CN108409571A - The compound for treating cancer extracted from Euphorbia antiquorum - Google Patents
The compound for treating cancer extracted from Euphorbia antiquorum Download PDFInfo
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- CN108409571A CN108409571A CN201810268575.XA CN201810268575A CN108409571A CN 108409571 A CN108409571 A CN 108409571A CN 201810268575 A CN201810268575 A CN 201810268575A CN 108409571 A CN108409571 A CN 108409571A
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- Prior art keywords
- compound
- cell
- euphorbia
- antiquorum
- euphorbia antiquorum
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/21—Acetic acid esters of hydroxy compounds with more than three hydroxy groups
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Abstract
The invention belongs to technical field of pharmaceuticals, the compound extracted from Euphorbia antiquorum more particularly to two kinds, which can be used as treating cancer reactive compound, using it as the pharmaceutical composition of active ingredient, and its application in preparing anticancer drug, the compound, such as one of lower structure：The compound that the present invention separates and extracts Euphorbia antiquorum carries out Activity determination using mtt assay to separated compound in Euphorbia antiquorum, it was demonstrated that its antitumor activity.
Description
Technical field
The invention belongs to technical field of pharmaceuticals, the compound extracted from Euphorbia antiquorum more particularly to two kinds, the compound
Treating cancer reactive compound is can be used as, using it as the pharmaceutical composition of active ingredient, and its in preparing anticancer drug
Using.
Background technology
Malignant tumour is global one of the common disease for seriously endangering human life and health, and harm has been more than heart and brain blood
Pipe disease and become first cause of death of the mankind, the World Health Organization has been called the number one killer of human life.
There are three essential characteristics, i.e. proliferation out of control, differentiation deficiency and apoptosis to be obstructed for tumour cell usually tool.Surgery is removed at present
Operation is outer, and radiation and chemotherapy is still the primary treatments of tumour, but they set primarily directed to the proliferation out of control of tumour cell
Meter, maximum disadvantage can also generate lethal effect while killing tumor cell in addition to drug resistance to normal cell,
Especially to hematopoietic tissue and cell, serious lethal complication can be caused.Tumour oneself be proved to be a kind of cell prosoplasia
Disease, for normal differentiated cells, tumour cell lacks ripe form and complete function to varying degrees, and to just
Normal differentiation regulation mechanism lacks reaction, and appearance differentiation missing, differentiation blocks and disdifferentiation.
The cancer of the esophagus is the common malignant tumour of (esophageal carcinoma) mankind, account for the 90% of esophageal neoplasm with
On, it is only second to gastric cancer in whole mortality of malignant tumors retrospective surveys and occupies the 2nd.The whole world every year about 200,000 according to estimates
People dies of the cancer of the esophagus, is the most common malignant tumour one of very harmful to the life and health of the people.The cancer of the esophagus has occurred frequently
This feature of area illustrate this area have its generation condition, such as exist strong carcinogen, promote cancer object, lack some anticancer factors with
And have genetic predisposition etc..But various countries various regions result of study is very inconsistent, the cause of disease for reflecting the cancer of the esophagus is diversified.
Western scholar thinks that it is main cause to smoke and drink more.Currently, though the cause of disease of the cancer of the esophagus is not yet completely understood, state in recent years
It is inside and outside to cancer of esophagi because having carried out multipath exploration.It is multi-party from nitrosamine, nutrition, trace element, fungi and virus, heredity etc.
Face is studied and is explored at many levels, obtains meaningful progress.
Liver malignancy can be divided into primary and secondary two major classes.Characters of Primary Malignant Tumors of Liver originates from liver
Epithelium or mesenchymal tissue, the former is known as primary carcinoma of liver, is that China is occurred frequently, very harmful malignant tumour；The latter is known as meat
Tumor, it is more rare compared with primary carcinoma of liver.Secondary or metastatic hepatic carcinoma means the pernicious of the multiple organ origins of whole body
Tumor invading is to liver.Generally it is more common in the organ malignant tumours such as stomach, biliary tract, pancreas, Colon and rectum, ovary, uterus, lung, mammary gland
Hepatic metastases.
The Euphorbiaceae that Euphorbia is under the jurisdiction of, now temporary point 5 subfamilies, China share 4 subfamilies, including Common Leafflower Herb subfamily, big
Halberd subfamily, iron look for dish subfamily and crotons subfamily.Undergraduate course total about 300 belongs to more than 5000 kinds, originates from the Tertiary Period, on its ecologicaI distribution
In addition to the arctic and the alpine zone of cold, it is dispersed throughout the whole world, mainly originates in subtropical and tropical zones.They are distributed in pole not
The meat in same place, existing extremely special desert type starches plant, also has hygrophyte, is also much Tropical forests arbor, very
It is widely distributed weeds in field to many.The distribution center of Euphorbiaceae is India and Malaysian region and Brazil.China is about
72, which belong to more than 450, plants, and spreads all over each provinces and regions of China, mainly originates in southwest to Taiwan.
Euphorbia antiquorum (Euphorbia antiquorum) is Euphorbiaceae euphorbia, belongs to root of Beijing euphorbia subgenus, alias hundred
Walk Hui Yang, camwood leads to, the small Green Dragon, justifies Buddha's warrior attendant one《Yunnan Chinese herbal medicine》；Huo Yang le one《Sward pharmacological property is slightly wanted》；Rattle stick one《Zhejiang
River medicinal plant will》；Sword in thousand, Buddha's warrior attendant tree one《The main poisonous plant in south》Deng.It is be grown near cottages or near field more,
More works are ornamental or hedge plant is cultivated.The ground such as India, Sri Lanka are originated in, there is cultivation in the present all over the world.Euphorbia antiquorum
Phytomorph is perennial shrub.Stem is that meat is upright, includes the milk of thick white；Old stem is cylindric, sprig green meat
Matter has 3-5 items thickness and makees corrugated wing, and the recess of wing has a pair of sharp thorn more.Single leaf alternate, more lifes have short handle at branch end,
It is born by wing side, is obovate, blade face is dark green, and back side color is slightly shallow.Euphorbia antiquorum is the traditional dai medicine in China, and medicinal part is stem
Portion, there are two types of main pharmaceutical procedures：Go its thorn, using fresh herb；Slice, dries, is used after processing.It is recorded according to Chinese medicine ancient book, Buddha's warrior attendant
It is China's tradition dai medicine to compile (E.antiquorum), and stem has the benefits of defaecation, detumescence, desinsection.Expansion, acute stomach can be treated
Inflammation, pyogenic infections, help insane, mycotic ulcer caused by venereal disease, skin disease.Its leaf has the effect of removing toxic substances row addiction, thermalization that disappears is stagnant.Tropical diarrhea, bruise can be treated
The dirty vomiting and diarrhoea convulsion of product addiction nameless sores or boils, rash treats sore, cholera.
The correlative study of Euphorbia antiquorum is seldom, and current existing Euphorbia antiquorum patent only has 6, wherein introducing the grafting side of plant
Method three.Another 3 are：The patent application document of number of patent application CN200810130374.X《A kind of ascitic type liver cancer for the treatment of
Chinese herbal and crude drugs preparations》In Chinese herbal compound preparation in simply medicine be Euphorbia antiquorum (pistil)；Number of patent application
The patent application document of CN201210299297.7《Euphorbia plant (Euphorbiaceae) active material and preparation method thereof
With application》Animal viral infections can be treated by introducing Euphorbia antiquorum, and prepare the purposes on animal disease resistant cytotoxic drug；Number of patent application
The patent application document of CN201310369369.5《Euphorbia plant activity for inhibiting cancer and/or growth of tumour cell
Substance and its application》It is a kind of Euphorbia antiquorum composition to talk about, for the active material of ethyl alcohol extraction or the active matter of n-hexane extraction
Matter, and contain autophagy inhibitor.But there is no clearly isolate Euphorbia antiquorum structure and identify its activity in all patents.
Two compounds that this research is isolated from Euphorbia antiquorum, and to its active anticancer, especially anti-esophageal squamous cell carcinoma is lived
Property and liver cancer activity studied, as a result confirm that compound that this research is isolated from Euphorbia antiquorum has good anti-esophageal squamous cell
Cancer and liver cancer activity.
Invention content
1. to solve the problems, such as
It is an object of the invention to：
First, problem to be solved of the present invention is the compound for finding to extract from Euphorbia antiquorum and the use of the compound
On the way.Second, for Euphorbia antiquorum in the prior art active component it is indefinite, using being restricted the problems such as, the present invention provide two
The active material detached in kind Euphorbia antiquorum, two kinds of active materials have active anticancer, active effect good.Third, it is of the invention
Purpose also resides in offer using this compound as the anticancer pharmaceutical composition of active ingredient；It is prepared by such compound and combinations thereof
Anticancer drug, the application in especially anti-esophageal squamous cell carcinoma drug and liver-cancer medicine.
2. technical solution
To solve the above-mentioned problems, the present invention is realized especially by following technical scheme：
Compound for inhibiting cancer and/or growth of tumour cell, structure are：
Compound 1
(1-(4-hydroxy-3-methoxyphenyl)-2-{4[(E)-3-acetoxypropen-1-yl]-2-
Methoxyphenoxy } propanl, 3-diol)
Compound 2
(1-(4-hydroxy-3-methoxyphenyl)-2-{4[(E)-3-acetoxypropen-1-yl]-2-
Methoxyphenoxy } propanl, 3-diol 3-acetate)
Preferably, it is euphorbia plant (Euphorbiaceae) active material
Preferably, the euphorbia plant is Euphorbia antiquorum.
Preferably, the compound, application in preparation of anti-tumor drugs.
Preferably, the tumour is the incidence originating from people, esophagus, brain, thyroid gland, pancreas, lungs, liver, food
Pipe, stomach, mammary gland, kidney, gall-bladder, colon or rectum, ovary, uterus, cervix, prostate, bladder, testis it is primary or secondary
Cancer and sarcoma.
Preferably, the compound, it is characterised in that：It can be used for the application in treating esophageal squamous cell carcinoma drug.
Preferably, the compound, it is characterised in that：It can be used for the application in treating liver-cancer medicine.
3. advantageous effect
Compared with the prior art, beneficial effects of the present invention are：
(1) compound 1 is noval chemical compound, and compound 2 is known compound, but does not have the above-mentioned antitumor work of document report
Property.
There are blank, medical value underexploitations for the research of Euphorbia antiquorum at present, to its chemical composition and pharmacological research
It is less.
Current existing Euphorbia antiquorum related patents only have 6, wherein only 3 of research pharmacological action.Respectively：Patent
The patent application document of application number CN200810130374.X《A kind of Chinese herbal and crude drugs preparations for treating ascitic type liver cancer》In medium-height grass
Medicine is Euphorbia antiquorum (pistil) simply in medicine compound preparation；The patent application document of number of patent application CN201210299297.7《Greatly
Halberd section plant (Euphorbiaceae) active material and the preparation method and application thereof》Animal virus can be treated by introducing Euphorbia antiquorum
Infection, and prepare the purposes on animal disease resistant cytotoxic drug；The patent application document of number of patent application CN201310369369.5《With
In the euphorbia plant active material and its application that inhibit cancer and/or growth of tumour cell》It is a kind of Euphorbia antiquorum combination to talk about
Object, the active material of the active material or n-hexane extraction that are extracted for ethyl alcohol, and contain autophagy inhibitor.But all patents
In there is no clearly isolate Euphorbia antiquorum structure and identify its activity.
The present invention is extracted two kinds of biologically active compounds from Euphorbia antiquorum, solves chemical composition in Euphorbia antiquorum
Complexity, the uncontrollable problem of quality, the compound of extraction, pharmacological mechanism is more precisely.
The present invention gropes by a large amount of experiment, from be found that in Euphorbia antiquorum compound and its in antitumor drug
Using, the experimental results showed that, compound 1 and compound 2 can treat tumour；The tumour is the incidence originating from people, food
Road, brain, thyroid gland, pancreas, lungs, liver, oesophagus, stomach, mammary gland, kidney, gall-bladder, colon or rectum, ovary, uterus, uterus
The primary or secondary cancer and sarcoma of neck, prostate, bladder, testis；
The compound that the present invention separates and extracts Euphorbia antiquorum, using mtt assay to chemical combination separated in Euphorbia antiquorum
Object carries out Activity determination, it was demonstrated that its antitumor activity.
Description of the drawings
Fig. 1 is the separated active material 1 of Euphorbia antiquorum to normal cell (HEEC) and three plants of esophageal squamous cell carcinoma cells
The proliferation function of (KYSE410 KYSE450 TE13).
Fig. 2 is the separated active material 2 of Euphorbia antiquorum to normal cell (HEEC) and three plants of esophageal squamous cell carcinoma cells
The proliferation function of (KYSE410 KYSE450 TE13).
Specific implementation mode
With reference to embodiment, the present invention is described further, as described below, is only the preferable implementation to the present invention
Example, not limits the present invention, any person skilled in the art is possibly also with the disclosure above
Technology contents be changed to the equivalent embodiment changed on an equal basis.Without departing from the concept of the present invention, according to the present invention
Technical spirit any simple modification that following embodiment is done or equivalent variations, all fall in protection scope of the present invention.
The proliferation function of 1 compound 1 of embodiment and compound 2 to normal cell and esophageal squamous cell carcinoma cell
One, experiment material, instrument and reagent
1 experiment material
1.1 drug：The compound 1 and compound 2 of this laboratory separation
Docetaxel (Hengrui Medicine Co., Ltd., Jiangsu Prov.)
1.2 cell strain：
People's normal esophageal epithelial cell (HEEC), people's esophageal squamous cell carcinoma cell strain (TE-13, KYSE-450, KYSE-410) by
This seminar preserves.
2 main experimental preparation of reagents methods
2.1 RPMI-1640 preparation methods：Take 10.4g RPMI-1640 dry powder, 2g NaHCO3, 50mg penicillin,
100mg streptomysins, dd H2O 800mL, magnetic stirring apparatus make it mix well, HCl tune pH to 7.4, and 0.22 μm of filter is crossed and filtered out
Bacterium, packing, 4 DEG C save backup.
2.2 PBS liquid making methods：NaCl 8.0g, KCl 0.2g, Na2HPO41.44g KH2PO40.24g adds water constant volume
To 1L, autoclave sterilization, 4 DEG C save backup.
2.3 trypsase preparation methods：It is dissolved with PBS liquid, 4 DEG C are stirred overnight, 0.22 μm of millipore filter filtration sterilization,
4 DEG C save backup.Use a concentration of 0.25%.
2.4, which weigh 0.5mg MTT powder, is dissolved in PBS, and is settled to 100mL, is kept in dark place in -20 DEG C after packing.
Three, experimental method
The preparation of 3.1 test samples
It weighs that sample is appropriate, the stoste of 100mg/mL is dissolved into DMSO, a certain amount of stoste is taken to be matched with 1640 culture mediums
It is made as the mother liquor of 100 μ g/mL, 0.22 μm of organic system filter filtration sterilization of sterilizing is used in combination.With 1640 culture mediums times of serum-free
Than the test solution for diluting 5 gradients.
Using taxol as positive control, 10 μ g/mL are diluted to 1640 culture mediums of serum-free, with the 1640 of serum-free
Culture solution dilutes 10 times successively, is diluted to the test solution of 5 gradients altogether.
3.2 cell culture
Normal cell and tumour cell are with 1640 culture mediums of 10% fetal calf serum in 37 DEG C, 5% CO2In incubator
Culture, logarithmic growth phase cell is for testing.
The preparation of 3.3 cell suspensions
Cell in exponential phase pancreatin digestive juice is digested, cell count is carried out, with 10% fetal calf serum
1640 culture mediums, which are diluted in every mL, contains 3 × 104The cell suspension of a cell concentration.
3.4 cell administration
100 μ L cell suspensions will be added in 96 orifice plates per hole, cell concentration is 3 × 103A/hole, after cell is adherent respectively
The test solution of various concentration, 100 holes μ L/ is added, each dosage makees 3 multiple holes.Positive controls taxol is equally administered.
Negative control group adds 100 holes μ L/ of serum-free 1640 culture medium, makees 5 multiple holes.96 orifice plates are placed in 37 DEG C, 5% CO2Incubator
Middle culture.96 orifice plates are placed under microscope after 48h, observation control group and experimental group cell growth state.
3.5 cell dyeings and measurement
After 96 orifice plate culture 48h plus MTT, 20 holes μ L/ are taken out after setting 37 DEG C of incubator culture 4h, and exhaust culture medium, adds
150 holes μ L/ DMSO, at 570nm survey light absorption value, and using at 630nm as reference wavelength.
Four, experimental result
4.1 cell toxicant results
From fig. 1, it can be seen that the compound 1 can inhibit the proliferation function of three plants of esophageal squamous cell carcinoma cells.(50 μ of high concentration
G/mL) sample can reach 80% or more to the proliferation inhibition rate of KYSE410, KYSE450, can be with to the increment inhibiting rate of TE13
Reach 60% or more.But it is 60% or so that the compound, which also has normal cell certain toxicity, inhibiting rate,.
As can be seen from Figure 2, which can inhibit the proliferation function of three plants of esophageal squamous cell carcinoma cells.(50 μ of high concentration
G/mL) sample can reach 90% or more to the proliferation inhibition rate of KYSE410, KYSE450, can be with to the increment inhibiting rate of TE13
Reach 80% or more.But it is 60% or so that the compound, which also has normal cell certain toxicity, inhibiting rate,.
4.2 IC50Value compares
IC50Value is specifically shown in Table 1-1.
The IC of table 1-1 compounds 1 and 250It is worth (μ g/mL)
The proliferation function of 2 compound 1 of embodiment and compound 2 to liver cancer cells
Two, experiment material, instrument and reagent
1 experiment material
1.1 drug：The compound 1 and compound 2 of this laboratory separation
1.2 cell strain：HepG-2 cells, are preserved by this seminar.
2 main experimental preparation of reagents methods
2.1 DMEM culture medium preparation methods：Take DMEM dry powder, 2g NaHCO3, 50mg penicillin, 100mg streptomysins, dd
H2O 800mL, magnetic stirring apparatus make it mix well, HCl tune pH to 7.0, with distilled water constant volume to 1000ml, 0.22 μm of filter
Filtration sterilization, packing, 4 DEG C save backup.
2.2 PBS liquid making methods：NaCl 8.0g, KCl 0.2g, Na2HPO41.44g KH2PO40.24g adds water constant volume
To 1L, autoclave sterilization, 4 DEG C save backup.
2.3 trypsase preparation methods：It is dissolved with PBS liquid, 4 DEG C are stirred overnight, 0.22 μm of millipore filter filtration sterilization,
4 DEG C save backup.Use a concentration of 0.25%.
2.4, which weigh 0.5mg MTT powder, is dissolved in PBS, and is settled to 100mL, is kept in dark place in -20 DEG C after packing.
Three, experimental method
The preparation of 3.1 test samples
It weighs that sample is appropriate, the stoste of 100mg/mL is dissolved into DMSO, a certain amount of stoste DMEM culture mediums is taken to match
It is made as the mother liquor of 100 μ g/mL, 0.22 μm of organic system filter filtration sterilization of sterilizing is used in combination.With the DMEM culture mediums times of serum-free
Than the test solution for diluting totally 6 gradients.
3.2 cell culture
Tumour cell is with the DMEM culture mediums of 10% fetal calf serum in 37 DEG C, 5% CO2It is cultivated in incubator, takes logarithm
Growth period cell is for testing.
The preparation of 3.3 cell suspensions
Cell in exponential phase pancreatin digestive juice is digested, cell count is carried out, with 10% fetal calf serum
1640 culture mediums, which are diluted in every mL, contains 3 × 104The cell suspension of a cell concentration.
3.4 cell administration
100 μ L cell suspensions will be added in 96 orifice plates per hole, cell concentration is 3 × 103A/hole, after cell is adherent respectively
The test solution of various concentration, 100 holes μ L/ is added, each dosage makees 3 multiple holes.Negative control group adds serum-free 1640 to train
5 multiple holes are made in 100 holes μ L/ of nutrient solution.96 orifice plates are placed in 37 DEG C, 5% CO2It is cultivated in incubator.96 orifice plates are placed in after 48h
Under microscope, observation control group and experimental group cell growth state.
3.5 cell dyeings and measurement
After 96 orifice plate culture 48h plus MTT, 20 holes μ L/ are taken out after setting 37 DEG C of incubator culture 4h, and exhaust culture medium, adds
150 holes μ L/ DMSO, at 570nm survey light absorption value, and using at 630nm as reference wavelength.
Four, experimental result
4.1 cell toxicant results
From table 2-1 it is found that compound 1 and compound 2 can inhibit the proliferation function of HepG-2 cells.
Table 2-1 compounds 1 and compound 2 test the toxic effect of HepG-2 cells
4.2 IC50Value
Experimental result shows, Euphorbia antiquorum compound 1 setting six concentration (100,25,6.25,1.56,0.39,
0.098 μ g/mL), the destructive rate to HepG-2 cells is respectively 85.90,74.33,33.50,6.88,4.33,2.21%, IC50
A concentration of 11.94 μ g/mL.
Euphorbia antiquorum compound 2 setting six concentration (100,25,6.25,1.56,0.39,0.098 μ g/mL), it is right
The destructive rate of HepG-2 cells is respectively 88.90,85.43,36.90,7.35,6.66,4.55%, IC50A concentration of 9.11 μ g/
mL。
The present invention is described according to preferred embodiment.It should be understood that the description of front and embodiment are only
In order to demonstrate the invention.On the premise of without departing from the spirit and scope of the present invention, those skilled in the art can be with
The a variety of alternatives and improvement project for designing the present invention, should be understood within protection scope of the present invention.
Claims (5)
1. a kind of compound, such as one of lower structure：
2. chemical combination application in preparation of anti-tumor drugs according to claim 1.
3. compound application in preparation of anti-tumor drugs according to claim 1, it is characterised in that：The tumour
For the incidence originating from people, oesophagus, brain, thyroid gland, pancreas, lungs, liver, oesophagus, stomach, mammary gland, kidney, gall-bladder, colon
Or rectum, ovary, uterus, cervix, prostate, bladder, testis primary or secondary cancer and sarcoma.
4. application according to claim 3, it is characterised in that：The tumour is esophageal squamous cell carcinoma.
5. application according to claim 3, it is characterised in that：The tumour is liver cancer.
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| Application Number | Priority Date | Filing Date | Title |
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810268575.XA CN108409571A (en) | 2018-03-23 | 2018-03-23 | The compound for treating cancer extracted from Euphorbia antiquorum |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140056995A1 (en) * | 2012-08-27 | 2014-02-27 | Mackay Memorial Hospital | Use of compounds isolated from euphorbia neriifolia for treating cancer and/or thrombocytopenia |
| CN103936590A (en) * | 2014-05-05 | 2014-07-23 | 中国科学院昆明植物研究所 | Diterpenoid compounds in euphorbia pekinensis, medicine composition thereof, and application of same in pharmacy |
| CN105732381A (en) * | 2014-12-30 | 2016-07-06 | 合生技股份有限公司 | Compounds from antrodia camphorata, method for preparing the same and use thereof |
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2018
- 2018-03-23 CN CN201810268575.XA patent/CN108409571A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140056995A1 (en) * | 2012-08-27 | 2014-02-27 | Mackay Memorial Hospital | Use of compounds isolated from euphorbia neriifolia for treating cancer and/or thrombocytopenia |
| CN103936590A (en) * | 2014-05-05 | 2014-07-23 | 中国科学院昆明植物研究所 | Diterpenoid compounds in euphorbia pekinensis, medicine composition thereof, and application of same in pharmacy |
| CN105732381A (en) * | 2014-12-30 | 2016-07-06 | 合生技股份有限公司 | Compounds from antrodia camphorata, method for preparing the same and use thereof |
| EP3240772A1 (en) * | 2014-12-30 | 2017-11-08 | Oneness Biotech Co., Ltd | Compounds from antrodia camphorata, method for preparing the same and use thereof |
Non-Patent Citations (3)
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| JAKUPOVIC, J.ET AL: "New coumaric acid derivatives and other constituents from Argentinian Baccharis species", 《REVISTA LATINOAMERICANA DE QUIMICA》 * |
| KIM K，ET AL.: "Lignan glucosides from Sinomenium acutum rhizomes", 《BIOSCIENCE, BIOTECHNOLOGY, AND BIOCHEMISTRY》 * |
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Application publication date: 20180817 |