CN102309479A - Application of isoflavone compound in preparation of medicaments or foods for resisting tumors - Google Patents
Application of isoflavone compound in preparation of medicaments or foods for resisting tumors Download PDFInfo
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- CN102309479A CN102309479A CN201110165163A CN201110165163A CN102309479A CN 102309479 A CN102309479 A CN 102309479A CN 201110165163 A CN201110165163 A CN 201110165163A CN 201110165163 A CN201110165163 A CN 201110165163A CN 102309479 A CN102309479 A CN 102309479A
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Abstract
The invention relates to the field of pharmacy and medical technology and particularly relates to application of an isoflavone compound (irisflorentin) from Belamcanda chinensis (L.)DC. in the preparation of medicaments or foods for resisting tumors. Proven by in-vitro experiments, the isoflavone compound has an effect of obvious inhibiting the growth of cell strains A549 (human lung cancer cell), LOVO (human colon cancer cell), 6T-CEM (human Tcell leukemic cell) and HL-60 (human leukemic cell), therefore the isoflavone compound can be used for preparing the medicaments or foods for resisting tumors. The invention provides a new source for preparing the medicaments or foods for resisting tumors.
Description
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..The application is that application number is dividing an application of 201010144912.8 one Chinese patent application.
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.New flavone and isoflavone glycoside from Belamcanda chinensis; Chinese Chemical Letters 2007,18:158-160; Jin Li (Jin Li), Chen Hai-sheng (Chen Haisheng), et al.Chemical constituents from Belamcanda chinensis Journal 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, Wang Zhengtao. the chemical constitution study of Rhizoma Belamcandae (I), 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:
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.
Table 1 is seen in the group collocation of above-mentioned each chemical compound respectively.
The chemical constitution and the title of five kinds of isoflavone of table 1
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; Method for preparing sees [Jin Li (Jin Li) for details; Chen Hai-sheng (Chen Haisheng); Et al.Chemical constituents from Belamcanda chinensis 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
Combine embodiment at present, 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.Chemical constituents from Belamcanda chinensis Journal of Asian Natural Products Research 2008,10 (1): 89-91)
Chinese medicine Rhizoma Belamcandae dry rhizome 4Kg pulverizes the back and extracts 3 times decompression and solvent recovery with 80% alcohol heating reflux; 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 CHCl of gradient solvent 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 CHCl of gradient solvent 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 ELIASA: model: (WellscanMK-2) production firm: Finland Labsystems company 96 porocyte culture plates (U.S. Nune company)
5, experimental technique
1) preparation cell suspension:
By routine above-mentioned each cell strain is used that RPMI1640+15%NBS+ is two anti-to be mixed with concentration and to be 4-5 * 10
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 150ulDMSO; Concussion 10min fully after the dissolving, surveys 570nm OD value with the full-automatic ELIASA of MK-2.
6, experimental result
Measure isoflavonoid tectorigenin, wild flag aglycon, irisflorentin, iridin, iridin cell in vitro cytotoxic activity through 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
Visible by table 2; 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. the isoflavonoid irisflorentin is in preparation anti-tumor drug or Application in Food, and its chemical structural formula is following:
R wherein
1Be OCH
3
R
2And R
3Be O-CH
2-O;
R
4, R
5, R
6Be OCH
3
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| CN201110165163A CN102309479A (en) | 2011-06-17 | 2011-06-17 | Application of isoflavone compound in preparation of medicaments or foods for resisting tumors |
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| CN201110165163A CN102309479A (en) | 2011-06-17 | 2011-06-17 | Application of isoflavone compound in preparation of medicaments or foods for resisting tumors |
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| CN102309479A true CN102309479A (en) | 2012-01-11 |
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ID=45423302
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104592189A (en) * | 2015-01-30 | 2015-05-06 | 中国科学院成都生物研究所 | Isoflavonoid compound as well as preparation method and application thereof |
Citations (4)
| 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 |
| CN1879764A (en) * | 2006-05-16 | 2006-12-20 | 南京大学 | Medical use of iris |
| CN100999492A (en) * | 2006-12-22 | 2007-07-18 | 南京大学 | Quinoline kind iriyellowsin electronic isostericmer its preparation process and use |
| CN101797247A (en) * | 2010-04-09 | 2010-08-11 | 中国人民解放军第二军医大学 | Application of isoflavone compound in preparation of anti-tumor drug or food |
-
2011
- 2011-06-17 CN CN201110165163A patent/CN102309479A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1879764A (en) * | 2006-05-16 | 2006-12-20 | 南京大学 | Medical use of iris |
| CN1850817A (en) * | 2006-05-26 | 2006-10-25 | 南京大学 | Roofirisrhizome flavin non polar isostere, and its preparing method and use |
| CN100999492A (en) * | 2006-12-22 | 2007-07-18 | 南京大学 | Quinoline kind iriyellowsin electronic isostericmer its preparation process and use |
| CN101797247A (en) * | 2010-04-09 | 2010-08-11 | 中国人民解放军第二军医大学 | Application of isoflavone compound in preparation of anti-tumor drug or food |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104592189A (en) * | 2015-01-30 | 2015-05-06 | 中国科学院成都生物研究所 | Isoflavonoid compound as well as preparation method and application thereof |
| CN104592189B (en) * | 2015-01-30 | 2017-01-04 | 中国科学院成都生物研究所 | A kind of isoflavonoid, its preparation method and application |
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Application publication date: 20120111 |