CN101797247A - Application of isoflavone compound in preparation of anti-tumor drug or food - Google Patents

Application of isoflavone compound in preparation of anti-tumor drug or food Download PDF

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CN101797247A
CN101797247A CN201010144912A CN201010144912A CN101797247A CN 101797247 A CN101797247 A CN 101797247A CN 201010144912 A CN201010144912 A CN 201010144912A CN 201010144912 A CN201010144912 A CN 201010144912A CN 101797247 A CN101797247 A CN 101797247A
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food
iridin
preparation
human
tectorigenin
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CN101797247B (en
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陈海生
金丽
刘建国
金永生
赵卫权
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Second Military Medical University SMMU
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Abstract

The invention relates to the technical field of drugs, in particular to application of isoflavone compounds in rhizoma belamcandae belamcanda chinensis (L.) DC. such as tectorigenin, wild iris genin, irisflorentin, wild iris glycoside or tecoridin in preparation of anti-tumor drugs or food. In vitro experiments show that the compounds have significant effect on inhibition of growth of cell lines A549 (human lung cancer cells), LOVO (human colon cancer cells), 6T-CEM (human T-cell leukemia cells) and HL-60 (human leukemia cells). Therefore, the compounds can be used for preparation of the anti-tumor drugs or food. The invention provides a novel source for preparation of the anti-tumor drugs or food.

Description

Isoflavonoid is in preparation anti-tumor drug or Application in Food
Technical field
The present invention relates to medical technical field, is that isoflavonoid tectorigenin, wild flag aglycon, irisflorentin, iridin or iridin are preparing antitumor drug or Application in Food among Rhizoma Belamcandae Belamcanda chinensis (L.) DC..
Background technology
Rhizoma Belamcandae is the dry rhizome of Iridaceae Rhizoma Belamcandae platymiscium Rhizoma Belamcandae Belamcanda chinensis (L.) DC..The main component that the Rhizoma Belamcandae of having reported contains has 19 isoflavonoid [Jin Li (Jin Li) such as wild flag aglycon, tectorigenin, irisflorentin, iristectorin A, dichotomitin, iridin and iridin, Chen Hai-Sheng (Chen Haisheng) et al.Newflavone and isoflavone glycoside from Belamcanda chinensis, ChineseChemical Letters 2007,18:158-160; Jin Li (Jin Li), Chen Hai-sheng (Chen Haisheng), et al.Chemical constituents from Belamcanda chinensisJournal of Asian Natural Products Research 2008,10 (1): 89-91; Hu Xiaolan, etc.The separation of chemical constituent and evaluation in the Rhizoma Belamcandae, bulletin of Chinese materia medica, 1982,7 (1): 29～30; Propitious essay is bright, Qin Minjian, the chemical constitution study (I) of Wang Zheng great waves Rhizoma Belamcandae, China Medicine University's journal, 2001,32 (3): 197～199; Surplus subclass, etc.The research of lipophilic ingredients in the B.Chinensis rhizome, Acta Pharmaceutica Sinica, 1983,18 (12): 969～972; Yamaki M, et al., Planta Med., 1990,56 (3): 335; Hydeyuki Ito, Satomi Onoue, et al., Isoflavonoids from Belamcanda chinensis, Chem.Pharm.Bull, 2001,49 (9): 1229～1231; Zhou Lixin, Lin Mao, He Lanfeng, the chemical constitution study of Rhizoma Belamcandae (I), Chinese herbal medicine, 1996,27 (1): 8～10; Qin Minjian, propitious essay is bright, Wang Zhengtao, the chemical constitution study of Rhizoma Belamcandae (II), Chinese herbal medicine, 2004,35 (5): 487～489].The chemical structure of general formula of isoflavonoid wild flag aglycon (irigenin), tectorigenin (tectorigenin), irisflorentin (irisflorentin), iridin (iridin) and iridin (tectoridin) is:
Figure GSA00000081695900021
Wherein, R 1Be OH or OCH 3
R 2Be OCH 3, OH or H;
R 3Be OH or Oglu;
R 4Be OCH 3, OH or H;
R 5Be OCH 3, OH, H or Oglu (glu is a glucosyl group);
R 6Be OCH 3, OH or H.
The group collocation of above-mentioned each chemical compound sees Table 1 respectively.
The chemical constitution and the title of five kinds of isoflavone of table 1
Figure GSA00000081695900022
But do not see that so far wild flag aglycon, tectorigenin, irisflorentin, iridin or iridin have the report of antitumor action aspect.
Summary of the invention
The objective of the invention is provides a kind of purposes for preparing antitumor drug or food for isoflavonoid wild flag aglycon, tectorigenin, irisflorentin, iridin or iridin.
The cell strain that the present invention selects for use is A549 (human lung carcinoma cell), LOVO (people's colon-cancer cell), 6T-CEM (human T cell leukemia cell), HL-60 (human leukemia cell); The experimental technique that adopts is conventional mtt assay.Chemical compound wild flag aglycon, tectorigenin, irisflorentin, iridin, iridin self-control, preparation method sees [Jin Li (Jin Li) for details, Chen Hai-sheng (Chen Haisheng), et al.Chemical constituents from Belamcandachinensis Journal of Asian Natural Products Research 2008,10 (1): 89-91].
Test through anti tumor activity in vitro, wild flag aglycon, tectorigenin, irisflorentin, iridin or iridin all have cytotoxic activity to above-mentioned cell strain, particularly tectorigenin has remarkable inhibition MDA-MB-435 (human breast cancer cell) cell growth effect, therefore can be used for preparing antitumor drug or food.
The present invention provides a kind of new source for preparing anti-tumor drug or food.
The specific embodiment
Now in conjunction with the embodiments, the present invention is described in detail.
Embodiment 1. preparation wild flag aglycons, tectorigenin, irisflorentin, iridin, iridin (see Jin Li (Jin Li) for details, Chen Hai-sheng (Chen Haisheng), et al.Chemicalconstituents from Belamcanda chinensis Journalof Asian NaturalProducts Research 2008,10 (1): 89-91)
Chinese medicine Rhizoma Belamcandae dry rhizome 4Kg, pulverizing the back extracts 3 times with 80% alcohol heating reflux, decompression and solvent recovery, get the about 200g of fluid extract, it is scattered among the distilled water 800ml, extract (each 500ml) respectively 3 times with petroleum ether, chloroform and ethyl acetate successively, after reclaiming solvent respectively, obtain petroleum ether extract 22g, chloroform extract 65g, acetic acid ethyl ester extract 28g.
Get chloroform extract 65g and carry out silica gel column chromatography, with the gradient solvent CHCl of system 3→ CHCl 3/ CH 3OH: H 2O (20: 1) eluting obtains stream part C1, C2 and C3 respectively.C1 is carried out Sephadex LH20 column chromatography again, use CHCl 3/ CH 3OH (1: 1) eluting is collected corresponding eluent, obtains compd B C-3 respectively, BC-1 and BC-2.
Get acetic acid ethyl ester extract 28g, through silica gel column chromatography, with the gradient solvent CHCl of system 3/ CH 3OH (20: 1 → 1: 1) eluting obtains stream part E1, E2 and E3.E3 is carried out Sephadex LH20 column chromatography again, use CHCl 3/ CH 3OH (1: 1) eluting is collected corresponding eluent, obtains compd B C-4 and BC-5.
Embodiment 2: wild flag aglycon, tectorigenin, irisflorentin, iridin, the experiment of iridin anti tumor activity in vitro
1, trial drug:
Wild flag aglycon (BC-1), tectorigenin (BC-2), irisflorentin (BC-3), iridin (BC-4), iridin (BC-5) are by embodiment 1 preparation;
Positive control drug: doxycycline (DOX), Changzhou pharmaceutical factory;
2, cell strain: provide by Shanghai Institute of Pharmaceutical Industry's Pharmacology Lab
1. A549 (human lung carcinoma cell)
2. LOVO (people's colon-cancer cell)
3. 6T-CEM (human T cell leukemia cell)
4. MDA-MB-435 (human breast cancer cell)
3, culture fluid: RPMI1640+15%NBS+ two anti-(10000U/mL penicillins+10000U/mL streptomycin)
4, other materials
Full-automatic microplate reader: model: (WellscanMK-2) production firm: Finland Labsystems company 96 porocyte culture plates (U.S. Nune company)
5, experimental technique
1) preparation cell suspension:
Two anti-to be mixed with concentration be 4-5 * 10 with RPMI1640+15%NBS+ with above-mentioned each cell strain routinely 4The cell suspension of individual/ml.
2) compounding pharmaceutical solution:
Wild flag aglycon (BC-1), tectorigenin (BC-2), irisflorentin (BC-3), iridin (BC-4), iridin (BC-5) and doxycycline (DOX) precision are weighed, respectively with an amount of DMSO dissolving, facing the time spent is diluted to desired concn with the PBS (-) that contains DMEM, and the DMSO final concentration is lower than 0.1% (V/V).Drug solution concentration is: 1mg/ml.
3) anti-tumor activity experiment:
Adopt mtt assay, on 96 orifice plates, add cell suspension 100 μ l/ holes respectively, put 5%CO 237 ℃ of cultivations in the incubator; Be cultured to 24h, add drug solution 10 μ l/ holes respectively, establish two multiple holes, continue to put 37 ℃ of cultivations in the 5%CO2 incubator; Be cultured to 72h, every hole adds the MTT solution 20 μ l of 5mg/ml, continues to cultivate 4h, stops cultivating, the centrifugal 5min of 1000rpm discards the culture fluid of cultivating in the plate hole then, and every hole adds 150 μ lDMSO, concussion 10min fully after the dissolving, surveys 570nm OD value with the full-automatic microplate reader of MK-2.
6, experimental result
Measure isoflavonoid tectorigenin, wild flag aglycon, irisflorentin, iridin, iridin cell in vitro cytotoxic activity by mtt assay, the IC50 and the inhibition rate of tumor cell of each chemical compound are as shown in table 2.
Five isoflavone compounds of table 2 are to the in-vitro multiplication inhibitory action of human body tumour cell
Figure GSA00000081695900061
By table 2 as seen, 5 kinds of isoflavonoids (BC-1-BC-5) all have inhibitory action to selected tumor cell, especially all apparent in view to the suppression ratio of people's colon-cancer cell (LOVO), tectorigenin (BC-2) and irisflorentin (BC-3) are very obvious to the inhibitory action of human breast carcinoma thin (MDA-MB-435).
Above-mentioned experimental result shows that isoflavonoid tectorigenin, wild flag aglycon, irisflorentin, iridin or iridin all have than remarkable antitumor effect, therefore can be used for preparing anti-tumor drug or food.

Claims (1)

1. isoflavonoid tectorigenin, wild flag aglycon, irisflorentin, iridin or iridin are preparing anti-tumor drug or Application in Food,
Their chemical structure of general formula is as follows:
Figure FSA00000081695800011
R wherein 1Be OH or OCH 3
R 2Be OCH 3, OH or H;
R 3Be OH or Oglu;
R 4Be OCH 3, OH or H;
R 5Be OCH 3, OH, H or Oglu;
R 6Be OCH 3, OH or H;
The group collocation of each chemical compound is respectively:
Figure FSA00000081695800012
CN2010101449128A 2010-04-09 2010-04-09 Application of isoflavone compound in preparation of anti-tumor drug or food Expired - Fee Related CN101797247B (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102309479A (en) * 2011-06-17 2012-01-11 中国人民解放军第二军医大学 Application of isoflavone compound in preparation of medicaments or foods for resisting tumors
CN102584767A (en) * 2011-01-07 2012-07-18 福建归真堂药业股份有限公司 Application of 4'-methoxy-7-hydroxy isoflavone in preparation of anti-tumor drugs and preparation method of 4'-methoxy-7-hydroxy isoflavone
CN102697768A (en) * 2012-06-07 2012-10-03 中国人民解放军第二军医大学 Application of luteolin flavonoid compounds in preparation of anti-tumor medicaments

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1850817A (en) * 2006-05-26 2006-10-25 南京大学 Roofirisrhizome flavin non polar isostere, and its preparing method and use
CN101011378A (en) * 2006-12-11 2007-08-08 中国人民解放军第二○八医院 Process for preparing iris aglycone and use thereof in preparation of medicament for treating atherosclerosis

Patent Citations (2)

* Cited by examiner, † Cited by third party
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CN1850817A (en) * 2006-05-26 2006-10-25 南京大学 Roofirisrhizome flavin non polar isostere, and its preparing method and use
CN101011378A (en) * 2006-12-11 2007-08-08 中国人民解放军第二○八医院 Process for preparing iris aglycone and use thereof in preparation of medicament for treating atherosclerosis

Non-Patent Citations (4)

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Title
《Biol. Pharm. Bull.》 20011031 Kyung-Tae Lee, et al. Tectorigenin, an Isoflavone of Pueraria thunbergiana BENTH., Induces Differentiation and Apoptosis in Human Promyelocytic Leukemia HL-60 Cells 1117-1121 1 第24卷, 第10期 2 *
《Journal of Natural Products》 20050301 Orawan Monthakantirat, et al. Phenolic Constituents of the Rhizomes of the Thai Medicinal Plant Belamcandachinensis with Proliferative Activity for Two Breast Cancer Cell Lines 361-364 1 第68卷, 第3期 2 *
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102584767A (en) * 2011-01-07 2012-07-18 福建归真堂药业股份有限公司 Application of 4'-methoxy-7-hydroxy isoflavone in preparation of anti-tumor drugs and preparation method of 4'-methoxy-7-hydroxy isoflavone
CN102584767B (en) * 2011-01-07 2015-05-13 福建归真堂药业股份有限公司 Application of 4'-methoxy-7-hydroxy isoflavone in preparation of anti-tumor drugs and preparation method of 4'-methoxy-7-hydroxy isoflavone
CN102309479A (en) * 2011-06-17 2012-01-11 中国人民解放军第二军医大学 Application of isoflavone compound in preparation of medicaments or foods for resisting tumors
CN102697768A (en) * 2012-06-07 2012-10-03 中国人民解放军第二军医大学 Application of luteolin flavonoid compounds in preparation of anti-tumor medicaments

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