CN103012358A - Compound extracted from antrodia camphorate, medical composition containing compound and application of compound - Google Patents
Compound extracted from antrodia camphorate, medical composition containing compound and application of compound Download PDFInfo
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- CN103012358A CN103012358A CN2011102969730A CN201110296973A CN103012358A CN 103012358 A CN103012358 A CN 103012358A CN 2011102969730 A CN2011102969730 A CN 2011102969730A CN 201110296973 A CN201110296973 A CN 201110296973A CN 103012358 A CN103012358 A CN 103012358A
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Abstract
The invention discloses a new compound extracted from antrodia camplhorate, a related compound shown in formula (1) and a medical composition containing the compound shown in formula (1) and a medically acceptable carrier or excipient. The invention also discloses an application of the compound shown in formula (1) to prepare a preparation used for inhibiting cancer cells. The compound extracted from the antrodia camplhorate disclosed by the invention has the function of inhibiting growth activity of tumour cells of a human body, so that a tumour can be effectively prevented and treated. Formula (1) is described in the specification.
Description
Technical field
The present invention relates to field of medicaments, particularly relate to a kind of new compound from the Antrodia camphorata extraction, and formula (1) compound relevant with this compound, the medical composition that comprises this formula (1) compound and this formula (1) compound purposes in the preparation that the preparation anticancer is used.
Background technology
Antrodia camphorata (antrodia Cinnamomea) is a kind of natural fungi in Taiwan, is also referred to as mushroom (Chang-nei mushroom) in Cinnamomum kanahirai hay mushroom (antrodia camphorate/Niu-chang mushroom), camphor tree sesame (Chang chih), red camphor tree (Hong-chang), red camphor tree mushroom (Hong-chang mushroom) or the camphor tree.The spore of Antrodia camphorata is to reach 450 meters growths in the treehole of the rotten Cinnamomum kanahirai hays trees (cinnamomum Kanehirai Hey) of 2,000 meters height being positioned at height above sea level.Antrodia camphorata is a kind of perennial mushroom, belongs to polyporaceae (Polyporaceae family), and Antrodia belongs to (Antrodia genus).Wild Cinnamomum kanahirai hay tree is very rare, is a kind of shielded plant species in Taiwan.In recent years, because illegal felling is rampant, cause the Cinnamomum kanahirai hay tree of waste Yezhong fewer and feweri.In addition, the vegetative period of Antrodia camphorata is relatively short, only grows between the June to October in every year.Therefore, Antrodia camphorata becomes a kind of preciousness and expensive Chinese medicine.
The complicated component of Antrodia camphorata comprises the material (for example antodia acid) of polyose (for example beta-glucan), triterpenes, superoxide-dismutase, adenosine, protein-based (comprising immunoglobulin (Ig)), vitamins (for example vitamins B and nicotinic acid), trace element (for example calcium, phosphorus and germanium), nucleic acid, lectin, amino acids, steroid, xylogen and stabilizing blood pressure.Through showing, these physiologically active substances can suppress tumour, enhancing immunity, regulate anaphylaxis, anticoagulant, lowering blood glucose, reduction serum cholesterol and protect liver.
Although Antrodia camphorata contains many physiologically active substances, these physiologically active substances are not yet differentiated fully.Need to differentiate, purifying and analysis Antrodia camphorata extract be to obtain to have the activeconstituents of anti-tumor activity, as the safe and efficient alternative method for the treatment of or preventing cancer.
Summary of the invention
One of the technical problem to be solved in the present invention provides a kind of compound from the Antrodia camphorata extraction, and it can effectively treat cancer.
For solving the problems of the technologies described above, formula of the present invention (1) compound comprises: the prodrug of this formula (1) compound, and perhaps this formula (1) compound or this prodrug are at pharmaceutically acceptable salt; Wherein, R
1, R
2And R
3Be independently selected from respectively hydrogen, alkoxyl group, hydroxyl, carboxyl or alkyl.
Two of the technical problem to be solved in the present invention provide a kind of from Antrodia camphorata extraction and through separating and the compound of purifying.
For solving the problems of the technologies described above, formula (1) compound through separation and purifying of the present invention comprises: the prodrug of this formula (1) compound, and perhaps this formula (1) compound or this prodrug are at pharmaceutically acceptable salt; Wherein, R
1, R
2And R
3Be independently selected from respectively hydrogen, alkoxyl group, hydroxyl, carboxyl or alkyl.
Formula (1)
Better, above-mentioned R
1And R
2Be methoxyl group, and R
3Be methyl.
Three of the technical problem to be solved in the present invention provides a kind of medical composition that comprises above-mentioned formula (1) compound.
For solving the problems of the technologies described above, medical composition of the present invention comprises:
(a) formula (1) compound or its prodrug, perhaps this formula (1) compound or this prodrug are at pharmaceutically acceptable salt; And (b) pharmaceutically acceptable vehicle or supporting agent.
Described formula (1) compound can be through separating and purifying.
Four of the technical problem to be solved in the present invention provides the purposes of above-mentioned formula (1) compound in the preparation that the preparation anticancer is used.
For solving the problems of the technologies described above, the purposes of formula of the present invention (1) compound in the preparation that the preparation anticancer is used is that tool is treated this formula (1) compound of significant quantity for the Mammals that needs anticancer.
Described cancer cells is rectum cancer cell.
Of the present invention from Antrodia camphorata extraction compound and contain the medical composition of this compound, have following advantages and beneficial effect:
(1) the compounds of this invention is the new compound from the Antrodia camphorata extraction, and has the activity that suppresses the human body rectum cancer cell, thereby provides new approach for preventing and treating the rectum cancer.
(2) add in other consistency salt or the pharmaceutically acceptable vehicle or supporting agent by the compounds of this invention that will have growth inhibitory activity to tumor cell, make and to supply the oral medical composition (its better form of taking is tablet or powder form) of patient, can increase by this restraining effect to the patient body inner tumour cell.
Description of drawings
The one dimension proton magnetic resonance (PMR) of Fig. 1 display type (1) compound (proton nuclear magnetic resonance,
1H-NMR) collection of illustrative plates;
Correlated Spectroscopy (correlation spectroscopy, COSY) the two dimensional NMR collection of illustrative plates of Fig. 2 display type (1) compound;
The one dimension of Fig. 3 display type (1) compound
13C nucleus magnetic resonance (One-dimensional
13C NMR) collection of illustrative plates;
The two-dimentional heteronuclear Multiple-quantum of Fig. 4 display type (1) compound (Heteronuclear Multiple Quantum Coherence, the HMQC) nuclear magnetic resonance map of being correlated with;
The two-dimentional heteronuclear multikey of Fig. 5 display type (1) compound (Heteronuclear Multiple Bond Coherence, the HMBC) nuclear magnetic resonance map of being correlated with;
50% inhibition concentration (half-maximal inhibitory concentrations, the IC of Fig. 6 display type (2) compound and compound (3), (4)
50) curve, these curved measurements compound suppress the validity of people's rectum cancer cell (HT29);
The IC of Fig. 7 display type (2) compound and compound (3), (4)
50Curve, these curved measurements compound suppress the validity of people's rectum cancer cell (Colo205).
Embodiment
Understand for technology contents of the present invention, characteristics and effect being had more specifically, existing details are as follows in conjunction with illustrated embodiment:
Definition
When existing, unless otherwise mentioned, following term is defined as (but being not limited to) to give a definition:
" alkyl (alkyl) " refer to have 1 to 5 carbon atom straight or branched of (comprising 1 and 5) is perhaps censured the groups such as saturated or aliphatic unsaturated hydrocarbon.
" alkoxyl group (alkoxy) " refers to " alkyl-O-" group; Wherein, this alkyl is to replace with optional alkyl in aforementioned definitions as defined above.
" pharmaceutically acceptable salt (pharmaceutically acceptable salts) " refers to keep the required biological activity of parent compound (parent compound), and can not give the salt of undesirable toxicological action.The form of pharmaceutically acceptable salt comprises by acid or alkali addition and obtains various polycrystalline and the amorphous form that different salt has.Acid salt (acid addition salts) available mineral acid or organic acid form.The illustrative that this is sour but limiting examples comprises hydrochloric acid, Hydrogen bromide, sulfuric acid, phosphoric acid, citric acid, acetic acid, propionic acid, phenylformic acid, naphthoic acid, oxalic acid, succsinic acid, maleic acid, FUMARIC ACID TECH GRADE, oxysuccinic acid, hexanodioic acid, lactic acid, tartrate, Whitfield's ointment, methanesulfonic, 2-hydroxyethanesulfonic acid, toluenesulphonic acids, Phenylsulfonic acid, camphorsulfonic acid and ethane sulfonic acid.Pharmaceutically acceptable base addition salt (base addition salts) available metal counterion or organic balanced ion (metal and organ counterions) form, and include, but is not limited to an alkali metal salt, for example sodium salt or sylvite; Alkaline earth salt, for example magnesium salts or calcium salt; With ammonium salt or tetraalkylammonium salt, i.e. NX
4+(wherein X is C
1-4).
Term used herein " treatment " comprises application or the result of preventative (such as preventive medicine), the property alleviated and healing property.
Term " individuality " refers to comprise Mammals by animal, is preferably the mankind.
Term " prodrug " refers to transform in vivo generate has bioactive product, such as formula of the present invention (1) compound or formula (1) compound at pharmaceutically acceptable salt.Its conversion can occur by various mechanism, for example by in blood, being hydrolyzed, or bio-transformation (for example enzyme activity).The prodrug of formula (1) compound can be via traditional method, and the functional group's (such as hydroxyl) that for example is present in the compound by modification forms, and obtains a free hydroxyl group.
" pharmaceutically acceptable supporting agent " or " pharmaceutically acceptable vehicle " refer to, gives in the individuality or throw supporting agent or the vehicle that can not cause undesirable physiological action after giving on the individuality in throwing.Supporting agent in the medical composition is necessary for " acceptable ", and its meaning is that this medical composition and activeconstituents are compatible, especially can make the activeconstituents person of stablizing better.Can come feeding type (1) compound as pharmaceutical carriers with one or more solubilizing agent.
New compound
The present invention relates to a kind of formula (1) compound, the prodrug of this formula (1) compound, perhaps this formula (1) compound or this prodrug are at pharmaceutically acceptable salt.
Formula (1)
R wherein
1, R
2And R
3Be independently selected from respectively hydrogen, alkoxyl group, hydroxyl, carboxyl or alkyl.
According to the present invention, formula (1) compound can produce by following reaction mechanism is synthetic:
The retrosynthesis strategy
Synthetic way Trail
Ginseng examines the people ， You Machine With biomolecules Learn (Org.Biomol.Chem.) such as document------Lee (C.L.Lee), 2011,9,70-73
N-iodo amber vinegar Asia amine: N-iodosuccinimide
Valylene: 2-methylbut-1-en-3-yne
In preferred embodiment, the compounds of this invention has the structure suc as formula (2),
Formula (2)
Formula (1) compound is water or organic solvent to be extracted obtain from Antrodia camphorata.This organic solvent can be alcohol, ester, alkane or alkyl halide.
The alcoholic solvent that uses among the present invention comprises methyl alcohol, ethanol or propyl alcohol.The esters solvent that uses among the present invention comprises ethyl acetate.The alkane solvents that uses among the present invention comprises hexane.The alkyl halide kind solvent that uses among the present invention comprises methyl chloride or monochloroethane.The compounds of this invention is preferably and uses the alcoholic solvent extraction.
Medical composition
Medical composition comprises formula (1) compound and pharmaceutically acceptable supporting agent or vehicle.Suitable pharmaceutically acceptable supporting agent is by being known in the affiliated technical field among the present invention, and the supporting agent that changes with form and the dispensing pattern thereof of this medical composition.Pharmaceutically acceptable supporting agent or vehicle include, but is not limited to: salt brine solution; Aqueous electrolyte liquid; Isotonic regulator (isotonicity modifiers); Water; Polyethers (for example polyoxyethylene glycol); Polyvinyl compound class (polyvinyls), for example polyvinyl alcohol and polyvidone (povidone); Derivatived cellulose class, for example methylcellulose gum and Vltra tears; Acrylate copolymer class, for example carboxyvinyl polymer gel (carboxypolymethylene gel); Polysaccharides, for example poly-candy (dextrans) of grape; And glucosamine poly-carbohydrate, for example Hyaluronic Acid sodium; And salt, for example sodium-chlor and Repone K.
Preparation by medical composition provides mode of movement in suction, external application, oral, rectum, implanted storage and the bodies such as non-oral (such as intravenous injection, intramuscular injection, subcutaneous injection, joint injection, synovial membrane injection, the injection of brain pond, intrathecal injection, injection into liver, intralesional injection and intracranial injections).Wherein, oral delivery is especially better.
This medical composition can be by the known any technological method preparation of pharmacy field.The method comprises the step that makes active compound and supporting agent association (association), and this supporting agent can comprise one or more ancillary component (accessory ingredients).For example, when preparing the composition that is applicable to inject, its solution and the sterilization of suspension process, and to have osmotic pressure person identical with blood for better.When the preparation injectable formulation, can use supporting agent commonly used in the technical field of the invention, for example water, ethanol, propylene glycol.In these situations, can be by adding an amount of isotonic regulator, for example sodium-chlor, grape candy or glycerine reach preparation and blood etc. are oozed.The water-based aseptic injectable solution can comprise in addition oxygenant, buffer reagent and can accept to add the additive of non-oral composition.
For example, oral tablet, hard or soft capsule lozenge, water-based or oily suspensions, viscous gel, Chewing gum, dispersible powder or granule, emulsion, the perhaps form of syrup or elixir of can be.
The preparation method of powder is that compound is ground to form the powder with suitable size, mixes with the pharmaceutical carrier of the similar powder diameter of tool again, and this pharmaceutical carrier system is such as consumption carbohydrate such as starch or N.F,USP MANNITOL.Seasonings, dispersion agent and tinting material also can exist simultaneously.
To orally use, the preparation of its waterborne suspension is by water is added powder and the granule that can disperse and interpolation dispersion agent or wetting agent, suspension agent, one or more sanitass and other vehicle gained in water.Suspension agent comprises for example Xylo-Mucine, methylcellulose gum and sodium alginate.Dispersion agent or wetting agent comprise the condensation product, oxyethane of naturally occurring phospholipid, allylene oxide (allylene oxide) and condensation product, oxyethane and the long chain aliphatic alcohol of lipid acid and the condensation product of the partial ester that formed by lipid acid and hexitol, and the condensation product of oxyethane and the partial ester that obtained by lipid acid and hexitan.Sanitas comprises for example ethyl p-hydroxybenzoate (ethyl p-hydroxybenzoate) and P-hydroxybenzoic acid n-propyl.Other vehicle comprises sweeting agent (for example sucrose, asccharin), seasonings and tinting material.The persond having ordinary knowledge in the technical field of the present invention is deserved with from above-mentioned recapitulative description, recognizes that many concrete and clear and definite vehicle and wetting agent system is covered by wherein.
With oral application, the preparation of its tablet is to mix by the pharmaceutically acceptable non-toxic excipients of active compound and being fit to being made tablet.These vehicle can be for example inert diluent (such as calcium carbonate, yellow soda ash, lactose, calcium phosphate or sodium phosphate), granulating agent and disintegrating agent (such as W-Gum or Lalgine); Tackiness agent (such as starch, gelatin or gum arabic) and lubricant (such as Magnesium Stearate, stearic acid or talcum).Tablet can perhaps utilize known technology that it is carried out dressing without dressing, delaying disintegration and the absorption in gi tract, and makes thus one long period of its continuous action.For example, can use the material of slack time, for example glyceryl monostearate or distearin.The formulation that orally uses also can be the hard gelatine capsule form, its active compound with mix such as inert solid diluent such as calcium carbonate, calcium phosphate or kaolin; Perhaps be the soft gelatin capsule form, its active compound mixes with water or such as peanut oil, whiteruss or olive wet goods oil medium.The formulation that orally uses can form the Chewing gum form by active compound is embedded in addition in the jelly, so that active compound slowly discharges when chewing.
Purposes in the preparation of preparation anticancer
The purposes of the present invention in the preparation of preparation anticancer is that individuality is thrown formula (1) compound that gives the tool significant quantity, uses the symptom and the symptom that alleviate individual cancer.These active compounds comprise that the prodrug of formula (1) compound, formula (1) compound or this formula (1) compound or this prodrug are at pharmaceutically acceptable salt.
" significant quantity " used herein refers to be enough to alleviate formula (1) the compound dosage of cancer symptoms and symptom (for example lump, pain and lose weight).
In the present invention, the chemical formula title that provides should contain its all optical isomers and steric isomer, and the racemic mixture that has aforementioned isomer and mixture.
Hereinafter example will further specify the present invention.These examples only are used for explanation the present invention, and it should be interpreted as restriction of the present invention.
Example
Example 1: extraction and duscriminant (2) compound
As mentioned below, extraction formula (2) compound from the Antrodia camphorata of cultivating satinwood:
1. mix with the Antrodia camphorata grinds, and with ethanol, obtain the ethanolic extract of Antrodia camphorata;
2. the ethanolic extract with step 1 is scattered in the mixture of ethyl acetate and water (volume ratio 1: 1), the beginning distribution process;
3. high polarity ethanolic extract is dissolved in the water, forms the aqueous solution (lower floor), and will hang down the polarity ethanolic extract and be dissolved in (upper strata) in the ethyl acetate.
Ethyl acetate solution in the step 3 is divided into 7 parts, analyzes with post layer analysis method.These 7 parts of solution are further separated with post layer analysis method, and see through the HPLC purifying.Confirm that this compound has the aromatic series characteristic.
Chemical structure by following steps duscriminant (2) compound:
1. (M+H) of separating compound
+Molecular weight is 261.1038.This molecular weight is to utilize high resolving power electrospray ionization mass spectrometry instrument (high-resolution electron spray ionization mass spectrometer, HRESIMS) to calculate under positive ion mode.The molecular formula of separating compound is C
15H
16O
4, and degree of unsaturation is 8.
2. utilize the structure of following methods assessment separating compound: use 500MHz nuclear magnetic resonance spectrometer (NMR spectrometer), Correlated Spectroscopy (COSY), relevant NMR (Nuclear Magnetic Resonance) spectrum (the HMQC NMR spectrum) NMR (Nuclear Magnetic Resonance) spectrum relevant with the heteronuclear multikey (HMBC NMR spectrum) of heteronuclear Multiple-quantum carry out the one dimension proton magnetic resonance (PMR) (
1H-NMR) and one dimension
13The C nucleus magnetic resonance (
13C-NMR).The deuterium solvent is CDCl
3
The one dimension of Fig. 1 display separation compound
1The H-NMR collection of illustrative plates.
1H-NMR(500MHz，CDCl
3)：δH?5.91(2H，s)，5.35(1H，br?s)，5.24(1H，br?s)，3.96(3H，s)，3.85(3H，s)，2.25(3H，s)，1.98(3H，br?s)。The proton signal of NMR collection of illustrative plates also demonstrates, and methylene radical connects two protons, two methoxyl groups, the methyl that is connected with phenyl ring on two Sauerstoffatoms, the two key alkene, and with methyl that alkene is connected in a proton.
The two-dimentional COSY NMR collection of illustrative plates of Fig. 2 display separation compound.According to Fig. 2, δ H 1.98 and δ H 5.35,5.24 relevant.That is confirm, methyl is connected with alkene at δ H 1.98.
The one dimension of Fig. 3 display separation compound
13The C-NMR collection of illustrative plates, wherein the chemical shift of aromatic ring was δ C 139.8,139.5,137.2,136.3,127.8,101.4 o'clock, the carbon signal of four methyl is positioned at δ C 60.3,60.0,13.8,23.6, and the methylene radical that is connected with two Sauerstoffatoms is positioned at δ C 101.4.Two characteristic carbon signals of alkynes are positioned at δ C97.5 and 83.5.Analyze according to HRESIMS, the degree of unsaturation of separating compound is as follows: aromatic ring has 4 degrees of unsaturation, and two two key alkene respectively have 1 degree of unsaturation, and all the other two degrees of unsaturation then partly are identified at alkynes.
The HMQC NMR collection of illustrative plates of Fig. 4 display separation compound.(δ C) is relevant with chemical shift of proton in the carbon geochemistry displacement, and is positioned at following 6 positions: 101.4,121.0,60.3,60.0,13.8 and 23.6.
The HMBC NMR collection of illustrative plates of Fig. 5 display separation compound.Separating compound is that δ C 97.5 places (alkynes) have long-range coupling at δ H 1.98 places and carbon geochemistry displacement.According to the experimental result of general introduction in the table 1, the structure of separating compound is 1,2-methylene radical dioxy base-3,6-bi-methoxy-4-(3-methyl-3-alkene-ethyl acetylene)-5-methylbenzene, i.e. formula (2) compound.
Example 2: Anticancer Activity in vitro
Cognation:
This test is with the ability of formula (2) compound at the vitro inhibition human cancer cell.
Scheme:
Using HT29 and Colo205 people's rectum cancer cell is the antitumous effect of assessment formula (2) compound and compound (3) and (4).
Compound (3) and (4) are the known compounds from the Antrodia camphorata extraction, and have chemical formula shown below:
Compound (3)
Compound (4)
Human rectum cancer cell HT29 and Colo205 are pressed 1 * 10
4-5The concentration of individual cells/well is inoculated in 96 orifice plates.At 37 ℃ and 5%CO
2Environment under cultivate human rectum cancer cell and spend the night.Next day, wash these cancer cells 3 times with serum free medium or phosphate buffered saline buffer (PBS).Formula (2) compound and compound (3) and (4) are added to respectively in HT29 and the human rectum cancer cell of Colo205.Carry out three experiments, and calculate average IC
50Value.
The result:
Fig. 6 display type (2) compound and compound (3) and (4) are for the IC of the human rectum cancer cell of HT29
50Curve.Fig. 7 display type (2) compound and compound (3) and (4) are for the IC of the human rectum cancer cell of Colo205
50Curve.It was reported and point out, IC
50The chemical substance that is lower than 100M represent cytotoxicity (vegetable chemistry (Phytochemistry) 2005,66 (10), 1186-1191).
Referring to Fig. 6, the IC of formula (2) compound
50Value is 66 μ M, and compound (3) is 59 μ M, and compound (4) is higher than 100 μ M.This shows, compares with compound (4), and formula (2) compound has the antitumour activity of enhancing to the human rectum cancer cell cording of the HT29 of test.
Referring to Fig. 7, the IC of formula (2) compound
50Value is 9 μ M, and compound (3) is 42 μ M, and compound (4) is higher than 100 μ M.This shows, compares with compound (3) and (4), and formula (2) compound has the antitumour activity of enhancing to the human rectum cancer cell cording of the Colo205 of test.
Generally speaking, formula (2) compound has lower IC
50, and more effective than known compound aspect the inhibition rectum cancer cell.
Based on above-mentioned, formula (1) compound is the new compound from the Antrodia camphorata extraction, and can effectively treat cancer.
Claims (10)
1. a formula (1) compound comprises: the prodrug of this formula (1) compound, and perhaps this formula (1) compound or this prodrug are at pharmaceutically acceptable salt; It is characterized in that R
1, R
2And R
3Be independently selected from respectively hydrogen, alkoxyl group, hydroxyl, carboxyl or alkyl.
Formula (1)
2. compound as claimed in claim 1 is characterized in that, R
1And R
2Be methoxyl group, and R
3Be methyl.
3. one kind through separating and formula (1) compound of purifying, comprising: the prodrug of this formula (1) compound, and perhaps this formula (1) compound or this prodrug are at pharmaceutically acceptable salt; It is characterized in that R
1, R
2And R
3Be independently selected from respectively hydrogen, alkoxyl group, hydroxyl, carboxyl or alkyl.
Formula (1)
4. compound as claimed in claim 3 is characterized in that, R
1And R
2Be methoxyl group, and R
3Be methyl.
5. a medical composition is characterized in that, comprising:
(a) formula (1) compound or its prodrug, perhaps this formula (1) compound or this prodrug are at pharmaceutically acceptable salt; And
(b) pharmaceutically acceptable supporting agent.
6. medical composition as claimed in claim 5 is characterized in that, this formula (1) compound is through separating and purifying.
7. the purposes of a formula as claimed in claim 1 (1) compound in the preparation that the preparation anticancer is used is characterized in that, needing to be used for the Mammals of anticancer with this formula (1) compound of tool treatment significant quantity.
8. purposes as claimed in claim 7 is characterized in that, described cancer cells is rectum cancer cell.
9. the purposes of a formula as claimed in claim 3 (1) compound in the preparation used of preparation anticancer is characterized in that, is used for a Mammals that needs anticancer with this formula (1) compound of tool treatment significant quantity.
10. purposes as claimed in claim 9 is characterized in that, described cancer cells is rectum cancer cell.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013119544A (en) * | 2011-12-09 | 2013-06-17 | Taiwan Leader Biotech Corp | Polyacetylene compound, extract containing the same, and application thereof |
| CN104177240A (en) * | 2013-05-28 | 2014-12-03 | 曾卉菱 | Compound and extract isolated from Antrodia camphorata and application |
| CN109276563A (en) * | 2017-07-21 | 2019-01-29 | 珠海市鑫展生物科技有限公司 | Application of pharmaceutical composition in preparing medicine for treating or preventing individual infection virus |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101214238A (en) * | 2007-01-05 | 2008-07-09 | 国鼎生物科技股份有限公司 | Application of 'niuzhangzhi' extract for inhibiting tumor cell growth |
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2011
- 2011-09-27 CN CN2011102969730A patent/CN103012358A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101214238A (en) * | 2007-01-05 | 2008-07-09 | 国鼎生物科技股份有限公司 | Application of 'niuzhangzhi' extract for inhibiting tumor cell growth |
Non-Patent Citations (1)
| Title |
|---|
| LIN, TING-YU：等: "《Metabolite profiles for Antrodia cinnamomea fruiting bodies harvested at different culture ages and from different wood substrates》", 《JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY》, vol. 59, no. 14, 13 June 2011 (2011-06-13), pages 7626 - 7635 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013119544A (en) * | 2011-12-09 | 2013-06-17 | Taiwan Leader Biotech Corp | Polyacetylene compound, extract containing the same, and application thereof |
| CN104177240A (en) * | 2013-05-28 | 2014-12-03 | 曾卉菱 | Compound and extract isolated from Antrodia camphorata and application |
| CN104177240B (en) * | 2013-05-28 | 2016-10-19 | 曾卉菱 | The compound of separated from Antrodia sesame, extract and application thereof |
| CN109276563A (en) * | 2017-07-21 | 2019-01-29 | 珠海市鑫展生物科技有限公司 | Application of pharmaceutical composition in preparing medicine for treating or preventing individual infection virus |
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Application publication date: 20130403 |