CN102232940B - Antrodia camphorata cyclohexenone compound for inhibiting colorectal cancer tumor cell growth - Google Patents
Antrodia camphorata cyclohexenone compound for inhibiting colorectal cancer tumor cell growth Download PDFInfo
- Publication number
- CN102232940B CN102232940B CN 201010174697 CN201010174697A CN102232940B CN 102232940 B CN102232940 B CN 102232940B CN 201010174697 CN201010174697 CN 201010174697 CN 201010174697 A CN201010174697 A CN 201010174697A CN 102232940 B CN102232940 B CN 102232940B
- Authority
- CN
- China
- Prior art keywords
- colorectal cancer
- antrodia camphorata
- tumor cell
- cancer tumor
- cell growth
- 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.)
- Active
Links
Landscapes
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to a new application of a compound and a medicinal composition for inhibiting colorectal cancer tumor cell growth. 4-hydroxy-2,3-dimethoxy-6-methy-5(3,7,11-trimethyl-dodeca-2,6,10-trienyl)-cyclohex-2-enone is separated and purified from antrodia camphorata extract. The cyclohexenone compound can be applied to inhibition of colorectal cancer tumor cell growth, and also can be applied to medicinal compositions for inhibiting colorectal cancer tumor cell growth.
Description
Technical field
The present invention system is about a kind of new application of chemical compound, especially about a kind of purposes that is suppressed the colorectal cancer growth of tumour cell by the chemical compound of institute's separation and purification in Antrodia Camphorata (Antrodiacinnamomea) extract of utilizing.
Background technology
Large intestine (large intestine) comprises caecum, coton and rectal three large sections, and it is the latter end outpost of the tax office of digestion.Normal colorectal mucosa can form adenoma (being flat meat) in large intestine inwall hypertrophy because many factors make benign cell, even further becomes colorectal cancer (colorectal cancer).Colorectal cancer also can be commonly referred to as colorectal carcinoma etc., it is one of the most general in the world malignant tumor, in recent years in the Taiwan, because westernization and the sophistication of compatriots' life and diet style, and the year by year increase of animal fat and protein uptake amount, and the day by day minimizing of dietary fiber picked-up so that the colorectal cancer attack rate is soaring year by year, has nowadays become in the cancer mortality reason the 3rd.
The cardinal symptom of colorectal cancer comprises that hemafecia, relieving constipation are unusual, abdomen rises by sense, anemia even touches abdominal part lump etc.Be difficult for during the colorectal cancer Development that subjective symptoms is arranged, but when the prostatitis symptom is arranged, all non-early cancer's stage, cause the degree of difficulty in the treatment when conscious.In addition, colorectal cancer generally occurs in the patient more than 50 years old, but the mean age of studying the PATIENTS WITH LARGE BOWEL of pointing out the Taiwan is lower than foreign country, rejuvenation trend is obvious, and it is all poor that youngster obtains the large intestine cancer prognosis, this and youthful cancer are normally broken up the related to cancer system relatively poor, that grade of malignancy is higher, simultaneously, have been that Terminal cancer is relevant when also often being ID owing to youthful cancer.
The Therapeutic Method of colorectal cancer is mainly take surgical resection as main, and the patient for the cancerous cell diffusion then is aided with radiotherapy and chemotherapy.One of chemotherapeutical Main Function is interfere with cancer cells the carrying out in cycle, affect the synthetic of its DNA, RNA and protein, reach the purpose of inhibition tumor cell propagation, yet radiotherapy and chemotherapy tend to follow other to cause the generation of uncomfortable side effect; On the other hand, liver and lungs are positions of the long-range transfer of the easiest generation of colorectal cancer, and in a single day long-range transfer occurs colorectal cancer, even if carry out combined chemistry treatment and cancerous cell target therapy, effect to the long-range transfer sufferer of majority is limited, and its prognosis is in poor shape.So exploitation is effective and the little therapeutant of side effect is imperative for clinical practice.
Antrodia Camphorata (Antrodia cinnamomea), among the peoplely in Taiwan be called again wild rice, Antrodia camphorata or red Camphor tree in Camphor tree mushroom, Camphor tree wild rice, the Camphor tree, be the exclusive medicinal mushrooms of this province, it is the perennial mushroom fungus class that belongs to Aphyllophorales (Aphyllophorales), Polyporaceae (Polyporaceae).Because Antrodia camphorata only parasitizes on the dried hollow heartwood interior wall tissue of Taiwan distinctive child care class Cinnamomum kanahirai hay ebon at occurring in nature, add artificial felling trees unlawfully, more shape is rare so that parasitize the wild Antrodia Camphorata quantity that wherein can grow, and because the growth phase of Antrodia camphorata sporophore is worked as slowly under naturalness, so wild Antrodia camphorata quantity is rare and expensive.
The sporophore of Antrodia Camphorata is perennial, and stockless is suberin to wooden, and the Lignum cinnamomi camphorae 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 cerise that its periphery can present radiation warp shape afterwards, and to expansion growth all around, color also changes light red brown or khaki into, and many pores are arranged, and it is the abundantest position of medical value of Antrodia Camphorata.
In the Taiwan folk custom medically, Antrodia Camphorata has that the circulation of qi promoting of dispeling the wind, blood stasis dispelling are invigorated blood circulation, the effect of warming middle-JIAO removing food stagnancy, removing toxic substances and promoting subsidence of swelling and sedation-analgesia, and be considered as first-class antidote, all alimentary toxicosis, diarrhoea, vomiting, pesticide intoxication all has Detoxication, all has adjuvant treatment efficacy to improving liver, stomach malfunction and blood circulation disease in addition.Antrodia Camphorata as the gill fungus mushrooms of edible medicinal, composition with many complexity, in the known physiologically active ingredient, comprise: triterpenoid compound (triterpenoids), polysaccharides (polysaccharides, such as the poly-candy in β-D-Portugal), adenosine (adenosine), vitamin is (such as vitamin B, niacin), protein (containing immunoglobulin), super oxygen disproportionation ferment (superoxide dismutase, SOD), trace element (as: calcium, phosphorus, germanium), nucleic acid, steroid and blood pressure stabilization material (such as antodia acid) etc., these a little physiologically active ingredients are considered to have antitumor, increase immunocompetence, antiallergic, Anti-bacterium, resisting hypertension, the multiple efficacies such as blood sugar lowering and cholesterol reducing, and help the treatment of hepatoprotective and liver related disease.
The composition Study of relevant Antrodia camphorata, mostly focus on macromolecular polysaccharides (polysaccharides) and micromolecular triterpenes (triterpenoids) and steroid (steroids), wherein, Antrodia camphorata contains macromolecular polysaccharides, form with different monosaccharide and to be present in its sporophore and the mycelium, but after spectrum analysis, all contain the β of tool physiologically active-poly-candy in D-Portugal (β-D-glucans); Triterpenoid compound is the general name that is combined into hexagon or pentagon native compound by 30 carbons, and the bitterness that Antrodia Camphorata has is namely mainly from this composition of triterpenes, and it also is studied maximum composition.The triterpenoid compound that obtains from sporophore has antrocin, 4,7-dimethoxy-5-methyl isophthalic acid, 3-benzo dioxy ring (4,7-dimethoxy-5-methy-1,3-benzodioxole) and 2,2 ', 5,5 '-tetramethoxy-3,4,3 ', 4 '-two-methylene-dioxy-6,6 '-dimethyl diphenyl (2,2 ', 5,5 '-teramethoxy-3,4,3 ', 4 '-bi-methyl enedioxy-6,6 '-dimethylbiphenyl) (Chiang et al., 1995), the new triterpenoid compound antcin A take lumistane (ergostane) as skeleton, antcin B, antcin C antcin E, antcin F, methyl antcinate G and methyl antcinate H (Cherng et al., 1995,1996).The chemical compound that sporophore contains in addition take lumistane as skeleton comprises Zhankuic acid A, B and C zhankuic acid D and zhankuic aci d E (Chen and Yang, 1995; Yang 1996), noval chemical compound 15 α take lanostane (lanostane) as skeleton-acetyl-dehydrosulphurenic acid (15 α-acetyl-dehydrosulphurenic acid), dehydroeburicoic acid (dehydroeburicoic acid) and the sulfurenic acid (dehydrasulphurenic acid) that anhydrates.
Although can learn that by at present many experiments the Antrodia Camphorata extract has aforementioned effect, and its ingredient is also analyzed successively to be gone out, but which kind of effective ingredient in the extract can be facilitated the inhibition cancer effect of Antrodia Camphorata actually, do not deliver concrete relevant effective ingredient, remaining further experiment research differentiates, if so can find out the composition of contained real establishment tumor growth in this extract, to be conducive to the research that Antrodia Camphorata presses down the cancer Related Mechanism, and Antrodia Camphorata is applied to cancer, and for example treatment and the prevention of colorectal cancer there is greatest help.
Summary of the invention
For be that what composition has the effect that presses down cancer in the clear Antrodia Camphorata extract actually, the present invention provides the chemical compound of following structural (1) by separation and purification in the Antrodia Camphorata extract;
Wherein, X is oxygen (O) or sulfur (S), and Y is oxygen or sulfur; R
1Be hydrogen base (H), methyl (CH
3) or (CH
2) m-CH
3, R
2Be hydrogen base, methyl or (CH
2) m-CH
3, R
3Be hydrogen base, methyl or (CH
2) m-CH
3, m=1～12; N=1～12.
In the chemical compound suc as formula (1) structural formula, the preferably is the chemical compound of formula as follows (2):
The chemical compound of formula (2), its chemistry 4-hydroxyl-2 by name, 3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-cyclonene (4-hydroxy-2,3-dimethoxy-6-methy-5 (3,7,11-trimethyl-dodeca-2,6,10-trienyl)-cyclohex-2-enone), molecular formula is C
24H
38O
4, outward appearance is the pale yellow powder shape, molecular weight is 390.
The chemical compound of Chinese style of the present invention (1), formula (2) is that separation and purification is from Antrodia Camphorata water extract or organic solvent extraction thing, organic solvent can comprise alcohols (for example methanol, ethanol or propanol), esters (for example ethyl acetate), alkanes (for example hexane) or alkyl halide (for example chloromethanes, ethyl chloride), but not as limit, wherein the preferably is alcohols, and better person is ethanol.
By aforesaid compound, the present invention is applied in the inhibition tumor cell growth, enables further to use during the medicine that is included in the treatment cancer forms part the therapeutic effect of gain cancer.The present invention comprises growth inhibited for the colorectal cancer tumor cell to the scope of the application of this chemical compound, by the ramp that suppresses these tumor cells, and then suppresses the hypertrophy of tumor, and delays the deterioration of tumor.Wherein, better chemical compound is the 4-hydroxyl-2 of formula (2), 3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-cyclonene.
On the other hand, also the chemical compound of formula (1) or/and formula (2) can be used among the present invention in the composition of the medical component that suppresses the colorectal cancer growth of tumour cell.Aforementioned medical component still can comprise pharmaceutically acceptable carrier except the chemical compound of the formula that comprises effective dose (1) or/and formula (2).Carrier can be excipient (such as water), filler (such as sucrose or starch), adhesive (such as cellulose derivative), diluent, disintegrating agent, absorption enhancer or sweeting agent, but does not only limit to this.Medical component of the present invention can be manufactured according to the preparation method of general known pharmacy, with formula (1) or/mix mutually with more than one carrier with formula (2) effective ingredient dosage, prepare required dosage form, this dosage form can comprise lozenge, powder, granule, capsule or other liquid preparation, but not as limit.
Below will further specify embodiments of the present invention; following cited embodiment is in order to illustrate the present invention; be not to limit scope of the present invention; anyly have the knack of this skill person; without departing from the spirit and scope of the present invention; when can doing a little change and retouching, so protection scope of the present invention is as the criterion with claims.
The specific embodiment
Through extraction Antrodia Camphorata water extract or organic solvent extraction thing later, can be further by in addition separation and purification of high performance liquid chroma-tography, again each separatory (fraction) is carried out the test of cancer resistant effect afterwards.At last, then the separatory for the tool cancer resistant effect carries out component analysis, and the composition that may produce cancer resistant effect is further done respectively the inhibition test of colorectal cancer tumor cell.Series of compounds suc as formula (1)/formula (2) among the final the present invention of discovery has the effect that suppresses the colorectal cancer growth of tumour cell.
For convenience of description the present invention below will be with the 4-hydroxyl-2 of formula (2), and 3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-pimelie kelone compounds describes.In addition, for confirming 4-hydroxyl-2,3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-the 2-pimelie kelone compounds is to the inhibition of growth of tumour cell, is with the MTT analytic process among the present invention, according to National Cancer Institute (National Cancer Institute, NCI) antitumor drug screening pattern is carried out the test of cell survival rate to the colorectal cancer tumor cell.Confirmed by those tests, 4-hydroxyl-2,3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-, 12 carbon triolefins)-and the 2-cyclonene is for the colorectal cancer tumor cell: WiDr cell line can reduce its survival rate, also can reduce simultaneously growth half suppression ratio desired concn (being the IC50 value) under comparing, therefore must be by 4-hydroxyl-2,3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-and the 2-cyclonene, be applied on the growth inhibited of colorectal cancer tumor cell, and further can be used in the treatment of colorectal cancer.Aforementioned embodiments is elaborated as follows:
Embodiment 1:
4-hydroxyl-2, the separation of 3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-cyclonene
With Antrodia Camphorata mycelium, sporophore or the mixture of the two about 100 grams, insert in the triangular pyramidal bottle, the water and the alcohols (70%～100% alcohol solution) that add proper proportion, wherein this alcohols is preferably ethanol, extract more than at least 1 hour in 20～25 ℃ of lower stirrings, with filter paper and 0.45 μ m membrane filtration, collect filtrate and namely get the Antrodia Camphorata extract afterwards.
Antrodia Camphorata extract with aforementioned collection, utilize high-effect liquid chromatography (LC) instrument (High PerformanceLiquid chromatography), chromatography pipe (column) with RP 18 is analyzed, and take methanol (A) and 0.1%～0.5% aqueous acetic acid (B) as mobile phase (mobile phase) (its solution proportion as: 0～10 minute, the B ratio was 95%～20%; 10～20 minutes, the B ratio was 20%～10%; 20～35 minutes, the B ratio was 10%～90%; 35～40 minutes, the B ratio was 10%～95%), carry in the speed undershoot of per minute 1ml, simultaneously with the long detector analysis of ultraviolet-visible light all-wave.
25 minutes to 30 minutes the extract that rushes is collected the concentrated solid product of pale yellow powder shape of getting final product to get, and this is 4-hydroxyl-2,3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-cyclonene.By analysis, its molecular formula is C
24H
38O
4, molecular weight 390, fusing point (m.p.) are 48 ℃～52 ℃.Nuclear magnetic resonance, NMR (NMR) assay value is then as follows:
1H-NMR (CDCl
3) δ (ppm): 1.51,1.67,1.71,1.75,1.94,2.03,2.07,2.22,2.25,3.68,4.05,5.07 and 5.14.
13C-NMR (CDCl
3) δ (ppm): 12.31,16.1,16.12,17.67,25.67,26.44,26.74,27.00,39.71,39.81,4.027,43.34,59.22,60.59,120.97,123.84,124.30,131.32,135.35,135.92,138.05,160.45 and 197.12.
Embodiment 2:
The active testing of In Vitro Anti colorectal cancer tumor cell
By in the further test implementation example 1 the discovery chemical compound to the inhibition of tumor cell, present embodiment will be according to National Cancer Institute (National Cancer Institute, NCI) antitumor drug screening pattern, at first get the 4-hydroxyl-2 that separates among the embodiment 1,3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-the 2-pimelie kelone compounds, add and contain in the culture fluid of human colorectal cancer tumor cell WiDr, carry out the test of tumor cell viability.Wherein, the test of cell survival can be adopted known MTT analytic process and be analyzed, and colorectal cancer tumor cell WiDr is human colorectal carcinoma cells strain (human colon adenocarcinoma cell line).
The MTT analytic process is a kind of common analytical method for analysis of cells hypertrophy (cell proliferation), survival rate (percent of viable cells) and cytotoxicity (cytotoxicity).Wherein, MTT (3-[4,5-dimethylthiazol-2-yl] 2,5-diphenyltetrazolium bromide) is yellow stain, it can be absorbed by living cells and is reduced into water insoluble by the succinic acid tetrazolium reductase (succinate tetrazoliumreductase) in the Mitochondria and be hepatic formazan, therefore whether form by formazan, can judge and calculate the survival rate of cell.
At first human colorectal carcinoma cells WiDr is cultivated in RPMI 1640 culture medium that contain 10% hyclone (fetal bovine serum), this culture medium also comprises the dish Ni Xilin (Penicillin) of 100IU/ml, and the streptomycin (Streptomycin) of 100mg/ml, and in 5%CO
2, cultivated 24 hours in 37 ℃ of environment.Cell after the hypertrophy is cleaned once with PBS, and process cell with 1 times trypsin-EDTA, under 1,200rpm centrifugal 5 minutes subsequently, with cell precipitation and abandon supernatant.Add afterwards the new culture fluid of 10ml, slight wobble suspends cell again, in the 96 holes trace dish that again cell is placed in.During test, organize in contrast (without total extract of purifies and separates) respectively at the Antrodia Camphorata extract that adds 30,10,3,1,0.3,0.1 and 0.03 μ g/ml in each hole; And the 4-hydroxyl-2 that in each hole, adds 30,10,3,1,0.3,0.1 and 0.03 μ g/ml, 3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-cyclonene is as test group, in 37 ℃, 5%CO
2Lower cultivation 48 hours.Thereafter, the MTT in add 2.5mg/ml under the environment of lucifuge in each hole reacts the lysis buffer cessation reaction that adds again 100 μ l after 4 hours in each hole.Under 570nm extinction wavelength, measure its light absorption value with the ferment immunity analysis instrument at last, use the survival rate of calculating cell, and to extrapolate its half suppression ratio desired concn of growing (be IC
50Value), its result as shown in Table 1.
Table one: external test result to colorectal cancer tumor cell survival rate
By in the table one as can be known, by 4-hydroxyl-2, the effect of 3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-cyclonene, it is for the IC of the human colorectal cancer tumor cell of WiDr
50Value is 0.92 μ g/ml, compared to the measured IC of matched group Antrodia Camphorata extraction mixture
50Low many of value (not showing in the table), so the 4-hydroxyl-2 in the susceptible of proof Antrodia Camphorata extract, 3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-the 2-cyclonene can be used in the inhibition of colorectal cancer growth of tumour cell really.
In sum, the 4-hydroxyl-2 of separated from Antrodia camphorate of the present invention, 3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-pimelie kelone compounds, but the growth of establishment colorectal cancer tumor cell.On the other hand, be the material of natural extraction because of antrodia camphorata cyclohexenone compound, when so it is applied to suppress colorectal cancer, can't cause that the patient is uncomfortable or produce other side effect such as toxicity, complication, and its also can with chemotherapeutic agents and usefulness, to reduce the chemotherapeutics using dosage and to reduce the side effect that these chemotherapeutic agents are caused; In addition, also it can be prepared into the medical component for the treatment of colorectal cancer, wherein, this medical component still can comprise pharmaceutically acceptable carrier except the antrodia camphorata cyclohexenone compound that comprises effective dose.Carrier can be excipient (such as water), filler (such as sucrose or starch), adhesive (such as cellulose derivative), diluent, disintegrating agent, absorption enhancer or sweeting agent, but does not only limit to this.Medical component of the present invention can be manufactured according to the preparation method of general known pharmacy, the antrodia camphorata cyclohexenone compound of effective ingredient dosage is mixed mutually with more than one carrier, prepare required dosage form, this dosage form can comprise lozenge, powder, granule, capsule or other liquid preparation, but not as limit.Use the purpose that reaches treatment colorectal cancer tumor disease.
Claims (2)
1. one kind with compound 4-hydroxy base-2, and 3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-cyclonene is for the preparation of the application of the medicine that suppresses the colorectal cancer growth of tumour cell.
2. application as claimed in claim 1, wherein this colorectal cancer tumor cell is WiDr cell line.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010174697 CN102232940B (en) | 2010-05-06 | 2010-05-06 | Antrodia camphorata cyclohexenone compound for inhibiting colorectal cancer tumor cell growth |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010174697 CN102232940B (en) | 2010-05-06 | 2010-05-06 | Antrodia camphorata cyclohexenone compound for inhibiting colorectal cancer tumor cell growth |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102232940A CN102232940A (en) | 2011-11-09 |
| CN102232940B true CN102232940B (en) | 2013-03-27 |
Family
ID=44884365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 201010174697 Active CN102232940B (en) | 2010-05-06 | 2010-05-06 | Antrodia camphorata cyclohexenone compound for inhibiting colorectal cancer tumor cell growth |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102232940B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI241344B (en) * | 2002-03-29 | 2005-10-11 | Food Industry Res & Dev Inst | Processes for producing an antrodia camphorata culture having pharmacological activity, processes for obtaining a pharmacologically active composition from a culture of A camphorata, products produced thereby and pharmaceutical compositions of cancer... |
| CN101225066B (en) * | 2007-01-18 | 2010-09-22 | 国鼎生物科技股份有限公司 | Cyclohexenone extract of antrodia camphorata |
-
2010
- 2010-05-06 CN CN 201010174697 patent/CN102232940B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI241344B (en) * | 2002-03-29 | 2005-10-11 | Food Industry Res & Dev Inst | Processes for producing an antrodia camphorata culture having pharmacological activity, processes for obtaining a pharmacologically active composition from a culture of A camphorata, products produced thereby and pharmaceutical compositions of cancer... |
| CN101225066B (en) * | 2007-01-18 | 2010-09-22 | 国鼎生物科技股份有限公司 | Cyclohexenone extract of antrodia camphorata |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102232940A (en) | 2011-11-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI335314B (en) | ||
| CN101417934B (en) | New compounds separated from Antrodia camphorate extract | |
| CN101225066B (en) | Cyclohexenone extract of antrodia camphorata | |
| TWI394566B (en) | Used to inhibit the growth of ovarian cancer tumor cells of the cattle camphor cyclohexene ketone compounds | |
| TW201102075A (en) | Cyclohexenone compound of Antrodia cinnomomea that suppresses growth of tumor cell of pancreatic cancer | |
| CN102000046B (en) | Application of antrodia camphorata cyclohexenone compound in preparing medicine for inhibiting growth of pancreatic cancer tumor cells | |
| TW201109023A (en) | Cyclohexenone compound of Antrodia cinnomomea that suppresses growth of tumor cell of colorectal cancer | |
| CN102000047B (en) | Antrodia camphorata cyclonene compound for restraining growth of bone cancer cells | |
| TW201109011A (en) | Cyclohexenone chemical compounds of Antrodia cinnamomea for suppressing the growth of gastric cancer tumor cell | |
| CN102875615B (en) | Extraction method and application of falcate dolichos root or leaf glucoside A and total saponins of falcate dolichos root or leaf | |
| CN102603856B (en) | Anti-tumor saponin in anemone plants and preparation method thereof as well as application | |
| CN101343247B (en) | Cyclohexenone extract of antrodia camphorata | |
| CN102232940B (en) | Antrodia camphorata cyclohexenone compound for inhibiting colorectal cancer tumor cell growth | |
| CN103739653B (en) | A kind of 23-fall oleanane acid compound and preparation method thereof and the purposes in preparing glycosidase inhibitor | |
| CN107266516B (en) | Triterpenoid with anti-tumor activity and the preparation method and application thereof | |
| TWI379679B (en) | ||
| CN102232942B (en) | Antrodia camphorata cyclohexenone compound for suppressing growth of lymphoma tumor cells | |
| TW201109013A (en) | Cyclohexenone chemical compounds of Antrodia cinnamomea for suppressing the growth of the Lymphoma tumor cell | |
| TW201102076A (en) | Cyclohexenone compound of Antrodia cinnomomea suppressing growth of tumor cell of osteosarcoma | |
| CN102232943B (en) | Antrodia camphorata cyclohexenone compound for inhibiting skin cancer tumor cell growth | |
| CN102232945B (en) | Antrodia camphorata cyclohexenone compound for suppressing growth of bladder cancer tumor cells | |
| CN102232946B (en) | Use of antrodia camphorata cyclohexenone compound in preparing medicine for inhibiting stomach cancer tumor cell growth | |
| CN102232941B (en) | Antrodia camphorata cyclohexenone compound for inhibiting ovarian cancer tumor cell growth | |
| TW201109024A (en) | Cyclohexenone compound of Antrodia cinnomomea that suppresses growth of tumor cell of bladder cancer | |
| CN102232944B (en) | Antrodia cinnamomea pimelie kelone compound for inhibiting growth of oral cancer tumor cells |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |