CN102464617A - Dicranostigma leptopodum berberrubine with anticancer activity and preparation method thereof - Google Patents

Dicranostigma leptopodum berberrubine with anticancer activity and preparation method thereof Download PDF

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CN102464617A
CN102464617A CN2010105516225A CN201010551622A CN102464617A CN 102464617 A CN102464617 A CN 102464617A CN 2010105516225 A CN2010105516225 A CN 2010105516225A CN 201010551622 A CN201010551622 A CN 201010551622A CN 102464617 A CN102464617 A CN 102464617A
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alkali
favus
scalp
premium
medicinal extract
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柳军玺
邸多隆
巩红飞
刘大护
张天才
魏小宁
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Lanzhou Institute of Chemical Physics LICP of CAS
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Abstract

The invention discloses dicranostigma leptopodum berberrubine with anticancer activity and a preparation method thereof. The compound is of an aporphine alkaloid compound, and the molecular formula of the compound is C20H20NO5. The dicranostigma leptopodum berberrubine is prepared through a collection and processing step, an extraction step, and a seperation and purification step of a dicranostigma leptopodum raw material. Extrinsic and intrinsic pharmacological experiments indicate that the dicranostigma leptopodum berberrubine has stronger anticancer activity.

Description

Has favus of the scalp premium alkali of antitumour activity and preparation method thereof
Technical field
The present invention relates to a kind of compound favus of the scalp premium alkali and preparation method thereof with antitumour activity.Specifically, the present invention relates to a kind of aporphine Alkaloid of extraction separation compound favus of the scalp premium alkali and preparation method thereof from the bloodroot slenderstalk dicranostigma herb.
Background technology
Slenderstalk dicranostigma herb [Dicranostigma leptopodum (Maxim) Fedde] has another name called Hong Maocao, the baldhead spends, reins in the horse back in (Shaanxi), is papaveracease slenderstalk dicranostigma herb platymiscium.Slenderstalk dicranostigma herb is biennial or perennial herb, high 25-80 centimetre; Slenderstalk dicranostigma herb is distributed in the temperate zone, Asia, and the first-class place of hills, hillside, roadside, farmland, meadow, wall of height above sea level 400-1300 rice is drought-enduring, barren-resistant; China produces entirely, mainly is distributed in provinces and regions such as Gansu, Shaanxi, Henan, Shanxi, Qinghai, Ningxia, Sichuan, Yunnan, Tibet; Slenderstalk dicranostigma herb mainly grows in north and south, the Qinling Mountains, basin, the Weihe River in Gansu Province; This plant spring, summers two Ji Junke excavate whole herb with root, dry in the shade or using fresh herb." national herbal medicine compilation " carries: " bitter, puckery, cool, poisonous "; " Shaanxi herbal medicine " carries: " bitter, puckery, cool in nature "; Effects such as that herb has is clearing heat and detoxicating, swelling and pain relieving, desinsection; Treating tonsillitis, toothache, throat pain, lymphoid tuberculosis; Be used for diseases such as the favus of the scalp, mange, ulcer, fistula, intractable stomatitis, suppurative otitis media, stomach ulcer, wound, zoster, scrotum tinea, vulvitis, colpitis mycotica outward.
Modern pharmacological research shows: the slenderstalk dicranostigma herb extract to BCG-CWS (BCG) and LPS (LPS) inductive mouse immune liver damage have the certain protection effect [Mao Aihong, Tang Deping, Xia Xiaohui. the slenderstalk dicranostigma herb extract is to CCl 4The influence of inductive chmice acute liver injury. Lanzhou University's journal (medicine), 2008,34 (2): 18-20]; Slenderstalk dicranostigma herb can significantly reduce because of CCl 4And the rising of the serum glutamic pyruvic transminase that causes (ALT), SEAP (ALP), glutamic-oxal(o)acetic transaminase (AST), serum lactic dehydrogenase (LDH) and liver mda (MDA) level; And can keep serum superoxide dismutases (SOD) level; Make hepatic tissue pathology change the [Zhang Yu that is improved; Zhang Wei, Tian Yuzhang. slenderstalk dicranostigma herb effective constituent is to mouse CCl 4The provide protection of liver injury, Qinghai Medicine College's journal, 2004,25 (1): 7-10]; The slenderstalk dicranostigma herb extract can suppress by H respectively in vivo and in vitro 2O 2The mouse red corpuscle oxidisability haemolysis that causes with pyrodin [cuckoo is flat for Zhao Qi, Han Yin. and the slenderstalk dicranostigma herb extract is machine-processed to hemolytic inhibitions of red corpuscle oxidisability. Lanzhou University's journal (medicine), 2006,32 (3): 40-45.].
The natural product chemistry composition Study show mainly contain in the slenderstalk dicranostigma herb luxuriant and rich with fragrance type of morphinane alkaloid of Ah pouncing on [pass unimpeded if; Wang Hongxin, period-luminosity is controlled. slenderstalk dicranostigma herb chemical ingredients and tissue morphology research. and pharmaceutical analysis magazine, 1982; 2 (5): 273-277]; This Alkaloid mostly has analgesia, calmness and the effect of adrenergic receptor appearance, and part of compounds has antitumour activity.
Summary of the invention
The object of the present invention is to provide a kind of new compound favus of the scalp premium alkali with antitumour activity.
Another object of the present invention is to provide a kind of preparation method with favus of the scalp premium alkali of antitumour activity.
We are the new compound favus of the scalp premium alkali of extraction separation from the bloodroot slenderstalk dicranostigma herb first, has antitumour activity.
A kind of favus of the scalp premium alkali with antitumour activity is characterized in that this compound for the luxuriant and rich with fragrance Alkaloid compounds of Ah pouncing on, has C 20H 20NO 5Molecular formula, chemical structural formula is suc as formula I
Figure BSA00000352873000021
Formula I
The chemical structure of compound favus of the scalp premium alkali provided by the invention through UV, IR, 1HNMR, 13The evaluation of modern spectrum such as CNMR, DEPT, COSY, HMQC, HMBC, HR-ESIMS and spectroscopic technique obtains confirming and having following physicochemical constant and SPECTROSCOPIC CHARACTERIZATION:
C 20H 20NO 5, red-purple pulverulent solids, HR-ESIMS:m/z=354.1335 [M] +, C 20H 20NO 5Calculated value be 354.1336; UV (MeOH) Max(Log) nm 225 (3.55), 281 (2.78), 328 (3.01) nm; IR (KBr) MaxCm -1: 1680,1603,1564cm -1 1H NMR spectrum with 13C NMR spectrum data are seen table 1:
Table 1 favus of the scalp premium alkali 1HNMR (400MHz) and 13CNMR (100MHz) data (TMS, ppm, JHz)
Figure BSA00000352873000022
Figure BSA00000352873000031
The preparation method of favus of the scalp premium alkali of the present invention is characterized in that through the processing of slenderstalk dicranostigma herb feedstock capture, extraction, three steps of separation and purification:
A, feedstock capture processing: gather slenderstalk dicranostigma herb, drying, pulverizing;
B, medicinal extract extraction step: the proton sour water that adopts 70-95% (V/V) ethanol or 5% to raw material cold soaking or reflux heat carry total medicinal extract;
C, purification procedures: total medicinal extract is used sherwood oil successively with alkalization water suspendible, and chloroform, propyl carbinol carry out liquid liquid and distribute extraction to obtain F A, F B, F CThree components; F BWith the mixed mixed solvent of forming of different volumes ratio, by polarity from small to large, gradient elution carries out common silica gel column chromatography and separates component with sherwood oil and acetone system or chloroform and methanol system, collects polarity at 4: 1 to 6: 1 component F B2F B2With the mixed solvent of sherwood oil and acetone 4: 1 by volume carry out again column chromatography separate favus of the scalp premium alkali bullion, obtain favus of the scalp premium alkali with the mixed solvent recrystallization of 2: 1 by volume compositions of chloroform and methyl alcohol.
The present invention shows that through external, intravital pharmacological evaluation favus of the scalp premium alkali has stronger antitumour activity.
The invention has the advantages that:
1, from slenderstalk dicranostigma herb extraction separation to compound favus of the scalp premium alkali with antitumour activity;
2, by preparation method provided by the invention, extraction separation prepares favus of the scalp premium alkali, and technology is simple, and method is reliable, and productive rate is high, and compound purity is good.
Description of drawings
Fig. 1 is ir spectra (IR) figure of formula I compound favus of the scalp premium alkali.
Fig. 2 is high resolution mass spectrum (HR-ESIMS) figure of formula I compound favus of the scalp premium alkali.
Embodiment
Understand the present invention for clearer, below in conjunction with embodiment the present invention is further described, but the invention is not restricted to following examples.
Embodiment 1: the extraction separation of favus of the scalp premium alkali in the slenderstalk dicranostigma herb
A, feedstock capture procedure of processing: it is an amount of to gather slenderstalk dicranostigma herb, dries in the shade, and suitably pulverizes.
B, medicinal extract extraction step: get slenderstalk dicranostigma herb 5Kg, add 8 times of amount 95% ethanol, cold soaking (7d * 3) filters, and decompression and solvent recovery gets total medicinal extract 180g.
C, separating step: be suspended from the 1000mL water 180g medicinal extract is muddy,, reclaim the medicinal extract F of solvent with 300mL sherwood oil (60-90 ℃) extraction 3 times A20g, residuum reclaim solvent and get medicinal extract F with 300mL chloroform extraction 3 times B30g, residuum gets medicinal extract F 3 times with the 300mL n-butanol extraction C30g.With chloroform F BPart medicinal extract is mixed appearance with 30g silica gel (100-200 order); 600g silica gel (200-300 order) is gone up the simple glass chromatography column, sherwood oil (60-90 ℃): (10: 1-2: 1) carry out gradient elution, 500mL is first-class part to acetone; Reclaim solvent; With thin-layer chromatography uv lamp (UV) down or spray with iodo-bismuth potassium iodide vegeto-alkali test solution, inspect and same composition, F B1(5g, 10: 1), F B2(4g, 4: 1), F B3(4g, 2: 1), three components.Component F B2Mix appearance with 5g silica gel (100-200 order); 40g silica gel (200-300 order) is gone up the simple glass chromatography column; Sherwood oil (60-90 ℃): acetone (4: 1) wash-out, with thin-layer chromatography uv lamp (UV) down or spray with iodo-bismuth potassium iodide vegeto-alkali test solution, the colour developing back merges same composition and gets favus of the scalp premium alkali 5mg.
Embodiment 2: the extraction separation of favus of the scalp premium alkali in the slenderstalk dicranostigma herb
A, feedstock capture procedure of processing: it is an amount of to gather slenderstalk dicranostigma herb, dries in the shade, and suitably pulverizes.
B, medicinal extract extraction step: get slenderstalk dicranostigma herb 5Kg, add 8 times of amount 5% aqueous sulfuric acids, reflux (1.5h * 3) is filtered, buck alkalization extracting solution, and decompression and solvent recovery gets total medicinal extract 300g.
C, separating step: be suspended from the 1000mL alkalization water 300g medicinal extract is muddy, with 300mL sherwood oil (60-90 ℃) extraction 3 times, the medicinal extract F of recovery solvent A15g, residuum reclaim solvent and get medicinal extract F with 300mL chloroform extraction 3 times B20g, residuum gets medicinal extract F 3 times with the 300mL n-butanol extraction C80g.With chloroform F BPart medicinal extract is mixed appearance with 20g silica gel (100-200 order); 400g silica gel (200-300 order) is gone up the simple glass chromatography column, chloroform: (10: 1-2: 1) carry out gradient elution, 500mL is first-class part to methyl alcohol; Reclaim solvent; With thin-layer chromatography uv lamp (UV) down or spray with iodo-bismuth potassium iodide vegeto-alkali test solution, inspect and same composition, F B1(2g, 10: 1), F B2(2g, 6: 1), F B3(3g, 2: 1), three components.Component F B2Mix appearance with 2g silica gel (100-200 order); 30g silica gel (200-300 order) is gone up the simple glass chromatography column; Sherwood oil (60-90 ℃): acetone (4: 1) wash-out, with thin-layer chromatography uv lamp (UV) down or spray with iodo-bismuth potassium iodide vegeto-alkali test solution, the colour developing back merges same composition and gets favus of the scalp premium alkali 5mg.
Embodiment 3: the extraction separation of favus of the scalp premium alkali in the slenderstalk dicranostigma herb
A, feedstock capture procedure of processing: it is an amount of to gather slenderstalk dicranostigma herb, dries in the shade, and suitably pulverizes.
B, medicinal extract extraction step: get slenderstalk dicranostigma herb 5Kg, add 10 times of amount 95% ethanol, reflux heat is carried (2h * 3), filters, and decompression and solvent recovery gets total medicinal extract 250g.
C, separating step: be suspended from the 1000mL buck 200g medicinal extract is muddy,, reclaim the medicinal extract F of solvent with 300mL sherwood oil (60-90 ℃) extraction 3 times A15g, residuum reclaim solvent and get medicinal extract F with 300mL chloroform extraction 3 times B20g, residuum gets medicinal extract F 3 times with the 300mL n-butanol extraction C80g.With chloroform F BPart medicinal extract is mixed appearance with 20g silica gel (100-200 order); 400g silica gel (200-300 order) is gone up the simple glass chromatography column, sherwood oil (60-90 ℃): (10: 1-2: 1) carry out gradient elution, 500mL is first-class part to acetone; Reclaim solvent; With thin-layer chromatography uv lamp (UV) down or spray with iodo-bismuth potassium iodide vegeto-alkali test solution, the colour developing back merges same composition, F B1(5g, 10: 1),, F B2(2g, 4: 1), F B3(6g, 2: 1) four components.Component F B2Mix appearance with 2g silica gel (100-200 order); 20g silica gel (200-300 order) is gone up the simple glass chromatography column; Sherwood oil (60-90 ℃): acetone (6: 1) wash-out; With thin-layer chromatography uv lamp (UV) down or spray with iodo-bismuth potassium iodide vegeto-alkali test solution, the colour developing back merges same composition and gets favus of the scalp premium alkali 4.5mg.
Embodiment 4: favus of the scalp premium alkali is to human liver cancer cell HepG 2Cell in vitro toxic action with the human lung cancer cell A549
A, preparation human hepatoma cell strain HepG 2Suspension with the human lung cancer cell A549: 0.25% tryptic digestion is made into 8 * 10 with nutrient solution 4Individual cell/mL cell suspension; Inoculating cell: every hole 100L is inoculated in 96 orifice plates;
B, cultivation in advance: 37 ℃, 5%CO 2And cultivate 24h under the saturated humidity;
C, with medicine favus of the scalp premium alkali: by 0.2,0.4,0.6,1.2,1.6, the dosing of 2.0mol/mL concentration, every hole 100L, each concentration is established three multiple holes.37 ℃, 5%CO 2And 24h is cultivated in continuation under the saturated humidity;
Behind D, the 24h, take out culture plate, every hole adds trichoroacetic acid(TCA) (TCA) the 50L fixed cell of 50% (mass/volume), and the final concentration of TCA is 10%, is added on the liquid level of every hole, in 4 ℃ of refrigerators, places 1h; TCA is removed, behind air drying with deionized water wash 5 times in each hole of culture plate; Every hole adds 0.4% SRB100L, and room temperature held 10～30min discards in each hole and washs 5 times with 1% acetate behind the liquid; Remove unconjugated dyestuff, using pH behind the air drying is 10.5, the dissolving of 10mmol/L tri methylol amino methane; 5min vibrates on oscillator plate; Under enzyme-linked immunosorbent assay instrument 490nm wavelength, measure the OD value,, obtaining growth of tumour cell inhibiting rate is defined as the extracorporeal inhibiting rate of medicine to tumour cell with the blank zeroing.Measure medicine favus of the scalp premium alkali to human hepatoma cell strain HepG 2IC with the human lung cancer cell A549 50Be respectively: 10mol/mL and 12mol/mL.
Embodiment 5: favus of the scalp premium alkali is to antitumor activity in the mouse S180 sarcoma body
Transplanting and the inoculation of A, S180 band knurl animal: get inoculation back 9-10d S180 in the age tumor-bearing mice that goes down to posterity; Oncocyte in the aseptic extraction mouse peritoneal; Place ice-water bath, the S180 cell concn that extracts is transferred to 1.0 * 10 with ice-cold saline water (containing 100U/ml penicillium mould and 100mg/L Streptomycin sulphate) 7Individual/mL.At mouse right fore armpit subcutaneous injection 0.2mL refrigerative cell suspension, TCS is 2.0 * 10 6Individual/only.
B, grouping and administration: the mouse that will inoculate S180 is divided into 5 groups at random by body weight, and 16 every group, i.e. dose groups, HT high dose group among model control group, HT low dose group, the HT.Other establishes the blank group, and the blank group is the inoculated tumour cell not, every day ip. saline water; Model control group, every day ip. saline water; Basic, normal, high dose groups, every day is respectively with the dosage ip. favus of the scalp premium alkali of 15mg/kg, 30mg/kg, 60mg/kg; Positive controls, per 2 days the i.p. endoxan (CTX) once, dosage is 30mg/kg.Successive administration 12 days, whole mouse cervical vertebra dislocations in the 13rd day are put to death, and get the knurl piece and weigh, and are calculated as follows tumour inhibiting rate: tumour inhibiting rate (%)=(the average knurl of the average knurl weight-administration of model control group group is heavy)/average knurl of model control group heavy * 100%.
D, result are through statistical study, and favus of the scalp premium alkali is respectively the tumour inhibiting rate of S180 sarcoma: high dose group 65.0%, middle dose groups 50.1%, low dose group 30.1%.This result shows that favus of the scalp premium alkali has certain restraining effect to mouse S180 sarcoma, to the body weight gain of S180 tumor-bearing mice, liver index, renal index, thymus index, index and spleen index all less than obviously influence.

Claims (2)

1. the favus of the scalp premium alkali with antitumour activity is characterized in that this compound for the luxuriant and rich with fragrance Alkaloid compounds of Ah pouncing on, has C 20H 20NO 5Molecular formula, chemical structural formula is suc as formula I
Figure FSA00000352872900011
Formula I.
2. the preparation method of favus of the scalp premium alkali according to claim 1 is characterized in that through the processing of slenderstalk dicranostigma herb feedstock capture, extraction, three steps of separation and purification:
A, feedstock capture processing: gather slenderstalk dicranostigma herb, drying, pulverizing;
B, medicinal extract extraction step: the proton sour water that adopts 70-95% (V/V) ethanol or 5% to raw material cold soaking or reflux heat carry total medicinal extract;
C, purification procedures: total medicinal extract is used sherwood oil successively with alkalization water suspendible, and chloroform, propyl carbinol carry out liquid liquid and distribute extraction to obtain F A, F B, F CThree components; F BWith the mixed mixed solvent of forming of different volumes ratio, by polarity from small to large, gradient elution carries out common silica gel column chromatography and separates component with sherwood oil and acetone system or chloroform and methanol system, collects polarity at 4: 1 to 6: 1 component F B2F B2With the mixed solvent of sherwood oil and acetone 4: 1 by volume carry out again column chromatography separate favus of the scalp premium alkali bullion, obtain favus of the scalp premium alkali with the mixed solvent recrystallization of 2: 1 by volume compositions of chloroform and methyl alcohol.
CN2010105516225A 2010-11-16 2010-11-16 Dicranostigma leptopodum berberrubine with anticancer activity and preparation method thereof Pending CN102464617A (en)

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Publication number Priority date Publication date Assignee Title
CN102389426A (en) * 2011-08-01 2012-03-28 王芳 Application of isoquinoline type alkaloids and derivatives thereof to preparation of medicine for inhibiting HPV (Human Papilloma Virus) infection
CN105250391A (en) * 2014-07-17 2016-01-20 中国科学院兰州化学物理研究所 Dicranostigma leptopodum (maxim) fedde alkaloid effective part preparation method
US11759349B2 (en) 2017-02-01 2023-09-19 Ceragem Co., Ltd. Ceramic lifting and lowering device for thermotherapeutic apparatus

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102389426A (en) * 2011-08-01 2012-03-28 王芳 Application of isoquinoline type alkaloids and derivatives thereof to preparation of medicine for inhibiting HPV (Human Papilloma Virus) infection
CN105250391A (en) * 2014-07-17 2016-01-20 中国科学院兰州化学物理研究所 Dicranostigma leptopodum (maxim) fedde alkaloid effective part preparation method
CN105250391B (en) * 2014-07-17 2019-06-21 中国科学院兰州化学物理研究所 A kind of preparation method of slenderstalk dicranostigma herb alkaloid valid target
US11759349B2 (en) 2017-02-01 2023-09-19 Ceragem Co., Ltd. Ceramic lifting and lowering device for thermotherapeutic apparatus

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