CN101628863B - New compounds separated from leaves of rubus corchorifolius and preparation method and application thereof - Google Patents
New compounds separated from leaves of rubus corchorifolius and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates three new compounds separated from leaves of rubus corchorifolius of which chemical names are separately ent-9 beta,16 alpha,17-trihydroxy-kauran-2-one, II, ent-16 alpha,17,19-trihydroxy-kauran-2-one and ent-2 beta,3 alpha,16 alpha,17-tetrahydroxy-kauranol. The compounds are prepared by using silica gel column chromatography, thin layer chromatography and crystallization repeatedly and the active experiment shows that the three compounds have anti-tumor effect.
Description
Technical field
The present invention relates to extraction separation goes out in the compound in rubus corchorifolius leaf one group of three new compound, preparation method with and in the purposes aspect the preparation antitumor drug.
Background technology
Rubus corchorifolius (Rubus corchorifolius L.f) belongs to a kind of machaka in the Rosaceae rubus.Grow in endroit, small stream limit, mountain valley, wasteland and the shrubbery height above sea level 300m～1500m more.Except northeast, the Inner Mongol, Qinghai, Xinjiang, Tibet, all there is distribution in the whole nation.Fujian the whole province various places all have Rubus corchorifolius to distribute, and the wild resource standing stock are quite big.China utilizes the with a long history of Rubus corchorifolius, and the write up of Rubus corchorifolius pharmaceutical use is just arranged in ancient book supplement to the Herbal, Compendium of Material Medica, " Mingyi Bielu ", " Shiliao Bencao ", its medicinal existing history of more than one thousand years.Rubus corchorifolius fruit, root and Ye Junke are used as medicine.The contained coumarin compound of over-ground part (leaf, young fruit and stem), the effect that has certain analgesia, anti-inflammatory, eliminates the phlegm and relieving asthma as eastern gelsemium henbane lactone.In the western Hunan, the Northwest of Hubei Province Rubus corchorifolius is as Miao ethnic group's medicine commonly used, be used for curing common frequently-occurring disease, as diarrhoea, hot eyes, alcoholism etc., determined curative effect.
The research of at present relevant Rubus corchorifolius mainly is the development and use aspect that concentrates on resource, and ChenBing Hua utilizes its composite fruit, is used for food-processing; Utilize its tannin as industrial chemicals, the chemical constitution study that closes Rubus corchorifolius again is on the increase in recent years, ChenBing Hua etc. have been separated to a kind of tonka bean camphor first from the Rubus corchorifolius cauline leaf, be accredited as 6-methoxyl group-umbelliferone through physics and chemistry test and multiple Spectrum Analysis, i.e. scopolactone (Scopletin); Report that simultaneously the Rubus corchorifolius complete stool contains tannin, flavonoid compound, over-ground part (leaf, stem, young fruit) contains coumarin compound, contains phenolic constituent and saponin in the root.Zhang Min records that general flavone content is 1.18mg/g in the compound in rubus corchorifolius leaf.Zhang Yan etc. have reported that the nutritive ingredient of certain kind of berries fruit obtains tea-polyphenol for people such as guarantor's gift extract from compound in rubus corchorifolius leaf, and content reaches 5.15%.Contain a large amount of tanning acid in the report Rubus corchorifolius fruits such as Bi Jinfeng.Composition in the report compound in rubus corchorifolius leaf alcohol extracts such as old snow perfume (or spice) mainly contains organic acid, carbohydrate, flavones and glucoside thereof, tannin, phenols, cardiotonic glycoside, tonka bean camphor, steroidal, terpene.Zhang Min etc. study the chemical ingredients at Rubus corchorifolius ethyl acetate extraction position, therefrom separate having obtained 2 kaurane diterpene new compounds.
Summary of the invention
The purpose of this invention is to provide isolated three new compounds from Rubus corchorifolius, by the thick method gained that extracts through silica gel column chromatography, thin-layer chromatography and crystallization repeatedly of compound in rubus corchorifolius leaf, activity experiment proves that this group compound has antitumor action.
Provided by the present invention one group of three new compound are through silica gel column chromatography repeatedly from the crude extract of compound in rubus corchorifolius leaf, the method gained of thin-layer chromatography and crystallization, chemical name is respectively: compound 1: mapping-9 β, 16 α, 17 trihydroxyies-kauri pine-2 ketone (ent-9 β, 16 α, 17-trihydroxy-kaur-2-one), compound 2: mapping-16 α, 17,19 trihydroxyies-kauri pine-2 ketone (ent-16 α, 17,19-trihydroxyl-kaur-2-one), compound 3: mapping-2 β, 3 α, 16 α, 17-tetrahydroxy-kauri pine alcohol (t-2 β, 3 α, 16 α 17-tetrahydroxyl-kauranol), have determined compound 1 through wave spectrum analysis and chemical process, compound 2, the structure of compound 3 is respectively:
Compound 1
Compound 2
Compound 3
Above-mentioned three compounds are by the preparation method's gained that may further comprise the steps:
(1) take by weighing the compound in rubus corchorifolius leaf of pulverizing, add the ethanol of 10 times of volumes 80%, stir evenly, first supersound extraction 30min, lixiviate 48h under room temperature filters then, and filter residue repeats to extract once again, merging filtrate, concentrated frozen is done standby;
(2) with medicinal extract liquid with using sherwood oil successively, chloroform, ethyl acetate, the extraction of propyl carbinol repeated multiple times concentrate extraction liquid respectively, lyophilize, respectively sherwood oil, chloroform, ethyl acetate, n-butyl alcohol extract;
(3) acetic acid ethyl ester extract is carried out silica gel column chromatography and separate, carry out gradient elution with normal hexane and ethyl acetate, ethyl acetate and methyl alcohol, collect elutriant, detect through TLC, colour developing merges identical component, and is concentrated freeze-dried;
(4) component among the column chromatography I is carried out the silica gel column chromatography separating purification second time, carry out gradient elution with chloroform and methyl alcohol, collect elutriant, detect the identical component of merging through TLC, concentrated freeze-dried;
(5) component among the column chromatography II is carried out silica gel column chromatography again and separate, carry out gradient elution with chloroform and methyl alcohol, elutriant detects through TLC, merge identical component, be concentrated into small volume, carry out recrystallization respectively, get compound 1, compound 2, compound 3 respectively.
In the step (3), when carrying out the gradient washing, the volume ratio of normal hexane and ethyl acetate is followed successively by: 100: 0,50: 50, the volume ratio of ethyl acetate and methyl alcohol was followed successively by 100: 0, and 80: 1,40: 1,10: 1,5: 1,1: 1,0: 1.
In the step (4), when carrying out gradient elution, the volume ratio of chloroform and methyl alcohol was followed successively by 100: 0, and 80: 1,40: 1,10: 1,5: 1,1: 1,0: 1.
In the step (5), when carrying out gradient elution, the volume ratio of chloroform and methyl alcohol was followed successively by 40: 1, and 20: 1,10: 1,5: 1,1: 1,0: 1.
Activity experiment proves that these three new compounds all have favorable anti-tumor effect.
The purposes of the mixture of one or more of this group compound aspect the preparation antitumor drug.
The purposes of the mixture of one or more of this group compound aspect the preparation healthcare products.
The mixture of one or more of this group compound is in the purposes of one of preparation antineoplastic component.
The structure determination of three compounds of the present invention:
(1), mapping-9 β, 16 α, the structure determination of 17 trihydroxyies-kauri pine-2 ketone
1, physics and chemistry and spectroscopic data
(1) this compound is white crystal, M.p.170～172 ℃, and specific rotation: 170.18 °: all wave band scanning λ max=224nm (methyl alcohol), sherwood oil: ethyl acetate=1: 5, Rf=0.28,1% Vanillin sulphuric acid soln show and are single blue spot.
(2) compound
13The C-NMR signal is (CD
3OD, 400MHZ): 216.7 (s), 82.9 (s), 78.5 (s), 66.7 (t), 57.2 (t), 51.4 (t), 51.0 (s), 50.3 (s), 48.3 (d), 47.9 (t), 45.1 (d), 39.6 (s), 39.0 (t), 37.6 (t), 34.0 (q), 30.3 (t), 28.6 (t), 23.6 (q), 21.7 (t), 21.5 (q).
(3) compound
1The H-NMR signal is (CD
3OD, 100MHZ): 0.886 (s, 3h); 1.076 (s, 3h); 1.102,1.138 (d, 1h); 1.115 (s, 3h); 1.206-1.297 (m, 1h); 1.36-1.42 (m, 1h); 1.445-1.485 (m, 1h); 1.5-1.6 (m, 1h); 1.64-1.82 (m, 3h); 1.831,1.848,1.868,1.886 (dd, 1h); 1.941,1.951,1.974,1.984 (dd, 1h); 2.0-2.12 (m, 4h); 2.178,2.181,2.207,2.213 (dd, 1h); 2.234,2.239,2.272,2.277 (dd, 1h); 2.329,2.362 (d, 1h); 2.847,2.878 (d, 1h); 3.568,3.588 (d, 1h); 3.688,3.697 (d, 1h).
(4)IR(KBr)：Vmax?cm
-1：35403330(OH)，29432926(V?C-H)，1692(C＝O)。
2, structure is derived
(1) determining of molecular formula: APCI-MS provides quasi-molecule amount 354 (M+H
2O), 336 (M), 318 (M-H
2O), illustrate that this compound molecular weight is 336, therefore releasing molecular formula is C
20H
32O
4, Ω equals 5.
(2) structural formula determines
1. the compound two dimensional structure is definite: by HHCOSY, and HMQC, the HMBC collection of illustrative plates, find to have following structure fragment:
Fragment I fragment II
Fragment III fragment IV
So far, surplus 30.3 (t) also, two carbon of 28.6 (t) are easy to, according to degree of unsaturation, its plane structure as follows:
2. the compound three-dimensional arrangement determines
By consulting document, compare with a large amount of analogues, its NMR data are consistent with the ent-kaurane type
Proved that its space multistory structure is ent-kaurane type tetracyclic diterpene.The NOE test is visible coherent signal also, and structure is as follows:
(2) mapping-16 α, the structure determination of 17,19 trihydroxyies-kauri pine-2 ketone
1, physics and chemistry and spectroscopic data
(1) white crystal, M.p.223～225 ℃, specific rotation: 200.0 °:, all wave band scanning λ max=207nm (methyl alcohol), sherwood oil: ethyl acetate=1: 5, Rf=0.23,1% Vanillin sulphuric acid soln show and are single punctation.
(2) compound
13The C-NMR signal is (CD
3OD, 400MHZ): 214.9 (s), 82.7 (s), 66.8 (t), 66.1 (t), 57.1 (d), 57.0 (t), 56.6 (d), 53.5 (t), 50.9 (t), 46.2 (d), 45.8 (s), 45.3 (s), 44.9 (s), 42.9 (t), 37.7 (t), 27.7 (q), 26.9 (t), 22.0 (t), 20.0 (q), 19.6 (t).
(3) compound
1The H-NMR signal is (CD
3OD, 100MHZ): 1.042 (s, 3h); 1.11 (s, 3h); 1.312,1.332 (d, 1h); 1.4-1.7 (m, 11h); 1.776,1.771,1.803.1.806 (m, 1h); 1.841,1.871 (d, 1h); 2.039 (brs, 1h); 2.039,2.071 (d, 1h); 2.111,2.146 (d, 1h); 2.447,2.452,2.479,2.484 (dd, 1h); 2.513,2.518,2.548,2.554 (dd, 1h); 3.360,3.389 (d, 1h); 3.475,3.503 (d, 1h); 3.582,3.610 (d, 1h); 3.687,3.716 (d, 1h).
(4)IR(KBr)：FTIRVmax?cm
-1：35403440(OH)，29432921(VC-H)，1692(C＝O)。
2, structure is derived
(1) determining of molecular formula: APCI-MS provides quasi-molecule amount 354 (M+H
2O), 336 (M), 318 (M-H
2O), illustrate that this compound molecular weight is 336, therefore releasing molecular formula is C
20H
32O
4, Ω equals 5.
(2) two dimensional structure determines
By HHCOSY, HMQC, the HMBC collection of illustrative plates, find to have following structure fragment:
Fragment I fragment II
Fragment III fragment IV
So far 20 carbon atoms have all found relevantly, and aforementioned degree of unsaturation is 5, so its two dimensional structure is a kaurane type tetracyclic diterpene constituents:
(3) three-dimensional arrangement determines
By consulting document, with a large amount of analogues relatively, its NMR data are consistent with the ent-kaurane type, be embodied among the C-NMR, as following table:
Table 1 C-NMR data
Also can see in the NOE spectrum relevant, so determine that compound structure is as follows:
The three-dimensional arrangement of compound 2
Therefore, the compound called after: mapping-16 α, 17,19 trihydroxyies-kauri pine-2 ketone (Ent-16 α, 17,19 α-trihydroxyl-kauran-2-one).
(3) mapping-2 β, 3 α, 16 α, 17-tetrahydroxy-kauri pine alcohol structure determination
1, physics and chemistry and spectroscopic data
(1) white crystal, M.p.169～170 ℃, specific rotation :-16.13 °, all wave band scanning λ max=278nm (methyl alcohol), 1% Vanillin sulphuric acid soln show and are single blue spot.
(2) compound
13The C-NMR signal is (CD
3OD, 400MHZ): 82.7 (s), 78.9 (d), 70.4 (d), 66.9 (t), 58.4 (d), 53.7 (t), 51.6 (d), 47.9 (t), 46.3 (d), 45.7 (s), 42.3 (t), 40.5 (s), 38.7 (s), 37.7 (t), 27.1 (t), 25.3 (q), 23.8 (q), 23.3 (q), 22.6 (t), 20.0 (t).
(3) compound
1The H-NMR signal is (CD
3OD, 100MHZ): 0.887 (s, 3h); 0.992 (s, 3h); 1.124-1.189 (m, 2h); 1.236 (s, 3h); 1.367,1.402 (d, 1h); 1.42-1.72 (m, 12h); 1.854,1.883 (d, 1h); 2.021,2.027 (brs, 1h); 3.509,3.532 (d, 1h); 3.581,3.609 (d, 1h); 3.68-3.74 (m, 2h).
(4)IR(KBr)：FTIRVmax?cm
-1：3180(OH)，29252857(VC-H)。
2, structure is derived
(1) determining of molecular formula: APCI-MS provides quasi-molecule amount 356 (M+H2O), and 320 (M-H2O) illustrate that this compound molecular weight is 338, and therefore releasing molecular formula is C20H34O4, and Ω equals 4.
(2) two dimensional structure determines
By HHCOSY, HMQC, the HMBC collection of illustrative plates, find to have following structure fragment:
Fragment I fragment II
Fragment III fragment IV
So far also having three CH2 signals, do not obtain explanation, is 4 according to degree of unsaturation, the structure of compound can be decided to be as follows:
(3) three-dimensional arrangement determines
(1) by with analogue relatively, its NMR data are consistent with the ent-kaurane type, be embodied among the C-NMR, as following table:
Table 2 NMR data and ent-kaurane type are relatively
Determining of 2,3 dihydroxyl configurations: (d 1h) is connected on the carbon 78.9 (d) hydrogen 3.509,3.532, and bimodal is to split branch because be subjected to the coupling of 2 hydrogen, and calculating coupling constant J is 11.5HZ, so 2 and 3 two hydroxyls must all be on the e key.So be 2 β, 3 α.Also can see in the NOE spectrum relevant, so determine that No. 3 structures are as follows:
So these compound 4 called afters: mapping-2 β, 3 α, 16 α, 17-tetrahydroxy-kauri pine alcohol (Ent-2 β, 3 α, 16 α, 17-tetradroxyl-kauranol).
Embodiment
Isolated three kinds of new compounds from Rubus corchorifolius, chemical name is respectively: compound 1, mapping-9 β, 16 α, 17 trihydroxyies-kauri pine-2 ketone (ent-9 β, 16 α, 17-trihydroxy-kaur-2-one), compound 2, mapping-16 α, 17,19 trihydroxyies-kauri pine-2 ketone (ent-16 α, 17,19-trihydroxyl-kaur-2-one), compound 3, mapping-2 β, 3 α, 16 α, 17-tetrahydroxy-kauri pine alcohol (t-2 β, 3 α, 16 α, 17-tetrahydroxyl-kauranol), determined compound 1 through wave spectrum analysis and chemical process, compound 2, the structure of compound 3 is respectively:
Compound 1
Compound 2
Compound 3
These three compounds are separating obtained by following method:
(1) preparation of compound in rubus corchorifolius leaf ethanol crude extract: take by weighing the compound in rubus corchorifolius leaf 3500.0g of pulverizing, add the ethanol of 10 times of volumes 80%, stir evenly, the supersound extraction 30min of elder generation, lixiviate 48h under room temperature filters then, filter residue repeats to extract once again, merging filtrate, and concentrated frozen is done standby.
(2), Rubus corchorifolius activeconstituents liquid-liquid extraction separation and purification: with using sherwood oil successively, chloroform, ethyl acetate, the extraction of propyl carbinol repeated multiple times concentrate extraction liquid respectively lyophilize with medicinal extract liquid.Get sherwood oil, chloroform, ethyl acetate, n-butyl alcohol extract respectively.
(3), acetic acid ethyl ester extract being carried out silica gel column chromatography separates, normal hexane and ethyl acetate, ethyl acetate and methyl alcohol with different concns carries out gradient elution successively, the volume ratio of normal hexane and ethyl acetate is followed successively by: 100: 0,50: 50, the volume ratio of ethyl acetate and methyl alcohol was followed successively by 100: 0,80: 1,40: 1,10: 1,5: 1,1: 1,0: 1.Collect elutriant, detect through TLC, colour developing merges identical component, and is concentrated freeze-dried;
(4), a component among the column chromatography I is carried out the silica gel column chromatography separating purification second time, carry out gradient elution with chloroform and methyl alcohol, the volume ratio of chloroform and methyl alcohol was followed successively by 100: 0,80: 1,40: 1,10: 1,5: 1,1: 1,0: 1, collect elutriant, detect the identical component of merging through TLC, concentrated freeze-dried;
(5), a component among the column chromatography II carried out silica gel column chromatography again separate, carry out gradient elution with chloroform and methyl alcohol, the volume ratio of chloroform and methyl alcohol was followed successively by 40: 1,20: 1,10: 1,5: 1,1: 1,0: 1, elutriant detected through TLC, merged identical component, be concentrated into small volume, carry out recrystallization respectively, get compound 1, compound 2, compound 3 respectively.
The mensuration of three new compound anti-tumor activities among the present invention:
1, experiment material
1.1 medicine: above-mentioned isolated compound 1,2,3.
1.2 cell: human hepatoma cell strain HepG
2Company provides by the safe standing grain biological medicine in Guangzhou.
1.3 reagent: PRMI1640, foetal calf serum, 96 orifice plates, pancreatin, DMSO, MTT, 5-FU, penicillin, Streptomycin sulphate.
2, method
With liver cancer HepG
2Cell cultures is in containing 10% foetal calf serum, 1 * 10
5In the RPMI1640 nutrient solution of U/L penicillin, Streptomycin sulphate, 37 ℃, 5%CO
2The routine cultivation of going down to posterity in the incubator.Cell is with 1 * 10
4The concentration in individual/hole is inoculated in 96 well culture plates, in the RPMI-1640 nutrient solution that contains 10% foetal calf serum, cultivate 24h, behind the cell attachment, the experimental group dosage be 100 μ g/mL, 200 μ g/mL, 400 μ g/mL,, negative control group adds equivalent RPMI (DMSO content is 1%), and the concentration that positive controls adds 5-Fu is 100 μ g/mL, 200 μ g/mL, 400 μ g/mL, 800 μ g/mL, 1600 μ g/mL.The blank group only adds equivalent RPMI.Behind the drug effect 24h, the 5%MTT 20 μ L that add preparation in every hole continue to cultivate 4h, abandon supernatant, add 150 μ L DMSO, after mixing the shaker about 10min of medicine that shakes, crystallisate is fully dissolved, join on the detector 492nm wavelength in enzyme and measure each hole light absorption value.
Calculate the inhibiting rate (CT%) of cancer cells, CT%=(1-OD processing/OD contrast) * 100%.
3, experimental result (see Table 3, table 4, table 5)
1 couple of liver cancer HepG of table 3 compound
2The cell inhibiting effect
2 couples of liver cancer HepG of table 4 compound
2The cell inhibiting effect
3 couples of liver cancer HepG of table 5 compound
2The cell inhibiting effect
Above-mentioned experimental result shows: compound mapping-9 β, 16 α, 17 trihydroxyies-kauri pine-2 ketone, mapping-16 α, 17,19 trihydroxyies-kauri pine-2 ketone and mapping-2 β, 3 α, 16 α, 17-tetrahydroxy-kauri pine alcohol all has the obvious suppression effect to liver cancer HepG2 cell, and has good dose-effect relationship.
Claims (7)
1. one group of isolated compound from Rubus corchorifolius, chemical name is respectively: compound 1, mapping-9 β, 16 α, 17-trihydroxy--kauri pine-2-ketone, compound 2, mapping-16 α, 17,19-trihydroxy--kauri pine-2-ketone, compound 3, mapping-2 β, 3 α, 16 α, 17-tetrahydroxy-kauri pine alcohol
Mapping-9 β, 16 α, the chemical structural formula of 17-trihydroxy--kauri pine-2-ketone is:
Mapping-16 α, the chemical structure of 17,19-trihydroxy--kauri pine-2-ketone be for:
Mapping-2 β, 3 α, 16 α, the chemical structural formula of 17-tetrahydroxy-kauri pine alcohol is:
According to claim 1 from Rubus corchorifolius the preparation method of isolated compound, it is characterized in that, may further comprise the steps:
(1) take by weighing the compound in rubus corchorifolius leaf of pulverizing, add the ethanol of 10 times of volumes 80%, stir evenly, first supersound extraction 30min, lixiviate 48h under room temperature filters then, and filter residue repeats to extract once again, merging filtrate, concentrated frozen is done standby;
(2) with medicinal extract liquid with successively with sherwood oil, chloroform, ethyl acetate, the extraction of propyl carbinol repeated multiple times, extraction liquid is concentrated respectively, lyophilize, respectively sherwood oil, chloroform, ethyl acetate, n-butyl alcohol extract;
(3) acetic acid ethyl ester extract is carried out silica gel column chromatography and separate, carry out gradient elution with normal hexane and ethyl acetate, ethyl acetate and methyl alcohol, collect elutriant, detect through TLC, colour developing merges identical component, and is concentrated freeze-dried;
(4) component among the column chromatography I is carried out the silica gel column chromatography separating purification second time, carry out gradient elution with chloroform and methyl alcohol, collect elutriant, detect the identical component of merging through TLC, concentrated freeze-dried;
(5) component among the column chromatography II is carried out silica gel column chromatography again and separate, carry out gradient elution with chloroform and methyl alcohol, elutriant detects through TLC, merges identical component, carries out recrystallization respectively, gets compound 1, compound 2, compound 3 respectively.
According to claim 2 from Rubus corchorifolius the preparation method of isolated compound, it is characterized in that, in the step (3), when carrying out the gradient washing, the volume ratio of normal hexane and ethyl acetate is followed successively by: 100: 0,50: 50, the volume ratio of ethyl acetate and methyl alcohol was followed successively by 100: 0,80: 1,40: 1,10: 1,5: 1,1: 1,0: 1.
According to claim 2 from Rubus corchorifolius the preparation method of isolated compound, it is characterized in that in the step (4), when carrying out gradient elution, the volume ratio of chloroform and methyl alcohol was followed successively by 100: 0,80: 1,40: 1,10: 1,5: 1,1: 1,0: 1.
According to claim 2 from Rubus corchorifolius the preparation method of isolated compound, it is characterized in that in the step (5), when carrying out gradient elution, the volume ratio of chloroform and methyl alcohol was followed successively by 40: 1,20: 1,10: 1,5: 1,1: 1,0: 1.
According to claim 1 from Rubus corchorifolius one or more mixture of isolated compound in the purposes of preparation aspect the antitumor drug.
According to claim 1 from Rubus corchorifolius one or more mixture of isolated compound in the purposes of preparation one of antineoplastic component.
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| CN102344365A (en) * | 2011-08-02 | 2012-02-08 | 曹庸 | Two novel compounds with antitumor effects in Rubus corchorifolius leaves, preparation method and application thereof |
| CN102718809B (en) * | 2012-05-26 | 2017-11-10 | 华南农业大学 | A kind of diterpene compound, preparation method and its usage in compound in rubus corchorifolius leaf |
| CN108078855B (en) * | 2018-01-13 | 2021-01-26 | 上海欧润化妆品有限公司 | Raspberry fruit extract and extraction process thereof |
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Non-Patent Citations (4)
| Title |
|---|
| Additional ent-Kaurane Diterpenoids from Rubus corchorifolius L. f.;Xue-Xiang Chen et al.;《Helvetica Chimica Acta》;20100120;第93卷(第1期);第84-89页 * |
| Xue-Xiang Chen et al..Additional ent-Kaurane Diterpenoids from Rubus corchorifolius L. f..《Helvetica Chimica Acta》.2010,第93卷(第1期),第84-89页. |
| 张敏.湘西山莓叶有效成分提取分离结构鉴定及活性研究.《中国优秀硕士学位论文医药卫生科技辑》.2006,(第11期),第1-69页. |
| 湘西山莓叶有效成分提取分离结构鉴定及活性研究;张敏;《中国优秀硕士学位论文医药卫生科技辑》;20061115(第11期);第1-69页 * |
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