CN104193679B - The method extracting isolating alkaloids from Aconitum soongaricum - Google Patents
The method extracting isolating alkaloids from Aconitum soongaricum Download PDFInfo
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- CN104193679B CN104193679B CN201410425142.2A CN201410425142A CN104193679B CN 104193679 B CN104193679 B CN 104193679B CN 201410425142 A CN201410425142 A CN 201410425142A CN 104193679 B CN104193679 B CN 104193679B
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- C07—ORGANIC CHEMISTRY
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- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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Abstract
A kind of method extracting isolating alkaloids from Aconitum soongaricum of disclosure, comprises the steps: (1) Aconitum soongaricum root alcohol steep, regulates leaching liquid pH value to 4-8, then uses dichloromethane extraction；(2) dichloromethane that step (1) is obtained by extraction crosses silicagel column mutually, with petroleum ether-ethyl acetate-diethylamine mixed liquor eluting, obtains alkaloid。Adopt the inventive method to extract respectively from the root of Aconitum soongaricum and isolate alkaloid 4 kinds single, respectively aconitine, songorine, 16,17-dihydro-12 β, 16 beta epoxide aneplines and 12-Biao-Ou Wu alkali。
Description
Technical field
The invention belongs to active ingredient of autonomic drug and extract field, the method being specifically related to extract isolating alkaloids from Aconitum soongaricum。
Background technology
Aconitum soongaricum (AconitumsoongoricumStapf.) for Ranunculaceae (Ranunculaceae) Aconitum (Aconitum) herbaceos perennial。Originate in the counties such as Yili of Xinjiang Xin Yuan, Nilka in China, be born in mountain region and the meadow tailo of height above sea level 1800～2600 meters[1]。Its root hyoscine, tuber has severe toxicity, can dispersing wind and cold, dehumidifying, pain relieving。Though the component of biology total alkali in Aconitum soongaricum has been analyzed by existing report, but how to extract to have isolated from Aconitum soongaricum and be still, by analyzing each alkaloid component detected, the problem that needs overcome。
Summary of the invention
It is an object of the invention to provide a kind of extraction from Aconitum soongaricum and isolate alkaloidal method。
The method extracting isolating alkaloids from Aconitum soongaricum, comprises the steps:
(1) Aconitum soongaricum root alcohol steep, regulates leaching liquid pH value to 4-8, then uses dichloromethane extraction；
(2) dichloromethane that step (1) is obtained by extraction crosses silicagel column mutually, with petroleum ether-ethyl acetate-diethylamine mixed liquor eluting, obtains alkaloid。
Further, step (1) leaching liquid pH value is adjusted to 4；In step (2), the volume ratio of petroleum ether-ethyl acetate-diethylamine is 8:2:0.5, and to collect 1000ml every time, the eluent collected the 18th～23 time merges, and crystallization obtains aconitine。
Further, step (1) leaching liquid pH value is adjusted to 8；In step (2), the volume ratio of petroleum ether-ethyl acetate-diethylamine is 10:1:0.5, and to collect 1000ml every time, the eluent collected the 6th～11 time merges, and crystallization obtains songorine。
Further, step (1) leaching liquid pH value is adjusted to 8；In step (2), the volume ratio of petroleum ether-ethyl acetate-diethylamine is 7:3:0.5, and to collect 1000ml every time, the eluent collected the 4th～9 time merges, and crystallization obtains 12-Biao-Ou Wu alkali。
Further, step (1) leaching liquid pH value is adjusted to 8；In step (2), the volume ratio of petroleum ether-ethyl acetate-diethylamine is 10:1:0.5, to collect 1000ml every time, the eluent collected the 1st～3 time merges, after SephadexLH-20 gel column, with chloroform-petroleum ether-methyl alcohol mixed liquor eluting that volume ratio is 5:5:1, obtain 16,17-dihydro-12 β, 16 beta epoxide aneplines。
Further, step (1), before regulating leaching liquid pH value, after leaching liquid concentration, first adds hydrochloric acid suspendible, then uses petroleum ether extraction defat, then regulate pH value with ammonia。
Adopt the inventive method to extract respectively from the root of Aconitum soongaricum and isolate alkaloid 4 kinds single, respectively aconitine, songorine, 16,17-dihydro-12 β, 16 beta epoxide aneplines and 12-Biao-Ou Wu alkali。
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described in further details。
Embodiment 1
Aconitum soongaricum root (10.0kg), pulverizes (crossing 20 mesh sieves), and 95wt% ethanol merceration extracts 3 times, 27L/ time, and extracting solution with 2wt% hydrochloric acid 5500ml suspendible, makes alkaloid be substantially soluble in suspension after thin film evaporation concentrates, then petroleum ether extraction defat；Residue water liquid ammonia adjusts PH=4, then with dichloromethane extraction, obtains dichloromethane phase。Dichloromethane is through silica gel column chromatography, with petroleum ether-ethyl acetate-diethylamine mixed liquor eluting, the volume ratio of petroleum ether-ethyl acetate-diethylamine is 8:2:0.5, flow velocity is 20ml/min, collects 1000ml eluent every time, and the eluent collected the 18th～23 time merges, crystallization, filter, obtain compound 1(1.5449g), determine that it is single compound by TLC thin layer chromatography。
Compound 1: colourless prismatic crystal, bismuth potassium iodide reaction is positive, mp.189 ~ 190 DEG C, C34H47NO11,1HNMR (400MHz, CDCl3)δPpm:1.10 (t,J=7.0Hz, 3H, NCH2 CH 3 ), 1.39 (s, 3H, COCH3), 3.11,3.27,3.34,3.75 (s, each 3H, OCH3), 4.04 (d,J=6.5Hz, 1H, 6-β H), 4.48 (s, 1H), 4.88 (d,J=4.8Hz, 1H, 14-α H), 8.03 (d,J=7.6Hz, 2H, Ar-H), 7.66 7.39 (m, 3H, Ar-H)；13CNMR (400MHz, CDCl3)δPpm:13.35 (C-21), 21.45 (COCH 3 ), 33.63 (C-2), 35.83 (C-12), 40.90 (C-10), 43.14 (C-4), 44.21 (C-9), 44.70 (C-7), 46.85 (C-5), 46.86 (C-19), 48.93 (C-20), 50.00 (C-11), 55.94 (C-1'), 58.00 (C-6'), 59.13 (C-18'), 61.02 (C-16'), 61.15 (C-17), 71.55 (C-3), 74.05 (C-13), 76.69 (C-18), 78.85 (C-15), 78.92 (C-14), 82.38 (C-1), 83.38 (C-6), 89.97 (C-16), 92.06 (C-8), 128.65 (C-3 "), 129.61 (C-2 "), 129.78 (C-1 "), 133.29 (C-4 "), 166.08 (ArCO), 172.43 (COCH3)。Data above is basically identical with document, therefore is accredited as aconitine。
Embodiment 2
Aconitum soongaricum root (10.0kg), pulverizes (crossing 20 mesh sieves), and 95wt% ethanol merceration extracts 3 times, 27L/ time, and extracting solution with 2% hydrochloric acid 5500ml suspendible, makes alkaloid be substantially soluble in suspension, petroleum ether extraction defat after thin film evaporation concentrates；Residue water liquid ammonia adjusts PH=8, then with dichloromethane extraction, obtains dichloromethane phase。Dichloromethane is through silica gel column chromatography, with the petroleum ether-ethyl acetate that volume ratio is 10:1:0.5-diethylamine mixed liquor eluting, flow velocity is 20ml/min, collect 1000ml eluent every time, the eluent collected the 6th～11 time merges, and crystallization filters, thus obtaining compound 2(1.3345g), determine that it is single compound by TLC thin layer chromatography。
Compound 2: colourless prismatic crystal, bismuth potassium iodide reaction is positive, mp.200 ~ 202 DEG C, C22H31NO3,1HNMR (400MHz, CDCl3)δPpm:0.77 (s, 4H, 4-CH3), 1.07 (t,J=6.8Hz, 3H, NCH2 CH 3 ), 3.10 (d,J=2.4Hz, 1H), 3.34 (dd,J=17.1,11.7Hz, 2H), 3.45 (s, 1H), 3.85 (s, 1H, 1-β H), 4.36 (d,J=8.1Hz, 1H, 15-α H), 5.20,5.30 (s, 2H, 17-CH2)；13CNMR (400MHz, CDCl3)δppm:13.63(NCH2 CH 3 ), 23.23 (C-6), 26.07 (C-18), 31.66 (C-2), 32.24 (C-3), 34.11 (C-4), 35.21 (C-9), 37.33 (C-11), 38.13 (C-14), 43.51 (C-7), 49.19 (C-5), 50.03 (C-8), 50.91 (NCH 2 CH3), 52.42 (C-10), 53.79 (C-13), 57.41 (C-19), 66.01 (C-20), 70.37 (C-1), 77.22 (C-15), 111.42 (C-17), 115.08 (C-16), 209.90 (C-12)。Data above is basically identical with document, therefore is accredited as songorine。
Embodiment 3
Aconitum soongaricum root (10.0kg), pulverizes (crossing 20 mesh sieves), and 95wt% ethanol merceration extracts 3 times, 27L/ time, and extracting solution with 2% hydrochloric acid 5500ml suspendible, makes alkaloid be substantially soluble in suspension, petroleum ether extraction defat after thin film evaporation concentrates；Residue water liquid ammonia adjusts PH=8, then with dichloromethane extraction, obtains dichloromethane phase。Dichloromethane is through silica gel column chromatography, with the petroleum ether-ethyl acetate that volume ratio is 10:1:0.5-diethylamine eluting, flow velocity is 20ml/min, to collect 1000ml every time, the eluent collected the 1st～3 time merges, the eluent merged is after SephadexLH-20 gel column, again with chloroform-petroleum ether-methyl alcohol mixed liquor eluting that volume ratio is 5:5:1, flow velocity is 5ml/min, 15ml/ collection pressed by eluent, the eluent crystallization that 7th time is collected, filter, with acetone recrystallization, thus obtaining compound 3(100mg), it is defined as single compound by TLC thin layer chromatography。
Compound 3: white amorphous powder, bismuth potassium iodide reaction is positive, mp.230 ~ 232 DEG C, C22H33NO3,1HNMR (400MHz, CDCl3)δPpm:0.74 (3H, s, 18-H), 1.04 (3H, t,J=8Hz, 22-H), 1.38 (3H, s, 17-H), 1.78 (1H, d,J=6Hz, 14 α-H), 2.71 (1H, dd,J=4,8Hz, 13-H), 3.42 (1H, brs, 20-H), 3.47 (1H, s, 15-H), 3.88 (1H, dd,J=16.3,9.4Hz, 1-H), 4.83 (1H, dd,J=7.7,3.9Hz, 12-H)。13CNMR (400MHz, CDCl3)δPpm:13.61 (C-22), 21.84 (C-17), 22.52 (C-6), 26.00 (C-18), 26.00 (C-11), 28.76 (C-14), 31.97 (C-2), 33.88 (C-4), 38.03 (C-3), 38.22 (C-9), 38.55 (C-13), 43.39 (C-7), 49.22 (C-8), 50.79 (C-21), 51.29 (C-10), 51.53 (C-5), 57.28 (C-19), 66.54 (C-20), 70.86 (C-1), 77.51 (C-12), 79.73 (C-15), 89.33 (C-16)。Data above is with basically identical, therefore is accredited as 16,17-dihydro-12 β, 16 beta epoxide aneplines。
Embodiment 4
Aconitum soongaricum root (10.0kg), pulverizes (crossing 20 mesh sieves), and 95wt% ethanol merceration extracts 3 times, 27L/ time, and extracting solution with 2% hydrochloric acid 5500ml suspendible, makes alkaloid be substantially soluble in suspension, petroleum ether extraction defat after thin film evaporation concentrates；Residue water liquid ammonia adjusts PH=8, then with dichloromethane extraction, obtains dichloromethane phase。Dichloromethane is through silica gel column chromatography, with the petroleum ether-ethyl acetate that volume ratio is 7:3:0.5-diethylamine mixed liquor eluting, flow velocity is 20ml/min, collect 1000ml eluent every time, the eluent collected the 4th～9 time merges, and crystallization filters, obtain compound 4(1.2910g), determine that it is single compound by TLC thin layer chromatography。
Compound 4: white amorphous powder, bismuth potassium iodide reaction is positive, C22H33NO3,1HNMR (400MHz, CDCl3)δPpm:0.77 (3H, s, 4-CH3), 1.09 (3H, t,J=4Hz, NCH2 CH 3 ), 3.91 (1H, br, s, 1-β H), 4.20 (1H, dd,J=15.9,7.2Hz, 12-α H), 5.13,5.34 (2H, s, 17-CH2)。13CNMR (400MHz, CDCl3)δppm:13.47(NCH2 CH 3 ), 23.58 (C-6), 26.40 (C-18), 29.57 (C-2), 31.60 (C-3), 32.64 (C-11), 33.77 (C-4), 36.05 (C-14), 37.02 (C-9), 43.84 (C-7), 43.88 (C-13), 48.58 (C-5), 50.93 (NCH 2 CH3), 51.04 (C-8), 52.54 (C-10), 58.29 (C-19), 66.33 (C-20), 67.10 (C-1), 69.89 (C-12), 77.23 (C-15), 111.55 (C-17), 155.00 (C-16)。Data above is basically identical with document, therefore is accredited as 12-Biao-Ou Wu alkali。
Claims (4)
1. from Aconitum soongaricum, extract the method separating aconitine, comprise the steps:
(1) Aconitum soongaricum root alcohol steep, leaching liquid first adds hydrochloric acid, then uses petroleum ether extraction defat, then is adjusted to 4 with ammonia adjustment leaching liquid pH value, then uses dichloromethane extraction；
(2) dichloromethane that step (1) is obtained by extraction crosses silicagel column mutually, with petroleum ether-ethyl acetate-diethylamine mixed liquor eluting, the volume ratio of petroleum ether-ethyl acetate-diethylamine is 8:2:0.5, to collect 1000ml every time, the eluent collected the 18th～23 time merges, and crystallization obtains aconitine。
2. from Aconitum soongaricum, extract the method separating songorine, it is characterised in that
(1) Aconitum soongaricum root alcohol steep, leaching liquid first adds hydrochloric acid, then uses petroleum ether extraction defat, then is adjusted to 8 with ammonia adjustment leaching liquid pH value, then uses dichloromethane extraction；
(2) dichloromethane that step (1) is obtained by extraction crosses silicagel column mutually, with petroleum ether-ethyl acetate-diethylamine mixed liquor eluting, the volume ratio of petroleum ether-ethyl acetate-diethylamine is 10:1:0.5, to collect 1000ml every time, the eluent collected the 6th～11 time merges, and crystallization obtains songorine。
3. from Aconitum soongaricum, extract the method separating 12-Biao-Ou Wu alkali, it is characterised in that
(1) Aconitum soongaricum root alcohol steep, leaching liquid first adds hydrochloric acid, then uses petroleum ether extraction defat, then is adjusted to 8 with ammonia adjustment leaching liquid pH value, then uses dichloromethane extraction；
(2) dichloromethane that step (1) is obtained by extraction crosses silicagel column mutually, with petroleum ether-ethyl acetate-diethylamine mixed liquor eluting, the volume ratio of petroleum ether-ethyl acetate-diethylamine is 7:3:0.5, to collect 1000ml every time, the eluent collected the 4th～9 time merges, and crystallization obtains 12-Biao-Ou Wu alkali。
4. from Aconitum soongaricum, extract separation 16,17-dihydro-12 β, the method for 16 beta epoxide aneplines, it is characterised in that
(1) Aconitum soongaricum root alcohol steep, leaching liquid first adds hydrochloric acid, then uses petroleum ether extraction defat, then is adjusted to 8 with ammonia adjustment leaching liquid pH value, then uses dichloromethane extraction；
(2) dichloromethane that step (1) is obtained by extraction crosses silicagel column mutually, with petroleum ether-ethyl acetate-diethylamine mixed liquor eluting, the volume ratio of petroleum ether-ethyl acetate-diethylamine is 10:1:0.5, to collect 1000ml every time, the eluent collected the 1st～3 time merges, after SephadexLH-20 gel column, with chloroform-petroleum ether-methyl alcohol mixed liquor eluting that volume ratio is 5:5:1, obtain 16,17-dihydro-12 β, 16 beta epoxide aneplines。
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| CN102579612A (en) * | 2012-03-27 | 2012-07-18 | 新疆医科大学 | Method for extracting total alkaloid of aconitum soongaricum |
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| CN101301370A (en) * | 2008-06-26 | 2008-11-12 | 中国科学院长春应用化学研究所 | Method for preparing monoester type alkaloids using Chinese medicinal material of aconitum as raw material |
| CN101829201A (en) * | 2010-05-19 | 2010-09-15 | 重庆市中药研究院 | Method for extracting alkaloid from monkshood medicinal material |
| CN102579612A (en) * | 2012-03-27 | 2012-07-18 | 新疆医科大学 | Method for extracting total alkaloid of aconitum soongaricum |
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