CN101704858B - Compound extracted from Tibetan medicine eriophyton wallichii with antioxidant activity and extracting method thereof - Google Patents
Compound extracted from Tibetan medicine eriophyton wallichii with antioxidant activity and extracting method thereof Download PDFInfo
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- CN101704858B CN101704858B CN2009102284149A CN200910228414A CN101704858B CN 101704858 B CN101704858 B CN 101704858B CN 2009102284149 A CN2009102284149 A CN 2009102284149A CN 200910228414 A CN200910228414 A CN 200910228414A CN 101704858 B CN101704858 B CN 101704858B
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Images
Abstract
The invention relates to a compound extracted from Tibetan medicine eriophyton wallichii with antioxidant activity and an extracting method thereof. The compound is identified as new iridoid through modern spectral analysis, wherein the molecular weight is 780, and the molecular formula is C34H52O20. The extracting method comprises the following steps of: pulverizing whole eriophyton wallichii; extracting with ethanol; sequentially extracting by using petroleum ether, ethylacetate and water saturated n-butanol; carrying out chromatography on the n-butanol part by macroporous absorption resin; and carrying out column chromatography on 30 percent of an elution part sequentially through MCI-GEL CHP20P, ODS-A and Sephadex LH-20 so as to obtain wallchiiside F. The new iridoid has simple preparation method, low cost and obvious activity and provides a new compound for developing medicaments having antioxidant effects.
Description
Technical field
The present invention relates to a kind of method of from the continuous ginseng of Tibetan medicine, extracting new compound, particularly a kind of compound with anti-oxidant activity and process for extracting thereof that from the continuous ginseng of Tibetan medicine, extracts.
Background technology
The medical health method of Tibetan medicine's pharmacy uniqueness that to be China's Tibetan people form in the process that long-term and physical environment are struggled against is the rarity of motherland's traditional medicine.Tibet is high and cold a, anoxic, strong, the free of contamination altitude environment of radiation, so Tibetan medicine has characteristics such as growth cycle length, special effect, active substance accumulation height.Though existing Tibetan medicinal health-care product on the market; But kind is more single, and efficacy factor and structure thereof to imitate dose-effect relationship all indeterminate, this is unfavorable for developing third generation healthcare products and moves towards the world market; Therefore; Furtheing investigate the application of Tibetan medicine aspect healthcare products, confirm the efficacy factor and the structure effect dose-effect relationship thereof of Tibetan medicinal health-care product, is an exploitation third generation Tibetan medicinal health-care product and a key moving towards the world market.
Continuous ginseng (Eriophyton wallichii Benth.), Tibetan medicine name list ginseng cloth is eaten, and is labiate; Herb or root are used as medicine, and are born in the ice pool riprap of height above sea level 4500-5300km, the rubble band; Originate in Tibet, Qinghai, SOUTH OF GANSU, western Sichuan, northwestern Yunnan Province; The flower Sheng phase gathers, and removes clean earth, dries.Bitter is cool in nature, gas, nourishing, moistening lung in regulating the qi flowing in the channels and blood, the lifting.Control deficiency of vital energy and physically weak, deficiency of both QI and blood, pulmonary abscess, pulmonary tuberculosis, cough due to lung-heat, hemoptysis, pectoralgia.
Continuous ginseng is early on the books in Tibetan medicine masterpiece " brilliant pearl book on Chinese herbal medicine ", at present, have only Chinese Academy of Sciences Chengdu biological once from the fat-soluble position that silk floss is joined, assigned to 28-epi-cyasterone; Eriophytonoide, Cyasterone, ajuforrestinsA and B; 20-hydroxyecdysone, polypodinB, ajugalactone; 8-O-acetylharpagid, apigenin ,-sitosterol daucosterol; And N-[2-hydroxy-(nonadecanoyl-tricosanoyl)]-compounds such as 4-hydroxytrans-8-sphingenine; And the systematic study of its fat-soluble position and water soluble part is not also reported, simultaneously, the research on its active substance basis is not reported both at home and abroad yet.
Therefore; In order to further investigate the chemical ingredients and the pharmacologically active thereof of continuous ginseng; Clear and definite its efficacy factor and structure thereof are imitated dose-effect relationship, for developing continuous ginseng series health-care products theoretical foundation are provided, and utilize modern separate analytical technique and pharmacological evaluation technology that the bioactive ingredients of silk floss ginseng is studied.A kind of compound with anti-oxidant activity and process for extracting thereof that from the continuous ginseng of Tibetan medicine, extracts promptly is provided, promptly becomes one of these those skilled in the art problem anxious to be addressed.
Summary of the invention
The objective of the invention is to overcome the weak point of prior art, a kind of compound with anti-oxidant activity and process for extracting thereof that from the continuous ginseng of Tibetan medicine, extracts is provided.
For realizing that the technical scheme that above-mentioned purpose the present invention is adopted is: a kind of compound with anti-oxidant activity that from the continuous ginseng of Tibetan medicine, extracts is characterized in that the compound chemical structure formula with anti-oxidant activity that is obtained is:
This compound is a colourless crystallization, by ESI-MS m/z:803 [M+Na]
+, 825 [M+HCOO
-]
-, can know that its molecular weight is 780, in conjunction with
1H-NMR (C
5D
5N) and
13C-NMR (C
5D
5N) data confirm that its molecular formula is C
34H
52O
20, degree of unsaturation is 9;
δ 94.5, δ 96.2, δ 97.9 are three acetal carbon signals, and HMQC shows δ
C141/ δ
H6.45 and δ
C103.9/ δ
H4.74 be the hydrocarbon signal of two keys, in conjunction with HMQC and HMBC spectrum, the NMR signal of aglycon shows two cyclopentane type secoiridoid skeletons of existence, a skeleton is identical with ajugoside, and another is then similar with the ajugoside skeleton, δ
H6.06/ δ
C97.9, δ
H2.45 (2H)/δ
C29 show that the two keys on C3 '-C4 ' become singly-bound, and the HMBC spectrum shows coherent signal δ
H6.42/ δ
C100.4, δ
H5.41/ δ
C94.5 and δ
H5.93/ δ
C100.1, δ
H5.59/ δ
C96.2, show that two secoiridoid skeleton C-1 hydroxyls have respectively connected a glucone, and coherent signal δ
H5.41/ δ
C84.6, δ
H6.06/ δ
C84.6, δ
H4.35/ δ
C97.9 and δ
H4.35/ δ
CDirectly do not link to each other 100.4 show two secoiridoid skeletons, but link to each other through (1 → a 2) glucone, this compound is a new iridoid glycoside, called after wallchiiside F.
A kind of process for extracting of the compound that from the continuous ginseng of Tibetan medicine, extracts with anti-oxidant activity, implementation step is following:
At first, with 10Kg exsiccant silk floss ginseng herb, pulverizing is extracted 3 times with 50-95% ethanol soaking at room temperature, and each 7-10 days, extracting solution is merged concentrating under reduced pressure, get fluid extract 970g, density 1.15g/ml gets 3L after the water suspendible disperses; Use sherwood oil, ETHYLE ACETATE and water saturated n-butanol extraction successively, obtain petroleum ether part 200g, ethyl acetate extract 33g, n-butanol portion 255g respectively;
Then, through D-1400 type macroporous adsorptive resins, blade diameter length ratio 1: 5 is divided into 4 parts 10%, 30%, 60%, 90% with water-ethanol system wash-out with n-butanol portion 255g;
30% wash-out part, 74g, through MCI-GEL CHP20P macroporous resin column chromatography, blade diameter length ratio 1: 8 with 10-60% methanol-water wash-out, increases progressively by 10% and to be divided into A1-A6 totally 6 parts; A4 is again through anti-phase ODS-A column chromatography; Blade diameter length ratio 1: 8 increases progressively with 10-60% methanol-water wash-out 5 column volumes of each wash-out by 10%; Be divided into B1-B6 totally 6 parts; B3 is Sephadex LH-20 gel filtration chromatography repeatedly again, and blade diameter length ratio 1: 30 gets wallchiiside F 10mg with 50% methanol-eluted fractions.
The invention has the beneficial effects as follows: extraction separation to a new iridoid from the continuous ginseng of Tibetan medicine; The extraction separation process is easy; Have the ability of removing radical through this compound of evidence, the medicine that has antioxygenation for exploitation provides lead compound.
Description of drawings
Fig. 1 is a wallchiiside F extraction separation schema of the present invention.
Embodiment
The following drawings and preferred embodiment, to details are as follows according to the specific embodiment provided by the invention and feature:
The chemical structural formula with anti-oxidant activity new compound that the present invention obtained is:
This compound is a colourless crystallization, by ESI-MS m/z:803 [M+Na]
+, 825 [M+HCOO
-]
-, can know that its molecular weight is 780, in conjunction with
1H-NMR (C
5D
5N) and
13C-NMR (C
5D
5N) data confirm that its molecular formula is C
34H
52O
20, degree of unsaturation is 9;
δ 94.5, δ 96.2, δ 97.9 are three acetal carbon signals, and HMQC shows δ
C141/ δ
H6.45 and δ
C103.9/ δ
H4.74 be the hydrocarbon signal of two keys, in conjunction with HMQC and HMBC spectrum, the NMR signal of aglycon shows two cyclopentane type secoiridoid skeletons of existence, a skeleton is identical with ajugoside (ajugoside), and another is then similar with ajugoside (ajugoside) skeleton, δ
H6.06/ δ
C97.9, δ
H2.45 (2H)/δ
C29 show that the two keys on C3 '-C4 ' become singly-bound, and the HMBC spectrum shows coherent signal δ
H6.42/ δ
C100.4, δ
H5.41/ δ
C94.5 and δ
H5.93/ δ
C100.1, δ
H5.59/ δ
C96.2, show that two secoiridoid skeleton C-1 hydroxyls have respectively connected a glucone, and coherent signal δ
H5.41/ δ
C84.6, δ
H6.06/ δ
C84.6, δ
H4.35/ δ
C97.9 and δ
H4.35/ δ
CDirectly do not link to each other 100.4 show two secoiridoid skeletons, but link to each other through (1 → a 2) glucone, this compound is a new iridoid glycoside, called after wallchiiside F.
As shown in Figure 1, a kind of process for extracting of the compound that from the continuous ginseng of Tibetan medicine, extracts with anti-oxidant activity, implementation step is following:
At first, with 10Kg exsiccant silk floss ginseng herb, pulverizing is extracted 3 times with 50-95% ethanol soaking at room temperature, and each 7-10 days, extracting solution is merged concentrating under reduced pressure, get fluid extract 970g, density 1.15g/ml gets 3L after the water suspendible disperses; Use sherwood oil, ETHYLE ACETATE and water saturated n-butanol extraction successively, obtain petroleum ether part 200g, ethyl acetate extract 33g, n-butanol portion 255g respectively;
Then, through D-1400 type macroporous adsorptive resins, blade diameter length ratio 1: 5 is divided into 4 parts 10%, 30%, 60%, 90% with water-ethanol system wash-out with n-butanol portion 255g;
30% wash-out part, 74g, through MCI-GEL CHP20P macroporous resin column chromatography, blade diameter length ratio 1: 8 with 10-60% methanol-water wash-out, increases progressively by 10% and to be divided into A1-A6 totally 6 parts; A4 is again through anti-phase ODS-A column chromatography; Blade diameter length ratio 1: 8 increases progressively with 10-60% methanol-water wash-out 5 column volumes of each wash-out by 10%; Be divided into B1-B6 totally 6 parts; B3 is Sephadex LH-20 gel filtration chromatography repeatedly again, and blade diameter length ratio 1: 30 gets wallchiiside F 10mg with 50% methanol-eluted fractions.
Measure wallchiiside F through the DPPH method and have stronger anti-oxidant activity.
Table 1wallchiiside F is at C
5D
5Nuclear magnetic resonance data among the N
Adopt instrument and material:
Mass spectrum: MAT-95 type mass spectrograph, Kratos 1H type mass spectrograph;
Nuclear magnetic resonance spectrum: BruckAM-400 NMR;
Reverse phase silica gel: ODS-A (120nm, S-50 μ m), YMC CO., LTD., Japan
Sephadex
TM?LH-20：GE?Healthcare?Bio-Scoences?AB，Uppsala，Sweden；
Macroporous adsorbent resin: D-1400, Yangzhou pharmaceutical factory; MCI-GEL CHP20P (75-150 μ m), Mitsubishi Chemical Corporation, Tokyo, Japan;
Specific rotatory power: Perkin-Elmer 241MC polarimeter or Perkin-Elmer 341polarimeter;
Ir spectra: Nicolet Magna 750FTIR type infrared spectrophotometer;
TLC thin layer plate: HSGF254 can adopt Yantai chemical research institute;
Developer: 10% sulfuric acid vanillin food grade,1000.000000ine mesh ethanolic soln;
Vegetable material: continuous ginseng (Eriophyton wallichii Benth.) herb picks up from Tibet Autonomous Region;
DPPH:sigma company.
The TP of wallchiiside F anti-oxidant activity:
10,20,40,80,160,320mg/L with water is solvent, accurately wallchiiside F and standard substance is made into following concentration:.In the 250mL volumetric flask, then the concentration of DPPH is 2 * 10 to the DPPH that takes by weighing 20mg with the anhydrous alcohol solution constant volume
-4Mol/L.Measuring method: in 96 orifice plates, add the sample solution of 150 μ L and the DPPH solution of 150 μ L, shake up, in room temperature, behind the placement 30min, measure its absorbancy at 517nm (maximum absorption wave strong point).Sample can be used computes to the clearance rate K of DPPH:
k＝[1-(A
i-A
j)/Ac]×100％
In the formula:
A
iThe absorbance of=150 μ L DPPH solution+150 μ L sample solutions;
A
jThe absorbance of=150 μ L sample solutions+150 μ L water;
The absorbance of Ac=150 μ L DPPH solution+150 μ L water.
Test-results:
The clearance rate of table 2wallchiiside F DPPH, %
Can find out from table 2, along with the free radical scavenging activity of the increase wallchiiside F of concentration also raises gradually, through analyzing IC
50Value finds that the radical scavenging activity of wallchiiside F obviously is better than kaempferol-3-O-violaguercitrin, explains that it has significant resistance of oxidation.
The pharmacologically active of iridoid glycoside compounds:
Iridoid is as one of effective constituent in numerous plant amedicas; Has wide biological activity; Like various active such as antiviral, antibiotic, antitumor, anti-oxidant, hepatic cholagogic, spasmolysis and analgesia, enhancing immunity, hypoglycemics, and neural system, the cardiovascular system Digestive tract of unifying had useful effect.
Have experiment to show that Geniposide in the cape jasmine, jasminoidin can suppress the growth of murine leukemia P388 cell, wherein the semi-acetal structure of aglycon is antitumor necessary.And Geniposidic acid (GA) and jasminoidin (GP) are as the protective agent of semilethal X-radiation effect is realized to the antitumous effect of rat tumor model.Find that simultaneously GA has higher protection activity than GP.
The experiment of Chinese People's Anti-Japanese Military and Political College's mouse alloxan diabetes shows that scropolioside D that from figwort Scrophularia deserti, finds and the Harper acid of 8-O-ethanoyl have strong active; C-3 cinnyl group makes the iridoid glycoside increased activity, and the ethanoyl on the C-8 is essential to anti-diabetic activity.The skunk bush iridoid glycoside has provide protection to the oxidative stress damage that is caused by diabetic vascular complications.Other have the experiment show the skunk bush iridoid glycoside can make diabetes rat thoracic aorta vascular endothelial cell damage be improved significantly; And can suppress the formation of diabetes rat renal cortex AGEs; Its Receptor mRNA level is descended, have the effect that alleviates the dn-change.
Geniposide in the cape jasmine kernel has the effect of softening stool, and its aglycon has the effect of significant promotion choleresis through the pharmacological evaluation proof.The effective constituent of psyllium clearing away damp-heat, diuresis effect is the aucubin of cyclopentane structure.Catalpol is the effective constituent of hypoglycemic activity in the glutinous rehmannia, and good diuretic properties and the slow effect down of tardy property are arranged.Fructus catalpae is used to treat diseases such as ephritis edema, and the pharmacological action of catalposide wherein is similar with Catalpol.Bitter glycosides of oily olive in the olive and elenolide have hypotensive effect.
Ajugoside (Ajugoside) has anti-infectious function, during 100 μ M, can suppress in the human blood platelets 75% TXB
2Release, IC
50Be 9.5 μ mol/L.The plain B of thromboxane
2(TXB
2) increase and be shown in: atherosclerosis, myocardial infarction, thrombotic diseases, mellitus, hyperlipidaemia, malignant tumour etc.During 100 μ M, can suppress in the NMPI mouse peritoneum scavenger cell 42% PGE
2(PGE
2) release.
The pharmacology activity research of 8-ethanoyl Harpagide (8-O-acetyl-harpagide) gets often, mainly contains effects such as antitumor, antiviral, anti-inflammatory.In the papillomatous experiment of rat of having moral integrity with dimethylbenzanthracene (DMBA) and growth of tumour cell promotor (TPA); With the positive contrast medicine of glycyrrhetinic acid; Rat is after inducing for 8 weeks with DMBA and TPA, and the lotus ratio of outflow is 80%, give 8-ethanoyl Harpagide after; Under identical condition, the lotus ratio of outflow has only 8%.8-ethanoyl Harpagide is to having better result of treatment by TPA inductive rat skin cancer than glycyrrhetinic acid.This compound also has the effect of certain inhibition lung cancer.To suppress Ai-Ba virus (EBV) strongly relevant with it for the antitumor action of 8-ethanoyl Harpagide.EBV belongs to simplexvirus, can make the bone-marrow-derived lymphocyte of people and primate change into the cancerous tumor cell of indeterminate growth, and its also reproducible in the non-lymphocyte of pars oralis pharyngis comprises other epithelial cells of salivary gland duct and pars oralis pharyngis.8-ethanoyl Harpagide is expressed the DNA by EBV in the TPA inductive Raji cell (Barkitt`s lymphoma cell) has very strong restraining effect; At 20 μ g/mL is that inhibiting rate is 100%; Inhibiting rate is 80% when 10 μ g/mL, and it is all better than positive control drug glycyrrhetinic acid, vitamin A acid that it suppresses effect.8-ethanoyl Harpagide (8-O-acetyl-harpagide) has anti-infectious function, TXB in the ability strongly inhibited human blood platelets
2Release, IC
50Be 19.5 μ mol/L.
The medical health method of Tibetan medicine's pharmacy uniqueness that to be China's Tibetan people form in the process that long-term and physical environment are struggled against is the rarity of motherland's traditional medicine.Tibet is high and cold a, anoxic, strong, the free of contamination altitude environment of radiation, so Tibetan medicine has characteristics such as growth cycle length, special effect, active substance accumulation height.Though existing a large amount of Tibetan medicinal health-care product on the market; But kind is more single, and efficacy factor and structure thereof to imitate dose-effect relationship all indeterminate, this is unfavorable for developing third generation healthcare products and moves towards the world market; Therefore; Furtheing investigate the application of Tibetan medicine aspect healthcare products, confirm the efficacy factor and the structure effect dose-effect relationship thereof of Tibetan medicinal health-care product, is an exploitation third generation Tibetan medicinal health-care product and a key moving towards the world market.The present invention's extraction separation and identified described new compound from the continuous ginseng of Tibetan medicine first particularly; And its functional component carried out systematic study; Result according to modern pharmacology research; We think that continuous ginseng has effects such as antiviral, Azelaic Acid, antitumor, anti-oxidant, hepatic cholagogic, spasmolysis and analgesia, enhancing immunity, hypoglycemic, lipopenicillinase, step-down, anti-platelet aggregation and thrombus, removing oxyradical, Azelaic Acid; Along with further going deep into of research, believe that continuous ginseng has broad prospects in the healthcare products application facet.
Above-mentioned with reference to embodiment to the detailed description that this compound with anti-oxidant activity that from the continuous ginseng of Tibetan medicine, extracts and process for extracting thereof carry out, be illustrative rather than determinate; Therefore in the variation and the modification that do not break away under the general plotting of the present invention, should belong within protection scope of the present invention.
Claims (2)
1. compound with anti-oxidant activity that from the continuous ginseng of Tibetan medicine, extracts is characterized in that the compound chemical structure formula with anti-oxidant activity that is obtained is:
This compound is a colourless crystallization, by ESI-MS m/z:803 [M+Na]
+, 825 [M+HCOO
-]
-, can know that its molecular weight is 780, in conjunction with
1H-NMR (C
5D
5N) and
13C-NMR (C
5D
5N) data confirm that its molecular formula is C
34H
52O
20, degree of unsaturation is 9;
δ 94.5, δ 96.2, δ 97.9 are three acetal carbon signals, and HMQC shows δ
C141/ δ
H6.45 and δ
C103.9/ δ
H4.74 be the hydrocarbon signal of two keys, in conjunction with HMQC and HMBC spectrum, the NMR signal of aglycon shows two cyclopentane type secoiridoid skeletons of existence, a skeleton is identical with ajugoside, and another is then similar with the ajugoside skeleton, δ
H6.06/ δ
C97.9, δ
H2.45 (2H)/δ
C29 show that the two keys on C3 '-C4 ' become singly-bound, and the HMBC spectrum shows coherent signal δ
H6.42/ δ
C100.4, δ
H5.41/ δ
C94.5 and δ
H5.93/ δ
C100.1, δ
H5.59/ δ
C96.2, show that two secoiridoid skeleton C-1 hydroxyls have respectively connected a glucone, and coherent signal δ
H5.41/ δ
C84.6, δ
H6.06/ δ
C84.6, δ
H4.35/ δ
C97.9 and δ
H4.35/ δ
CDirectly do not link to each other 100.4 show two secoiridoid skeletons, but link to each other through (1 → a 2) glucone, this compound is a new iridoid glycoside, called after wallchiiside F.
2. the process for extracting of the compound with anti-oxidant activity that from the continuous ginseng of Tibetan medicine, extracts according to claim 1 is characterized in that implementation step is following:
At first, with 10Kg exsiccant silk floss ginseng herb, pulverizing is extracted 3 times with 50-95% ethanol soaking at room temperature, and each 7-10 days, extracting solution is merged concentrating under reduced pressure, get fluid extract 970g, density 1.15g/ml gets 3L after the water suspendible disperses; Use sherwood oil, ETHYLE ACETATE and water saturated n-butanol extraction successively, obtain petroleum ether part 200g, ethyl acetate extract 33g, n-butanol portion 255g respectively;
Then, through D-1400 type macroporous adsorptive resins, blade diameter length ratio 1: 5 is divided into 4 parts 10%, 30%, 60%, 90% with water-ethanol system wash-out with n-butanol portion 255g;
30% wash-out part, 74g, through MCI-GEL CHP20P macroporous resin column chromatography, blade diameter length ratio 1: 8 with 10-60% methanol-water wash-out, increases progressively by 10% and to be divided into A1-A6 totally 6 parts; A4 is again through anti-phase ODS-A column chromatography; Blade diameter length ratio 1: 8 increases progressively with 10-60% methanol-water wash-out 5 column volumes of each wash-out by 10%; Be divided into B1-B6 totally 6 parts; B3 is Sephadex LH-20 gel filtration chromatography repeatedly again, and blade diameter length ratio 1: 30 gets wallchiiside F 10mg with 50% methanol-eluted fractions.
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| 张松 等.绵参化学成分的研究.《中国中药杂志》.2007,第32卷(第9期),824-826. * |
| 张松 等.藏药绵参化学成分的HPLC_MS_n分析.《分析测试学报》.2007,第26卷166-168. * |
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