CN107875143B - Application of -2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl in pharmacy - Google Patents
Application of -2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl in pharmacy Download PDFInfo
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- CN107875143B CN107875143B CN201711061739.3A CN201711061739A CN107875143B CN 107875143 B CN107875143 B CN 107875143B CN 201711061739 A CN201711061739 A CN 201711061739A CN 107875143 B CN107875143 B CN 107875143B
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
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Abstract
The invention discloses application of -2 (E)-alkene -1- pentanone of compound 1-4 '-hydroxy phenyl -5- phenyl in pharmacy, present invention discover that -2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl has good inhibiting effect to hepatitis C virus NS/4A protease, hepatitis C, liver cancer and gastric cancer, can individually be compounded with other components for preventing and treating hepatitis C, liver cancer and the drug of gastric cancer.
Description
Technical field
The present invention relates to technical field of pharmaceuticals, more particularly to compound 1-4 '--2 (E)-alkene-of hydroxy phenyl -5- phenyl
1- pentanone treats the application in hepatitis C, liver cancer and gastric cancer medicament.
Technical background
Hepatitis C caused by human infection Hepatitis C Virus, it has also become the most intractable health problem in the whole world is complete at present
The world have 1.7 hundred million people infection (McHutchison, J.G., and K.Patel.Hepatology, 2002,36, S245-
S252.；Seeff,L.B.,and J.H.Hoofnagle.Clin.Liver Dis.,2003,7:261–287.).If without drug
Treatment, Long-term Infection Hepatitis C Virus will develop into the diseases such as chronic hepatitis, hepatonecrosis, liver cancer (Lindenbach,
B.D.；Rice,C.M.Nature,2005,436,933.).Current most effective therapeutic agent is expensive Suo Fei boolean
(N Engl J Med.2015 Dec 31；373 (27): 2618-28.), for the developing countries, clinically common method
It is Peg-IFN alpha-2b joint Lijin Ba Wei, this method is lower than 50% to generally existing I type treating hepatitis c effective percentage,
Interferon is used for a long time, and there are many side effects, such as: the reduction and depression of leucocyte, blood platelet, neutrophils；It is long
Phase uses Lijin Ba Wei, will also generate the side effects such as hemolytic anemia, prevent patient is from continued treatment, therefore develop it is unique,
Effectively, especially urgent (Kai Lin, the et al.Antimicrobial Agents and of safer Remedies for hepatitis C object
Chemotherapy,2006,50,1813-1822.)。
Hcv protease NS3/4A plays an important role during virus is skillful, has been found to be discovery
Treat one of the Effective target site of hepatitis C drug (Yao, N.H.；Hesson,T.；Cable,M.； Hong,Z.；Kwong,
A.D.；Le,H.V.；Weber,P.C.Nat.Struct.Biol.,1997,4,463.；Chu, M.；Mierzwa,R.；
Truumees,I.；King,A.；Patel,M.；Berrie,R.；Hart,A.；
Butkiewicz,N.；Mahapatra,B.D.；Chan,T.M.；Puar,M.S.Tetrahedron Lett.
1996,37,7229.).Mesh first three hepatitis C NS3/4A protease inhibitors, BILN 2061 (Hinrichsen, H.,
Y.Benhamou,H.Wedemeyer,M.Reiser,R.E.Sentjens, J.L.Calleja,X.Forns,A.Erhardt,
J.Cronlein,R.L.Chaves,C.L.Yong,G. Nehmiz,and G.G.Steinmann.Gastroenterology,
2004,127:1347–1355.；Lamarre,D., P.C.Anderson,M.Bailey,P.Beaulieu,G.Bolger,
P.Bonneau, M.Bos,D.R.Cameron,M.Cartier,M.G.Cordingley,A.M.Faucher,N.
Goudreau,S.H.Kawai,G.Kukolj,L.Lagace,S.R.LaPlante,H.Narjes, M.A.Poupart,
J.Rancourt,R.E.Sentjens,R.St George,B.Simoneau,G. Steinmann,D.Thibeault,
Y.S.Tsantrizos,S.M.Weldon,C.L.Yong,and M. Llinas-Brunet.Nature,2003,426:186–
189.),VX-950(Reesink,H.W.,S.Zeuzem,C. J.Weegink,N.Forestier,A.van Vliet,J.van
de Wetering de Rooij,L.McNair,S. Purdy,H.-M.Chu,and
P.L.M.Jansen.2005.Presented at 36th Digestive Disease Week,Chicago,Ill.；
Reesink,H.W.,S.Zeuzem,C.J.Weegink,N.Forestier,A.van Vliet,J.van de Wetering
de Rooij,L.A.McNair,S.Purdy,H.-M.Chu,and P.L.M. Jansen.Hepatology,2005,42:
234A) and SCH 503034 (Yi, M., X.Tong, A.Skelton, R. Chase, T.Chen, A.Prongay, S.L.Bogen,
A.K.Saksena,F.G.Njoroge,R.L. Veselenak,R.B.Pyles,N.Bourne,B.A.Malcolm,and
S.M.Lemon.J.Biol.Chem. 2005.(Epub ahead of print；doi:10.1074/
Jbc.M510246200.)), it is significant in efficacy by clinic confirmation, but mostly peptide inhibitor, synthesis is difficult, and has certain
Toxic side effect.
Gastric cancer is also one of China's common malignant gastrointestinal tumors, and about 170,000 people die of gastric cancer every year, increases 400,000 diseases newly
People's (practical internal medicine journal of China, 20144, (4), 408-415).Early carcinoma of stomach symptom is unobvious, is not easy to be found, late gastric cancer
After patient generallys use operation removal lesion tissue, then carry out related chemotherapeutic treatment, but curative effect it is little (Chinese clinical tumor,
2010,37 (3), 171-175), therefore the curing gastric cancer drug found efficiently, less toxic is extremely urgent.
It is currently employed for clinical anti-tumor drug, 30% derivative from natural resources and native compound,
They have unique physiological activity, preferable curative effect and low toxicity, and mention for further chemical synthesis and structural modification
The chemical structure (Journal of Natural Products, 2007,70 (3), 461-477) of novel and unique is supplied.
Chinese medicine winter daphne (Daphne papyracea Wall.ex Steud.) is Thymelaeceae Daphne evergreen shrubs, also known as
Mountain spicy skin, Peng Lai flower, snowflake, takes that fragrant flower, wild dream flower, mountain dream flower, snowfield are bloomed, red general pipeline, snow freeze flower by force at musk deer capsule.Main point
It is distributed in the hillside shrubbery or careless slope on height above sea level 1000-3100 meters of the ground such as Sichuan, Guizhou, Yunnan, has and control abscess of throat, dentalgia,
Rheumatalgia and other effects (" China's book on Chinese herbal medicine " Shanghai Scientific & Technical Publishers 1999,5,414,4432.).Using classical Phytochemistry means,
- 2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl extracting and developing and is purified from Chinese medicine winter daphne, passes through matter
Spectrum, nuclear-magnetism and with bibliography compare, determine the structure of the compound.(CHINA JOURNAL OF CHINESE MATERIA MEDICA, 2012,37 (22), 3434-
3436.))
Summary of the invention
The technical problem to be solved by the present invention is to overcome, the pharmaceutical synthesis of existing treatment hepatitis C is difficult, side effect is more
Defect, winter daphne ketone compounds 1-4 '--2 (E)-alkene -1- pentanone of hydroxy phenyl -5- phenyl is provided and is preparing hepatitis C virus
Application in malicious NS3/4A protease inhibitors, treatment hepatitis C, liver cancer and gastric cancer medicament.
Technical solution of the present invention includes:
Compound 1-4 '--2 (E)-alkene -1- pentanone of hydroxy phenyl -5- phenyl answering in preparation treatment hepatitis C drug
With.Wherein, -2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl is in 100 μ g/ml, inhibit hepatitis C virus NS/
4A proteinase activity is 56.5%.
Application of compound 1-4 '--2 (E)-alkene -1- pentanone of hydroxy phenyl -5- phenyl in preparation treatment liver-cancer medicine.
Wherein, inhibit the IC of HepG2 cell50It is 2.7 ± 4.8 μM.Thus it proves that the compound can effectively inhibit liver cancer, can be used to prepare
The drug of anti-liver cancer and anti-.
Application of compound 1-4 '--2 (E)-alkene -1- pentanone of hydroxy phenyl -5- phenyl in preparation treatment gastric cancer medicament.
Wherein, -2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl inhibits human stomach cancer cell line SGC7901, AGS, HGC, N87
IC50Respectively 4.2 ± 6.7 μM, 7.0 ± 9.1 μM, 9.4 ± 7.5 μM and 12 ± 5.4 μM.Therefore, 1-4 '-hydroxy phenyl -5-
Phenyl -2 (E)-alkene -1- pentanone can be used to prepare the drug of anti-gastric cancer, have good application and development prospect.
Compared with prior art, present invention discover that winter daphne letones 1-4 '-hydroxy phenyl -5- from Chinese medicine winter daphne
Phenyl -2 (E)-alkene -1- pentanone has certain inhibition to hcv protease NS3/4A, can preferably inhibit people
Stomach cancer cell and liver cancer cells, therefore can be individually used for preparing hcv protease NS3/4A inhibitor, preparation gastric cancer
With the drug of liver cancer, and the drug of prevention and treatment hepatitis C, gastric cancer and liver cancer, can also be compounded with other components for pre-
Anti- and treatment hepatitis C is in the drug of preparation hepatitis, gastric cancer and liver cancer.
Detailed description of the invention
- 2 (E)-alkene -1- pentanone of Fig. 1 1-4 '-hydroxy phenyl -5- phenyl1H-NMR spectrum
- 2 (E)-alkene -1- pentanone of Fig. 2 1-4 '-hydroxy phenyl -5- phenyl13C-NMR spectrogram
Fig. 3 various concentration 1-4 '--2 (E)-alkene -1- pentanone of hydroxy phenyl -5- phenyl is thin to human gastric cancer SGC7901 cell strain
Born of the same parents' period
Fig. 4 1-4 '--2 (E)-alkene -1- pentanone of hydroxy phenyl -5- phenyl is to human gastric cancer SGC7901 cell scratch experiment knot
Fruit schematic diagram.
Specific embodiment
Present invention will be further explained below with reference to the attached drawings and examples, but not as any limitation of the invention.
In order to confirm the structure of extracted compound and verify its anti-hepatitis c virus, liver cancer and Effect on Gastric Cancer, this hair
It is bright done it is relevant experiment it is as follows:
1, the Structural Identification of compound
Using classical Phytochemistry means, extracting and developing is purified from Chinese medicine winter daphne, obtains target compound, warp1H-
NMR,13It C-NMR, MS and is compareed with document, determines structure: white solid；ESI-MS m/z 275[M+ Na]+；1H NMR
(Pyridine-d5, 400MHz) and δ: 2.63 (2H, t, J=8.0Hz, H-4), 2.84 (2H, t, J=8.0Hz, H-5), 6.87
(1H, d, J=8.7Hz, H-3), 7.04 (1H, d, J=6.0,15.0Hz, H-2), 7.20 (1H, d, J=6.0,15.0Hz, H-
), 4 " 7.13-7.26 (4H, m, H-2 ", 3 ", 5 ", 6 "), 7.83 (2H, d, J=8.7Hz, H-2 ', 6 '), 12.3 (1H ,-OH)；13C NMR(Pyridine-d5,100MHz)δ:34.6(C-4), 34.8(C-5),116.2(C-3′),116.3(C-5′),
126.5(C-2),126.6(C-4″),128.8(C-3″,5″), 128.9(C-2″,6″),130.0(C-1′),131.8(C-2′,
6′),141.7(C-1″),146.9(C-3),163.7(C-4′), 188.2(C-1).The above spectroscopic data and number reported in the literature
According to unanimously (Wang Mingshi, LIU WEIGUO, Xin jasmine Juan, Nanjing pharmaceutical college journal, 1984,15 (2): 1.), compound is confirmed as 1-
- 2 (E)-alkene -1- pentanone of 4 '-hydroxy phenyl -5- phenyl.
Molecular formula are as follows: C17H16O2, structural formula is as follows:
2, purity test:
2.1 thin-layered chromatography: " one annex VI B tlc determination of Chinese Pharmacopoeia 2005 version is shone.
- 2 (E)-alkene -1- pentanone of the 1-4 ' for taking purification to obtain-hydroxy phenyl -5- phenyl adds methanol that the molten of 1mg/ml is made
Liquid, as test solution.
Test liquid 5mL is taken, is put in silica G F254On lamellae, using ascending development mode, 1-4 '-hydroxy phenyl -5- benzene
Base -2 (E)-alkene -1- pentanone is with chloroform-acetone (5:1), chloroform-methanol (40:1) and petroleum ether: acetone (1:1) is solvent exhibition
It opens, the silica G F of subsequent -2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl254Lamellae is examined in the UV lamp (254nm)
After knowledge, after iodine is aobvious, it is placed under daylight and checks.The result shows that: combine a variety of colour developing modes to examine knowledge through three kinds of solvent development systems,
In single spot.Therefore it is examined through thin-layered chromatography and knows -2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl for sterling.
3, evaluating drug effect:
3.1 compound anti-hepatitis c virus NS3/4A albumen enzyme effects
Test philosophy: fluorescence method
Detecting instrument: TECAN GENios, electronic analytical balance METTLER AE-240 Switzerland.
Kit: SensoLyte 520HCV protease reagent box (lot number: AK71145-1011, U.S. San Jose
AnaSpec)。
Protease: HCV NS3/4A protease (lot number: 046-079, U.S. San Jose AnaSpec).
Test medicine: winter daphne is newly plain.
Positive control: Embelin (Japan folic hill university and Chinese institute of Pharmaceutical Research drug metabolism engineering dividing line chemical standard
Product)
Data process&analysis: data indicate (X ± S) with mean standard deviation, pass through 2003 Excel of Microsoft Windows
Software completes statistical procedures, and measurement data uses STDEV-t checking computation inhibiting rate.
Inhibiting rate calculation formula:
Inhibiting rate %=100 × (Fvehicle-Fsample)/Fvehicle；F in formula is control group and sample sets fluorescent value.
Experimental method and result:
Test the preparation (operating by kit instruction manual) of solution:
Buffer solution: 2X test buffer (Component D), 1M DDT (Component F) and deionized water are pressed
1:0.06:1 is mixed, and ice bath is spare.
The dissolution of HCV NS3/4A protease substrate: add the DMSO (Component C) of 0.12ml to HCV NS3/4A albumen
Zymolyte [Ac-Asp-Glu-Dap (QXLTM520)-Glu-Glu-Abu-COO-Ala-Ser-Cys (5-FAMsp)-NH2]
(Component A), freezes as -20 DEG C of stock solution.Stock solution is taken before experiment every time, it is dilute in 1:100 ratio with buffer solution
It releases, it is ready-to-use.
HCV NS3/4A protein enzyme solution: protein enzyme solution is diluted 20 or 60 times with buffer solution.
Measuring method (is operated) by kit instruction manual: in 384 hole black plates (BD Falcon company, the U.S.),
First be separately added into substrate blank solution (Substrate Control, SC), solvent blank solution (Vehicle Control,
VC), positive control (Positive Control, PC), inhibitor control (Inhibitor Control, IC), test chemical combination
Object compares (Test Compound Control, TCC), adds HCV NS3/4A protease and substrate.Each concentration is 3
A multiple holes after concussion mixes, are warmed up at 37 DEG C and are incubated 30 minutes, through TECAN GENios in excitation wavelength 485nm and launch wavelength
Fluorescence intensity is tested under 535nm.Experimental result is shown in Table 1.
Inhibiting rate (n=3) of the 1 daphneolon class compound (100g/ml) of table to HCV NS3/4A protease
Positive control (PC): HCV NS3/4A protease positive control Embelin, data are as follows: average value ± relative standard
Deviation (independent experiment value three times).
Isolated experiment is thought at present, the IC of monomeric compound50Just there is stronger HCV-Ab IgG NS3/4A in 10g/mL or less
Albumen enzyme effect.In 100g/mL, -2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl is to HCV NS3/4A protease
Inhibiting rate has certain inhibiting effect up to 56.3%, to hepatitis C HCV NS3/4A protease.
- 2 (E)-alkene -1- pentanone resisting human gastric cancer SGC7901, AGS of 3.2 compound 1-4 '-hydroxy phenyl -5- phenyl, HGC,
The effect of N87 and hepatoma H22 cells.
3.2.1 cell culture
Human stomach cancer cell line SGC7901, AGS, HGC, N87 and hepatoma H22 cells are purchased from cell institute, the Shanghai Chinese Academy of Sciences,
With (the U.S. Gibco of RPMI 1640；31800-014) full culture medium culture is (containing 10% FBS (Zhejiang day Hangzhoupro biology；11011-
And 1%P/S (U.S. Cyagen 8611)；S0022)), 37 DEG C are put in, 5%CO2In incubator (U.S. Thermo).
3.2.2 MTT experiment
Method: logarithmic growth phase human stomach cancer cell line SGC7901, AGS, HGC, N87 and hepatoma cell strain respectively
Cell suspension is made in cell by HepG2, and 4000/hole is inoculated in 96 orifice plates overnight.After cell culture culture 24 hours adherent
Suck original culture medium.Experiment is divided into blank control group, drug-treated group.Blank group replacement contains the 1640 of 10% fetal calf serum
Culture medium；Drug-treated group be 0.5,1,2,5,10,20 μM -2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl or
Taxol (U.S. Sellect；S1150) 100 hole μ L/, in 37 DEG C, 5%CO2Incubator culture 48 or after 72 hours is added 10
μ L MTT (final concentration 0.5mg/mL；Give birth to work in Shanghai；It 298-93-1) sets after incubator reacts 4 hours and abandons culture medium, 200 μ are added
L DMSO (traditional Chinese medicines；30072418) sufficiently dissolution, dark place dispose 10min, utilize microplate reader (U.S. Bioteck；Power
Wave XS2) measurement light absorption value OD (wavelength 490nm), and cell survival is calculated according to light absorption value, each processing is arranged 6
Repeating hole.
Cell survival rate (%)=△ ODDrug-treated/△ODBlank control×100。
Experimental result: -2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl to human stomach cancer cell line SGC7901,
The IC of AGS, HGC, N87 and hepatoma H22 cells50Respectively 4.2 ± 6.7 μM, 7.0 ± 9.1 μM, 9.4 ± 7.5 μM, 12 ±
5.4 μM and 2.7 ± 4.8 μM.- 2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl to human stomach cancer cell line SGC7901,
The growth of AGS, HGC, N87 and hepatoma H22 cells has good inhibiting effect.
3.2.3 flow cytometry
Cell suspension is made in cell by logarithmic growth phase human gastric cancer SGC7901, and 1 × 105A/hole is inoculated in 6 orifice plates
In overnight, give certain density medicine irritation after 24 hours, collect cell arrive 15ml centrifuge tube, centrifugation abandon supernatant, addition
Cell is resuspended in 300ml PBS, the dehydrated alcohol of 700ml pre-cooling is added dropwise, side edged vortex, 4 DEG C fixed overnight；On centrifugation is abandoned
Clearly, and with PBS cell is washed；With contain 100mg/ml RNaseA and 20mg/ml PI (U.S. Sigma；P-4170 PBS)
Cell is resuspended in 500ml, and 37 DEG C are protected from light incubation 1 hour, and supernatant is abandoned in centrifugation, and cell is resuspended with 500ml PBS, uses flow cytometer
(U.S. BD；FACS Calibur Flowcytometer) the measurement cell cycle, as a result see Fig. 4.
Flow cytometry experiments the results show that cell cycle influence, SubG1 increase, prompt compound 1-4 '-hydroxyl
- 2 (E)-alkene -1- pentanone of phenyl -5- phenyl can induce cell apoptosis, and cause cell death.
3.2.4 scratch experiment
Gastric carcinoma cells SGC7901 is laid in 24 orifice plates, cell density 90-95%, is drawn in plate using 10 μ l pipette tips
One of scratch out is taken pictures, and is calculated as 0 hour (0h)；Then, drug is added in each hole in plate, uses inverted microscope (Japan
Olympus；IX73 it) was taking pictures respectively at 24 and 48 hours.Scratch experiment prompt: illustrate ability of creeping toward intermediate cell
It is stronger, that is to say, that transfer ability is stronger.
As shown in figure 4, scratch experiment result: -2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl can inhibit thin
Dysuria with lower abdominal colic is moved.
Several embodiments of the present invention are given below.
Embodiment 1: experiments verify that, in 100 μ g/mL, -2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl
Inhibiting rate to hcv protease NS3/4A is respectively 56.5%, can be used for preparing the drug for the treatment of hepatitis C.
Embodiment 2: experiments verify that, -2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl inhibits human liver cancer cell
HepG2IC50It is 2.7 ± 4.8 μM, it can be used for preparing the drug for the treatment of liver cancer.
Embodiment 3: experiments verify that, -2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl is to gastric carcinoma cells
The IC of SGC7901, AGS, HGC, N8750Respectively 4.2 ± 6.7 μM, 7.0 ± 9.1 μM, 9.4 ± 7.5 μM and 12 ± 5.4 μM；Together
When Flow cytometry experiments result also verify MTT experiment as a result, therefore -2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl can
It is used to prepare the drug for the treatment of gastric cancer.
Embodiment 4: taking -2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl, dry, pulverize, and is added appropriate auxiliary
Material, is made acceptable dosage form on the medicaments such as granule, capsule, tablet, oral solution, soft capsule, pill.
Embodiment 5: -2 (E)-alkene -1- pentanone of 1-4 '-hydroxy phenyl -5- phenyl is taken, dry, pulverize, other raw materials are added
Medicine compounding, is made acceptable dosage form on the medicaments such as granule, capsule, tablet, oral solution, soft capsule, pill.
It is above specific application example of the invention, there are other embodiments of the invention, all to use equivalent replacement
Or the technical solution that equivalent transformation is formed, it all falls within protection scope of the presently claimed invention.
Claims (2)
1. compound 1-4 '-hydroxy phenyl -5- phenyl -2 (EApplication of the)-alkene -1- pentanone in preparation treatment gastric cancer medicament.
2. application according to claim 1, it is characterised in that: 1-4 '-hydroxy phenyl -5- phenyl -2 (E)-alkene -1- pentanone,
Inhibit the IC of human stomach cancer cell line SGC7901, AGS, HGC, N8750Respectively 4.2 ± 6.7 μM, 7.0 ± 9.1 μM,
9.4 ± 7.5 μM and 12 ± 5.4 μM.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102249885A (en) * | 2011-05-16 | 2011-11-23 | 中国农业大学 | Composite method of (E)-1-(4-hydroxybenzene radial)-5-phenyl-2-alkene-1-pentanone |
| CN103027999A (en) * | 2011-11-28 | 2013-04-10 | 贵阳中医学院 | Traditional Chinese medicine winter daphne and novel application of extract of winter daphne in preparation of medicines |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102249885A (en) * | 2011-05-16 | 2011-11-23 | 中国农业大学 | Composite method of (E)-1-(4-hydroxybenzene radial)-5-phenyl-2-alkene-1-pentanone |
| CN103027999A (en) * | 2011-11-28 | 2013-04-10 | 贵阳中医学院 | Traditional Chinese medicine winter daphne and novel application of extract of winter daphne in preparation of medicines |
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