CN102344365A - Two novel compounds with antitumor effects in Rubus corchorifolius leaves, preparation method and application thereof - Google Patents
Two novel compounds with antitumor effects in Rubus corchorifolius leaves, preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to two novel compounds separated out by extracting Rubus corchorifolius leaves and a preparation method thereof. The two novel compounds are obtained through adopting methods of repeated silicagel column chromatography, thin layer chromatography and crystallization in the crude extract of the Rubus corchorifolius leaves, wherein the chemical name of the compound I is (ZM-1) 3beta, 16alpha, 17, 19-tetrahydroxy-ent-kaurene-19-acetate, and the chemical name of the compound II is (99-106) 3beta, 16alpha, 17,19-tetrahydroxy-ent-kaurene-19-acetate-17-O-beta-D-glucoside. Proved by an activity experiment, the two novel compounds have very good antitumor effects, and can be applied to preparing antitumor drugs.
Description
Technical field
The present invention relates to extraction separation goes out in the compound in rubus corchorifolius leaf two new compounds, preparation method with and the purposes of antitumor drug aspect.
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 300～1500m more.Except that 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 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 like eastern gelsemium henbane lactone.In the western Hunan, the Northwest of Hubei Province Rubus corchorifolius is as Miao ethnic group's medicine commonly used, is used to cure common frequently-occurring disease, like 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 Chen Ping 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; Chen Ping 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 and obtained 2 kaurane diterpene new compounds: 3 α; 16 α, 17,19-mapping-kaurane-tetrol and 2 carbonyls-16 Alpha-hydroxies-mapping-kaurane-17-β-D-glucoside.Separation obtains four new compound compounds to old snow perfume (or spice) etc. from Rubus corchorifolius ethyl acetate extraction position: be respectively 9 β; 16 α; 17 trihydroxyies-mapping kauri pine-2 ketone (9 β; 16 α, 17-trihydroxy-ent-kaur-2-one), 16 α; 17; 19 trihydroxyies-mapping kauri pine-2 ketone (16 α, 17,19-trihydroxyl-ent-kaur-2-one); 2 β; 3 α, 16 α, 17-tetrahydroxy-mapping-kauri pine alcohol (2 β; 3 α; 16 α 17-tetrahydroxyl-ent-kauranol), and all have antineoplastic action.
Summary of the invention
The purpose of this invention is to provide isolated two new compounds from Rubus corchorifolius, extract through silica gel column chromatography, thin-layer chromatography and crystalline method gained repeatedly by compound in rubus corchorifolius leaf is thick, this group compound of activity experiment proof has antitumor action.
Provided by the present invention one group of two new compound are through silica gel column chromatography, thin-layer chromatography and crystalline method gained repeatedly from the crude extract of compound in rubus corchorifolius leaf; Chemical name is respectively: compound 1 (ZM-1) 3 β; 16 α; 17; 19-tetrahydroxy-mapping kauri pine-19-acetic ester, compound 2 (99-106) 3 β, 16 α; 17,19-tetrahydroxy-mapping kauri pine-19-acetic ester-17-oxygen-β-D-glucoside.Confirmed to be respectively the structure of compound 1, compound 2 through wave spectrum analysis and chemical process:
Compound 1 compound 2
Above-mentioned two compounds are by the preparing 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, in 50 ℃ of following lixiviate 48h, filter, filter residue repeats to extract once again, and merging filtrate is concentrated freeze-dried subsequent use;
(2) concentrated freeze-dried gained medicinal extract liquid is used sherwood oil successively, chloroform, ethyl acetate, the extraction of propyl carbinol repeated multiple times concentrate extraction liquid respectively, and lyophilize gets sherwood oil, chloroform, ethyl acetate, n-butyl alcohol extract respectively;
(3) chloroform extract is carried out silica gel column chromatography and separate, carry out gradient elution, merge identical component with trichloromethane and methyl alcohol, concentrated freeze-dried;
(4) get and present component of crystalline after concentrated freeze-dried, dissolve fully with methyl alcohol, left standstill 24 hours under 25 ℃, obtain crystallization, filter, crystal is used dissolve with methanol again, recrystallization once promptly obtains compound 1;
(5) concentrated freeze-dried back gross weight is maximum, show a component of pale powder shape, with dissolve with methanol and get proper silica gel and mix thoroughly, volatilize solvent; Appearance on the dry method is carried out silica gel column chromatography again and is separated, and carries out gradient elution with chloroform and methyl alcohol; Collect elutriant, through merging identical component, concentrated freeze-dried;
(6) get and detect a high component of purity, use dissolve with methanol, left standstill 24 hours under 25 ℃, obtain crystallization, filtration is used dissolve with methanol again with crystal, and recrystallization once promptly obtains compound 2.
In the step (3), when carrying out gradient elution, the volume ratio of trichloromethane and methyl alcohol is followed successively by: 500: 0, and 500: 1,300: 1,100: 1,90: 1,70: 1,50: 1,, 30: 1,10: 1,5: 1, the volume ratio of methyl alcohol and water was 4: 1.
In the step (5), 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.
Activity experiment proves that above-mentioned two new compounds all have favorable anti-tumor effect.Therefore, compound 1 of the present invention can be used for preparing antitumor drug with compound 2, also can be used for preparing the healthcare products with corresponding effect.
The structure determination of two compounds of the present invention:
(1) compound 1 (ZM-1) 3 β, 16 α, 17, the structure determination of 19-tetrahydroxy-mapping kauri pine-19-acetic ester
1, physics and chemistry and spectroscopic data
(1) this compound is a colourless acicular crystal, M.p.140-141 ℃, and specific rotation :-17.3, all wave band scanning λ max=207nm (methyl alcohol), trichloromethane: it is single pink spot that methyl alcohol=20: 1, Rf=0.68,1% Vanillin sulphuric acid soln show.
(2) compound
13The C-NMR signal is (CD
3OD, 400MHZ): 173.1 (s), 82.8 (s), 71.4 (d); 68.9 (t), 66.8 (t), 58.0 (d), 53.9 (t); 50.4 (d), 46.4 (d), 45.7 (s), 43.4 (t); 42.7 (s), 40.1 (s), 38.0 (t), 34.4 (t); 27.2 (t), 26.3 (t), 23.1 (q), 21.3 (t); 20.7 (q), 19.3 (t), 18.5 (q)
(3) compound
1The H-NMR signal is (CD
3OD, 100MHZ): 1.017 (s, 3h); 1.070 (s, 3h); 1.130 (m, 1h); 1.301 (m, 1h); 1.35-1.47 (m, 3h); 1.48-1.67 (m, 11h); 1.89-1.99 (m, 2h); 2.029 (s, 3h); 2.030 (m, 1h); 3.59 (d, J=11.4Hz, 1h); 3.613 (t, J=3.0Hz, 1h); 3.69 (d, J=11.4Hz, 1h); 3.93 (d, J=11.4Hz, 1h); 4.22 (d, J=10.8Hz, 1h); 4.583 (s, 1h, OH).
(4)APCI-MS：267.3，285.2，345.1(100)，363.1，381.0
(5)IR(KBr)Vmax?cm
-1：3505，3430(OH)，2940，2850(C-H)，1715(C＝O).
2, structure is derived
(1) confirming of molecular formula: provide quasi-molecular ion peak 381 ([M+H] among the APCI-MS
+), 363 ([M+H-H
2O]
+), 345 ([M+H-2H
2O]
+) to release this compound molecular weight be 380amu.To sum up can release the compound molecule formula is C
22H
36O
5, Ω equals 5, contains 3 hydroxyls in the molecule.
(2) structural formula confirms
Confirming of compound two dimensional structure: analyze HSQC, HMBC, H-HCOSY spectrum, find to have following structure fragment:
Fragment I fragment II
Fragment III
Fragment IV fragment V
So far 22 carbon atoms have all found relevant; Aforementioned degree of unsaturation is 5; So its two dimensional structure is a kaurane type tetracyclic diterpene constituents,, compare with a large amount of analogues through consulting document; Its NMR data are consistent with the ent-kaurane type; And former plant has been assigned to a series of the type compounds, so confirm that structural formula of compound is following: called after 3 β, 16 α; 17,19-tetrahydroxy-mapping kauri pine-19-acetic ester.
(2) compound 2 (99-106) 3 β, 16 α, 17,19-tetrahydroxy-mapping kauri pine-19-acetic ester-17-oxygen-β-D-glucoside structure determination
1, physics and chemistry and spectroscopic data
(1) white powder, M.p.139-141 ℃, specific rotation :-25.8, all wave band scanning λ max=205nm (methyl alcohol), trichloromethane: it is single gray corrosion that methyl alcohol=3: 1, Rf=0.7,1% Vanillin sulphuric acid soln show.
(2) compound
13The C-NMR signal is (CD
3OD, 400MHZ) 173.1 (s), 105.3 (d), 82.0 (s), 78.0 (d); 77.9 (d), 75.3 (d), 75.0 (t), 71.7 (d), 71.4 (d); 68.9 (t), 62.8 (t), 58.0 (d), 53.6 (t), 50.4 (d); 46.8 (d), 45.7 (s), 43.3 (t), 42.7 (s), 40.1 (s); 37.9 (t), 34.4 (t), 27.1 (t), 26.3 (t), 23.1 (q); 21.3 (t), 20.8 (q), 19.3 (t), 18.5 (q)
(3) compound
1The H-NMR signal is (CD
3OD, 100MHZ):
1.017(s，3h)；1.068(s，3h)；1.133(brs，1h)；1.297(m，1h)；1.36-1.68(m，14h)；1.721(brd，1h)；1.88-2.00(m，2h)；2.029(s，3h)；2.081(brs，1h)；3.22(dd，J＝7.6，9.4Hz，1h)；3.26-3.30(m，2h)；3.372(m，1h)；3.51(d，J＝10.4Hz，1h)；3.611(brs，1h)；3.679(m，1h)；3.87(dd，J＝1.2，12Hz，1h)；3.93(d，J＝11.2Hz，1h)；4.15-4.25(t，2h)；4.285(d，J＝8.0Hz，1h)。
(4)APCI-MS：560，565，1107
(5)IR(KBr)：FTIR?V?max?cm
-1：3515，3480(OH)，2940，2860(C-H)，1730(C＝O).
2, structure is derived
(1) confirming of molecular formula: provide quasi-molecular ion peak 560 ([M+H among the APCI-MS
2O]
+), 565 ([M+Na]
+), 1107 ([2M+Na]
+) to release this compound molecular weight be 542amu.Can release the compound molecule formula is C
28H
46O
10, calculating degree of unsaturation is 6,
(2) two dimensional structure confirms
By HHCOSY, HMQC, the HMBC collection of illustrative plates, find to have following structure fragment:
Fragment III fragment IV
So far 28 carbon atoms have all found relevant; Aforementioned degree of unsaturation is 6; So its two dimensional structure is a kaurane type tetracyclic diterpene constituents: through consulting document; Compare with a large amount of analogues, its NMR data are consistent with the ent-kaurane type, and former plant has been assigned to a series of the type compounds; So confirm that structural formula of compound is following: called after 3 β; 16 α, 17,19-tetrahydroxy-mapping kauri pine-19-acetic ester-17-oxygen-β-D-glucoside.
Embodiment
Embodiment
(1) preparation of compound in rubus corchorifolius leaf ethanol crude extract: take by weighing the compound in rubus corchorifolius leaf 3000.0g of pulverizing, add the ethanol of 10 times of volumes 80%, stir, in 50 ℃ of following lixiviate 48h, filter, filter residue repeats to extract once again, merging filtrate, and concentrated frozen is done subsequent use.
(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), the separation and purification of chloroform extract column chromatography: chloroform extract is carried out silica gel column chromatography separate, carry out gradient elution, collect 500mL, collect 173 bottles altogether for every bottle with trichloromethane and methyl alcohol; Detect through TLC, adopt the colour developing of sulfuric acid Vanillin, merge identical component; Altogether 11 components, be expressed as respectively: Fr.1, Fr.2; Fr.3, Fr.4, Fr.5; Fr.6, Fr.7, Fr.8; Fr.9, Fr.10, Fr.11 is concentrated freeze-dried to be used for further separation and purification.
(4), column chromatography I component Fr.7 carries out recrystallization, after the crystallization compound 1:3 β, 16 α, 17,19-tetrahydroxy-mapping kauri pine-19-acetic ester.Fr.11 carries out second time silica gel column chromatography separating purification and carries out gradient elution with chloroform and methyl alcohol, and every 10mL collects one bottle, collects 122 bottles altogether, detects through TLC to merge identical component; Altogether 15 components, be respectively: be expressed as respectively: Fr.11.1, Fr.11.2, Fr.11.3; Fr.11.4, Fr.11.5, Fr.11.6, Fr.11.7; Fr.11.8, Fr.11.9, Fr.11.10; Fr.11.11, Fr.11.12, Fr.11.13; Fr.11.14, Fr.11.15 concentrated freeze-driedly is used for further separation and purification.Fr.11.15 appearance is carried out recrystallization, gets compound 2:3 β, 16 α, 17,19-tetrahydroxy-mapping kauri pine-19-acetic ester-17-oxygen-β-D-glucoside after the crystallization.
The mensuration of two new compound anti-tumor activities among the present invention
1, experiment material
1.1 medicine:
Above-mentioned isolated compound:
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, 1x10
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 1x10
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%MTT20 μ L that in every hole, adds preparation continues to cultivate 4h, abandons supernatant; Add 150 μ L DMSO; After mixing the about 10min of medicine that shakes on the shaker, crystallisate is fully dissolved, join each hole light absorption value of 492nm wavelength mensuration on the detector in enzyme.
Calculate cytotoxicity values (CT%), CT%=(1-OD processing/OD contrast) * 100%.
3, experimental result
Table 1 compound is to liver cancer HepG
2The cell inhibiting effect
2 couples of liver cancer HepG of table 2 compound
2The cell inhibiting effect
Above-mentioned experimental result shows: mapping-9 β, and 16 α, 17 trihydroxyies-kauri pine-2 ketone and mapping-16 α, 17,19 trihydroxyies-kauri pine-2 ketone all has the obvious suppression effect to liver cancer HepG2 cell, and has good dose-effect relationship.Therefore, above-mentioned two kinds of compounds can or be mixed for preparing separately antitumor drug, also can be used for preparing anti-tumor health care product.
Claims (10)
1. the new compound 1 of tool antitumor action in the compound in rubus corchorifolius leaf, chemical name is: 3 β, 16 α, 17,19-tetrahydroxy-mapping kauri pine-19-acetic ester, structural formula is:
2. the new compound 2 of tool antitumor action in the compound in rubus corchorifolius leaf, chemical name is: 3 β, 16 α, 17,19-tetrahydroxy-mapping kauri pine-19-acetic ester-17-oxygen-β-D-glucoside, structural formula is:
3. the preparation method of the new compound 1 of tool antitumor action in the compound in rubus corchorifolius leaf as claimed in claim 1 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, in 50 ℃ of following lixiviate 48h, filter, filter residue repeats to extract once again, and merging filtrate is concentrated freeze-dried subsequent use;
(2) concentrated freeze-dried gained medicinal extract liquid is used sherwood oil successively, chloroform, ethyl acetate, the extraction of propyl carbinol repeated multiple times concentrate extraction liquid respectively, and lyophilize gets sherwood oil, chloroform, ethyl acetate, n-butyl alcohol extract respectively;
(3) chloroform extract is carried out silica gel column chromatography and separate, carry out gradient elution, merge identical component with trichloromethane and methyl alcohol, concentrated freeze-dried;
(4) get and present component of crystalline after concentrated freeze-dried, dissolve fully with methyl alcohol, left standstill 24 hours under 25 ℃, obtain crystallization, filter, crystal is used dissolve with methanol again, recrystallization once promptly obtains compound 1.
4. the preparation method of the new compound 2 of tool antitumor action in the compound in rubus corchorifolius leaf as claimed in claim 2 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, in 50 ℃ of following lixiviate 48h, filter, filter residue repeats to extract once again, and merging filtrate is concentrated freeze-dried subsequent use;
(2) concentrated freeze-dried gained medicinal extract liquid is used sherwood oil successively, chloroform, ethyl acetate, the extraction of propyl carbinol repeated multiple times concentrate extraction liquid respectively, and lyophilize gets sherwood oil, chloroform, ethyl acetate, n-butyl alcohol extract respectively;
(3) chloroform extract is carried out silica gel column chromatography and separate, carry out gradient elution, merge identical component with trichloromethane and methyl alcohol, concentrated freeze-dried;
(5) concentrated freeze-dried back gross weight is maximum, show a component of pale powder shape, with dissolve with methanol and get proper silica gel and mix thoroughly, volatilize solvent; Appearance on the dry method is carried out silica gel column chromatography again and is separated, and carries out gradient elution with chloroform and methyl alcohol; Collect elutriant, through merging identical component, concentrated freeze-dried;
(6) get and detect a high component of purity, use dissolve with methanol, left standstill 24 hours under 25 ℃, obtain crystallization, filtration is used dissolve with methanol again with crystal, and recrystallization once promptly obtains compound 2.
5. the preparation method of the new compound 1 of tool antitumor action is characterized in that in the compound in rubus corchorifolius leaf according to claim 3, in the step (3); When carrying out gradient elution, the volume ratio of trichloromethane and methyl alcohol is followed successively by: 500: 0, and 500: 1; 300: 1,100: 1,90: 1; 70: 1,50: 1; 30: 1; 10: 1,5: 1, the volume ratio of methyl alcohol and water was 4: 1.
6. the preparation method of the new compound 2 of tool antitumor action is characterized in that in the compound in rubus corchorifolius leaf according to claim 4, in the step (3); When carrying out gradient elution, the volume ratio of trichloromethane and methyl alcohol is followed successively by: 500: 0, and 500: 1; 300: 1,100: 1,90: 1; 70: 1,50: 1; 30: 1,10: 1,5: 1; The volume ratio of methyl alcohol and water is 4: 1; In the step (5), 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.
7. the purposes of compound 1 as claimed in claim 1 aspect the preparation antitumor drug.
8. the purposes of compound 1 as claimed in claim 1 aspect the preparation healthcare products.
9. the purposes of compound 2 as claimed in claim 2 aspect the preparation antitumor drug.
10. the purposes of compound 2 as claimed in claim 2 aspect the preparation healthcare products.
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Cited By (1)
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| CN102718809A (en) * | 2012-05-26 | 2012-10-10 | 曹庸 | New diterpene compound in leaves of rubus corchorifolius L.f as well as preparation method and purpose thereof |
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| CN102718809A (en) * | 2012-05-26 | 2012-10-10 | 曹庸 | New diterpene compound in leaves of rubus corchorifolius L.f as well as preparation method and purpose 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 |
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