CN100490833C - Method of supercritical CO2 for extracting terpenoid of effective component of triperygium wilfordii, and composition - Google Patents
Method of supercritical CO2 for extracting terpenoid of effective component of triperygium wilfordii, and composition Download PDFInfo
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- CN100490833C CN100490833C CNB200610015592XA CN200610015592A CN100490833C CN 100490833 C CN100490833 C CN 100490833C CN B200610015592X A CNB200610015592X A CN B200610015592XA CN 200610015592 A CN200610015592 A CN 200610015592A CN 100490833 C CN100490833 C CN 100490833C
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Abstract
A process for extracting the terpene compounds from common threewingnut root by supercritical CO2 includes such steps as proportionally immersing broken common threewingnut root in alcohol, and extracting with supercritical CO2 at 30-50 deg.C under 20-40 MPa for 60-150 min. The obtained terpene compounds include sesquiterpene alkaloid, abietane-type diterpene, triterpenoid carboxylic acid, wilfordine A and tripterine.
Description
Technical field
The present invention relates to a kind of supercritical CO
2Extract the method and the composition of prepared from active ingredients of tripterygium wilfordii terpenoid, belong to the extraction and separation technology of Chinese medicine Radix Tripterygii Wilfordii active ingredient.
Background technology
Radix Tripterygii Wilfordii (Tripterygium wilfordii Hook f.) is the Celastraceae tripterygium plant, the record of Chinese medicine voluminous dictionary, have expelling wind and removing dampness, removing obstruction in the collateral to relieve pain, reducing swelling and alleviating pain, the parasiticidal effect of detoxifcation, the clinical autoimmune diseasees such as rheumatoid arthritis, chronic nephritis and lupus erythematosus that are used for the treatment of, be used for the anti-rejection treatment of organ transplantation in recent years, all obtained better curative effect.Modern study finds that in succession Radix Tripterygii Wilfordii has effects such as antiinflammatory, anti-immunity, antifertility, antitumor, antibacterial activity.So far isolated 200 number of chemical monomers from Radix Tripterygii Wilfordii, wherein Diterpenes, sesquiterpene alkaloids class, triterpenes are main active.
Aspect the Radix Tripterygii Wilfordii preparation research, commercially available Glucosidorum Tripterygll Totorum and thunder rattan sheet are arranged; After the nineties, the development of Radix Tripterygii Wilfordii preparation research is swift and violent, and special research aspect slow release, controlled release will produce important function to raising Radix Tripterygii Wilfordii curative effect, reduction toxic and side effects.The Radix Tripterygii Wilfordii preparation has tripterygium total terpenoids sheet, Radix Tripterygii Wilfordii microencapsule tablet, Radix Tripterygii Wilfordii drop pill, the double-deck bolt of Radix Tripterygii Wilfordii, Radix Tripterygii Wilfordii cataplasma at present.
The Radix Tripterygii Wilfordii complex chemical composition, pharmacological action is extensive, and important clinical application value is arranged.But, limited the popularization of clinical practice because the Radix Tripterygii Wilfordii toxic and side effects is bigger.Should further strengthen pharmaceutical chemistry and pharmacological action and Study of Clinical Application to Radix Tripterygii Wilfordii, extraction, purification, the effective ingredient that synthesizes high-efficiency low-toxicity or derivant improve its safety and using value, for the further development and use of Radix Tripterygii Wilfordii lay the foundation.
The method that the tradition prepared from active ingredients of tripterygium wilfordii extracts mainly contains decoction and alcohol sedimentation technique, water is put forward chloroform extraction method, alcohol extraction ethyl acetate extraction method etc., goes to dissolve with the solvent of opposed polarity according to polarity " similar mixing " principle of material and extracts the polarity composition similar to it.There is significant disadvantages in traditional extraction process:
(1) extraction efficiency is low: a lot of effective ingredient only extract a part sometimes, and remainder is but outwelled with medicinal residues, causes the waste of Chinese herbal medicine resource;
(2) production cycle long, production efficiency is lower;
(3) selectivity is bad: many invalid impurity and toxic component together extract with effective ingredient, and the concentration of effective ingredient is low, and toxic component content is higher, and multiple solvent extraction process all can't overcome the big shortcoming of toxicity;
(4) effective ingredient is easily destroyed: contact owing to the temperature height, with air etc., thermal sensitivity composition in the medicine, easy oxidizing component are damaged;
(5) drug quality and class are lower: organic solvent has residual after the lipotropy extracts active ingredients.
Summary of the invention
The object of the present invention is to provide a kind of supercritical CO
2Extract the method and the composition of prepared from active ingredients of tripterygium wilfordii terpenoid, the drug effect height of the prepared from active ingredients of tripterygium wilfordii terpenoid that this method is extracted and toxic and side effects is low.
The present invention is realized by the following technical programs, a kind of supercritical CO
2Extract the method for prepared from active ingredients of tripterygium wilfordii terpenoid, it is characterized in that comprising following process: Radix Tripterygii Wilfordii is crushed to 10～200 orders, be dipped in by Radix Tripterygii Wilfordii and ethanol mass ratio 2: 1-1.5 in the ethanol entrainer of mass concentration 55～85%, at extraction kettle with supercritical CO
2For solvent extracts, its operating condition is; Temperature is 30～50 ℃, and pressure is 20-40MPa, CO
2Flow velocity is 10-30kg/h, extracts 60～150min.
Extract the composition of prepared from active ingredients of tripterygium wilfordii terpenoid with said method, it is characterized in that comprising sesquiterpene alkaloids, abietane type diterpene and triterpene carboxylic acids, the mass ratio of three compounds is: sesquiterpene alkaloids 30-50%, abietane type diterpene 25-45%, triterpene carboxylic acids 5-15%; In addition, the mass content of triptolide is 0.05-0.15%, and the tripterine mass content is 0.1-0.5%.
The present invention compares with other extracting method, and technical process is simple, regulates the ratio of three class active chemicals in the extract effectively, obviously is different from the extraction of traditional handicraft; Effective component extraction rate height, triptolide extraction ratio are 200-400%.Drug effect is 3-4 a times of commercially available prod, and toxicity is the 20-50% of commercially available prod.
Description of drawings
Fig. 1 is the embodiment of the invention 1 supercritical CO
2The efficient liquid phase chromatographic analysis figure of extract.
Among the figure: the Δ alkaloids; O abietane type Diterpenes; * triterpene carboxylic acids.
Three compounds account for finger printing total peak area 90.15%, and wherein sesquiterpene alkaloids 45.65%, abietane type Diterpenes 35.5%, triterpene carboxylic acids 9.0%
The specific embodiment
The following example is intended to further describe for example the present invention, rather than limit the present invention by any way, under the prerequisite that does not deviate from purport of the present invention and principle, any change or change that those of ordinary skills that the present invention did are realized easily all will fall as within the claim scope that awaits the reply of the present invention.
Embodiment 1:
Finish extraction with the supercritical carbon dioxide extraction circulating device, get tripterygium wilfordii powder 180.53 gram that the 10-120 order originates in yueyang, hunan and be loaded in the extractor, with CO
2Be solvent, the temperature of setting extraction column, separator is respectively 40-45 ℃ and 35 ℃, pressure is respectively 25MPa and 5MPa, CO
2Consumption and raw material ratio are about 100, and entrainer adds 108 milliliters of quality 75% ethanol, and extraction time 1.67h obtains extract 1.95 grams, extraction yield 1.08%.
With triptolide, tripterine content assaying method-Soxhlet methanol extraction method in the Radix Tripterygii Wilfordii crude drug, the amount of the triptolide that Radix Tripterygii Wilfordii biology total alkali Soxhlet 95% ethanol extraction method obtains, Radix Tripterygii Wilfordii biology total alkali, tripterine is a benchmark, the amount of the triptolide that obtains with supercritical extraction, Radix Tripterygii Wilfordii biology total alkali, tripterine is made comparisons, and the definition extraction ratio is:
Extraction ratio (%)=(supercritical fluid extraction amount/Soxhlet extracted amount) * 100%.
Every performance test results of present embodiment effective ingredient extract is as follows:
(1) the extraction efficiency index of supercritical extract parameters and each composition
| Medical material | Entrainer | Temperature | Pressure | The plain extraction ratio (%) of first | Alkaloid extraction ratio (%) | Red pigment extraction ratio (%) |
| 180.53g | 75% ethanol 108mL | 40-45℃ | 25MPa | 361.37 | 66.34 | 46.45 |
Draw thus, supercritical fluid extraction technology can effectively increase the extraction ratio of abietane type Diterpenes composition, reduce the extraction ratio of one of main toxic component tripterine simultaneously, pointedly with three effective constituents proportion control in reasonable range, thereby reach the effect of Synergistic and attenuation.
(2) content of triptolide, tripterygium total alkaloid and tripterine in the supercritical extract
Adopt triptolide mass content 0.090% in the extract under these process conditions of high effective liquid chromatography for measuring that this laboratory sets up, tripterine mass content 0.348%, the mass content of total alkaloids are 30.42%.
Embodiment 2:
Extract with the supercritical carbon dioxide extraction circulating device, get tripterygium wilfordii powder 180.78 gram that the 10-120 order originates in yueyang, hunan and be loaded in the extractor, with CO
2Be solvent, the temperature of setting extraction column, separator is respectively 40-45 ℃ and 35 ℃, pressure is respectively 25MPa and 5MPa, CO
2Consumption and raw material are about 100, and entrainer adds 108 milliliters of quality 80% ethanol, and extraction time 1.67h obtains extract 1.70 grams, paste-forming rate 0.94%.
Every performance test results of present embodiment effective ingredient extract is as follows:
(1) the extraction efficiency index of supercritical extract parameters and each composition
| Medical material | Entrainer | Temperature | Pressure | The plain extraction ratio (%) of first | Alkaloid extraction ratio (%) | Red pigment extraction ratio (%) |
| 180.78g | 80% ethanol 108mL | 40-45℃ | 25MPa | 274.87 | 43.81 | 24.84 |
(2) content of triptolide, tripterygium total alkaloid and tripterine in the supercritical extract
Adopt triptolide mass content 0.079% in the extract under these process conditions of high effective liquid chromatography for measuring that this laboratory sets up, tripterine mass content 0.213%, the mass content of total alkaloids are 23.04%.
Embodiment 3:
Extract with the supercritical carbon dioxide extraction circulating device, tripterygium wilfordii powder 180.65 grams of getting 10-120 purpose yueyang, hunan product are loaded in the extractor, with CO
2Be solvent, the temperature of setting extraction column, separator is respectively 40-45 ℃ and 35 ℃, pressure is respectively 25MPa and 5MPa, CO
2Consumption and raw material are about 100, and entrainer adds 108 milliliters of quality 60% ethanol, and extraction time 1.67h obtains extract 1.31 grams, paste-forming rate 0.72%.
Every performance test results of present embodiment effective ingredient extract is as follows:
(1) the extraction efficiency index of supercritical extract parameters and each composition
| Medical material | Entrainer | Temperature | Pressure | The plain extraction ratio (%) of first | Alkaloid extraction ratio (%) | Red pigment extraction ratio (%) |
| 180.79g | 60% ethanol 108mL | 40-45℃ | 25MPa | 216.64 | 37.35 | 18.39 |
(2) content of triptolide, tripterygium total alkaloid and tripterine in the supercritical extract
Adopt triptolide mass content 0.077% in the extract under these process conditions of high effective liquid chromatography for measuring that this laboratory sets up, tripterine mass content 0.197%, the mass content of total alkaloids are 24.42%.
The relevant drug effect and the toxicity test of effective ingredient extract (embodiment 1)
The Radix Tripterygii Wilfordii supercritical extract is to LT inhibitory action
Control (ConA)=0.248 ± 0.010, no ConA=0.111 ± 0.012
Stimulation index: 2.23
Dexamethasone (OD)=0.093 ± 0.017; Suppression ratio=62.5%
ED
50=5.08 μ g/mL, cell number is 5 * 10
6Individual/mL
A producer produces Radix Tripterygii Wilfordii tablet and drenches the commentaries on classics experiment
Control(ConA)＝0.476±0.021
ED
50＝19.94μg/mL
B producer produces Radix Tripterygii Wilfordii tablet and drenches the commentaries on classics experiment
Control(ConA)＝0.476±0.021
ED50＝14.6μg/mL
The ED50 that external lymphocyte transformation experimental calculation draws the Radix Tripterygii Wilfordii supercritical extract is 5.08 μ g/mL, and the ED50 of A Radix Tripterygii Wilfordii tablet is 19.94 μ g/mL, and the ED50 of B Radix Tripterygii Wilfordii tablet is that 14.60 μ g/mL. have reached the purpose that improves drug effect.
Toxicity test
Get this law prepared from active ingredients of tripterygium wilfordii extract, investigate index as toxicity, measure median lethal dose(LD 50) (LD50) value with the median lethal dose(LD 50) of Kunming mouse.Experiment is divided into five groups, every group of 10 mices.Use simplification probability method and calculate LD50.
The LD50 of prepared from active ingredients of tripterygium wilfordii extract is 312.54 ± 34.21mg/kg;
The LD50 that A producer produces Tripterygium glycosides in the Radix Tripterygii Wilfordii tablet is 159.7 ± 14.3mg/kg.Reduce about 1 times of toxicity.
Claims (2)
1. supercritical CO
2Extract the method for prepared from active ingredients of tripterygium wilfordii terpenoid, it is characterized in that comprising following process: Radix Tripterygii Wilfordii is crushed to 10～200 orders, be dipped in by Radix Tripterygii Wilfordii and ethanol mass ratio 2: 1-1.5 in the ethanol entrainer of mass concentration 55～85%, at extraction kettle with supercritical CO
2For solvent extracts, its operating condition is: temperature is 30～50 ℃, and pressure is 20-40MPa, CO
2Flow velocity is 10-30kg/h, extracts 60～150min.
2. press the described supercritical CO of claim 1 for one kind
2Extract the composition of the chemical compound of prepared from active ingredients of tripterygium wilfordii terpenoid method extraction, it is characterized in that comprising sesquiterpene alkaloids, abietane type diterpene and triterpene carboxylic acids, the mass ratio of three compounds is: sesquiterpene alkaloids 30-50%, abietane type diterpene 25-45%, triterpene carboxylic acids 5-15%; In addition, the mass content of triptolide is 0.05-0.15%, and the tripterine mass content is 0.1-0.5%.
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| CN100439389C (en) * | 2007-04-20 | 2008-12-03 | 上海华拓医药科技发展股份有限公司 | Celastrine grape aminomethane salt and preparation method thereof |
| CN100453551C (en) * | 2007-05-31 | 2009-01-21 | 上海华拓医药科技发展股份有限公司 | Alkali metal salt compound of celastrol and preparation method thereof |
| CN102603852A (en) * | 2011-01-25 | 2012-07-25 | 苏州宝泽堂医药科技有限公司 | Preparation method of tripterine |
| CN103242414B (en) * | 2013-05-17 | 2015-09-30 | 成都彼斯特生物科技有限公司 | A kind of method from Stem of Oriental Bittersweet medicinal material separation and purification Tripterine |
| CN104173413B (en) * | 2013-05-28 | 2020-02-18 | 中国医学科学院药物研究所 | Application of centella asiatica leaf total terpenoids in preparation of anti-rheumatoid arthritis drugs |
| CN108478540B (en) * | 2018-05-21 | 2021-05-07 | 陕西国际商贸学院 | Preparation method of tripterygium wilfordii slow-release microcapsule |
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Non-Patent Citations (4)
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| SFE - CO2 萃取技术在中药提取分离中的应用. 钱亚琴，刘汉清，庄炜.南京中医药大学学报，第20卷第4期. 2004 |
| SFE - CO2 萃取技术在中药提取分离中的应用. 钱亚琴，刘汉清，庄炜.南京中医药大学学报，第20卷第4期. 2004 * |
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| 超临界二氧化碳萃取雷公藤中有效成分的研究. 王诗宏，杨祥良，韩定献，常雪玲.时珍国医国药，第13卷第11期. 2002 * |
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