CN101357167A - Method for increasing monoester alkaloid content in aconitum plant extract - Google Patents
Method for increasing monoester alkaloid content in aconitum plant extract Download PDFInfo
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- CN101357167A CN101357167A CNA2008100511618A CN200810051161A CN101357167A CN 101357167 A CN101357167 A CN 101357167A CN A2008100511618 A CNA2008100511618 A CN A2008100511618A CN 200810051161 A CN200810051161 A CN 200810051161A CN 101357167 A CN101357167 A CN 101357167A
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Abstract
The invention relates to a method for increasing content of monoester alkaloid in a wolfsbane extract. By regulating the pH of an extracting solution and adopting high pressure hydrolysis method, diester alkaloid in the extract can be transformed into the monoester alkaloid as much as possible. The reaction products are mainly products of a hydrolysis reaction, and the hydrolysis reaction happens to the diester alkaloid to generate the low-toxic monoester alkaloid. As the hydrolysis is applied to the extracting solution, no consideration is needed to be given to the influence of various factors such as moistening time of crude drugs and the like. Besides, the solution is evenly distributed, and the reaction is more stable and reliable, thus reducing by-products, shortening the production period, and increasing the yield of the monoester alkaloid by 0.17-13 times.
Description
Technical field
The invention belongs to technical field of Chinese medicines, be specifically related to increase the method for monoester alkaloid content in the aconitum plant extract.
Background technology
Ranunculaceae (Ranunculaceae) Aconitum (Aconitum) plant is a lot of in China's kind, about kind more than 160, main product is in southwestern each province, have 44 kinds approximately as medicinal, wherein Radix Aconiti Lateralis Preparata (Radix Aconiti Lateralis), Radix Aconiti (RadixAconiti) and Radix Aconiti Kusnezoffii (Radix Aconiti Kusnezoffii) are the most frequently used Chinese medicine.Radix Aconiti Lateralis Preparata is the daughter root of ranunculaceae plant Aconitum carmichjaelii Debx. (Aconitumcarmichaeli Debx), and Radix Aconiti is the dry parent root of ranunculaceae plant Aconitum carmichjaelii Debx., and Radix Aconiti Kusnezoffii is the dried root of ranunculaceae plant Aconitum kusnezoffii Reichb (Aconitum kusnezoffii Reichb).
Mainly contain three Alkaloids in the aconitum plant: diester-type alkaloids, monoester alkaloid and lipid alkaloid (table 1).Modern pharmacological research proves that diester-type alkaloids is the hypertoxic composition in Radix Aconiti Lateralis Preparata and the aconitum plant, the mice LD of aconitine, mesaconitine, hypaconitine
50Be respectively 1.8mg/kg, 1.9mg/kg and 5.8mg/kg (Ohno Y.J.Tox.2ToxinRev., 1998,17 (1): 1-11).Secondly poisoning symptom is gastrointestinal symptom based on nervous system and blood circulation, and the visible brain of postmortem and each organ of whole body all have in various degree hemorrhage " it is block nerves that this type of alkaloidal toxicity is summarised as curariform action mask) the neuromuscular junction conduction; The effect of aconitine sample shows as heart rate disorder, blood pressure drops, body temperature reduction, respiration inhibition, muscular paralysis and nervus centralis dysfunction etc. " aconitine can directly be poisoned myocardial cell; so its cardiotoxic mortality the most serious (Song Dongjiang. aconitine chemical compound toxicologic study overview [J]. Chinese pharmacology circular; 1989,5 (5): 272).Though monoester alkaloid content is low, toxicity is low, and is safe in utilization, and content is higher in processed product and the compatibility decocting liquid, but still have certain diester-type alkaloids remnants in the extract.In the heating hydrolysis process diester-type alkaloids such as aconitine at first hydrolysis lose C-8 position acetyl group and become less and benzoyl aconine class (benzoylaconitines) toxicity that still have certain pharmacological action of toxicity and be about 1/200 of aconitine, reach the detoxification purpose substantially.If further hydrolysis then loses C-14 position benzoyl ester group and forms to toxicity is littler, the aconine class (aconines) that pharmacological action is also more weak, its toxicity only are 1/2000～1/4000 of protozoa alkali.Hydrolyzed product is still effective.The purpose of this patent is promptly extracted the acid-base value of solution and the method for highly pressured hydrolysis by adjusting, makes the diester-type alkaloids in the extract change monoester alkaloid as much as possible into.
Summary of the invention
The present invention is by the acid-base value of regulating extract solution and the method for highly pressured hydrolysis, makes the diester-type alkaloids in the extract be converted into monoester alkaloid as much as possible.
Main diester-type alkaloids, monoester alkaloid and lipid alkaloid in table 1 aconitum plant
Oral half
The mass-to-charge ratio number causes death
Alkaloid R
1R
2R
3R
4R
5R
6R
7R
8
(m/z) amount
(mg/Kg)
Dibasic acid esters hypaconitine OCH
3CH
3H OCH
3OAc OBz OH OH 616 5.8
Type is given birth to mesaconitine OCH
3C
2H
5H OCH
3OAc OBz OH OH 632 1.9
Thing alkali aconitine OCH
3C
2H
5OH OCH
3OAc OBz OH OH 646 1.8
The 14-benzoyl
OCH
3 CH
3 H OCH
3 OH OBz OH OH 574 800
Aconine
Monoesters
In the 14-benzoyl
Type is given birth to
OCH
3 C
2H
5 H OCH
3 OH OBz OH OH 590 800
Aconine
Thing alkali
14-benzoyl crow
OCH
3 C
2H
5 OH OCH
3 OH OBz OH OH 604 1500
Amine
Inferior oleoyl-the 14-of 8-
Benzoyl time black OCH
3CH
3H OCH
3OLipo OBz OH OH 836 100-200
Amine
Inferior oleoyl-the 14-of fat type 8-
Black OCH in the biological benzoyl
3C
2H
5H OCH
3OLipo OBz OH OH 852 10-40
Alkali head amine
Inferior oleoyl-the 14-of 8-
Benzoyl aconite OCH
3C
2H
5OH OCH
3OLipo OBz OH OH 866＞400
Amine
A kind of method that increases monoester alkaloid content in the aconitum plant extract, its step and condition are as follows:
The dried powder of Aconitum carmichjaelii Debx. class plant is dipped in the alcoholic solution that volume fraction is 50-95% the dried powder quality (g) of Aconitum carmichjaelii Debx. class plant: the volume of the alcoholic solution of 50-95% (ml) is than being 1: 1-3; Leach ethanol extract after supersound extraction 1.5-4 hour; Handle again twice as stated above; Merge the ethanol extract that leaches for three times, 40 ℃-60 ℃ down decompression steam solvent, obtain extract; This extract becomes with the volume (ml) of the dried powder quality (g) of Aconitum carmichjaelii Debx. class plant and distilled water than being the solution of 3-6g/ml with distilled water diluting, add the ammonia adjust pH to 6.0-10.0, put in the autoclave in 100 ℃ of-120 ℃ of heating, heat time heating time, 40-80min obtained a kind of extracting solution that increases monoester alkaloid content in the aconitum plant extract.
Beneficial effect: a kind of method that increases monoester alkaloid content in the aconitum plant extract, product mainly are based on the hydrolysis product, and diester-type alkaloids generation hydrolysis generates the less monoester alkaloid of toxicity.Owing to be hydrolysis, need not consider the influence of various factors such as moistening time of raw medicinal herbs to extract solution.And solution is evenly distributed, and reacts more reliable and more stable.Reduce by-product, shorten the production cycle, improve monoester alkaloid productive rate 0.17-13 doubly.
Detection method
(1) mass spectrum semiquantitative method
180 ℃ of METAL HEATING PROCESS capillary temperatures; Spray voltage 4.5kV; Pipe lens compensation voltage 10V; Collision energy is 20%～42%; Nitrogen is shell gas; METAL HEATING PROCESS capillary voltage 10V; Syringe pump flow velocity 3 μ L/min.Get above-mentioned sample solution 20 μ L, add 100 μ L lappaconitines (internal standard substance), after 25 times of methanol dilutions, advance the electrospray mass spectrometer analysis.
(2) detection figure sees accompanying drawing 1 and accompanying drawing 2
Description of drawings
Accompanying drawing 1 increases the Electrospray Mass Spectrometry figure that the method for monoester alkaloid content obtains in the aconitum plant extract (616.88,632.68,646.61 are diester-type alkaloids among the figure) for Radix Aconiti without crossing.In the unhydrolysed as seen from the figure Radix Aconiti extracting solution sample mainly based on diester-type alkaloids, the content of monoester alkaloid very low (relative amount is 22.66%).
(590.63,574.62,604.58 are monoester alkaloid to the Electrospray Mass Spectrometry figure that accompanying drawing 2 obtains through the method that increases monoester alkaloid content in the aconitum plant extract for Radix Aconiti among the figure; 836.63,852.51 be ester-type alkaloids).Mainly be monoester alkaloid (relative amount is 317.90%) in the Radix Aconiti extracting solution sample after the hydrolysis as seen from the figure, diester-type alkaloids has been hydrolyzed into monoester alkaloid.
The specific embodiment
It is that supersound extraction leached ethanol extract after 1.5 hours in 50% the ethanol 5ml solution that embodiment 1 is dipped in volume ratio with the dried powder 5g of Radix Aconiti, handle again twice as stated above, merge the ethanol extract that leaches for three times, decompression steams solvent under 40 ℃, obtain the Radix Aconiti extract, it is the solution of 3g/ml that extract becomes the Radix Aconiti dried powder and the ratio of distilled water with distilled water diluting, add ammonia and transfer pH value to 6.0, to the high pressure reactor in 100 ℃ of heating, heat time heating time, 40min obtained the extracting solution of monoester alkaloid content in a kind of extract that increases Radix Aconiti.
The extracting solution of this Radix Aconiti is cooled to room temperature, get 20 μ L sample solutions, add 100 μ L lappaconitines as internal standard substance, behind the mixing, advance LCQ mass spectrum half-quantitative detection, relative amount before the whole hydrolysis of diester-type alkaloids, monoester alkaloid hydrolysis is 22.66%, and the relative amount after the hydrolysis is 317.90%.
It is that supersound extraction leached ethanol extract after 4 hours in 95% the ethanol 15ml solution that embodiment 2 is dipped in volume ratio with the dried powder 5g of Radix Aconiti, handle again twice as stated above, merge the ethanol extract that leaches for three times, decompression steams solvent under 60 ℃, obtain the Radix Aconiti extract, it is the solution of 6g/ml that extract becomes the Radix Aconiti dried powder and the ratio of distilled water with distilled water diluting, add ammonia and transfer pH value to 10.0, to the high pressure reactor in 120 ℃ of heating, heat time heating time, 80min obtained the extracting solution of monoester alkaloid content in a kind of extract that increases Radix Aconiti.
The extracting solution of this Radix Aconiti is cooled to room temperature, get 20 μ L sample solutions, add 100 μ L lappaconitines as internal standard substance, behind the mixing, advance LCQ mass spectrum half-quantitative detection, relative amount before the whole hydrolysis of diester-type alkaloids, monoester alkaloid hydrolysis is 22.66%, and the relative amount after the hydrolysis is 305.76%.
It is that supersound extraction leached ethanol extract after 3 hours in 75% the ethanol 10ml solution that embodiment 3 is dipped in volume ratio with the dried powder 5g of Radix Aconiti, handle again twice as stated above, merge the ethanol extract that leaches for three times, decompression steams solvent under 50 ℃, obtain the Radix Aconiti extract, it is the solution of 5g/ml that extract becomes the Radix Aconiti dried powder and the ratio of distilled water with distilled water diluting, add ammonia and transfer pH value to 7.0, to the high pressure reactor in 110 ℃ of heating, heat time heating time, 70min obtained the extracting solution of monoester alkaloid content in a kind of extract that increases Radix Aconiti.
The extracting solution of this Radix Aconiti is cooled to room temperature, get 20 μ L sample solutions, add 100 μ L lappaconitines as internal standard substance, behind the mixing, advance LCQ mass spectrum half-quantitative detection, relative amount before the whole hydrolysis of diester-type alkaloids, monoester alkaloid hydrolysis is 22.66%, and the relative amount after the hydrolysis is 276.98%.
The dried powder 5g of embodiment 4 Radix Aconiti Lateralis, processing method is with embodiment 1, obtains the extracting solution of monoester alkaloid content in a kind of extract that increases Radix Aconiti Lateralis.
The extracting solution of this Radix Aconiti Lateralis is cooled to room temperature, get 20 μ L sample solutions, add 100 μ L lappaconitines as internal standard substance, behind the mixing, advance LCQ mass spectrum half-quantitative detection, relative amount before the whole hydrolysis of diester-type alkaloids, monoester alkaloid hydrolysis is 21.09%, and the relative amount after the hydrolysis is 172.71%.
The dried powder 5g of Radix Aconiti Lateralis, processing method obtains the extracting solution of monoester alkaloid content in a kind of extract that increases Radix Aconiti Lateralis with embodiment 2.
The extracting solution of this Radix Aconiti Lateralis is cooled to room temperature, get 20 μ L sample solutions, add 100 μ L lappaconitines as internal standard substance, behind the mixing, advance LCQ mass spectrum half-quantitative detection, relative amount before the whole hydrolysis of diester-type alkaloids, monoester alkaloid hydrolysis is 21.09%, and the relative amount after the hydrolysis is 165.72%.
The dried powder 5g processing method of embodiment 6 Radix Aconiti Lateralis is with embodiment 3, obtains the extracting solution of monoester alkaloid content in a kind of extract that increases Radix Aconiti Lateralis.
The extracting solution of this Radix Aconiti Lateralis is cooled to room temperature, get 20 μ L sample solutions, add 100 μ L lappaconitines as internal standard substance, behind the mixing, advance LCQ mass spectrum half-quantitative detection, relative amount before the whole hydrolysis of diester-type alkaloids, monoester alkaloid hydrolysis is 21.09%, and the relative amount after the hydrolysis is 152.36%.
The dried powder 5g processing method of embodiment 7 Radix Aconiti Kusnezoffii Preparatas is with embodiment 1, obtains the extracting solution of monoester alkaloid content in a kind of extract that increases Radix Aconiti Kusnezoffii Preparata.
The extracting solution of this Radix Aconiti Kusnezoffii Preparata is cooled to room temperature, get 20 μ L sample solutions, add 100 μ L lappaconitines as internal standard substance, behind the mixing, advance LCQ mass spectrum half-quantitative detection, relative amount before the whole hydrolysis of diester-type alkaloids, monoester alkaloid hydrolysis is 57.71%, and the relative amount after the hydrolysis is 67.37%.
The dried powder 5g of embodiment 8 Radix Aconiti Kusnezoffii Preparatas, processing method is with embodiment 2, obtains the extracting solution of monoester alkaloid content in a kind of extract that increases Radix Aconiti Kusnezoffii Preparata.
The extracting solution of this Radix Aconiti Kusnezoffii Preparata is cooled to room temperature, get 20 μ L sample solutions, add 100 μ L lappaconitines as internal standard substance, behind the mixing, advance LCQ mass spectrum half-quantitative detection, relative amount before the whole hydrolysis of diester-type alkaloids, monoester alkaloid hydrolysis is 57.71%, and the relative amount after the hydrolysis is 65.39%.
The dried powder 5g of embodiment 9 Radix Aconiti Kusnezoffii Preparatas, processing method is with embodiment 3, obtains the extracting solution of monoester alkaloid content in a kind of extract that increases Radix Aconiti Kusnezoffii Preparata.
The extracting solution of this Radix Aconiti Kusnezoffii Preparata is cooled to room temperature, get 20 μ L sample solutions, add 100 μ L lappaconitines as internal standard substance, behind the mixing, advance LCQ mass spectrum half-quantitative detection, relative amount before the whole hydrolysis of diester-type alkaloids, monoester alkaloid hydrolysis is 57.71%, and the relative amount after the hydrolysis is 59.28%.
The dried powder 5g of embodiment 10 Radix Aconiti Kusnezoffii, processing method is with embodiment 1, obtains the extracting solution of monoester alkaloid content in a kind of extract that increases Radix Aconiti Kusnezoffii.
The extracting solution of this Radix Aconiti Kusnezoffii is cooled to room temperature, get 20 μ L sample solutions, add 100 μ L lappaconitines as internal standard substance, behind the mixing, advance LCQ mass spectrum half-quantitative detection, the whole hydrolysis of diester-type alkaloids, relative amount before the hydrolysis of lard type alkaloid is 191.82%, relative amount after the hydrolysis of lard type alkaloid is 299.36%, and the relative amount before the monoester alkaloid hydrolysis is 31.77%, and the relative amount after the monoester alkaloid hydrolysis is 45.81%.
The dried powder 5g of embodiment 11 Radix Aconiti Kusnezoffii, processing method is with embodiment 2, obtains the extracting solution of monoester alkaloid content in a kind of extract that increases Radix Aconiti Kusnezoffii.
The extracting solution of this Radix Aconiti Kusnezoffii is cooled to room temperature, get 20 μ L sample solutions, add 100 μ L lappaconitines as internal standard substance, behind the mixing, advance LCQ mass spectrum half-quantitative detection, the whole hydrolysis of diester-type alkaloids, relative amount before the hydrolysis of lard type alkaloid is 191.82%, relative amount after the hydrolysis of lard type alkaloid is 305.46%, and the relative amount before the monoester alkaloid hydrolysis is 31.77%, and the relative amount after the monoester alkaloid hydrolysis is 40.37%.
The dried powder 5g of embodiment 12 Radix Aconiti Kusnezoffii, processing method is with embodiment 3, obtains the extracting solution of monoester alkaloid content in a kind of extract that increases Radix Aconiti Kusnezoffii.
The extracting solution of this Radix Aconiti Kusnezoffii is cooled to room temperature, get 20 μ L sample solutions, add 100 μ L lappaconitines as internal standard substance, behind the mixing, advance LCQ mass spectrum half-quantitative detection, the whole hydrolysis of diester-type alkaloids, relative amount before the hydrolysis of lard type alkaloid is 191.82%, relative amount after the hydrolysis of lard type alkaloid is 287.56%, and the relative amount before the monoester alkaloid hydrolysis is 31.77%, and the relative amount after the monoester alkaloid hydrolysis is 37.88%.
The dried powder 5g of embodiment 13 Radix Aconiti Lateralis Preparata, processing method is with embodiment 1, obtains the extracting solution of monoester alkaloid content in a kind of extract that increases Radix Aconiti Lateralis Preparata.
The extracting solution of this Radix Aconiti Lateralis Preparata is cooled to room temperature, get 100 μ L sample solutions, add 20 μ L lappaconitines as internal standard substance, behind the mixing, advance LCQ mass spectrum half-quantitative detection, relative amount before the whole hydrolysis of diester-type alkaloids, monoester alkaloid hydrolysis is 47.24%, and the relative amount after the hydrolysis is 71.52%.
The dried powder 5g processing method of embodiment 14 Radix Aconiti Lateralis Preparata is with embodiment 2, obtains the extracting solution of monoester alkaloid content in a kind of extract that increases Radix Aconiti Lateralis Preparata.
The extracting solution of this Radix Aconiti Lateralis Preparata is cooled to room temperature, get 100 μ L sample solutions, add 20 μ L lappaconitines as internal standard substance, behind the mixing, advance LCQ mass spectrum half-quantitative detection, relative amount before the whole hydrolysis of diester-type alkaloids, monoester alkaloid hydrolysis is 47.24%, and the relative amount after the hydrolysis is 68.48%.
The dried powder 5g processing method of embodiment 15 Radix Aconiti Lateralis Preparata is with embodiment 3, obtains the extracting solution of monoester alkaloid content in a kind of extract that increases Radix Aconiti Lateralis Preparata.
The extracting solution of this Radix Aconiti Lateralis Preparata is cooled to room temperature, get 100 μ L sample solutions, add 20 μ L lappaconitines as internal standard substance, behind the mixing, advance LCQ mass spectrum half-quantitative detection, relative amount before the whole hydrolysis of diester-type alkaloids, monoester alkaloid hydrolysis is 47.24%, and the relative amount after the hydrolysis is 75.36%.
The dried powder 5g processing method of embodiment 16 Radix Aconiti Preparatas is with embodiment 1, obtains the extracting solution of monoester alkaloid content in a kind of extract that increases Radix Aconiti Preparata.
The extracting solution of this Radix Aconiti Preparata is cooled to room temperature, get 20 μ L sample solutions, add 100 μ L lappaconitines as internal standard substance, behind the mixing, advance LCQ mass spectrum half-quantitative detection, relative amount before the whole hydrolysis of diester-type alkaloids, monoester alkaloid hydrolysis is 69.17%, and the relative amount after the hydrolysis is 170.30%.
The dried powder 5g processing method of embodiment 17 Radix Aconiti Preparatas is with embodiment 2, obtains the extracting solution of monoester alkaloid content in a kind of extract that increases Radix Aconiti Preparata.
The extracting solution of this Radix Aconiti Preparata is cooled to room temperature, get 20 μ L sample solutions, add 100 μ L lappaconitines as internal standard substance, behind the mixing, advance LCQ mass spectrum half-quantitative detection, relative amount before the whole hydrolysis of diester-type alkaloids, monoester alkaloid hydrolysis is 69.17%, and the relative amount after the hydrolysis is 169.25%.
The dried powder 5g processing method of embodiment 18 Radix Aconiti Preparatas is with embodiment 3, obtains the extracting solution of monoester alkaloid content in a kind of extract that increases Radix Aconiti Preparata.
The extracting solution of this Radix Aconiti Preparata is cooled to room temperature, get 20 μ L sample solutions, add 100 μ L lappaconitines as internal standard substance, behind the mixing, advance LCQ mass spectrum half-quantitative detection, relative amount before the whole hydrolysis of diester-type alkaloids, monoester alkaloid hydrolysis is 69.17%, and the relative amount after the hydrolysis is 165.19%.
Claims (1)
1, a kind of method that increases monoester alkaloid content in the aconitum plant extract, its step and condition are as follows: the dried powder of Aconitum carmichjaelii Debx. class plant is dipped in the alcoholic solution that volume fraction is 50-95% the dried powder quality (g) of Aconitum carmichjaelii Debx. class plant: the volume of the alcoholic solution of 50-95% (ml) is than being 1: 1-3; Leach ethanol extract after supersound extraction 1.5-4 hour; Handle again twice as stated above; Merge the ethanol extract that leaches for three times, 40 ℃-60 ℃ down decompression steam solvent, obtain extract; This extract becomes with the volume (ml) of the dried powder quality (g) of Aconitum carmichjaelii Debx. class plant and distilled water than being the solution of 3-6g/ml with distilled water diluting, add the ammonia adjust pH to 6.0-10.0, put in the autoclave in 100 ℃ of-120 ℃ of heating, heat time heating time, 40-80min obtained a kind of extracting solution that increases monoester alkaloid content in the aconitum plant extract.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102283913A (en) * | 2011-09-08 | 2011-12-21 | 四川省中医药科学院 | Radix aconiti carmichaeli extract and application thereof |
| CN103768173A (en) * | 2014-01-20 | 2014-05-07 | 华东理工大学 | Method for preparing monkshood extract for injection |
-
2008
- 2008-09-12 CN CNA2008100511618A patent/CN101357167A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102283913A (en) * | 2011-09-08 | 2011-12-21 | 四川省中医药科学院 | Radix aconiti carmichaeli extract and application thereof |
| CN103768173A (en) * | 2014-01-20 | 2014-05-07 | 华东理工大学 | Method for preparing monkshood extract for injection |
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