CN104211627A - Antrodia camphorate compound, extract, and application thereof - Google Patents
Antrodia camphorate compound, extract, and application thereof Download PDFInfo
- Publication number
- CN104211627A CN104211627A CN201310206598.5A CN201310206598A CN104211627A CN 104211627 A CN104211627 A CN 104211627A CN 201310206598 A CN201310206598 A CN 201310206598A CN 104211627 A CN104211627 A CN 104211627A
- Authority
- CN
- China
- Prior art keywords
- extract
- compound
- antrodia camphorata
- antrodia
- methylene dichloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses an antrodia camphorate compound, which is separated from antrodia camphorate, and is represented by the formula I. The invention further discloses an application of the compound in preparation of drugs for inhibiting tumor growth, wherein the tumor can be lung adenocarcinoma, colon cancer, prostatic cancer, or liver cancer.
Description
Technical field
The invention relates to a kind of compound of separated from Antrodia camphorate, extract and uses thereof, particularly about the purposes this compound and extract being applied to Tumor suppression growth.
Background technology
Antrodia camphorata (Antrodia camphorata), also known as 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, be only grown 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, more shape is rare to make to parasitize the wild Antrodia camphorata quantity that wherein can grow, and due to its sporophore growth quite slow, vegetative period, therefore price was very expensive also only between June to October.
The sporophore of Antrodia camphorata is perennial, stockless, and in suberin to wooden, the camphor tree fragrance that its tool is strong, and form changeableization, have tabular, mitriform, horse-hof shape or tower-like.Nascent is platypelloid type and in bright red, its periphery can present radiation warp shape afterwards, and to surrounding expansion growth, color also changes reddish tan or khaki into, and has many pores, and its position that to be the pharmaceutical use of Antrodia camphorata the abundantest.
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, as candy gathers 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., this a little physiologically active ingredient is considered to have antitumor, increase immunological competence, antianaphylaxis, Anti-bacterium, hypertension, the multiple efficacies such as hypoglycemic and decreasing cholesterol.
With studied maximum of triterpene compound in the numerous composition of Antrodia camphorata, triterpene compound is the general name being combined into sexangle or pentagon natural compounds by 30 carbons, the bitter taste of Antrodia camphorata institute tool and main from this composition of triterpenes.During nineteen ninety-five, the people such as Cherng find the triterpene compound being skeleton with ergostane (ergostane) new containing three kinds in Antrodia camphorata sporophore extract: antcin A, antcin B and antcin C(Cherng, I.H., and Chiang, H.C.1995.Three new triterpenoids from Antrodia cinnamomea.J.Nat.Prod.58:365-371).The people such as Chen are to find three kinds of triterpene compounds (Chen such as zhankuic acid A, zhankuic acid B and zhankuic acid C after alcohol extraction camphor tree sesame sporophore, C.H., and Yang, S.W.1995.New steroid acids from Antrodia cinnamomea ,-a fungus parasitic on Cinnamomum micranthum.J.Nat.Prod.58:1655-1661).In addition, the people such as Chiang in nineteen ninety-five also by sporophore extract in find other three kinds of new triterpene compounds being respectively sesquiterpene lactones (sesquiterpene lactone) and two kinds of bisphenols derivatives, this i.e. 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 compounds from 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 then found that two kinds take ergostane as the new compound zhankuic acid D of skeleton, zhankuic acid E, with three kinds of new compounds that are skeleton with lanostane (lanostane): 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 Antrodia cinnamomea-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, through the activation of AMPK and the suppression to mTOR translation 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 to carve and die.
Although can learn that Antrodia camphorata extract has aforementioned effect by experiment many at present, and its ingredient also successively analyzed go out, but whether still have the compound of other tool antitumour activitys or other medical uses not found out in Antrodia camphorata extract, still need further experiment research differentiate.
Summary of the invention
Accordingly, one of the present invention object is providing a kind of compound of separated from Antrodia camphorate, represents with formula I:
(I)
Another object of the present invention is to provide a kind of by the purposes of above-claimed cpd for the preparation of Tumor suppression growth medicine, wherein this tumour be colorectal carcinoma, prostate cancer and liver cancer one of them.
Another object of the present invention is to the extract providing a kind of extraction from Antrodia camphorata, this extract carries out extracting with the following step and obtains: get Antrodia camphorata mycelium, sporophore or the mixture of the two extract to merge afterwards for 2 times with the alcohol of 10 times amount and concentratedly obtain one and slightly take out thing, this is slightly taken out thing and carry out distribution 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 through normal hexane/methylene dichloride (1:4), methylene dichloride, the solvent of ethanol/methylene (5:95) is separated and obtains this extract.
Accompanying drawing explanation
The Antrocamol LT3 Structural Identification that accompanying drawing 1-Fig. 2 provides for the embodiment of the present invention.
Embodiment
The extraction of Antrodia camphorata composition
Get Antrodia camphorata (Antrodia camphorata) mycelium, after sporophore or the mixture of the two (1.0kg) extract 2 times with the alcohol of 10 times amount, merge concentrated can obtaining slightly to take out thing and be about 230g (LT-E), slightly take out thing and carry out distribution extraction process 3 times with methylene dichloride/water (1:1), dichloromethane layer is divided into be about 102.6g (LT-E-D) and water layer is about 127.4g (LT-E-W), get dichloromethane layer 6.0g with silica gel column chromatography through normal hexane/methylene dichloride (1:4), methylene dichloride, the solvent of ethanol/methylene (5:95) is separated, be divided into LT-E-D-1, LT-E-D-2, LT-E-D-3, LT-E-D-4 etc. four layers.
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 consults following list 1 ~ 6.
Above-mentioned cell strain is cultivated 24 hours respectively in suitable nutrient solution.By the cell after hyperplasia with PBS cleaning once, and process cell with the trypsinase-EDTA of 1 times, under 1,200rpm centrifugal 5 minutes subsequently, cell Shen Dian is abandoned supernatant liquor.Add the new nutrient solution of 10ml afterwards, slight wobble makes cell again suspend, then is placed in by cell in 96 hole micro-plate.During test, respectively at the Antrodia camphorata extract adding 0.01 ~ 200 μ g/ml in each hole, in 37 DEG C, cultivate 48 hours under 5%CO2.Thereafter, under the environment of lucifuge, in each hole, add the MTT of 2.5mg/ml, react the lysis buffer termination reaction adding 100 μ l after 4 hours again in each hole.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 it and grow half inhibiting rate desired concn (i.e. IC50 value) all experimental datas and all represent with mean+/-standard error.Experimental data with match t test (paired-t test) carry out statistical study.Be less than 0.05 with p value and be considered as having statistically difference.
Table 1:A549 cell strain (adenocarcinoma of lung)
Table 2:CT26 cell strain (colorectal carcinoma)
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 when drug dilution to DMSO content is 2.34%, cell 50% can be caused dead, 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 are respectively different Antrodia camphorata extracts.
According to above-listed each table result display, ANCA-E-D-2, ANCA-E-D-3, ANCA-E-D-4 wherein have preferably inhibition for various different growth of cancer cells.Such as, ANCA-E-D-2 and ANCA-E-D-3 is wherein 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), compared to other groups relative, there is relatively preferably inhibition.And although ANCA-E-D-4 is a little less than ANCA-E-D-2 and ANCA-E-D-3, also there is certain inhibition for various tumour cell.Accordingly, can by the purposes of these extracts for the preparation of Tumor suppression growth medicine, comprise adenocarcinoma of lung, colorectal carcinoma, prostate cancer and liver cancer one of them, and effective single component wherein can be further purified.
From Antrodia camphorata extraction preparation Antrocamol LT3
According to the above results, LT-E-D-3 layer is carried with the solvent punching of anti-phase column chromatography (C-18 preparative tubing string) and methanol/water (80:20), Antrocamol LT3 (1) about 180mg can be obtained at 14.5 minutes.The Structural Identification result of Antrocamol LT3 is as follows:
Antrocamol LT3 is colourless product liquid, and the molecular formula of this compound is C24H38O5 by analysis; Molecular weight is 406; , complete China and British title is respectively (4R, 5R, 6R)-4-hydroxyl 5-[(2E, 6E, 9E)-11-hydroxyl-3,7,11-trimethylammonium-ten two-2,6,9-trialkenyl]-2,3-dimethoxy-6-methyl-cyclohexyl-2-ketenes, (4R, 5R, 6R)-4-hydroxy-5-[(2E, 6E, 9E)-11-hydroxy-3,7,11-trimethyldodeca-2,6,9-tri enyl]-2,3-dimethoxy-6-methylcyclohex-2-enone.
Antrocamol LT3 Structural Identification data (refers to accompanying drawing 1, Fig. 2): 1H-NMR (400MHz, CDCl3): 1.14 (3H, d, J=7.2Hz, ), 1.29 (6H, s), 1.56 (3H, s), 1.63 (3H, s), 1.70 (1H, m), 2.02 (2H), m), 2.08 (2H, t, J=6.4Hz), 2.21 (2H, t, J=7.6Hz), 2.51 (1H, dq, J=11.2, 7.2Hz), 2.64 (1H, d, J=5.2Hz), 3.64 (3H, s), 4.05 (3H, s), 4.32 (1H, d, J=3.2Hz), 5.08 (1H, t, J=6.8Hz), 5.14 (1H, t, J=6.4Hz), 5.57 (2H, m), 13C-NMR (100MHz, CDCl3): .12.32 (q), 16.14 (q), 16.14 (q), 26.35 (t), 26.95 (t), 29.85 (q), 39.63 (t), 40.24 (d), 42.20 (t), 43.40 (d), 59.29 (q), 60.59 (q), 67.88 (d), 70.76 (d), 121.14 (d), 124.78 (d), 125.22 (d), 134.04 (s), 135.84 (s), 137.77 (s), 139.17 (d), 160.59 (s), 197.21 (s).
MTT assay (no longer repeating at this) is carried out according to previous experiments method, analyser is utilized to measure its light absorption value under 570nm extinction wavelength, use the survival rate calculating cell, and extrapolate it and grow half inhibiting rate desired concn (i.e. IC50 value), the antitumour activity of test Antrocamol LT3, 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 with match t test (paired-t test) carry out statistical study.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 namely inducibility is stronger, and numerical value is lower.Can be found out by result in table, the extracts such as new compound Antrocamol LT3 and ANCA-E, ANCA-E-D and ANCA-E-D-3, all have rather good antitumour activity.Accordingly, can by the purposes of these compounds for the preparation of Tumor suppression growth medicine, comprise adenocarcinoma of lung, colorectal carcinoma, prostate cancer and liver cancer one of them, and can cancer therapy drug be further development of.
Utility value in the true tool industry of Antrodia camphorata compound provided by the present invention, extract and uses thereof, describing is only only preferred embodiment explanation of the present invention, allly be skillful in this those skilled in the art when can do other all improvement according to above-mentioned explanation, only these changes still belong in spirit of the present invention and following defined the scope of the claims.
Claims (4)
1. a compound for separated from Antrodia camphorate, represents with formula I:
(I)。
2. by the compound as described in claim the 1st for the preparation of Tumor suppression growth medicine a purposes, wherein this tumour be adenocarcinoma of lung, colorectal carcinoma, prostate cancer and liver cancer one of them.
3. one kind extracts the extract from Antrodia camphorata, this extract carries out extracting with the following step and obtains: 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 amount and concentrated obtain one and slightly take out thing, this is slightly taken out thing and carry out distribution 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 obtain this extract with silica gel column chromatography through the solvent separation of normal hexane/methylene dichloride (1:4), methylene dichloride, ethanol/methylene (5:95).
4. by the extract as described in claim the 3rd for the preparation of Tumor suppression growth medicine a purposes, wherein this tumour be adenocarcinoma of lung, colorectal carcinoma, prostate cancer and liver cancer one of them.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310206598.5A CN104211627A (en) | 2013-05-29 | 2013-05-29 | Antrodia camphorate compound, extract, and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310206598.5A CN104211627A (en) | 2013-05-29 | 2013-05-29 | Antrodia camphorate compound, extract, and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104211627A true CN104211627A (en) | 2014-12-17 |
Family
ID=52093583
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310206598.5A Pending CN104211627A (en) | 2013-05-29 | 2013-05-29 | Antrodia camphorate compound, extract, and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104211627A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1799562A (en) * | 2005-09-28 | 2006-07-12 | 莱阳农学院 | Antrodia camphorata mycelium fermented extract and application thereof |
| WO2012039793A1 (en) * | 2010-09-20 | 2012-03-29 | Golden Biotechnology Corporation | Methods and compositions for treating lung cancer |
| CN103083364A (en) * | 2011-11-04 | 2013-05-08 | 丽丰实业股份有限公司 | Pharmaceutical composition for treating cancer |
-
2013
- 2013-05-29 CN CN201310206598.5A patent/CN104211627A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1799562A (en) * | 2005-09-28 | 2006-07-12 | 莱阳农学院 | Antrodia camphorata mycelium fermented extract and application thereof |
| WO2012039793A1 (en) * | 2010-09-20 | 2012-03-29 | Golden Biotechnology Corporation | Methods and compositions for treating lung cancer |
| CN103083364A (en) * | 2011-11-04 | 2013-05-08 | 丽丰实业股份有限公司 | Pharmaceutical composition for treating cancer |
Non-Patent Citations (2)
| Title |
|---|
| 刘华等: "樟芝菌丝体的不同提取方法及其抗肿瘤活性的研究", 《分离与提取》 * |
| 夏永军: "樟芝菌发酵生产Antrodins等活性产物的研究", 《中国博士学位论文全文数据库 工程科技I辑》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101225066B (en) | Cyclohexenone extract of antrodia camphorata | |
| TWI330528B (en) | ||
| CN101417934B (en) | New compounds separated from Antrodia camphorate extract | |
| JP5014959B2 (en) | New compounds isolated from Benix nokitake extract | |
| CN101214238B (en) | Application of Antrodia camphorata extract for inhibiting tumor cell growth | |
| Zhang et al. | Current advances on the structure, bioactivity, synthesis, and metabolic regulation of novel ubiquinone derivatives in the edible and medicinal mushroom Antrodia cinnamomea | |
| CN104177240B (en) | The compound of separated from Antrodia sesame, extract and application thereof | |
| CN101343247B (en) | Cyclohexenone extract of antrodia camphorata | |
| JP5908002B2 (en) | Compounds contained in Benix nokitake and uses thereof | |
| TWI583376B (en) | Compounds isolated from Antelroxicus and their use | |
| CN104211627A (en) | Antrodia camphorate compound, extract, and application thereof | |
| CN102000046B (en) | Application of antrodia camphorata cyclohexenone compound in preparing medicine for inhibiting growth of pancreatic cancer tumor cells | |
| TWI361687B (en) | ||
| CN101362679A (en) | Antrodia camphoratea pimelie kelone compound for inhibiting B type hepatitis virus | |
| CN103159732A (en) | Polyacetylene compound, extract containing same and application of polyacetylene compound | |
| CN102232942B (en) | Antrodia camphorata cyclohexenone compound for suppressing growth of lymphoma tumor cells | |
| TW201442700A (en) | Antrodia camphorata compound, extract and applications thereof | |
| CN102232946B (en) | Use of antrodia camphorata cyclohexenone compound in preparing medicine for inhibiting stomach cancer tumor cell growth | |
| CN102232945B (en) | Antrodia camphorata cyclohexenone compound for suppressing growth of bladder cancer tumor cells | |
| CN102232944A (en) | Antrodia cinnamomea pimelie kelone compound for inhibiting growth of oral cancer tumor cells | |
| CN102232943A (en) | Antrodia camphorata cyclohexenone compound for inhibiting skin cancer tumor cell growth |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20141217 |