CN104177240A - Compound and extract isolated from Antrodia camphorata and application - Google Patents
Compound and extract isolated from Antrodia camphorata and application Download PDFInfo
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Abstract
The invention discloses a compound isolated from Antrodia camphorate and shown as formula I. Specifically, R1 is hydrogen or acetyl. The invention further discloses application of the compound to preparation of drugs for inhibiting tumor growth, wherein the tumor can be one of lung adenocarcinoma, colon cancer, prostate cancer and liver cancer.
Description
Technical field
The invention relates to compound, extract of a kind of separated from Antrodia camphorate and uses thereof, particularly about this compound and extract are applied to the purposes that suppresses tumor growth.
Background technology
Antrodia camphorata (Antrodia camphorata), claim again camphor tree sesame, Cinnamomum kanahirai hay mushroom or red camphor tree sesame etc., belong to the perennial gill fungus mushroom of Aphyllophorales (Aphyllophorales), polyporaceae (Polyporaceae), for Taiwan endemic species fungi, only grow on the rotten heartwood inwall of hollow of Taiwan child care class seeds-Cinnamomum kanahirai hay tree (Cinnamoum kanehirai Hay).Because Cinnamomum kanahirai hay tree distributed quantity is very rare, add artificial felling trees unlawfully, make to parasitize the more shape rareness of wild Antrodia camphorata quantity that wherein can grow, and because its sporophore growth is quite slow, vegetative period, therefore price was very expensive also only between June to October.
The sporophore of Antrodia camphorata is perennial, and stockless is suberin to wooden, and the camphor tree fragrance that its tool is strong, and changeableization of form have tabular, mitriform, horse-hof shape or tower-like.Nascent is platypelloid type and is bright red, and its periphery can present radiation warp shape afterwards, and to surrounding expansion growth, color also changes light red brown or khaki into, and has many pores, and its abundantest position of pharmaceutical use that is Antrodia camphorata.
In Taiwan folk custom medically, Antrodia camphorata has removing toxic substances, alleviating diarrhoea symptom, anti-inflammatory, treatment liver related disease and the function such as anticancer.Antrodia camphorata as the gill fungus mushroom class of edible medicinal, there is the composition of many complexity, in known physiologically active ingredient, comprise: triterpene compound (triterpenoids), polysaccharides (polysaccharides, candy as poly-in β-D-Portugal), adenosine (adenosine), VITAMIN is (as vitamins B, niacin), protein (containing immunoglobulin (Ig)), super oxygen disproportionation ferment (superoxide dismutase, SOD), trace element (as: calcium, phosphorus, germanium), nucleic acid, steroid and blood pressure stabilization material (as antodia acid) etc., these a little physiologically active ingredients are considered to have antitumor, increase immunological competence, antianaphylaxis, Anti-bacterium, hypertension, the multiple efficacies such as hypoglycemic and decreasing cholesterol.
In the numerous compositions of Antrodia camphorata with triterpene compound studied at most, triterpene compound is the general name that is combined into sexangle or pentagon natural compounds by 30 carbons, the bitter taste of Antrodia camphorata institute tool is mainly from this composition of triterpenes.When nineteen ninety-five, the people such as Cherng find to contain in Antrodia camphorata sporophore extract three kinds of new triterpene compounds taking ergostane (ergostane) as skeleton: antcin A, antcin B and antcin C(Cherng, I.H., and Chiang, H.C.1995.Three new triterpenoids fromAntrodia cinnamomea.J.Nat.Prod.58:365-371).The people such as Chen find three kinds of triterpene compound (Chen such as zhankuic acid A, zhankuic acid B and zhankuic acid C after with alcohol extraction camphor tree sesame sporophore, C.H., and Yang, S.W.1995.New steroid acids from Antrodiacinnamomea ,-a fungus parasitic on Cinnamomum micranthum.J.Nat.Prod.58:1655-1661).In addition, the people such as Chiang find other three kinds of new triterpene compounds that are respectively sesquiterpene lactones (sesquiterpene lactone) and two kinds of bisphenols derivatives in also by sporophore extract in nineteen ninety-five, this is antrocin, 4, 7-dimethoxy-5-methyl isophthalic acid, 3-benzo dioxy ring (4, 7-dimethoxy-5-methy-1, 3-benzodioxole) with 2, 2', 5, 5'-tetramethoxy-3, 4, 3', 4'-pair-methylene-dioxy-6, 6'-dimethyl diphenyl (2, 2', 5, 5'-teramethoxy-3, 4, 3', 4'-bi-methylenedioxy-6, 6'-dimethylbiphenyl) (Chiang, H.C., Wu, D.P., Cherng, I.W., and Ueng, C.H.1995.A sesquiterpene lactone, phenyl and biphenyl compoundsfrom Antrodia cinnamomea.Phytochemistry.39:613-616).By 1996, the people such as Cherng find four kinds of new triterpene compounds once again with same analytical procedure: antcin E, antcin F, methyl antcinate G, methyl antcinate H(Cherng, I.H., Wu, D.P., and Chiang, H.C.1996.Triteroenoids from Antrodia cinnamomea.Phytochemistry.41:263-267), the people such as Yang have found two kinds of new compound zhankuic acid D taking ergostane as skeleton, zhankuic acid E, with three kinds of new compounds taking lanostane (lanostane) as skeleton: 15 α – acetyl-dehydrosulphurenic acids (15 α-acetyl-dehydrosulphurenic acid), dehydroeburicoic acid (dehydroeburicoic acid) and sulfurenic acid (dehydrasulphurenic the acid) (Yang that anhydrates, S.W., Shen, Y.C., and Chen, C.H.1996.Steroids and triterpenoids of Antrodiacinnamomea-a fungus parasitic on Cinnamomum micranthum.Phytochemistry.41:1389-1392).Wherein, some composition is found to play an important role for AMPK and TOR message bang path successively, see through the activation of AMPK and mTOR translated to the inhibition in path, reach the good control to the G1 phase in Cancer Cell cycle, block the progress of Cancer Cell cycle completely, cause a series of cancer cells carving to die.
Although can learn that by many experiments at present Antrodia camphorata extract has aforementioned effect, and its ingredient also successively analyzed go out, but in Antrodia camphorata extract, whether still have the compound of other tool antitumour activitys or other medical uses not found out, still need further experiment research to be differentiated.
Summary of the invention
Accordingly, one of the present invention object is providing a kind of compound of separated from Antrodia camphorate, and with formula, I represents:
Wherein R1 is hydrogen or ethanoyl.
Preferably, the R1 of this compound is hydrogen, represents with formula (II):
Preferably, wherein the R1 of this compound is ethanoyl, represents with formula (III):
Another object of the present invention be to provide a kind of by above-claimed cpd for the preparation of the purposes that suppresses tumor growth medicine, wherein this tumour be adenocarcinoma of lung, colorectal carcinoma, prostate cancer and liver cancer one of them.
Another object of the present invention is to provide the extract of a kind of extraction from Antrodia camphorata, this extract extracts and obtains with the following step: get Antrodia camphorata mycelium, sporophore or the mixture of the two extract to merge afterwards for 2 times with the alcohol of 10 times of amounts and concentratedly obtain one and slightly take out thing, this is slightly taken out to thing and distributes extraction process 3 times with methylene dichloride/water (1:1), to be divided into a dichloromethane layer and a water layer, get this dichloromethane layer with silica gel column chromatography process normal hexane/methylene dichloride (1:4), methylene dichloride, the solvent of ethanol/methylene (5:95) separates and obtains this extract.
Brief description of the drawings
The Structural Identification of the Antrocamol LT1 that Fig. 1-Fig. 3 provides for the embodiment of the present invention;
The Structural Identification of the Antrocamol LT2 that Fig. 4-Fig. 6 provides for the embodiment of the present invention.
Embodiment
Get Antrodia camphorata (Antrodia camphorata) mycelium, sporophore or the mixture of the two (1.0kg) extract after 2 times with the alcohol of 10 times of amounts, merge concentrated can obtaining and slightly take out the about 230g of thing (LT-E), slightly take out thing and distribute extraction process 3 times with methylene dichloride/water (1:1), be divided into the about 102.6g of dichloromethane layer (LT-E-D) and the about 127.4g of water layer (LT-E-W), get dichloromethane layer 6.0g with silica gel column chromatography process normal hexane/methylene dichloride (1:4), methylene dichloride, the solvent of ethanol/methylene (5:95) separates, be divided into ANCA-E-D-1, ANCA-E-D-2, ANCA-E-D-3, four layers of ANCA-E-D-4 etc.
The antitumour activity of Antrodia camphorata extract
Carry out cell survival detection (MTT cell viability assay) for A549 cell strain (adenocarcinoma of lung), CT26 cell strain (colorectal carcinoma), DU145 cell strain (prostate cancer), HepG2 cell strain (liver cancer), mdck cell strain (kidney), PC3 cell strain (prostate cancer) respectively, result is consulted following list 1～6.
By above-mentioned cell strain respectively at cultivating in suitable nutrient solution 24 hours.Cell after hyperplasia is cleaned once with PBS, and process cell with the trypsinase-EDTA of 1 times, under 1,200rpm centrifugal 5 minutes subsequently, by cell Shen Dian and abandon supernatant liquor.The new nutrient solution that adds afterwards 10ml, slight wobble suspends cell again, then cell is placed in 96 hole trace dishes.When test, respectively at the Antrodia camphorata extract that adds 0.01～200 μ g/ml in each hole, under 37 DEG C, 5%CO2, cultivate 48 hours., in the environment of lucifuge under in each hole in add the MTT of 2.5mg/ml, react the lysis buffer termination reaction that adds again 100 μ l after 4 hours in each hole thereafter.Finally under 570nm extinction wavelength, measure its light absorption value with ferment immunity analysis instrument, use and calculate the survival rate of cell, and extrapolate all experimental datas of its half inhibiting rate desired concn of growing (being IC50 value) and all represent with mean+/-standard error.Experimental data carries out statistical study with pairing t test (paired-t test).Be less than 0.05 with p value and be considered as having statistically difference.
Table 1:A549 cell strain (adenocarcinoma of lung)
Table 3:DU145 cell strain (prostate cancer)
Table 4:HepG2 cell strain (liver cancer)
Table 5:MDCK cell strain (kidney)
Table 6:PC3 cell strain (prostate cancer)
In table 1～6,0～25% cell survival: +/-, 25～50% cell survivals :+, 50～75% cell survivals: ++, 75～100% cell survivals: +++, >100% cell survival: ++++.Solvent is DMSO, and its IC50 is 2.34%, means in the time that drug dilution to DMSO content is 2.34%, can cause cell 50% death, herein when the DMSO content of drug dilution to 100 μ g/ml is 0.5%.ANCA-E, ANCA-E-D, ANCA-E-W, ANCA-E-D-1, ANCA-E-D-2, ANCA-E-D-3, ANCA-E-D-4, LT-80 and LT-C80 are respectively different Antrodia camphorata extracts.
Show according to above-listed each table result, ANCA-E-D-2, ANCA-E-D-3, ANCA-E-D-4 wherein have preferably inhibition for various growth of cancer cells.For example, ANCA-E-D-2 wherein and ANCA-E-D-3 are for A549 cell strain (adenocarcinoma of lung), CT26 cell strain (colorectal carcinoma), DU145 cell strain (prostate cancer), HepG2 cell strain (liver cancer), mdck cell strain (kidney), PC3 cell strain (prostate cancer), than relative other groups, there is relatively preferably inhibition.Although and ANCA-E-D-4 is a little less than ANCA-E-D-2 and ANCA-E-D-3, also have certain inhibition for various tumour cells.Accordingly, can be by these extracts for the preparation of the purposes that suppresses tumor growth medicine, comprise adenocarcinoma of lung, colorectal carcinoma, prostate cancer and liver cancer one of them, and can be further purified effective single component wherein.
From Antrodia camphorata extraction preparation Antrocamol LT1 and Antrocamol LT2
According to the above results, ANCA-E-D-2 and ANCA-E-D-3 are further carried out to purifying, ANCA-E-D-3 layer can be obtained to the about 150mg of a new compound Antrocamol LT1 through preparative anti-phase column chromatography (C-18 reverse-phase chromatography tubing string) near 18.75 minutes with 80%MeOH/H20, and LT-E-D-2 layer can obtain the about 170mg of another new compound Antrocamol LT2 through preparative anti-phase column chromatography (C-18 reverse-phase chromatography tubing string) near 25.10 minutes with 80%MeOH/H20.The Structural Identification result of Antrocamol LT1 is as follows:
Antrocamol LT1 is colourless product liquid, and the molecular formula of this compound is C24H38O5 by analysis, and molecular weight is 406, complete Chinese illustrious name is called 4-hydroxyl-2,3-dimethoxy-6-methyl-5-(9-hydroxyl-3,7,11-trimethylammonium-2,6,10-, 12 carbon triolefins)-2-cyclonene, 4-hydroxy-5-[9-hydroxy-3,7,11-trimethyldodeca-2,6,10-trienyl]-2,3-dimethoxy-6-methyl-cyclohex-2-enone.
LT1 Structural Identification data (consulting accompanying drawing 1-Fig. 3): 1H-NMR (400MHz, CDCl3): 1.12 (3H, d, J=7.2Hz, ), 1.61 (3H, s), 1.64 (3H, s), 1.66 (3H, s), 1.68 (3H, s), 1.72 (1H, m), 1.98 – 2.30 (8H), 2.51 (1H, dq, J=11.6, 7.2Hz), 3.62 (3H, s), 4.02 (3H, s), 4.33 (1H, d, J=2.8Hz), 4.35 (1H, dt, J=9.2, 4.0Hz), 5.09 (1H, d, J=8.4Hz), 5.14 (1H, t, J=7.2Hz), 5.15 (1H, t, J=7.2Hz), 13C-NMR (100MHz, CDCl3): 12.17 (q), 15.95 (q), 16.19 (q), 18.13 (q), 25.72 (q), 25.93 (t), 26.78 (t), 39.41 (t), 39.98 (d), 43.29 (d), 47.94 (t), 58.81 (q), 60.48 (q), 65.35 (d), 67.24 (d), 121.64 (d), 127.64 (d), 128.42 (d), 132.03 (s), 134.99 (s), 135.97 (s), 137.42 (s), 160.82 (s), 197.15 (s).
Antrocamol LT2 (consulting accompanying drawing 4-Fig. 6): be colourless product liquid, the molecular formula of this compound is C26H40O6 by analysis; Molecular weight is 448, complete Chinese illustrious name is called 4-acetyl carboxyl-2,3-dimethoxy-6-methyl-5-(9-hydroxyl-3,7,11-trimethylammonium-2,6,10-, 12 carbon triolefins)-2-cyclonene, 4-acetoxy-5-[9-hydroxy-3,7,11-trimethyldodeca-2,6,10-trienyl]-2,3-dimethoxy-6-methyl-cyclohex-2-enone.
LT2 Structural Identification data: 1H-NMR (400MHz, CDCl3): 1.18 (3H, d, J=7.2Hz,), 1.54 (3H, s), 1.64 (3H, s), 1.67 (3H, s), 1.69 (3H, s), 1.72 (1H, m), 1.80 – 2.40 (8H), 2.50 (1H, dq, J=11.6,7.2Hz), 3.65 (3H, s), 3.98 (3H, s), 4.36 (1H, m), 5.10 (1H, t, J=6.8Hz), 5.12 (1H, d, J=8.0Hz), 5.20 (1H, t, J=6.4Hz), 5.72 (1H, t, J=3.2Hz), 13C-NMR (100MHz, CDCl3): 12.80 (q), 15.96 (q), 16.09 (q), 18.14 (q), 20.93 (q), 25.72 (q), 26.19 (t), 26.76 (t), 39.47 (t), 41.25 (d), 42.98 (d), 48.12 (t), 59.65 (q), 60.67 (q), 65.53 (d), 68.98 (d), 120.74 (d), 127.42 (d), 128.25 (d), 131.74 (s), 134.70 (s), 137.31 (s), 137.56 (s), 158.21 (s), 169.73 (s), 196.84 (s).
Carry out MTT assay (no longer repeating at this) according to previous experiments method, utilize analyser to measure its light absorption value under 570nm extinction wavelength, use the survival rate of calculating cell, and extrapolate its half inhibiting rate desired concn of growing (being IC50 value), the antitumour activity of test Antrocamol LT1 and Antrocamol LT2, and make comparisons with ANCA-E, ANCA-E-D and ANCA-E-D-3.All experimental datas all represent with mean+/-standard error.Experimental data carries out statistical study with pairing t test (paired-t test).Be less than 0.05 with p value and be considered as having statistically difference.And its 503nhibiting concentration (IC50) is arranged as following table (table 7).
Table 7
IC50 refers to the concentration of a suppressed half inhibitor.IC50 value is commonly used to weigh drug-induced cell and carves the ability of dying, and inducibility is stronger, and numerical value is lower.Can be found out by result in table, the extracts such as new compound Antrocamol LT1 and Antrocamol LT2 and ANCA-E, ANCA-E-D and ANCA-E-D-3, all have rather good antitumour activity.Accordingly, can be by these compounds for the preparation of the purposes that suppresses tumor growth medicine, comprise adenocarcinoma of lung, colorectal carcinoma, prostate cancer and liver cancer one of them, and can be further development of cancer therapy drug.
The compound of separated from Antrodia camphorate provided by the present invention, extract and uses thereof be the utility value in tool industry really, only above narration is only preferred embodiment explanation of the present invention, allly be skillful in this skill person when can do according to above-mentioned explanation other all improvement, only these changes still belong in spirit of the present invention and following defined the scope of the claims.
Claims (6)
1. a compound for separated from Antrodia camphorate, with formula, I represents:
Wherein R1 is hydrogen or ethanoyl.
2. the compound as described in the 1st of claim, wherein the R1 of this compound is hydrogen, represents with formula (II):
3. the compound as described in the 1st of claim, wherein the R1 of this compound is ethanoyl, represents with formula (III):
By the compound as described in the 1st of claim for the preparation of a purposes that suppresses tumor growth medicine, wherein this tumour be adenocarcinoma of lung, colorectal carcinoma, prostate cancer and liver cancer one of them.
5. an extraction is from the extract of Antrodia camphorata, this extract extracts and obtains with the following step: get Antrodia camphorata mycelium, sporophore or the mixture of the two and extract to merge afterwards for 2 times with the alcohol of 10 times of amounts and concentratedly obtain one and slightly take out thing, this is slightly taken out to thing and distributes extraction process 3 times with methylene dichloride/water (1:1), to be divided into a dichloromethane layer and a water layer, to get this dichloromethane layer and separate and obtain this extract through the solvent of normal hexane/methylene dichloride (1:4), methylene dichloride, ethanol/methylene (5:95) with silica gel column chromatography.
By the extract as described in the 5th of claim for the preparation of a purposes that suppresses tumor growth medicine, wherein this tumour be adenocarcinoma of lung, colorectal carcinoma, prostate cancer and liver cancer one of them.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107296805A (en) * | 2016-04-14 | 2017-10-27 | 郭盈妤 | Antrodia camphorata compound and its extract are used for the purposes for preparing the medicine for the treatment of and prevention of neurodegenerative diseases |
| CN107397764A (en) * | 2016-05-20 | 2017-11-28 | 台湾原生药用植物股份有限公司 | Medical composition for auxiliary for treating cancer |
| TWI648257B (en) * | 2014-12-30 | 2019-01-21 | 合一生技股份有限公司 | Compounds from antrodia camphorata, method for preparing the same and use thereof |
| CN110337991A (en) * | 2019-06-19 | 2019-10-18 | 三生源生物科技（天津）有限公司 | A kind of preparation and application of the inhibiting tumour cells agent based on Antrodia camphorata extract |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI648257B (en) * | 2014-12-30 | 2019-01-21 | 合一生技股份有限公司 | Compounds from antrodia camphorata, method for preparing the same and use thereof |
| CN105732381B (en) * | 2014-12-30 | 2021-07-20 | 合一生技股份有限公司 | Antrodia camphorata extract and preparation method and application thereof |
| CN107296805A (en) * | 2016-04-14 | 2017-10-27 | 郭盈妤 | Antrodia camphorata compound and its extract are used for the purposes for preparing the medicine for the treatment of and prevention of neurodegenerative diseases |
| CN107397764A (en) * | 2016-05-20 | 2017-11-28 | 台湾原生药用植物股份有限公司 | Medical composition for auxiliary for treating cancer |
| CN110337991A (en) * | 2019-06-19 | 2019-10-18 | 三生源生物科技（天津）有限公司 | A kind of preparation and application of the inhibiting tumour cells agent based on Antrodia camphorata extract |
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