CN102180850A - Dwarf lilyturf tuber medium-high isoflavone compounds, and preparation method and application thereof - Google Patents
Dwarf lilyturf tuber medium-high isoflavone compounds, and preparation method and application thereof Download PDFInfo
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Abstract
The invention provides high isoflavone compounds extracted from dwarf lilyturf tuber. The high isoflavone compounds are prepared by the following steps of: heating and extracting the dwarf lilyturf tuber medicinal material by using aqueous solution of ethanol; degreasing extracted concentrated liquid by using petroleum ether; extracting by using ethyl acetate; concentrating extract liquor; separating by using a silicagel column; eluting; concentrating and drying; separating continuously by using preparative liquid chromatography; collecting a solution; and concentrating and drying to obtain the compounds. Three high isoflavone compounds are extracted from the dwarf lilyturf tuber medicinal material for the first time; a pharmacological test proves that the high isoflavone compounds have anti-tumor activity and important significance for developing modern Chinese medicaments for treating tumor diseases, and can be used for preparing medicaments for preventing and treating tumors.
Description
Technical field
The invention belongs to the field of Chinese medicines, more specifically to from Chinese medicine the tuber of dwarf lilyturf extraction separation have active class homoisoflavone compounds of antitumor inhibition and preparation method thereof and medicinal use.
Background technology
Tumour is a kind of common disease, frequently-occurring disease, and wherein malignant tumour is the most serious class disease of present harm humans health.The tumour that China's hazardness is the most serious is lung cancer, nasopharyngeal carcinoma, the esophageal carcinoma, cancer of the stomach, large bowel cancer, liver cancer, mammary cancer, cervical cancer, leukemia and lymphoma etc.Particularly the incidence of liver cancer increases in recent years to some extent.Significant, the nosetiology of these tumours, pathogenesis and control thereof are the emphasis of China's tumor research.Cancer therapy drug and the anticancer ancillary drug of seeking high-efficiency low-toxicity are the important contents of current tumor research.
Modern pharmacological research and investigation of clinical epidemiology find that have non-organ specific prophylactic effect to kinds of tumors the tuber of dwarf lilyturf, are playing an important role aspect reduction tumour incidence, treatment and the prophylaxis of tumours recurrence.The tuber of dwarf lilyturf (
Ophiopgon japonicus) be the Liliaceae Ophiopogon, be usually used in illnesss such as dryness of the lung dry cough, cough due to consumptive disease, thirsty, the vexed insomnia of Tianjin wound, interior heat are quenched one's thirst, the dry constipation of intestines.Modern age, pharmacological research proved, can regulate neural, cardiovascular and endocrine system the tuber of dwarf lilyturf, promote the synthetic of body substance metabolism and protein and RNA, DNA, improve brain, physical work capacity and immunologic function, strengthen anti-stress, antifatigue, antitumor, anti-ageing, radiation-resistant ability.
The main component of the tuber of dwarf lilyturf is saponins, flavonoid compound and carbohydrate content.As, the tuber of dwarf lilyturf saponin A, B, C, D, glucoside unit is ruscogenin; Ophiopogonin B ', C ', D ', glucoside unit is diosgenin; The tuber of dwarf lilyturf methyl flavanone A, B, the tuber of dwarf lilyturf flavanone A, ophiopogonone A, B, methyl ophiopogonone A, B etc.
Summary of the invention
The purpose of this invention is to provide class homoisoflavone compounds in the tuber of dwarf lilyturf, mainly comprise three kinds of homoisoflavone compounds that from the tuber of dwarf lilyturf, extract: (3R)-2 with tumors inhibition activity, 3-dihydro-7-hydroxy-5-methyl oxygen base-3-(4-p-methoxy-phenyl)-6,8-dimethyl-4H-chromogen-4 ketone (compd A), (3R)-3-(1,3-benzo dioxy alcohol-5-ylmethyl)-2,3-dihydro-7-hydroxy-5-methyl oxygen base-6,8-dimethyl-4H-chromogen-4-ketone (compd B) and (3R)-3-(1,3-benzo dioxy alcohol-5-ylmethyl)-2,3-dihydro-7-hydroxy-5-methyl oxygen base-6-methyl-4H-chromogen-4-ketone (Compound C), its structural formula is as follows:
?
?
Compd A compd B Compound C.
Another object of the present invention provides the preparation method of a described class homoisoflavone compounds, realizes by following steps:
(1) will use 90% alcohol reflux the tuber of dwarf lilyturf;
(2) extract is evaporated to medicinal extract;
(3) medicinal extract is suspended in the suitable quantity of water, uses petroleum ether degreasing, use ethyl acetate extraction, the reclaim under reduced pressure ethyl acetate gets ethyl acetate extract;
(4) ethyl acetate extract and silica gel are mixed sample, with normal phase silicagel column it is separated, be that the methylene dichloride of 100:0～70:1 and methyl alcohol are as the eluent wash-out earlier with volume ratio, be methylene dichloride and the methanol-eluted fractions agent wash-out of 50:1 again with volume ratio, collected volume is than being the elutriant of 50:1, get sample behind the concentrate drying, with normal phase silicagel column it being carried out the second time again separates, being sherwood oil and the acetone eluent wash-out of 8:1～5:1 with volume ratio earlier, is sherwood oil and the acetone wash-out of 4:1 again with volume ratio; Collected volume gets sample than being the elutriant of 4:1 behind the concentrate drying, preparative liquid chromatography continues to separate the sample that obtains; The separation condition of preparative chromatography: chromatographic column is a preparative column, and moving phase is water and acetonitrile, isocratic elution.
Preparative liquid chromatography separation condition: chromatographic column: Agilent Zorbax SB-C
18Post (250 * 21.2 mm, 7 μ m); Moving phase: acetonitrile: water is 45:55, flow velocity: 6ml/min,, detect wavelength: 280 nm, collect the chromatographic peak of 59.0 min, decompression and solvent recovery, compd A; Collect the chromatographic peak of 62.1 min, decompression and solvent recovery gets compd B; Collect the chromatographic peak of 69.0 min, decompression and solvent recovery gets Compound C.
A further object of the present invention provide extract in described three kinds of tubers of dwarf lilyturf have the application of the active homoisoflavone compounds of antitumor inhibition in preparation prevention and treatment tumor disease medicine.
The active homoisoflavone compounds of antitumor inhibition that has that extracts in three kinds of tubers of dwarf lilyturf of the present invention can be used as activeconstituents, adds the auxiliary material of accepting on the pharmaceutics, makes preparation according to the preparation method of the preparation of putting down in writing on the pharmaceutics.
Described preparation comprises injection liquid, drip liquid, powder injection, granule, tablet, electuary, powder, oral liquid, sugar coated tablet, film coated tablet, enteric coated tablet, capsule, hard capsule, soft capsule, sucks agent, granule, pill, paste, sublimed preparation, sprays, pill, disintegrating agent, orally disintegrating tablet, micropill etc.
The present invention first from the tuber of dwarf lilyturf medicinal material extraction separation three kinds have the active homoisoflavone compounds of antitumor inhibition, pharmacological research confirms to have certain function of tumor inhibition, modern Chinese herbal medicine for exploitation treatment tumor disease has great importance, and this class homoisoflavone compounds can be used for preparing the medicine of treatment and prophylaxis of tumours disease.
Embodiment
Further describe flesh and blood of the present invention and beneficial effect below in conjunction with embodiment, this embodiment only is used to the present invention is described but not limitation of the present invention.
The preparation of embodiment one compd A
With 30 kg tubers of dwarf lilyturf with 90% alcohol reflux 2 times, each 2 h are evaporated to medicinal extract, get medicinal extract and are suspended in the suitable quantity of water, use the petroleum ether extraction degreasing, separate water layer and use ethyl acetate extraction again.With the ethyl acetate extraction part decompression and solvent recovery, get 120.5 g medicinal extract, and itself and silica gel are mixed sample, be added in the silicagel column and separate.Eluent is that volume ratio is methylene dichloride and the methyl alcohol of 100:0～70:1; Volume ratio is methylene dichloride and the methyl alcohol of 50:1, and collected volume is separated it with normal phase silicagel column than for getting sample behind the methylene dichloride of 50:1 and the meoh eluate concentrate drying again, and eluent is that volume ratio is sherwood oil and the acetone of 8:1～5:1; Volume ratio is sherwood oil and the acetone of 4:1, and collected volume continues to separate the sample that obtains than for getting sample behind the sherwood oil of 4:1 and the acetone elutriant concentrate drying with preparative liquid chromatography; The separation condition of preparative chromatography: chromatographic column is a preparative column, and moving phase is water and acetonitrile, isocratic elution.
The preparative liquid chromatography separation condition:
Instrument: Agilent 1100 preparative liquid chromatographs are equipped with the DAD detector.
Chromatographic column: Agilent Zorbax SB-C
18Post (250 * 21.2 mm, 7 μ m); Moving phase: acetonitrile: water is 45:55, flow velocity: 6ml/min, and, detect wavelength: 280 nm.Collect the chromatographic peak of 59.0 min, decompression and solvent recovery gets compd A.
The structural identification data of compd A are as follows:
Yellow unformed powder.
Nm (log ε): 286 (4.33), 250 (3.56), 225 (4.57);
+ 60.5 (c=0.08 g/100ml, C
2H
5OH).; IR (KBr): 3526,2926,1655,1598,1514,1467,1374,1301,1249,1186,1118.;
1H NMR (500MHz,
CDCl 3 ): 4.27 (dd, J=11.5,4.0), 4.09 (dd, J=11.4,7.0), 2.68-2.72 (m), 2.63 (dd, J=14.0,11.0), 3.11 (dd, J=13.5,4.0), 7.12 (d, J=8.5), 6.82 (d, J=8.5), 6.82 (d, J=8.5), 7.12 (d, J=8.5), 3.76 (s), 3.76 (s), 2.10 (s), 2.06 (s);
13C NMR (500MHz,
CDCl 3 ); 68.9,48.6,192.2,158.0,111.6,159.2,106.9,32.2,159.8,108.6,130.7,130.3,114.2,158.4,114.2,130.3,61.4,55.4,8.1,8.1; ESI-MS (pos.): 343 ([M+H]
+), ESI-TOF-MS:365.1308 ([M+Na]
+, C
20H
22O
5Na
+; Calc. 365.1365); CD (c=2.92 * 10-4 mol/l, C
2H
5OH) [θ] 25 nm+2099 (249) ,-4585 (288) ,+1767 (320) ,-1449 (353).
Structure elucidation shows that this compound is: (3R)-2, and 3-dihydro-7-hydroxy-5-methyl oxygen base-3-(4-p-methoxy-phenyl)-6,8-dimethyl-4H-chromogen-4 ketone.
The preparation of embodiment two compd Bs
The extraction of the tuber of dwarf lilyturf, extraction, silica gel sepn process and preparative liquid chromatography condition are with embodiment one, and different is the chromatographic peak of collecting 62.1 min, and decompression and solvent recovery gets compd B.
The structural identification data of compd B are as follows:
The unformed powder of white.
Nm (log ε): 287 (4.32), 251 (3.57), 206 (4.55);
+ 67.1 (c=0.076 g/100ml, C
2H
5OH); IR (KBr): 3411,2928,1658,1590,1486,1243,1188,1118,1037;
1H NMR (500MHz,
CDCl 3 ) 4.29 (dd, J=11.0,4.0), 4.11 (dd, J=11.0,7.5), 2.69-2.73 (m), 2.61 (dd, J=14.0,10.0), 3.15 (dd, J=14.0,4.5), 6.72 (d, J=1.5), 6.73 (d, J=8.0), 6.67 (dd, J=8.0,1.5), 5.92 (s), 3.81 (s), 2.10 (s), 2.07 (s);
13C NMR (500MHz,
CDCl 3 ) 68.9,48.6,191.9,158.1,111.5,159.0,106.9,32.8,159.7,108.7,132.6,109.6,146.4,148.0,108.5,122.3,101.1,61.4,8.1,8.1; ESI-MS (pos.): 357 ([M+H]
+)., ESI-TOF-MS:379.1158 ([M+Na]
+, C
20H
20O
6Na
+; Calc. 379.1157); CD (c=2.64 * 10-4 mol/l, C
2H
5OH) [θ] 25 nm+1323 (249) ,-5799 (292) ,+1867 (323) ,-1281 (352).
Structure elucidation shows that this compound is: (3R)-3-(1,3-benzo dioxy alcohol-5-ylmethyl)-2,3-dihydro-7-hydroxy-5-methyl oxygen base-6,8-dimethyl-4H-chromogen-4-ketone.
The preparation of embodiment three Compound C
The extraction of the tuber of dwarf lilyturf, extraction, silica gel sepn process and preparative liquid chromatography condition are with embodiment one, and different is the chromatographic peak of collecting 69.0 min, and decompression and solvent recovery gets Compound C.
The structural identification data of Compound C are as follows:
The unformed powder of white,
Nm (log ε): 285 (4.15), 251 (3.39), 206 (4.42);
+ 42.3 (c=0.078 g/100ml, C
2H
5OH); IR (KBr): 3230,2932,1662,1593,1492,1276,1165,1095,1095,1043;
1H NMR (500MHz, DMSO-d
6) 4.20 (dd, J=11.5,4.5), 4.01 (dd, J=11.5,8.5), 2.69-2.73 (m), 2.55 (dd, J=14.0,9.5), 2.99 (dd, J=14.0,5.5), 6.19 (s), 6.81 (d, J=1.0), 6.81 (d, J=8.0), 6.66 (dd, J=8.0,1.0), 5.96 (s), 3.80 (s), 1.92 (s);
13C NMR (500MHz, DMSO-d
6) 69.3,47.9,190.4,160.4,112.7,163.1,98.7,32.5,162.0,109.8,133.1,109.8,146.2,147.9,108.6,122.5,101.3,61.0,8.5; ESI-MS (pos.): 343 ([M+H]
+), ESI-TOF-MS:365.1001 ([M+Na]
+, C
19H
18O
6Na
+; Calc. 365.1014); CD (c=2.78 * 10-4 mol/l, C
2H
5OH) [θ] 25 nm+489 (248) ,-2334 (291) ,+985 (318) ,-694 (348).
Structure elucidation shows that this compound is: (3R)-3-(1,3-benzo dioxy alcohol-5-ylmethyl)-2,3-dihydro-7-hydroxy-5-methyl oxygen base-6-methyl-4H-chromogen-4-ketone.
The preparation of embodiment four dropping pill formulations
Get compd A or compd B or Compound C 0.1g and 10.5g polyoxyethylene glycol-20000 and mix, heating and melting moves in the dripping pill drip irrigation behind the change material, and in ℃ whiteruss of medicine liquid droplet to 6 ~ 8, oil removing makes 400 of dripping pills.
The preparation of embodiment five lyophilized injectable powders
Get compd A or compd B or Compound C 0.1g, glucose 4.5g, Sulfothiorine 0.9g and distilled water 1000ml, after said components mixes, 400 of packing, lyophilize, promptly.
The active appraisal experiment of embodiment homoisoflavone compounds six tubers of dwarf lilyturf
Vitro culture human oral cancer epithelial cell (Kb), human liver cancer cell (HepG2), human breast cancer cell (MCF-7) are carried out the homoisoflavone compounds anti-tumour cell proliferative activity evaluation experimental tuber of dwarf lilyturf.37 ℃ of culture condition, 5% carbonic acid gas, the nutrient solution proportioning: 90%DMEM substratum or RPMI1640 substratum+10% foetal calf serum (volume ratio)+200U/L is two anti-.With the tuber of dwarf lilyturf homoisoflavone compounds A, compd B, Compound C be diluted to the concentration gradient of 0.391～50 μ g/ml respectively with the cell culture fluid sesquialter, add in the tumour cell that 96 orifice plates cultivate and hatched 48 hours, adopt mtt assay to estimate its antitumor proliferation activity.The result: compd A is for the half-inhibition concentration (IC of HepG2, Kb and MCF-7 tumour cell
50) be respectively 33.14 μ g/ml, 29.96 μ g/ml and 29.67 μ g/ml; Compd B is for the IC of HepG2, Kb and MCF-7 tumour cell
50Be respectively 28.30 μ g/ml, 18.83 μ g/ml and 19.36 μ g/ml; Compound C is for the IC of HepG2, Kb and MCF-7 tumour cell
50Be respectively 24.71 μ g/ml, 14.74 μ g/ml and 31.19 μ g/ml.Show that tuber of dwarf lilyturf homoisoflavone compounds is inhibited for the propagation of Kb, HepG2, MCF-7 tumour cell.
Claims (6)
1. class homoisoflavone compounds in the tuber of dwarf lilyturf, it is characterized in that, the molecular formula of this compounds is: (3R)-2,3-dihydro-7-hydroxy-5-methyl oxygen base-3-(4-p-methoxy-phenyl)-6,8-dimethyl-4H-chromogen-4 ketone, (3R)-3-(1,3-benzo dioxy alcohol-5-ylmethyl)-2,3-dihydro-7-hydroxy-5-methyl oxygen base-6,8-dimethyl-4H-chromogen-4-ketone and (3R)-3-(1,3-benzo dioxy alcohol-5-ylmethyl)-2,3-dihydro-7-hydroxy-5-methyl oxygen base-6-methyl-4H-chromogen-4-ketone.
2. the preparation method of class homoisoflavone compounds in the tuber of dwarf lilyturf is characterized in that, realizes by following steps:
(1) will use 90% alcohol reflux the tuber of dwarf lilyturf;
(2) extract is evaporated to medicinal extract;
(3) medicinal extract is suspended in the water, uses petroleum ether degreasing, use ethyl acetate extraction, the reclaim under reduced pressure ethyl acetate gets ethyl acetate extract;
(4) ethyl acetate extract and silica gel are mixed sample, with normal phase silicagel column it is separated, be methylene dichloride and the methanol-eluted fractions agent wash-out of 100:0～70:1 with volume ratio earlier, be methylene dichloride and the methanol-eluted fractions of 50:1 again with volume ratio, collected volume is than being the elutriant of 50:1, get sample behind the concentrate drying, with normal phase silicagel column it being carried out the second time again separates, be sherwood oil and the acetone eluent wash-out of 8:1～5:1 with volume ratio earlier, be sherwood oil and the acetone wash-out of 4:1 again with volume ratio, collected volume is than being the elutriant of 4:1, get sample behind the concentrate drying, preparative liquid chromatography continues to separate the sample that obtains, and the separation condition of preparative chromatography: chromatographic column is a preparative column, moving phase is water and acetonitrile, isocratic elution.
3. the preparation method of a class according to claim 2 homoisoflavone compounds in the tuber of dwarf lilyturf is characterized in that preparative liquid chromatography separation condition: chromatographic column: Agilent Zorbax SB-C
18Post, 250 * 21.2 mm, 7 μ m; Moving phase: acetonitrile: water is 45:55, flow velocity: 6ml/min, detect wavelength: 280 nm, collect the chromatographic peak of 59.0 min, decompression and solvent recovery, get (3R)-2,3-dihydro-7-hydroxy-5-methyl oxygen base-3-(4-p-methoxy-phenyl)-6,8-dimethyl-4H-chromogen-4 ketone; Collect the chromatographic peak of 62.1 min, decompression and solvent recovery gets (3R)-3-(1,3-benzo dioxy alcohol-5-ylmethyl)-2,3-dihydro-7-hydroxy-5-methyl oxygen base-6,8-dimethyl-4H-chromogen-4-ketone; Collect the chromatographic peak of 69.0 min, decompression and solvent recovery gets (3R)-3-(1,3-benzo dioxy alcohol-5-ylmethyl)-2,3-dihydro-7-hydroxy-5-methyl oxygen base-6-methyl-4H-chromogen-4-ketone.
4. a class according to claim 1 is the application of homoisoflavone compounds in preparation prevention and treatment tumor disease medicine in the tuber of dwarf lilyturf.
5. application according to claim 4 is characterized in that, described medicine adds acceptable auxiliary on the pharmaceutics by homoisoflavone compounds in the tuber of dwarf lilyturf, according to the method preparation of putting down in writing on the pharmaceutics.
6. application according to claim 5 is characterized in that described preparation comprises liquid preparation or solid preparation.
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Cited By (6)
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| CN105301130A (en) * | 2015-10-20 | 2016-02-03 | 成都中医药大学 | High-performance liquid chromatography method for detecting flavonoid content in radix ophiopogonis |
| CN105663673A (en) * | 2016-01-26 | 2016-06-15 | 中国科学院生物物理研究所 | Method for preparing homoisoflavonoids from fragrant solomonseal rhizomes and application of homoisoflavonoids in medicines |
| CN112294794A (en) * | 2019-08-01 | 2021-02-02 | 四川大学 | Application of methyl ophiopogonone A in preparation of medicine for preventing and/or treating non-alcoholic fatty liver disease and liver injury |
| CN113024527A (en) * | 2021-03-24 | 2021-06-25 | 上海诗丹德标准技术服务有限公司 | Compound derived from Zhejiang ophiopogon root, application and pharmaceutical composition thereof |
| CN113045526A (en) * | 2021-03-29 | 2021-06-29 | 上海诗丹德标准技术服务有限公司 | Thunberg ophiopogon root source compound and application and pharmaceutical composition thereof |
| CN114259454A (en) * | 2022-01-24 | 2022-04-01 | 浙江省林业科学研究院 | Tear-type Zhejiang radix ophiopogonis whitening mask and preparation method thereof |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105301130A (en) * | 2015-10-20 | 2016-02-03 | 成都中医药大学 | High-performance liquid chromatography method for detecting flavonoid content in radix ophiopogonis |
| CN105663673A (en) * | 2016-01-26 | 2016-06-15 | 中国科学院生物物理研究所 | Method for preparing homoisoflavonoids from fragrant solomonseal rhizomes and application of homoisoflavonoids in medicines |
| CN105663673B (en) * | 2016-01-26 | 2019-08-09 | 中国科学院生物物理研究所 | The preparation method of radix polygonati officinalis homoisoflavone and its application in medicine |
| CN112294794A (en) * | 2019-08-01 | 2021-02-02 | 四川大学 | Application of methyl ophiopogonone A in preparation of medicine for preventing and/or treating non-alcoholic fatty liver disease and liver injury |
| CN112294794B (en) * | 2019-08-01 | 2021-07-30 | 四川大学 | Application of methyl ophiopogonone A in preparation of medicine for preventing and/or treating non-alcoholic fatty liver disease and liver injury |
| CN113024527A (en) * | 2021-03-24 | 2021-06-25 | 上海诗丹德标准技术服务有限公司 | Compound derived from Zhejiang ophiopogon root, application and pharmaceutical composition thereof |
| CN113045526A (en) * | 2021-03-29 | 2021-06-29 | 上海诗丹德标准技术服务有限公司 | Thunberg ophiopogon root source compound and application and pharmaceutical composition thereof |
| CN114259454A (en) * | 2022-01-24 | 2022-04-01 | 浙江省林业科学研究院 | Tear-type Zhejiang radix ophiopogonis whitening mask and preparation method thereof |
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Application publication date: 20110914 |