CN1986556A - Blackberry lily isoflavone compound and its application in medical field - Google Patents

Blackberry lily isoflavone compound and its application in medical field Download PDF

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CN1986556A
CN1986556A CN 200610147462 CN200610147462A CN1986556A CN 1986556 A CN1986556 A CN 1986556A CN 200610147462 CN200610147462 CN 200610147462 CN 200610147462 A CN200610147462 A CN 200610147462A CN 1986556 A CN1986556 A CN 1986556A
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isoflavones
iridin
och
isoflavone
trimethoxy
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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 present invention relates to natural medicine chemical technology, and is especially one kind of new isoflavonoid glycoside BC-17, chemically named as 5, 3', 5'-trimethoxy-6, 7-methylene dioxy isoflavonoid -4'-O-beta-D-glucoside, extracted from Belamcanda chinensis and its application in preparing medicine and health food for preventing and treating women's lower estrogen level and climacteric syndrome.

Description

Blackberry lily isoflavone compound and in the application of field of medicaments
Technical field:
The present invention relates to Natural Medicine Chemistry and medical technical field, relate to the chemical structure of a kind of blackberry lily isoflavone new compound that extraction separation goes out from the dry rhizome of Iridaceae blackberry lily platymiscium blackberry lily Belamcanda chinensis (L.) DC., and the blackberry lily isoflavone compound that comprises this new compound is low in preparation prevention and treatment estrogen level, the medicine of climacteric syndrome or the application in the protective foods.
Background technology:
Blackberry lily is the dry rhizome of Iridaceae blackberry lily platymiscium blackberry lily Belamcanda chinensis (L.) DC..Beginning is stated from Shennong's Herbal, and bitter is cold, goes into liver, lung channel, has clearing heat and detoxicating, relieve sore throat dissolving phlegm, the blood repercussive effect of loosing, and cures mainly swelling and pain in the throat, productive cough asthma etc.Be the conventional Chinese medicine material, and aboundresources.Studies show that, contain abundant isoflavonoid in the blackberry lily, is one of its characteristic component.The main component that the blackberry lily of having reported contains is the wild flag aglycon, tectorigenin, irisflorentin, iristectorin A, dichotomitin, Iridin, [Hu Xiaolan such as tectoridin, Xu's posthumous title, Huang Tianxia etc., the separation of chemical ingredients and evaluation in the blackberry lily, bulletin of Chinese materia medica, 1982,7 (1): 29～30; Propitious essay is bright, Qin Minjian, Wang Zhengtao, the chemical constitution study of blackberry lily (I), China Medicine University's journal, 2001,32 (3): 197～199; Surplus subclass, Wang Conghui, Liu Dai 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; HydeyukiIto, 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 blackberry lily (I), herbal medicine, 1996,27 (1): 8～10; Qin Minjian, propitious essay is bright, Wang Zhengtao, the chemical constitution study of blackberry lily (II), herbal medicine, 2004,35 (5): 487～489; Won SickWoo, Eun Hee Woo, An Isoflavone Noririsflorentin from Belamcanda chinensis, Phytochemistry, 1993,33 (4): 939～940; Zhou Lixin etc., Chinese chemical wall bulletin, 1997,8 (2): 133].So far do not see to the estrogen-like effects of belamcanda chinensis total isoflavone and composition thereof and at the report aspect the control climacteric syndrome.
Summary of the invention:
The objective of the invention is to from natural product, seek the natural product that is used to prepare the prevention disease low relevant safely and effectively with treatment and estrogen level, through continuous effort, finally a kind of blackberry lily isoflavone new compound that extraction separation goes out from the dry rhizome of Iridaceae blackberry lily platymiscium blackberry lily Belamcanda chinensis (L.) DC., called after 5,3 ', 5 '-trimethoxy-6,7-methylene-dioxy isoflavones-4 '-O-β-D-glucose; Simultaneously, the inventor has extracted other known blackberry lily isoflavone compound of q.s, find that all blackberry lily isoflavone compounds have estrogenic activity, can be low in preparation prevention and treatment estrogen level, used in the medicine of climacteric syndrome or the protective foods, thereby finished the present invention.
The present invention finishes by following technical solution, and particular content comprises: a kind of extraction separation of blackberry lily isoflavone new compound, and structure is identified; The research of the research of blackberry lily isoflavone new compound and other blackberry lily isoflavone compound estrogenic activity and associated medicinal use.
The present invention is by carrying 3 times with 80% ethanol heat after the blackberry lily pulverizing medicinal materials, concentrating under reduced pressure ethanol, gained medicinal extract with water-dispersion after, last macroporous resin, water and 90% ethanol elution successively, collect 90% ethanol eluate, concentrating under reduced pressure promptly gets belamcanda chinensis total isoflavone, from this component, further separate and obtained a kind of blackberry lily isoflavone new compound, called after 5,3 ', 5 '-trimethoxy-6,7-methylene-dioxy isoflavones-4 '-O-β-D-glucose, have the chemical structure shown in the chemical structural formula (1):
Its proton nmr spectra ( 1H-NMR) (DMSO-d 6) δ: 8.34 (1H, s, H-2), 7.02 (1H, s, H-8), 6.86 (2H, s, H-2 ', 6 '), 6.19 (2H, s ,-OCH 2O-), 4.97 (1H, d, J=6Hz, glc H-1 "), 3.91,3.80,3.80 (each 3H, s, OCH 3), carbon-13 nmr spectra ( 13C-NMR) (DMSO-d 6) δ: 152.06 (C-2), 123.89 (C-3), 173.72 (C-4), 140.48 (C-5), 135.91 (C-6), 152.62 (C-7), 93.54 (C-8), 153.83 (C-9), 113.15 (C-10), 127.28 (C-1 '), 107.85 (C-2 ', 6 '), 152.20 (C-3 ', 5 '), 134.43 (C-4 '), 102.61 (C-1 "); 77.15 (C-2 "), 74.12 (C-3 "), 69.82 (C-4 "), 76.50 (C-5 "), 60.71 (C-6 "), 102.55 (OCH 2O-"), 60.74,56.53,56.54 (OCH 3)].
And further separation has obtained 18 isoflavones components from this component, and the content of osajin composition (with the wild flag aglycon, tectorigenin, irisflorentin, Iridin, five principal constituent meters of tectoridin) is about 91%.
19 isoflavone compounds are respectively BC-1: wild flag aglycon (irigenin), BC-2: tectorigenin (tectorigenin), BC-3: irisflorentin (irisflorentin) [Yamaki M., Kato T., KashiharaM.and Takagi S., Planta Med, 56,335 (1990)], BC-4: nonirisflorentin (nonirisflorentin) [Woo W.S., Woo E.H., Pytochemistry, 33,939-940 (1993)], BC-5: iristectorin A (iristectorin A) [Xu Y L., Ma Y.B., Xiong J., ActaBotanica Yunnanica, 21,125～130 (1999)], BC-6: dichotomitin (dichotomitin) [ZhouL.X., Lin M., He L.F., Chinese Traditional and Herbal Drugs, 27,8-10 (1996)], BC-7:5,6,7,3 '-tetrahydroxy-4 '-methoxyl group isoflavones [Ito H., Onoue S., Yoshida T., Chem.Pharm.Bull., 49,1229-1231 (2001)], BC-8:5,7-dihydroxyl-6,3 ', 4 ', 5 '-tetramethoxy isoflavones [Sethi M.L., Taneja S.C., Dhar K.L., Atal C.K., Phytochemistry, 20,341～342 (1981)], BC-9:5,7,3 '-trihydroxy--8,4 ', 5 '-trimethoxy isoflavones (isoirigenin) [Atta-ur-Rahman, Nasim S., Baig I., Jalil S., Orhan I., Sener B.and Choudhary M., Journal of Ethnopharmacology, 86,177～180 (2003)], BC-10:5,7,4 '-trihydroxy--8-methoxyl group isoflavones (psi-tectorigenin) [Subba Raju K.V., Srimanarayana G., Phytochemistry, 17,1065～1066 (1978)], BC-11: irisolon (irisolone) [MoritaN., Arisawa M., Kondo Y., Takenoto T., Chem.Pharm.Bull, 21,600～603 (1973)], BC-12:5,7,4 '-trihydroxy--6,3 ', 5 '-trimethoxy isoflavones [Sethi M.L., Taneja S.C., Dhar K.L.and Atal C.K., Phytochemistry, 22,289 (1983)], BC-13: Iridin (iridin), BC-14: tectoridin (tectoridin), BC-15: iris aglycone-4 '-glucoside (tectorigenin-4 '-glucoside) [ShawlA.S., Kumar T., Phytochemistry, 31,1399～1401 (1992)], BC-16:3 '-hydroxyl tectoridin (3 '-hydroxy tectoridin) [Bidasee K.R., Maxwell A., Reynolds W.F., Patel V.andBesch JR.H.R., The Journal of Pharmacology and Experimental Therapeutics, 293,1074～1083 (2000)], BC-17:5,3 ', 5 '-trimethoxy-6,7-methylene-dioxy isoflavones-4 '-O-β-D-glucose, this compound is a new compound, BC-18:6 " O-P-(2-hydroxybenzoyl) Iridin (6 "-O-p-hydroxybenzoyl-iridin), BC-19:6 " O-vanilloyl Iridin (6 "-O-vanilloyl-iridin) [ItoH., Onoue S., Yoshida T., Chem.Pharm.Bull., 49,1229-1231 (2001)].The general structure of 19 isoflavone compounds (2) is as follows:
The title and the structure of 19 isoflavones components see Table 1:
The title and the structure of 19 isoflavones components of table 1
The compound code name R 1 R 2 R 3 R 4 R 5 R 6 R 7 The compound title
BC-1 OH OCH 3 OH H OH OCH 3 OCH 3 Wild flag aglycon (irigenin)
BC-2 OH OCH 3 OH H H OH H Tectorigenin (tectorigenin)
BC-3 OCH 3 O-CH 2-O H OCH 3 OCH 3 OCH 3 Irisflorentin (irisflorentin)
BC-4 OH O-CH 2-O H OCH 3 OCH 3 OCH 3 Nonirisflorentin (nonirisflorentin)
BC-5 OH OCH 3 OH H OH OCH 3 H Iristectorin A (iristectorin A)
BC-6 OH O-CH 2-O H OH OCH 3 OCH 3 Dichotomitin (dichotomitin)
BC-7 OH OH OH H OH OCH 3 H 5,6,7,3 '-tetrahydroxy-4 '-the methoxyl group isoflavones
BC-8 OH OCH 3 OH H OCH 3 OCH 3 OCH 3 5,7-dihydroxyl-6,3 ', 4 ', 5 '-the tetramethoxy isoflavones
BC-9 OH H OH OCH 3 OH OCH 3 OCH 3 5,7,3 '-trihydroxy--8,4 ', 5 '-trimethoxy isoflavones (isoirigenin)
BC-10 OH H OH OCH 3 H OH H 5,7,4 '-trihydroxy--8-methoxyl group isoflavones (psi-tectorigenin)
BC-11 OCH 3 O-CH 2-O H H OH H Irisolon (irisolone)
BC-12 OH OCH 3 OH H OCH 3 OH OCH 3 5,7,4 '-trihydroxy--6,3 ', 5 '-the trimethoxy isoflavones
BC-13 OH OCH 3 O-glu H OH OCH 3 OCH 3 Iridin (iridin)
BC-14 OH OCH 3 O-glu H H OH H Tectoridin (tectoridin)
BC-15 OH OCH 3 OH H H O-glu H Iris aglycone-4 '-glucoside (tectorigenin-4 '-glucoside)
BC-16 OH OCH 3 O-glu H OH OH H 3 '-the hydroxyl tectoridin (3 '-hydroxy tectoridin)
BC-17 OCH 3 O-CH 2-O H OCH 3 O-glu OCH 3 5,3 ', 5 '-trimethoxy-6,7-methylene-dioxy isoflavones-4 '-O-β-D-glucose
BC-18 OH OCH 3 Glc-p-hydroxy benxoic acid H OH OCH 3 OCH 3 6 " O-is right-the (2-hydroxybenzoyl) Iridin (6 "-O-p-hydroxybenzoyl-iridin)
BC-19 OH OCH 3 Glc-vanillic acid H OH OCH 3 OCH 3 6 " O-vanilloyl Iridin (6 "-O-vanilloyl-iridin)
Adopt the experiment of female castrated rats to find, belamcanda chinensis total isoflavone has and improves the estrogen level effect preferably removing the ovary rat.Therefore, as new purposes, belamcanda chinensis total isoflavone can be used for preparing prevention and treatment women estrogen level is low, the application on climacteric syndrome medicine or the food.
Embodiment:
Below by embodiment, the invention will be further described.
The preparation method of embodiment 1 belamcanda chinensis total isoflavone
The dry medicinal material 10Kg of blackberry lily extracts three times with 10 times of amount 95% ethanol heat, and each extraction time is 100 minutes, filter, decompression filtrate recycling ethanol, behind thin up to the 10 times volume, on the AB-8 macroporous resin column handled well, earlier with 5 column volumes of water elution, with 5 column volumes of 90% ethanol elution, collect this 90% ethanol part elutriant, decompression recycling ethanol again, concentrate drying gets belamcanda chinensis total isoflavone 198g (yield 2.5%).After testing, isoflavone levels is 91% in this extract.The gained belamcanda chinensis total isoflavone is again through silica gel, and column chromatography for separation such as gel get above 19 isoflavonoids.Compare by Spectrum Analysis mensuration with document, determined their chemical structure respectively.Wherein new isoflavones---5,3 ', 5 '-trimethoxy-6,7-methylene-dioxy isoflavones-4 '-the concrete separation and purification process of O-β-D-glucose is as follows:
Gained belamcanda chinensis total isoflavone 100g is carried out silica gel (200～300 order) column chromatography (post: 12cm * 120cm), with chloroform-methanol solvent systems (chloroform: 15: 1 → chloroform of methyl alcohol: gradient elution methyl alcohol 5: 1), collect chloroform: 10: 1 wash-out of methyl alcohol stream part, reclaim solvent and get component T1, about 9g.The T1 component is gone up silica gel 800 gram (200～300 order) column chromatographies again, and (post 4cm * 80cm), with chloroform-ethyl acetate (1: 1) solvent elution, part is collected, every part of 100ml, every part is carried out thin-layer chromatography (TLC) inspection, stream part 7～8 merging, reclaim solvent and get component T2, about 860mg.Again with SephadexLH-20 gel column on the T2 component, with chloroform: 1: 1 wash-out purifying of methyl alcohol obtains pure compound BC-17.By nucleus magnetic resonance (NMR) and mass spectrum analytical procedures such as (MS) determined the chemical structure of BC-17 be 5,3 ', 5 '-trimethoxy-6,7-methylene-dioxy isoflavones-4 '-O-β-D-glucose.Through chemical abstracts (CA) database retrieval, this compound is a new compound.
Embodiment 2 belamcanda chinensis total isoflavones are to the experiment of rat estrogen level influence
2.1 experiment purpose: research belamcanda chinensis total isoflavone gastric infusion is used for the treatment of female dimacteric syndrome to female castrated rats effect of estrogen after intending.
2.2 experiment material:
2.2.1 belamcanda chinensis total isoflavone: self-control.
2.2.2 soybean isoflavones: Handan City billowing wheat plant extract limited liability company, lot number: 20040412
2.2.3 benzylpenicillin sodium for injection: middle promise medicine company (Shijiazhuang) company limited, lot number: 05019321
2.2.4 0.9% physiological saline: the rich medicine company (group) of Shanghai Hua Yuanchang company limited, lot number: 05112503
2.3 dosage: group of solvents is given physiological saline, and belamcanda chinensis total isoflavone divides three dosage groups (300mg/kg, 600mg/kg and 900mg/kg), positive control soybean isoflavones 1000mg/kg.The molten long-pending 10ml/kg that is of administration
2.4 laboratory animal grouping and dosage setting:
45 of rats, body weight 180-250 gram, female, available from INM (conformity certification: SYXK-(army) 2002-044), be divided into 5 groups at random, 9 every group, i.e. solvent blank group, belamcanda chinensis total isoflavone is established high, medium and low three groups: 300mg/kg, 600mg/kg, 900mg/kg.Be mixed with suspension, gastric infusion, molten long-pending 10ml/kg with 0.5%CMC-Na when the positive control group of soybean isoflavones 1000mg/kg, above drug use.
2.5 experimental technique:
Female rats is with 24% Chloral Hydrate 350mg/kg intraperitoneal injection of anesthesia, ordinary method is opened the abdominal cavity, close the abdominal cavity after the excision bilateral ovaries, intramuscular injection injection benzylpenicillin sodium 50,000 is with preventing infection, and 9 days each groups of postoperative were by corresponding dosage administration, continuous 5 days, every day 1 time, put to death rat in 24 hours after the last administration, eye socket is got the centrifugal serum that stays of blood 1500rm/min, surveys estradiol level in the serum.
2.6 experimental result:
Compare with the solvent blank group, belamcanda chinensis total isoflavone 900mg/kg and soybean isoflavones 1000mg/kg group have highly significant to improve the estrogen level effect, and belamcanda chinensis total isoflavone 600mg/kg organizes the estrogen level action effect that is significantly increased, and sees the following form 2.
Table 2 belamcanda chinensis total isoflavone is to removing the influence of ovary rat model estradiol level
Group Estradiol level (pmol/L)
Group of solvents 32.97±5.814
Soybean isoflavones 1000mg/kg 61.217±24.980 **
Belamcanda chinensis total isoflavone 900mg/kg 62.312±20.640 **
Belamcanda chinensis total isoflavone 600mg/kg 53.403±21.758 *
Belamcanda chinensis total isoflavone 300mg/kg 34.046±18.068
*p＜0.05， **p＜0.01
2.7 conclusion: belamcanda chinensis total isoflavone 600mg/kg and 900mg/kg have estrogen-like effects to removing the ovary rat model estradiol level that is significantly improved.
The chemical structure of a kind of blackberry lily isoflavone new compound that extraction separation goes out in the dry rhizome of Iridaceae blackberry lily platymiscium blackberry lily Belamcanda chinensis (L.) DC., and comprise the blackberry lily isoflavone compound of this new compound can be low in preparation prevention and treatment estrogen level, be applied in the medicine of climacteric syndrome or the protective foods.

Claims (2)

  1. A novel blackberry lily isoflavone new compound 5,3 ', 5 '-trimethoxy-6,7-methylene-dioxy isoflavones-4 '-O-β-D-glucose, it is characterized in that this compound has the chemical structure shown in the chemical structural formula (1):
    Figure A2006101474620002C1
  2. 2. one kind comprises new isoflavone compounds described in the claim 1: 5,3 ', 5 '-trimethoxy-6,7-methylene-dioxy isoflavones-4 '-β-O-glucose and also comprise 18 isoflavone compounds BC-1: wild flag aglycon (irigenin), BC-2: tectorigenin (tectorigenin), BC-3: irisflorentin (irisflorentin), BC-4: nonirisflorentin (nonirisflorentin), BC-5: iristectorin A (iristectorin A), BC-6: dichotomitin (dichotomitin), BC-7:5,6,7,3 '-tetrahydroxy-4 '-the methoxyl group isoflavones, BC-8:5,7-dihydroxyl-6,3 ', 4 ', 5 '-the tetramethoxy isoflavones, BC-9:5,7,3 '-trihydroxy--8,4 ', 5 '-trimethoxy isoflavones (isoirigenin), BC-10:5,7,4 '-trihydroxy--8-methoxyl group isoflavones (psi-tectorigenin), BC-11: irisolon (irisolone), BC-12:5,7,4 '-trihydroxy--6,3 ', 5 '-the trimethoxy isoflavones, BC-13: Iridin (iridin), BC-14: tectoridin (tectoridin), BC-15: iris aglycone-4 '-glucoside (tectorigenin-4 '-glucoside), BC-16:3 '-hydroxyl tectoridin (3 '-hydroxytectoridin), BC-18:6 " O-P-(2-hydroxybenzoyl) Iridin (6 "-O-p-hydroxybenzoyl-iridin), BC-19:6 " O-vanilloyl Iridin (6 "-O-vanilloyl-iridin) low at preparation control estrogen level at interior isoflavonoid, application in climacteric syndrome medicine or the protective foods.
CN 200610147462 2006-12-19 2006-12-19 Blackberry lily isoflavone compound and its application in medical field Pending CN1986556A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101797265A (en) * 2010-04-09 2010-08-11 中国人民解放军第二军医大学 Application of belamcanda chinensis total isoflavone or isoflavone compounds in preparing medicaments and food for preventing and treating women's disease
CN102127047A (en) * 2011-01-10 2011-07-20 中国药科大学 Method for separating 5-hydroxyl isoflavonoids monomeric compound in blackberry lily
CN102631363A (en) * 2012-04-11 2012-08-15 李超生 Application of tectoridin in preparing medicine for preventing osteoporosis
CN106995425A (en) * 2017-04-20 2017-08-01 四川省中医药科学院 The extraction process and its isolation and purification method of a kind of Rhizoma Belamcandae flavone aglycone

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101797265A (en) * 2010-04-09 2010-08-11 中国人民解放军第二军医大学 Application of belamcanda chinensis total isoflavone or isoflavone compounds in preparing medicaments and food for preventing and treating women's disease
CN102127047A (en) * 2011-01-10 2011-07-20 中国药科大学 Method for separating 5-hydroxyl isoflavonoids monomeric compound in blackberry lily
CN102127047B (en) * 2011-01-10 2012-06-27 中国药科大学 Method for separating 5-hydroxyl isoflavonoids monomeric compound in blackberry lily
CN102631363A (en) * 2012-04-11 2012-08-15 李超生 Application of tectoridin in preparing medicine for preventing osteoporosis
CN106995425A (en) * 2017-04-20 2017-08-01 四川省中医药科学院 The extraction process and its isolation and purification method of a kind of Rhizoma Belamcandae flavone aglycone

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