CN102372606A - Method for extracting kirenol from glandularstalk st.paulswort herb - Google Patents
Method for extracting kirenol from glandularstalk st.paulswort herb Download PDFInfo
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- CN102372606A CN102372606A CN2010102630515A CN201010263051A CN102372606A CN 102372606 A CN102372606 A CN 102372606A CN 2010102630515 A CN2010102630515 A CN 2010102630515A CN 201010263051 A CN201010263051 A CN 201010263051A CN 102372606 A CN102372606 A CN 102372606A
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Abstract
The invention discloses a method for extracting kirenol from glandularstalk st.paulswort herb. The method comprises the following steps: performing ultrasonic extraction or backflow extraction for 2-4 times by using the tender stems and leaves of glandularstalk st.paulswort herb as the raw material and 80-100% methanol as the extraction solvent, filtering, combining the filtrate, concentrating, adding the concentrate in a macroporous resin column to perform adsorption, eluting active ingredients with 40-70% ethanol, concentrating the eluent, adding the obtained eluent in a high-pressure silica gel column, eluting with ethyl acetate and ethanol, concentrating the eluent to crystallize, and refluxing methanol to dissolve and recrystallize and obtaining kirenol. By adopting the method for producing kirenol, the extraction rate is high, the technology is simple and the specialization is high.
Description
Technical field:
The present invention relates to from plant, extract the method for kirenol, particularly a kind of method of Cong the Herba Siegesbeckiae young stem and leaf, extracting kirenol.
Background technology:
Kirenol (kirenol) belongs to diterpene-kind compound, and its chemical name is molecular formula: C
20H
34O
4, molecular weight: 338.48, structural formula is:
The main chemical compositions of kirenol Shi Herba Siegesbeckiae is to produce multiple bioactive important substance such as anti-inflammatory, rheumatism basis.The kirenol monomeric compound has the obvious suppression effect to the granuloma induced by implantation of cotton pellets of rat; The Herba Siegesbeckiae extract that contains kirenol 85% can alleviate the pathologic reaction of adjuvant arthritis rats ankle joint inflammation, can reach antiheumatic effect through adjustment body's immunity, the local pathologic reaction of improvement.
At present kirenol mainly separates from composite family Zhi Wu pig Xian Siegesbeckia orientalis L., Herba Siegesbeckiae Siegesbeckiapubescens Makino or siegesbeckia glabrescens Makino Siegesbeckia glabrescens Makino and obtains.It is very abundant to cross resource at me, mainly is distributed in ground such as Jiangsu, Zhejiang, Jiangxi, Hubei, Hunan, Sichuan, Yunnan, and its over-ground part, fruit and root all can be used as medicine, and its flavor is hot, bitter, cold in nature.Wind-damp dispelling is arranged, sharp joint, the effect of detoxifcation.Be used for rheumatic arthralgia, muscles and bones is unable, soreness of the waist and knees, tetraplegia, hemiplegy hemiplegia, the rubella sore that wets.The process for extracting of Herba Siegesbeckiae anti-inflammatory component kirenol generally has decocting cooking method, 10 times of amount methyl alcohol cold-macerations, 3 methods of 95% alcohol reflux.Aforesaid method exists that extraction yield is low, extraction time is long or shortcoming such as solvent load is big.Still the relevant report of not having at present the separation purification method aspect of kirenol.
Summary of the invention:
The process for extracting that the purpose of this invention is to provide a kind of kirenol, this method specificity is strong, and product purity is high.
Process for extracting of the present invention comprises the steps:
(1) pulverizes the Herba Siegesbeckiae young stem and leaf, and ultrasonic or refluxing extraction is 2-4 time with methyl alcohol, united extraction liquid, and filtration, concentrated methanol extract medicinal extract:
(2) methanol extract medicinal extract is added macroporous adsorptive resins, 3-6 times of column volume of 40-70% ethanol elution used in the abundant drip washing of first water again, collects elutriant, concentrates;
(3) with appearance on the above-mentioned liquid concentrator to the high pressure silicagel column, the ethyl acetate-ethanol wash-out, Liquid Detection is collected the high density flow point, reclaims reagent, concentrates the refrigeration crystallization;
(4) above-mentioned crystallisate is dissolved with methanol eddy, recrystallization 3-6 time leaches and is drying to obtain kirenol.
Methyl alcohol is the methyl alcohol of volume percent 80-100% described in the step (1).
The said macroporous adsorbent resin of step (2) is selected D101 or AB-8 type for use, and resin and methanol extract medicinal extract ratio are: (0.5-2): 1 (v/v).
The said column chromatography condition of step (2): the resin column blade diameter length ratio is 1: 6-1: 10; The removal of impurities flow velocity is 1.5-6BV/h, and elution flow rate is 3-9BV/h.
The said high pressure silica gel column chromatography of step (3) condition is: silica gel order number is the 300-400 order, and the chromatography column blade diameter length ratio is 1: 10-1: 18, and post is pressed and is 2.2-3.5MPa.
Described in the step (3) in the elutriant ETHYLE ACETATE and alcoholic acid volume ratio be 9: 1.
The present invention has following advantage:
1) the present invention uses solvent toxicity low, cheap and recyclable recycling;
2) the present invention uses macroporous resin as parting material, and absorption property is preferably arranged, and is prone to wash-out regeneration, can recycle.
3) the present invention uses the high pressure silica gel column chromatography, and the cycle is short, good separating effect, and product purity is high, and kirenol purity is greater than 97%.
Embodiment:
Embodiment 1
Take by weighing 1kg Herba Siegesbeckiae young stem and leaf, pulverized 20 mesh sieves, methanol solution 5kg, 3kg, the 3kg with 85% divides supersound extraction three times, and each 2 hours, united extraction liquid; Filter, concentrating under reduced pressure gets the methanol extract fluid extract, adds the D101 macroporous adsorptive resins, and the post blade diameter length ratio is 1: 7, earlier with after the change clearly of water wash to effluent; Use 3 times of column volumes of 50% ethanol elution instead, elution flow rate is 4BV/h, collects elutriant, concentrating under reduced pressure; Last appearance is a 300-400 purpose high pressure silicagel column to filler, and blade diameter length ratio 1: 15, post are pressed and be 2.2-3.5MPa, ethyl acetate-ethanol (9: 1) wash-out; The segmentation of kirenol high concentration flow is collected in the performance liquid monitoring, concentrates, and is positioned over crystallization under-10 ℃ of conditions; Leach crystallisate, dissolving crystallized 4 times of methanol eddy, the forced air drying crystallization promptly gets kirenol 1.9g, content 98.1%.
Embodiment 2
Take by weighing 1kg Herba Siegesbeckiae young stem and leaf, pulverized 40 mesh sieves, methanol solution 4kg, 3kg, 2kg with 90%, 2kg divide refluxing extraction four times; Refluxed first 2 hours, second and third, refluxed respectively for four times 1 hour, united extraction liquid filters; Concentrating under reduced pressure gets the methanol extract fluid extract, adds the D101 macroporous adsorptive resins, and the post blade diameter length ratio is 1: 6, earlier with after the change clearly of water wash to effluent; Use 3 times of column volumes of 60% ethanol elution instead, elution flow rate is 4BV/h, collects elutriant, concentrating under reduced pressure; Last appearance is a 300-400 purpose high pressure silicagel column to filler, and blade diameter length ratio 1: 12, post are pressed and be 2.2-3.5MPa, ethyl acetate-ethanol (9: 1) wash-out; The segmentation of kirenol high concentration flow is collected in the performance liquid monitoring, concentrates, and is positioned over crystallization under-5 ℃ of conditions; Leach crystallisate, dissolving crystallized 3 times of methanol eddy, the lyophilize crystallization promptly gets kirenol 1.8g, content 97.6%.
Embodiment 3
Take by weighing 2kg Herba Siegesbeckiae young stem and leaf, pulverized 20 mesh sieves, methanol solution 10kg, 8kg, the 4kg with 100% divides supersound extraction three times, and each 1.5 hours, united extraction liquid; Filter, concentrating under reduced pressure gets the methanol extract fluid extract, adds the AB-8 macroporous adsorptive resins, and the post blade diameter length ratio is 1: 9, earlier with after the change clearly of water wash to effluent; Use 3 times of column volumes of 40% ethanol elution instead, elution flow rate is 4BV/h, collects elutriant, concentrating under reduced pressure; Last appearance is a 300-400 purpose high pressure silicagel column to filler, and blade diameter length ratio 1: 10, post are pressed and be 2.2-3.5MPa, ethyl acetate-ethanol (9: 1) wash-out; The segmentation of kirenol high concentration flow is collected in the performance liquid monitoring, concentrates, and is positioned over crystallization under-4 ℃ of conditions; Leach crystallisate, dissolving crystallized 6 times of methanol eddy, the reduced vacuum drying crystalline promptly gets kirenol 3.2g, content 98.4%.
Embodiment 4
Take by weighing 3.8kg Herba Siegesbeckiae young stem and leaf, pulverized 30 mesh sieves, methanol solution 19kg, 10kg with 80%, refluxing extraction 2 times, return time was respectively 2 hours, 1 hour; United extraction liquid filters, and concentrating under reduced pressure gets the methanol extract fluid extract, adds the AB-8 macroporous adsorptive resins, and the post blade diameter length ratio is 1: 8; After becoming clearly with water wash to effluent earlier, use 3 times of column volumes of 60% ethanol elution instead, elution flow rate is 4BV/h, collects elutriant, concentrating under reduced pressure; Last appearance is a 300-400 purpose high pressure silicagel column to filler, and blade diameter length ratio 1: 15, post are pressed and be 2.2-3.5MPa, ethyl acetate-ethanol (9: 1) wash-out; The segmentation of kirenol high concentration flow is collected in the performance liquid monitoring, concentrates, and is positioned over crystallization under-10 ℃ of conditions; Leach crystallisate, dissolving crystallized 4 times of methanol eddy, the reduced vacuum drying crystalline promptly gets kirenol 7.2g, content 97.8%.
Claims (6)
1. method of from Herba Siegesbeckiae, extracting kirenol is characterized in that comprising following steps:
(1) pulverizes the Herba Siegesbeckiae young stem and leaf, and ultrasonic or refluxing extraction is 2-4 time with methyl alcohol, united extraction liquid, filtration, concentrated methanol extract medicinal extract;
(2) methanol extract medicinal extract is added macroporous adsorptive resins, 3-6 times of column volume of 40-70% ethanol elution used in the abundant drip washing of first water again, collects elutriant, concentrates;
(3) with appearance on the above-mentioned liquid concentrator to the high pressure silicagel column, the ethyl acetate-ethanol wash-out, Liquid Detection is collected the high density flow point, reclaims reagent, concentrates the refrigeration crystallization;
(4) above-mentioned crystallisate is dissolved with methanol eddy, recrystallization 3-6 time leaches and is drying to obtain kirenol.
2. extract the method for kirenol according to claim 1, it is characterized in that extraction conditions is described in the step (1): methyl alcohol is the methyl alcohol of volume percent 80-100%.
3. extract the method for kirenol according to claim 1, it is characterized in that the said macroporous adsorbent resin of step (2) is D101 or AB-8 type, resin and methanol extract medicinal extract ratio are: (0.5-2): 1 (v/v).
4. extract the method for kirenol according to claim 1, it is characterized in that the said column chromatography condition of step (2): the resin column blade diameter length ratio is 1: 6-1: 10; The removal of impurities flow velocity is 1.5-6BV/h, and elution flow rate is 3-9BV/h.
5. extract the method for kirenol according to claim 1, it is characterized in that the said high pressure silica gel column chromatography of step (3) condition is: silica gel order number is the 300-400 order, and the chromatography column blade diameter length ratio is 1: 10-1: 18, and post is pressed and is 2.2-3.5MPa.
6. extract the method for kirenol according to claim 1, it is characterized in that described in the step (3) that ETHYLE ACETATE and alcoholic acid volume ratio are 9: 1 in the elutriant.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102630515A CN102372606A (en) | 2010-08-26 | 2010-08-26 | Method for extracting kirenol from glandularstalk st.paulswort herb |
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| CN2010102630515A CN102372606A (en) | 2010-08-26 | 2010-08-26 | Method for extracting kirenol from glandularstalk st.paulswort herb |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109761752A (en) * | 2017-11-10 | 2019-05-17 | 义守大学 | The method of purifying nonyl alcohol |
| CN110467520A (en) * | 2018-05-10 | 2019-11-19 | 上海现代药物制剂工程研究中心有限公司 | The method that nonyl alcohol isolates and purifies in Yi Zhong Common St.Paulswort Herb leaf |
| CN114057672A (en) * | 2020-07-31 | 2022-02-18 | 山东省医学科学院药物研究所（山东省抗衰老研究中心、山东省新技术制药研究所） | Kirenol derivatives |
| CN115969892A (en) * | 2021-10-15 | 2023-04-18 | 北京中医药大学东直门医院 | Application of herba siegesbeckiae aqueous extract in preparation of medicine for improving myocardial reperfusion injury |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1380277A (en) * | 2002-04-26 | 2002-11-20 | 林文翰 | Method for separating, extracting and purifying nonyl alcohol from plant and its application |
| CN1961906A (en) * | 2006-11-27 | 2007-05-16 | 杭州耀恒医药科技有限公司 | Diterpene extract of Siegesbeckia, its preparation process and use thereof in phamacy |
-
2010
- 2010-08-26 CN CN2010102630515A patent/CN102372606A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1380277A (en) * | 2002-04-26 | 2002-11-20 | 林文翰 | Method for separating, extracting and purifying nonyl alcohol from plant and its application |
| CN1961906A (en) * | 2006-11-27 | 2007-05-16 | 杭州耀恒医药科技有限公司 | Diterpene extract of Siegesbeckia, its preparation process and use thereof in phamacy |
Non-Patent Citations (1)
| Title |
|---|
| 刘丹阳，等: "豨莶草不同入药部位醇溶性浸出物及奇壬醇的含量测定", 《中国药房》, vol. 19, no. 24, 31 August 2008 (2008-08-31), pages 1876 - 1877 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109761752A (en) * | 2017-11-10 | 2019-05-17 | 义守大学 | The method of purifying nonyl alcohol |
| CN110467520A (en) * | 2018-05-10 | 2019-11-19 | 上海现代药物制剂工程研究中心有限公司 | The method that nonyl alcohol isolates and purifies in Yi Zhong Common St.Paulswort Herb leaf |
| CN114057672A (en) * | 2020-07-31 | 2022-02-18 | 山东省医学科学院药物研究所（山东省抗衰老研究中心、山东省新技术制药研究所） | Kirenol derivatives |
| CN114057672B (en) * | 2020-07-31 | 2023-10-17 | 山东省医学科学院药物研究所（山东省抗衰老研究中心、山东省新技术制药研究所） | Qionanol derivative |
| CN115969892A (en) * | 2021-10-15 | 2023-04-18 | 北京中医药大学东直门医院 | Application of herba siegesbeckiae aqueous extract in preparation of medicine for improving myocardial reperfusion injury |
| CN115969892B (en) * | 2021-10-15 | 2023-10-20 | 北京中医药大学东直门医院 | Application of herba siegesbeckiae aqueous extract in preparation of medicines for improving myocardial reperfusion injury |
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