
ligation (66.63%) induced ulcer models. Chebulinic acid significantly
reduced free acidity (48.82%), total acidity (38.29%) and upregulated
mucin secretion (by 59.75%). Additionally, chebulinic acid significantly
inhibited H+ K+-ATPase activity in vitro with an IC50 value of 65.01
μg/ml compared to that of Omeprazole 30.24 μg/ml, proving its antisecretory activity [43]. In addition, the methanolic extract of T. arjuna
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
caused a significant reduction in the lesion index in diclofenac-induced
ulcer, and a significant increase in pH, non-protein sulfhydryls, reduced
glutathione, protein bound carbohydrate complexes, adherent mucus
content with a significant decrease in the volume of gastric juice, free
and total acidity, pepsin concentration, acid output, lipid peroxidase
levels and myeloperoxidase activities [44]. The ethanolic extract of T.
pallida exhibited a significant anti-ulcer activity against indomethacin,
histamine and ethanol in Swiss albino rats by enhancing the antioxidant
state of the gastric mucosa, thereby reducing mucosal damage [45].
Antimicrobial and Antiviral activity
Various Terminalia species were reported to exert a potent
antimicrobial effect on different microorganism. T. chebula water
extract had a significant antibacterial activity on Helicobactor pylori with
MIC and MBC of 125 and 150 μg/ml respectively [46]. Additionally, the
acetone extract of T. chebula exhibited a potent antibacterial activity
on Enterococcus faecalis, Bacillus sabtilis and Klebsiella pneumoniae
bacterias [47]. Casuarinin isolated from the bark of T. arjuna, showed
a strong antiviral activity on Herpes simplex type 2 at a concentration
of 25 μM and reduced the viral titers up to 100,000-fold by inhibiting
the viral attachment and penetration [48]. Recently, Fyhrquist reported
that the methanolic root and stem bark extracts of T. sambesiaca
showed lower MIC values than its aqueous, butanol and chloroform
fractions against mycobacterium [49]. The strong antibacterial activity
of T. muelleri ethylacetate leaf extract was attributed to its gallic acid
content [50].
The antifungal activity of different leaf extracts prepared from six
Terminalia species (T. prunioides, T. brachystemma, T. sericea, T. gazensis,
T. mollis and T. sambesiaca) were examined against numerous fungi. It
was found that the acetone extracts possessed the highest antifungal
activity. T. sericea extracts were the most active against nearly all tested
microorganisms [51]. Another study revealed that anolignan B isolated
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 17 of 21
from the ethyl acetate root extract of T. sericea had a strong antimicrobial
activity with MIC values ranging from 3.80 μg/ml against Bacillus
sabtilis to 31 μg/ml against Escherichia coli [40]. Gallic acid isolated
from the methanolic extract of T. nigrovenulosa bark showed a high
antifungal activity against Fusarium solani [52]. Ethanolic root extract of
T. macroptera had a significant antimicrobial activity, where the lowest
MICs were obtained for Shigella dysenteriae, Staphylococcus aureus and
Vibrio cholera with a significant activity against Campylobacter species
[53]. Also, the leaf extract of T. macroptera showed an antimicrobial
activity against Neisseria gonorrhoeae with an MIC value between 100
and 200 μg/ml, the diethyl ether fraction was the most active fraction
with an MIC values between 25 and 50 μg/ml [54]. Moreover, it was
assumed that punicalagin and terchebulin, the major compounds of
the T. macroptera root extract were responsible for the in vitro activity
of the extract against Helicobacter pylori [55]. The methanolic extract
of T. superba stem bark, together with its major component 3’,4-di-Omethyl-3-O-(β-ᴅ-xylopyranosyl) ellagic acid prevented the growth of
various mycobacteria and fungal species [56]. Punicalagin, isolated
from the acetone extract of T. brachystemma leaves, displayed a good
antifungal activity against Candida parapsilosis (MIC=6.25 µg/ml),
Candida krusei (MIC=6.25 µg/ml) and Candida albicans (MIC=12.50
µg/ml) [9]. T. australis methanol and aqueous extracts were effective
against the several Aspergillus and Candida strains [57]. The compounds
5,7,2’-tri-O-methyl-flavanone-4’-O-α-L-rhamnopyranosyl-(1→4)-β-ᴅglucopyranoside and 2α,3β,19β,23-tetrahydroxyolean-12-en-28-oicacid-3-O-β-ᴅ-galactopyranosyl-(1→3)-β-ᴅ-glucopyranoside-28-O-βᴅ-glucopyranoside isolated from the roots of T. alata were reported to
have a strong antifungal activity [58].
Cytotoxic activity
T. chebula methanolic fruit extract showed a reduction in cell
viability, inhibition of cell proliferation, and induction of cell death in
a dose-dependent manner on many malignant cell lines. In addition,
it induced apoptosis at lower concentrations, and necrosis at higher
concentrations. Chebulinic acid, tannic acid and ellagic acid, with
IC50 values of 53.20, 59.00 and 78.50 µg/ml respectively, were the most
cytotoxic compounds of T. chebula fruit [59]. Furthermore, chebulagic
acid isolated from the T. chebula fruit extract possessed an antiproliferative activity against HCT-15, COLO-205, MDA-MB-231, DU145 and K562 cell lines [60]. T. catappa leaf water extract, along with
its isolated component punicalagin were effective against bleomycininduced genotoxicity in Chinese hamster ovary cells [61]. Furthermore,
T. catappa leaf extract exerted a dose-dependent inhibitory effect on
the invasion and motility of highly metastatic A549 and Lewis lung
carcinoma cells [62]. Moreover, the ethanol extract of T. catappa leaves
significantly inhibited the cell migration capacity of oral squamous cell
carcinoma cells [63]. Luteolin, gallic acid and gallic acid ethyl ester
isolated from the bark, stem and leaves of T. arjuna methanolic extract
possessed a strong antineoplastic activity [64]. Moreover, ivorenoside
C isolated from the bark of T. ivorensis had an antiproliferative activity
against MDA-MB-231 and HCT116 human cancer cell lines with IC50
values of 3.96 and 3.43 μM respectively [65]. Additionally, the acetone
extract of T. calamansanai leaves inhibited the viability of HL-60 cells
[66].
Cardioprotective activity
T. arjuna bark has been used widely in traditional medicine as a
cardioprotective. The ethanolic extract of T. arjuna bark enhanced the
cardiac intracellular antioxidant status in CCl4-induced oxidative stress
in rats [67]. The protective effect was comparable to that of vitamin C.
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
In addition, The butanol fraction of T. arjuna bark extract exhibited
a protective effect against doxorubicin-induced cardiotoxicity by
increasing cardiac antioxidant enzymes, decreasing serum creatine
kinase-MB levels and reducing lipid peroxidation [68]. Many clinical
trials were also conducted to prove the beneficial effect of T. arjuna bark
on the heart. A group of scientists showed that patients with refractory
chronic congestive heart failure, when received T. arjuna bark extract
as an adjuvant therapy, showed a long lasting improvement in the signs
and symptoms of heart failure with an improvement in left ventricular
ejection phase indices and quality of life [69]. Moreover, a clinical
study was done to evaluate the role of T. arjuna in ischemic mitral
regurgitation (IMR) following acute myocardial infarction. Patients
receiving adjuvant T. arjuna showed significant decrease in IMR and
reduction in anginal frequency [70]. In addition, pretreatment with T.
pallida fruit extract ameliorated myocardial injury in isoproterenolinduced myocardial infarction in rats and exhibited cardioprotective
activity [71]. Similarly, pretreatment with T. chebula extract ameliorated
the effect of isoproterenol on lipid peroxide formation [72].
Anti-hypertensive activity
T. superba bark extract showed a potent antihypertensive activity
in spontaneously hypertensive rats, as well as in glucose-induced
hypertensive rats due to the withdrawal of sympathetic tone and the
improvement of the antioxidant status [73,74].
Antiparasitic and molluscicidal activity
The in vitro nematicidal activity of T. nigrovenulosa bark against
Meloidogyne incognita was attributed to 3,4-dihydroxybenzoic acid
isolated from it. [75]. The ethyl acetate, acetone and methanol leaf
and seed extracts of T. chebula showed in vitro ovicidal and larvicidal
activities on Haemonchus contortus [76]. In addition, T. chebula fruit
molluscicidal activity was due its tannic acid content that significantly
inhibited the AChE, ACP and ALP activity in the nervous tissue of
freshwater snail Lymnaea acuminate [77]. Additionally, ethanolic leaf
extract of T. catappa possessed a molluscicidal activity against the
snail intermediate hosts of schistosomiasis (Biomphalaria pfeifferi and
Bulinus globosus) with B. pfeifferi being more susceptible [78].
Wound healing activity
Topical administration of T. chebula alcoholic leaf extract on the
rat dermal wounds showed a beneficial effect in the acceleration of the
healing process, by increasing the tensile strength of tissues by about
40% and decreasing the period of epithelialization [79]. Moreover, the
tannin-rich fraction obtained from T. chebula fruits endorsed wound
healing in rats due to the powerful antibacterial and angiogenic activity
of the extract [80]. Topical application of T. arjuna hydro-alcholic
extract resulted in a significant increase in the tensile strength of the
incision wounds and epithelialization of excision wounds. This wound
healing property was more pronounced in the tannin-rich fraction
compared to the other fractions [81].
Conclusion
An extensive literature survey on genus Terminalia has revealed
a variety of chemical constituents produced by this genus. Tannins,
flavonoids, phenolic acids, triterpenes, triterpenoidal glycosides, lignan
and lignan derivatives constitute the major classes of phytoconstituents
of this genus [82-105]. In addition, the current review showed that most
of the biological studies performed on different extracts and isolated
compounds from different species of Terminalia were focused on the
assessment of the antimicrobial, antioxidant, hepatoprotective, anti-
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 18 of 21
inflammatory, hypoglycemic, hypolipidimic, cytotoxic and wound
healing activities of these species. The various pharmacological studies
validated the folk medicinal uses of different Terminalia species.
Although many phytochemical and biological investigations were
reported from the genus Terminalia, the studies have focused mainly
on certain species, with chebula, bellerica, arjuna, catappa, horrida,
superba, macroptera, pallida, ivorensis, sericea and alata being the most
phytochemically and biologically studied species, leaving a fertile area
for further investigations on other species that have not been fully
explored yet [106-133]. The present review provides a comprehensive
understanding of the chemistry and biology of different Terminalia
species, which may help in the discovery and development of new
alternative medications for the treatment of various diseases and health
problems.
Declaration of Interest
The authors have declared no conflicts of interest.
References
1. De Morais Lima GR, de Sales IR, Caldas Filho MR, de Jesus NZ, de Sousa
Falcão H, et al. (2012) Bioactivities of the genus Combretum (Combretaceae):
a review. Molecules 17: 9142-9206.
2. Saxena VG, Mishra KK, Vishwakarma, Saxena A (2013) A comparative study
on quantitative estimation of tannins in Terminalia chebula, Terminalia belerica,
Terminalia arjuna and Saraca indica using spectrophotometer. Asian J Pharm
Clin Res 6: 148-149.
3. Stace CA (2007) Combretaceae: Springer 9: 67-82.
4. Eloff JN, Katerere DR, McGaw LJ (2008) The biological activity and chemistry
of the southern African Combretaceae. J Ethnopharmacol 119: 686-699.
5. Yang MH, Vasquez Y, Ali Z, Khan IA, Khan SI (2013) Constituents from
Terminalia species increase PPARα and PPARγ levels and stimulate glucose
uptake without enhancing adipocyte differentiation. J Ethnopharmacol 149:
490-498.
6. Bag A, Bhattacharyya SK, Chattopadhyay RR (2013) The development of
Terminalia chebula Retz. (Combretaceae) in clinical research. Asian Pac J Trop
Biomed 3: 244-252.
7. Pellati F, Bruni R, Righi D, Grandini A, Tognolini M, et al. (2013) Metabolite
profiling of polyphenols in a Terminalia chebula Retzius ayurvedic decoction
and evaluation of its chemopreventive activity. J Ethnopharmacol 147: 277-285.
8. Dixit D, Dixit AK, Lad H, Gupta D, Bhatnagar D (2013) Radioprotective effect of
Terminalia Chebula Retzius extract against irradiation-induced oxidative stress.
Biomed Aging Pathol 3: 83-88.
9. Liu M, Katerere DR, Gray AI, Seidel V (2009) Phytochemical and antifungal
studies on Terminalia mollis and Terminalia brachystemma. Fitoterapia 80: 369373.
10. Garcez FR, Garcez WS, Miguel DL, Serea AA, Prado FC (2003)Chemical
constituents from Terminalia glabrescens. J Braz Chem Soc 14: 461-465.
11. Li DQ, Zhao J, Xie J, Li SP (2014) A novel sample preparation and on-line
HPLC–DAD–MS/MS–BCD analysis for rapid screening and characterization of
specific enzyme inhibitors in herbal extracts: Case study of a-glucosidase. J
Pharm Biomed Anal 88: 130-135.
12. Gao H, Huang YN, Xu, Kawabata J (2007) Inhibitory effect on a-glucosidase by
the fruits of Terminalia chebula Retz. Food Chem 105: 628-634.
13. Senthilkumar GP (2008) Biochemical studies on the effect of Terminalia chebula
on the levels of glycoproteins in streptozotocin-induced experimental diabetes
in rats. J Agric Food Chem 6: 105-115.
14. Ramachandran S, Rajasekaran A, Manisenthilkumar KT (2012) Investigation
of hypoglycemic, hypolipidemic and antioxidant activities of aqueous extract
of Terminalia paniculata bark in diabetic rats. Asian Pac J Trop Biomed 2: 262268.
15. Nampoothiri SV, Prathapan A, Cherian OL, Raghu KG, Venugopalan VV, et al.
(2011) In vitro antioxidant and inhibitory potential of Terminalia bellerica and
Emblica officinalis fruits against LDL oxidation and key enzymes linked to type
2 diabetes. Food Chem Toxicol 49: 125-131.
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
16. Latha RC, Daisy P (2011) Insulin-secretagogue, antihyperlipidemic and other
protective effects of gallic acid isolated from Terminalia bellerica Roxb. in
streptozotocin-induced diabetic rats. Chem Biol Interact 189: 112-118.
17. Anam K, Widharna RM, Kusrini D (2009) α-Glucosidase Inhibitor Activity of
Terminalia Species. Int J Pharm 5: 277-280.
18. Wansi JD, Lallemand MC, Chiozem DD, Toze FA, Mbaze LM, et al. (2007)
alpha-Glucosidase inhibitory constituents from stem bark of Terminalia superba
(Combretaceae). Phytochemistry 68: 2096-2100.
19. Nagappa AN, Thakurdesai PA, Venkat Rao N, Singh J (2003) Antidiabetic
activity of Terminalia catappa Linn fruits. J Ethnopharmacol 88: 45-50.
20. Kameswara Rao B, Renuka Sudarshan P, Rajasekhar MD, Nagaraju N, Appa
Rao Ch (2003) Antidiabetic activity of Terminalia pallida fruit in alloxan induced
diabetic rats. J Ethnopharmacol 85: 169-172.
21. Latha R, Daisy P (2011) Insulin-secretagogue, antihyperlipidemic and other
protective effects of gallic acid isolated from Terminalia bellerica Roxb. in
streptozotocin-induced diabetic rats. Chemico-Biological Interactions 189: 112118.
22. Israni DA, Patel KV, TR G (2010) Anti-hyperlipidemic activity of aqueous extract
of Terminalia chebula and Gaumutra in high cholesterol diet fed rats. Int J
Pharm Pharm Sci 1: 48-59.
23. Ram A, Lauria P, Gupta R, Kumar P, Sharma VN (1997) Hypocholesterolaemic
effects of Terminalia arjuna tree bark. J Ethnopharmacol 55: 165-169.
24. Shaila HP, Udupa SL, Udupa AL (1998) Hypolipidemic activity of three
indigenous drugs in experimentally induced atherosclerosis. Int J Cardiol 67:
119-124.
25. Viswanatha GL, Vaidya SK, Krishnadas N, Rangappa S (2010) Antioxidant and
antimutagenic activities of bark extract of Terminalia arjuna. Asian Pac J Trop
Biomed 3: 965-970.
26. Dixit D, Dixit AK, Lad H, Gupta D, Bhatnagar D (2013) Radioprotective effect
of Terminalia Chebula Retzius extract against γ-irradiation-induced oxidative
stress. Biomedicine and Aging Pathology 3: 83-88.
27. Pfundstein B, El Desouky SK, Hull WE, Haubner R, Erben G, et al. (2010)
Polyphenolic compounds in the fruits of Egyptian medicinal plants (Terminalia
bellerica, Terminalia chebula and Terminalia horrida): Characterization,
quantitation and determination of antioxidant capacities. Phytochemistry 71:
1132-1148.
28. Bajpai M, Pande A, Tewari SK, Prakash D (2005) Phenolic contents and
antioxidant activity of some food and medicinal plants. Int J Food Sci Nutr 56:
287-291.
29. Fahmy NM, Al-Sayed E, Abdel-Daim MM, Karonen M, Singab A (2015)
Protective effect of Terminalia muelleri against carbon tetrachloride-induced
hepato– nephro toxicity in mice and characterization of its bioactive constituents.
Pharm Biol 1-11.
30. Eesha BR, Mohanbabu AV, Meena KK, Babu S, Vijay M, et al. (2011)
Hepatoprotective activity of Terminalia paniculata against paracetamol induced
hepatocellular damage in Wistar albino rats. Asian Pac J Trop Biomed 4: 466469.
31. Ghosh J, Das J, Manna P, Sil PC (2010) Protective effect of the fruits of
Terminalia arjuna against cadmium-induced oxidant stress and hepatic cell
injury via MAPK activation and mitochondria dependent pathway. Food Chem
123: 1062-1075.
32. Manna P, Sinha M, Pal P, Sil PC (2007) Arjunolic acid, a triterpenoid saponin,
ameliorates arsenic-induced cyto-toxicity in hepatocytes. Chem Biol Interact
170: 187-200.
33. Lee HS, Jung SH, Yun BS, Lee KW (2007) Isolation of chebulic acid from
Terminalia chebula Retz. and its antioxidant effect in isolated rat hepatocytes.
Arch Toxicol 81: 211-218.
34. Kinoshita S, Inoue Y, Nakama S, Ichiba T, Aniya Y (2007) Antioxidant and
hepatoprotective actions of medicinal herb, Terminalia catappa L. from Okinawa
Island and its tannin corilagin. Phytomedicine 14: 755-762.
35. Jadon A, Bhadauria M, Shukla S (2007) Protective effect of Terminalia belerica
Roxb. and gallic acid against carbon tetrachloride induced damage in albino
rats. J Ethnopharmacol 109: 214-218.
36. Nair JJ, Aremu AO, Van Staden J (2012) Anti-inflammatory effects of Terminalia
phanerophlebia (Combretaceae) and identification of the active constituent
principles. S Afr J Bot 81: 79-80.
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 19 of 21
37. Talwar S, Nandakumar K, Nayak PG, Bansal P, Mudgal J, et al. (2011) Antiinflammatory activity of Terminalia paniculata bark extract against acute and
chronic inflammation in rats. J Ethnopharmacol 134: 323-328.
38. Tan AC, Hou DX, Konczak I, Tanigawa S, Ramzan I, et al. (2011) Native
Australian fruit polyphenols inhibit COX-2 and iNOS expression in LPSactivated murine macrophages. Food Res Int 44: 2362-2367.
39. Nair V, Singh S, Gupta YK (2010) Anti-arthritic and disease modifying activity
of Terminalia chebula Retz. in experimental models. J Pharm Pharmacol 62:
1801-1806.
40. Eldeen IM, Elgorashi EE, Mulholland DA, van Staden J (2006) Anolignan B: a
bioactive compound from the roots of Terminalia sericea. J Ethnopharmacol
103: 135-138.
41. Lin CC, Hsu YF, Lin TC (1999) Effects of punicalagin and punicalin on
carrageenan-induced inflammation in rats. Am J Chin Med 27: 371-376.
42. Fan YM, Xu LZ, Gao J, Wang Y, Tang XH, et al. (2004) Phytochemical and
antiinflammatory studies on Terminalia catappa. Fitoterapia 75: 253-260.
43. Mishra V, Agrawal M, Onasanwo SA, Madhur G, Rastogi P, et al. (2013) Antisecretory and cyto-protective effects of chebulinic acid isolated from the fruits of
Terminalia chebula on gastric ulcers. Phytomedicine 20: 506-511.
44. Devi RS, Narayan S, Vani G, Shyamala Devi CS (2007) Gastroprotective effect
of Terminalia arjuna bark on diclofenac sodium induced gastric ulcer. Chem Biol
Interact 167: 71-83.
45. Gupta M, Mazumder UK, Manikandan L, Bhattacharya S, Senthilkumar GP, et
al. (2005) Anti-ulcer activity of ethanol extract of Terminaliapallida Brandis. in
Swiss albino rats. J Ethnopharmacol 97: 405-408.
46. Malekzadeh F, Ehsanifar H, Shahamat M, Levin M, Colwell RR (2001)
Antibacterial activity of black myrobalan (Terminalia chebula Retz) against
Helicobacter pylori. Int J Antimicrob Agents 18: 85-88.
47. Kathirvel A, Sujatha V (2012) In vitro assessment of antioxidant and
antibacterial properties of Terminalia chebula Retz. leaves. Asian Pac J Trop
Biomed 2: S788-S795.
48. Cheng HY, Lin CC, Lin TC (2002) Antiherpes simplex virus type 2 activity of
casuarinin from the bark of Terminalia arjuna Linn. Antiviral Res 55: 447-455.
49. Fyhrquist P, Laakso I, Garcia Marco S, Julkunen-Tiitto R, Hiltunen R (2014)
Antimycobacterial activity of ellagitannin and ellagic acid derivate rich crude
extracts and fractions of five selected species of Terminalia used for treatment
of infectious diseases in African traditional medicine. S Afr J Bot 90: 1-16.
50. Anam K, Suganda A, Sukandar E, Kardono LBS (2010) Antibacterial effect of
component of Terminalia muelleri Benth. against Staphylococcus aureus. Int J
Pharm 6: 407-412.
51. Masoko P, Picard J, Eloff JN (2005) Antifungal activities of six South African
Terminalia species (Combretaceae). J Ethnopharmacol 99: 301-308.
52. Nguyen DM, Seo DJ, Lee HB, Kim IS, Kim KY, et al. (2013) Antifungal activity of
gallic acid purified from Terminalia nigrovenulosa bark against Fusarium solani.
Microb Pathog 56: 8-15.
60. Reddy DB, Reddy TC, Jyotsna G, Sharan S, Priya N, et al. (2009) Chebulagic
acid, a COX-LOX dual inhibitor isolated from the fruits of Terminalia chebula
Retz., induces apoptosis in COLO-205 cell line. J Ethnopharmacol 124: 506512.
61. Chen PS, Li JH, Liu TY, Lin TC (2000) Folk medicine Terminalia catappa and its
major tannin component, punicalagin, are effective against bleomycin-induced
genotoxicity in Chinese hamster ovary cells. Cancer Letters 152: 115-122.
62. Chu SC, Yang SF, Liu SJ, Kuo WH, Chang YZ, et al. (2007) In vitro and in
vivo antimetastatic effects of Terminalia catappa L. leaves on lung cancer cells.
Food Chem Toxicol 45: 1194-1201.
63. Yang SF, Chen MK, Hsieh YS, Yang JS, Zavras AI, et al. (2010) Antimetastatic
effects of Terminalia catappa L. on oral cancer via a down-regulation of
metastasis-associated proteases. Food Chem Toxicol 48: 1052-1058.
64. Pettit GR, Hoard MS, Doubek DL, Schmidt JM, Pettit RK, et al. (1996)
Antineoplastic agents 338. The cancer cell growth inhibitory. Constituents of
Terminalia arjuna (Combretaceae). J Ethnopharmacol 53: 57-63.
65. Ponou BK, Teponno RB, Ricciutelli M, Quassinti L, Bramucci M, et al. (2010)
Dimeric antioxidant and cytotoxic triterpenoid saponins from Terminalia
ivorensis A. Chev. Phytochemistry 71: 2108-2115.
66. Chen LG, Huang WT, Lee LT, Wang CC (2009) Ellagitannins from Terminalia
calamansanai induced apoptosis in HL-60 cells. Toxicol In Vitro 23: 603-609.
67. Manna P, Sinha M, Sil PC (2007) Phytomedicinal activity of Terminalia arjuna
against carbon tetrachloride induced cardiac oxidative stress. Pathophysiology
14: 71-78.
68. Singh G, Singh AT, Abraham A, Bhat B, Mukherjee A, et al. (2008) Protective
effects of Terminalia arjuna against Doxorubicin-induced cardiotoxicity. J
Ethnopharmacol 117: 123-129.
69. Bharani A, Ganguly A, Bhargava KD (1995) Salutary effect of Terminalia Arjuna
in patients with severe refractory heart failure. Int J Cardiol 49: 191-199.
70. Dwivedi S, Aggarwal A, Agarwal MP, Rajpal S (2005) Role of Terminalia arjuna
in ischaemic mitral regurgitation. Int J Cardiol 100: 507-508.
71. Shaik AH, Rasool SN, Reddy AVK, Kareem KA, Krushna GS, et al. (2012).
Cardioprotective effect of HPLC standardized ethanolic extract of Terminalia
pallida fruits against isoproterenol-induced myocardial infarction in albino rats.
J Ethnopharmacol 141: 33-40.
72. Suchalatha S, Shyamala Devi CS (2004) Protective effect of Terminalia chebula
against experimental myocardial injury induced by isoproterenol. Indian J Exp
Biol 42: 174-178.
73. Tom ENL, Thernier CG, Martin H, Dimo T, Alvergnas M, et al. (2014) Treatment
with an extract of Terminalia superba Engler & Diels decreases blood pressure
and improves endothelial function in spontaneously hypertensive rats. J
Ethnopharmacol 151: 372-379.
74. Tom EN, Demougeot C, Mtopi OB, Dimo T, Djomeni PD, et al. (2011) The
aqueous extract of Terminalia superba (Combretaceae) prevents glucoseinduced hypertension in rats. J Ethnopharmacol 133: 828-833.
53. Silva O, Duarte A, Pimentel M, Viegas S, Barroso H, et al. (1997) Antimicrobial
activity of Terminalia macroptera root. J Ethnopharmacol 57: 203-207.
75. Nguyen DM, Seo DJ, Kim KY, Park RD, Kim DH, et al. (2013) Nematicidal
activity of 3,4-dihydroxybenzoic acid purified from Terminalia nigrovenulosa
bark against Meloidogyne incognita. Microb Pathog 59-60: 52-9.
54. Silva O, Ferreira E, Vaz Pato M, Caniça M, Gomes ET (2002) In vitro antiNeisseria gonorrhoeae activity of Terminalia macroptera leaves. FEMS
Microbiol Lett 217: 271-274.
76. Kamaraj C, Rahuman AA (2011) Efficacy of anthelmintic properties of medicinal
plant extracts against Haemonchus contortus. Res Vet Sci 91: 400-404.
55. Silva O, Viegas S, de Mello-Sampayo C, Costa MJ, Serrano R, et al. (2012)
Anti-Helicobacter pylori activity of Terminalia macroptera root. Fitoterapia 83:
872-876.
56. Kuete V, Tabopda TK, Ngameni B, Nana F, Tshikalange TE, et al. (2010)
Antimycobacterial, antibacterial and antifungal activities of Terminalia superba
(Combretaceae). S Afr J Bot 76: 125-131.
57. Carpano SM, Spegazzini ED, Rossi JS, Castro MT, Debenedetti SL (2003)
Antifungal activity of Terminalia australis. Fitoterapia 74: 294-297.
58. Srivastava SK, Srivastava SD, Chouksey BK (2001) New antifungal constituents
from Terminalia alata. Fitoterapia 72: 106-112.
59. Saleem A, Husheem M, Härkönen P, Pihlaja K (2002) Inhibition of cancer cell
growth by crude extract and the phenolics of Terminalia chebula retz. fruit. J
Ethnopharmacol 81: 327-336.
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
77. Upadhyay A, Singh DK (2011) Molluscicidal activity of Sapindus mukorossi
and Terminalia chebula against the freshwater snail Lymnaea acuminata.
Chemosphere 83: 468-474.
78. Adetunji V, Salawu O (2010) Efficacy of ethanolic leaf extracts of Carica papaya
and Terminalia catappa as molluscicides against the snail intermediate hosts of
schistosomiasis. Journal of Medicinal Plants Research 4: 2348-2352.
79. Suguna L, Singh S, Sivakumar P, Sampath P, Chandrakasan G (2002)
Influence of Terminalia chebula on dermal wound healing in rats. Phytother
Res 16: 227-231.
80. Li K, Diao Y, Zhang H, Wang S, Zhang Z, et al. (2011) Tannin extracts from
immature fruits of Terminalia chebula Fructus Retz. promote cutaneous wound
healing in rats. BMC Complement Altern Med 11: 86.
81. Chaudhari M, Mengi S (2006) Evaluation of phytoconstituents of Terminalia
arjuna for wound healing activity in rats. Phytother Res 20: 799-805.
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 20 of 21
82. Pellati F, Bruni R, Righi D, Grandini A, Tognolini M, et al. (2013) Metabolite
profiling of polyphenols in a Terminalia chebula Retzius ayurvedic decoction
and evaluation of its chemopreventive activity. J Ethnopharmacol 147: 277-285.
83. Kandil FE, Nassar MI (1998) A tannin anti-cancer promotor from Terminalia
arjuna. Phytochemistry 47: 1567-1568.
84. Paarakh PM (2010) Terminalia arjuna (Roxb.) Wt. and Arn.: A Review. Int J
Pharm 6: 515-534.
85. Chyau CC, Ko PT, Mau JL (2006) Antioxidant properties of aqueous extracts
from Terminalia catappa leaves. LWT - Food Sci Technol 39: 1099-1108.
86. Murdiati T, McSweeney C, Lowry J (1992) Metabolism in sheep of gallic acid,
tannic acid and hydrolysable tannin from Terminalia oblongata. Crop Pasture
Sci 43: 1307-1319.
87. Gupta M, Mazumder UK, Manikandan L, Bhattacharya S, Senthilkumar GP, et
al. (2005) Anti-ulcer activity of ethanol extract of Terminaliapallida Brandis. in
Swiss albino rats. J Ethnopharmacol 97: 405-408.
88. Marzouk MS, El-Toumy SA, Moharram FA, Shalaby NM, Ahmed AA (2002)
Pharmacologically active ellagitannins from Terminalia myriocarpa. Planta Med
68: 523-527.
89. Nair V, Singh S, Gupta YK (2010) Anti-arthritic and disease modifying activity
of Terminalia chebula Retz. in experimental models. J Pharm Pharmacol 62:
1801-1806.
90. Bag A, Bhattacharyya SK, Chattopadhyay RR (2013) The development of
Terminalia chebula Retz. (Combretaceae) in clinical research. Asian Pac J Trop
Biomed 3: 244-252.
91. Tanaka T, Nonaka GI, Nishioka I (1986) Tannins and related Compounds. XLII.
: Isolation and Characterization of four new hydrolyzable tannins, terflavins A
and B, tergallagin and tercatain from the teaves of Terminalia catappa L. Chem
Pharm Bull 34: 1039-1049.
92. Filippich LJ, Zhu J, Oelrichs P, Alsalami MT, Doig AJ, et al. (1991) Hepatotoxic
and nephrotoxic principles in Terminalia oblongata. Res Vet Sci 50: 170-177.
93. Lin TC, Chien SC, Chen HF, Hsu FL (2000) Tannins and related compounds
from combretaceae plants. Chin Pharm J 52: 1-26.
94. Conrad J, Vogler B, Reeb S, Klaiber I, Papajewski S, et al. (2001) Isoterchebulin
and 4,6-O-isoterchebuloyl-D-glucose, novel hydrolyzable tannins from
Terminalia macroptera. J Nat Prod 64: 294-299.
95. Lin T, Nonaka G, Nishioka I, Ho F (1990) Tannins and related compounds. CII.
Structures of terchebulin, an ellagitannin having a novel tetraphenylcarboxylic
acid (terchebulic acid) moiety, and biogenetically related tannins from Terminalia
chebula Retz. Chem Pharm Bull 38: 3004-3008.
96. Yoshida T, Amakura Y, Yoshimura M (2010) Structural features and biological
properties of ellagitannins in some plant families of the order Myrtales. Int J Mol
Sci 11: 79-106.
97. Row LR, Raju RR (1967) Chemistry of Terminalia species-XI : Isolation of
3,4,3’-O-trimethyl flavellagic acid from Terminalia paniculata Roth. Tetrahedron
23: 879-884.
98. Baratelli TDG, Candido Gomes AC, Wessjohann LA, Kuster RM, Simas
NK (2012) Phytochemical and allelopathic studies of Terminalia catappa L.
(Combretaceae). Biochem Syst Ecol 41: 119-125.
106. Nagar A, Gujral VK, Gupta SR (1979) A new flavone from Terminalia arjuna
fruits. Phytochemistry 18: 1245.
107. Garcez FR, GarcezWS, Martins M, Lopes FA (2003) Triterpenoids, lignan and
flavans from Terminalia argentea (Combretaceae). Biochem Syst Ecol 31:
229-232.
108. Valsaraj R, Pushpangadan P, Smitt UW, Adsersen A, Christensen SB, et
al. (1997) New anti-HIV-1, antimalarial, and antifungal compounds from
Terminalia bellerica. J Nat Prod 60: 739-742.
109. Srivastava SK, Srivastava SD, Chouksey BK (1999) New constituents of
Terminalia alata. Fitoterapia 70: 390-394.
110. Tripathi VK, Pandey VB, Udupa KN, Rucker G (1992) Arjunolitin, a triterpene
glycoside fromTerminalia arjuna. Phytochemistry 31: 349-351.
111. Singh C (1990) 2α-Hydroxymicromeric acid, a pentacyclic triterpene from
Terminalia chebula. Phytochemistry 29: 2348-2350.
112. Collins DJ, Pilotti CA, Wallis AFA (1992) Triterpene acids from some Papua
New Guinea Terminalia species. Phytochemistry 31: 881-884.
113. Singh DV, Verma RK, Singh SC, Gupta MM (2002) RP-LC determination of
oleane derivatives in Terminalia arjuna. J Pharm Biomed Anal 28: 447-452.
114. Conrad J, Vogler B, Klaiber I, Roos G, Walter U, et al. (1998) Two triterpene
esters from Terminalia macroptera bark. Phytochemistry 48: 647-650.
115. Nandy AK, Podder G, Sahu NP, Mahato SB (1989) Triterpenoids and their
glucosides from Terminalia bellerica. Phytochemistry 28: 2769-2772.
116. Row RL, Subba Rao GSR (1962) Chemistry of Terminalia species—VI :
The constitution of tomentosic acid, a new triterpene carboxylic acid from
Terminalia tomentosa Wight et Arn. Tetrahedron 18: 827-838.
117. Bombardelli E, Bonati A, Gabetta B, Mustich G (1974) Triterpenoids of
Terminalia sericea. Phytochemistry 13: 2559-2562.
118. Mahato SB, Nandy AK, Kundu AP (1992) Pentacyclic triterpenoid sapogenols
and their glycosides from Terminalia Bellerica. Tetrahedron 48: 2483-2494.
119. Idemudia OG (1970) Terpenoids
Phytochemistry 9: 2401-2402.
of
Nigerian
Terminalia
species.
120. Anjaneyulu ASR, Reddy AVR, Mallavarapu GR, Chandrasekhara RS (1986)
3-acetylmaslinic acid from the root bark of Terminalia alata. Phytochemistry
25: 2670-2671.
121. Anjaneyulu ASR, Reddy AVR (1983) Structure of terminic acid, a
dihydroxytriterpene carboxylic acid from Terminalia arjuna. Phytochemistry
22: 993-998.
122. Atta UR, Zareen RS, Choudhary MI, Ngounou FN, Yasin A, et al. (2002)
Terminalin A, a novel triterpenoid from Terminalia glaucescens. Tetrahedron
Lett 43: 6233-6236.
123. Kundu AP, Mahato SB (1993) Triterpenoids and their glycosides from
Terminalia chebula. Phytochemistry 32: 999-1002.
124. Row J, Murty P (1970) Chemical examination of Terminalia bellerica Roxb.
Indian J Chem 8: 1047-1048.
99. Wang W, Ali Z, Shen Y, Li XC, Khan IA (2010) Ursane triterpenoids from the
bark of Terminalia arjuna. Fitoterapia 81: 480-484.
125. Mokgoatsane SI (2011) The isolation and characterization of an antibacterial
compound from Terminalia sambesiaca (Combretaceae), North-West
University. 192pp.
100. Kumar A, Lakshman K, Jayaveera K, Tripathi SM, Satish K (2010) Estimation
of gallic acid, rutin and quercetin in Terminalia chebula by HPTLC. Jordan J
Pharm Sci 3.
126. Anjaneyulu A, Rama Prasad A (1982) Chemical examination of the roots of
Terminalia arjuna the structures of arjunoside III and arjunoside IV, two new
triterpenoid glycosides. Phytochemistry 21: 2057-2060.
101. Dwivedi S (2007) Terminalia arjuna Wight & Arn.--a useful drug for
cardiovascular disorders. J Ethnopharmacol 114: 114-129.
127. Srivastava SK, Chouksey BK, Srivastava SD (2001) Triterpenoid glycoside
from the roots of Terminalia alata. Fitoterapia 72: 191-193.
102. Ross S, El-Fishawy A, Said A, Hawas U, Tekwani B, et al. (2013) A new fatty
alcohol from Terminalia arjuna leaves with antileishmanial activity. Med Chem
Res 22: 5844-5847.
128. Cao S, Brodie PJ, Callmander M, Randrianaivo R, Rakotobe E, et al.
(2010) Saponins and a lignan derivative of Terminalia tropophylla from the
Madagascar Dry Forest. Phytochemistry 71: 95-99.
103. Sharma P, Shoeb A, Kapil R, Popli S (1982) Arjunolone-a new flavone from
stem bark of Terminalia arjuna. Indian J Chem 21: 263-264.
104. Kumar DS, Prabhakar YS (1987) On the ethnomedical significance of the Arjun
tree, Terminalia arjuna (Roxb.) Wight & Arnot. J Ethnopharmacol 20: 173-190.
105. Lin YL, Kuo YH, Shiao MS, Chen CC, Ou JC (2000) Flavonoid glycosides from
Terminalia catappa L. J Chin Chem Soc 47: 253-256.
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
129. Honda T, Murae T, Tsuyuki T, Takahashi T, Sawai M (1976) Arjungenin,
arjunglucoside I and arjunglucoside II, a new triterpene and new triterpene
glucosides from Terminalia arjuna. Bull Chem Soc Jpn 49: 3213-3218.
130. Ali A, Kaur G, Hamid H, Abdullah T, Ali M, et al. (2003) Terminoside A, a new
triterpene glycoside from the bark of Terminalia arjuna inhibits nitric oxide
production in murine macrophages. J Asian Nat Prod Res 5: 137-142.
Volume 4 • Issue 5 • 1000218
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 21 of 21
131. Ali A, Ali M, Alam MS (2006) Two new oleanane triterpene glycosides from the
bark of Terminalia arjuna. Z Naturforsch B 61: 1282-1286.
pentacyclic triterpenes isolated from African Combretaceae. Phytochemistry
63: 81-88.
132. Katerere DR, Gray AI, Nash RJ, Waigh RD (2003) Antimicrobial activity of
133. Yadav RN, Rathore K (2001) A new cardenolide from the roots of Terminalia
arjuna. Fitoterapia 72: 459-461.
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
Volume 4 • Issue 5 • 1000218
Eman Al-sayed