CN105237377B - The technique that silica gel method extracts germacrone from thymeleaf rhododendron herb leaf - Google Patents
The technique that silica gel method extracts germacrone from thymeleaf rhododendron herb leaf Download PDFInfo
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- CN105237377B CN105237377B CN201510719269.XA CN201510719269A CN105237377B CN 105237377 B CN105237377 B CN 105237377B CN 201510719269 A CN201510719269 A CN 201510719269A CN 105237377 B CN105237377 B CN 105237377B
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- germacrone
- petroleum ether
- thymeleaf
- rhododendron
- herb leaf
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The technique for extracting germacrone from thymeleaf rhododendron herb leaf the invention provides a kind of silica gel method, belongs to plant effective active composition extraction and separation technology field.The present invention is to crush thymeleaf rhododendron herb leaf, is first extracted using steam distillation and obtains volatile oil；It is added in silicagel column, is eluted with petroleum ether petroleum ether and ethyl acetate mixed solvent, collection portion shunts part, crystallizes after volatile oil is dehydrated with anhydrous sodium sulfate again, filtering, is then crystallized, then with petroleum ether dissolution and recrystallize with petroleum ether, refilter, wash, obtain high-purity germacrone.Determined using efficient liquid phase chromatographic analysis instrument, the germacrone purity that the present invention is extracted and separated is 95% ~ 98%, and yield is up to 0.40%~0.70%.Preparation technology of the present invention is simple, and cost is low, and product yield is high, purity is high, can industrialization production.
Description
Technical field
The present invention relates to a kind of method that germacrone is extracted in leaf from thymeleaf rhododendron herb, more particularly to a kind of silica gel method is from thousand
In the technique of germacrone is extracted in fragrant rhododendron leaves, belong to plant effective active composition extraction and separation technology field.
Background technology
Germacrone is the principle active component in Traditional Chinese medicine Rhizoma curcumae, root tuber of aromatic turmeric.It is obvious anti-that pharmacological evaluation proves that germacrone has
Cancer activity.Its propagation to typeⅡ pneumocyte has obvious inhibitory action, while can induce typeⅡ pneumocyte apoptosis；
It can also suppress external liver cancer Bel7402 cells propagation；Also there is anti-herpes simplex, amantadine persister, Type B influenza
The activity of Strain and influenza A H3N2 hypotype strain virus（CN102274206B）；Germacrone is to palace caused by HPV infection
Neck cancer has good preventive and therapeutic action（CN102058568B）.
CN101973861A provides a kind of preparation method of germacrone, and ericad Xingan is used wherein also mentioning
Rhododendron leaves are raw material, are extracted with organic solvent-acetone, then pass through silica gel aluminum oxide mixing column chromatography, organic solvent elution, oil
Ether-acetone or hexamethylene-ethyl alcohol recrystallization are produced.The method complex process, consumption of organic solvent is big, and preparation time is long, and cost is high,
The yield of germacrone is low（40kg rhododendron dauricum leaves are only capable of extracting germacrone 3.2g, and yield is 0.008%）.
Thymeleaf rhododendron herb（Rhododendron thymifoliumMaxim.）It is main in China for ericad
The ground such as Shaanxi, Gansu, Qinghai and Sichuan are distributed in, reserves are larger.The plant has relieving cough and asthma, eliminating the phlegm function, for chronic
Bronchitis, treating asthma.Aboundresources, distribution are relatively broad at home for thymeleaf rhododendron herb, and raw material is easy to get, to thymeleaf rhododendron herb
Further development and utilization it is significant.Found by studying, it is lucky in the volatile oil extracted from thymeleaf rhododendron herb leaf
The content of horse ketone can reach more than 20%.Therefore, volatile oil is first extracted from thymeleaf rhododendron herb leaf, then is prepared from volatile oil
Germacrone, for realizing that efficiently preparing for germacrone is significant.
The content of the invention
The purpose of the present invention is simple there is provided a kind of technique for problems of the prior art, and cost is low, yield
Height, is adapted to the method for industrialized production germacrone.
The method that the present invention extracts from thymeleaf rhododendron herb leaf and separates germacrone, is to crush thymeleaf rhododendron herb leaf, mistake
After 40~60 mesh sieves, 5 ~ 8h is extracted using steam distillation, volatile oil is obtained；Volatile oil is dehydrated with anhydrous sodium sulfate again
Afterwards, it is added in 160~200 mesh silicagel columns, then is eluted with petroleum ether and ethyl acetate mixed solvent, collects elution fractions, knot
Crystalline substance, filtering, is then crystallized with petroleum ether, then with petroleum ether dissolution and is recrystallized, and is refiltered, and is washed, and obtains high-purity lucky
Horse ketone.
The volume ratio of the eluent petroleum ether and ethyl acetate in the mixed solvent, petroleum ether and ethyl acetate is 200:1
~50:1.
Determined using efficient liquid phase chromatographic analysis instrument, the present invention extracts from thymeleaf rhododendron herb leaf and separates germacrone purity
For 96% ~ 98%, yield is up to 0.40%~0.70%.
Present invention beneficial effect following compared with the prior art：
1st, steam distillation is taken to extract volatile oil, then by silica gel column chromatography, crystallization, recrystallization can obtain lucky horse
Ketone, preparation technology of the present invention is simple, and cost is low, and product yield is high, purity is high, can industrialization production.
2nd, gained germacrone product, yield is high, purity is high.
3rd, raw materials used thymeleaf rhododendron herb leaf aboundresources, does not destroy vegetation, beneficial to sustainable development.
Embodiment
The method for extracting separation germacrone from thymeleaf rhododendron herb leaf to the present invention below by specific embodiment is done into one
Walk explanation.
Embodiment 1
（1）Thymeleaf rhododendron herb leaf is crushed, 40 mesh sieves is crossed, weighs 100g thymeleaf rhododendron herb leaf powder, steamed using water vapour
Evaporate method and extract 6h, obtain volatile oil 1.8mL；
（2）40g silicagel columns are added to after being dehydrated in volatile oil with anhydrous sodium sulfate（160~200 mesh）In, first use
500mL petroleum ethers:Ethyl acetate mixed solvent（180:1）Elution, then use 1000mL petroleum ethers:Ethyl acetate mixed solvent
（100:1）Elution, by petroleum ether:Ethyl acetate（100:1）Eluent recycling design；
（3）Filtering for crystallizing, and after being crystallized with petroleum ether, then with petroleum ether dissolution and recrystallize, refilter, wash,
Obtain 0.55g germacrones.
Its content is analyzed using efficient liquid phase chromatographic analysis instrument：High-efficient liquid phase chromatogram condition：Chromatographic column is
Kromasil-C18 posts；Acetonitrile-water (80:20)；Flow velocity：1. 0 mL·min-1；Column temperature：Room temperature (25 DEG C)；Ultraviolet detection ripple
It is long：210 nm；Sample size：20μL.
Gained germacrone purity is 97%.Yield is 0.55%.
Embodiment 2
（1）Thymeleaf rhododendron herb leaf is crushed, 40 mesh sieves is crossed, weighs 100g thymeleaf rhododendron herb leaf powder, steamed using water vapour
Evaporate method and extract 8h, obtain volatile oil 2mL；
（2）40g silicagel columns are added to after being dehydrated in volatile oil with anhydrous sodium sulfate（160~200 mesh）In, first use
1000mL petroleum ethers:Ethyl acetate mixed solvent（150:1）Elution, then use 500mL petroleum ethers:Ethyl acetate mixed solvent
（100:1）Elution, by petroleum ether:Ethyl acetate（100:1）Eluent recycling design；
（3）Filtering for crystallizing, and after being crystallized with petroleum ether, then with petroleum ether dissolution and recrystallize, refilter, wash,
Obtain 0.60g germacrones.
Its content is analyzed using efficient liquid phase chromatographic analysis instrument, gained germacrone purity is 97%.Yield is
0.60%。
Embodiment 3
（1）Thymeleaf rhododendron herb leaf is crushed, 40 mesh sieves is crossed, weighs 100g thymeleaf rhododendron herb leaf powder, steamed using water vapour
Evaporate method and extract 7h, obtain volatile oil 1.7mL；
（2）35g silicagel columns are added to after being dehydrated in volatile oil with anhydrous sodium sulfate（160 ~ 200 mesh）In, first use
1000mL petroleum ethers:Ethyl acetate mixed solvent（150:1）Elution, then use 1000mL petroleum ethers:Ethyl acetate mixed solvent
（80:1）Elution, by petroleum ether:Ethyl acetate（80:1）Eluent recycling design；
（3）Filtering for crystallizing, and after being crystallized with petroleum ether, then with petroleum ether dissolution and recrystallize, refilter, wash,
Obtain 0.48g germacrones.
Its content is analyzed using efficient liquid phase chromatographic analysis instrument, gained germacrone purity is 97%.Yield is
0.48%。
Claims (3)
- It is to crush thymeleaf rhododendron herb leaf, using water vapour 1. silica gel method extracts the technique of germacrone from thymeleaf rhododendron herb leaf The way of distillation extracts 5 ~ 8h and obtains volatile oil；It is added to after volatile oil is dehydrated with anhydrous sodium sulfate again in 160~200 mesh silicagel columns, Eluted, collection portion shunts part, crystallized as eluent with ethyl acetate mixed solvent with petroleum ether petroleum ether, filtering, so Crystallized, then with petroleum ether dissolution and recrystallized with petroleum ether afterwards, refiltered, washed, obtain high-purity germacrone.
- 2. the technique that silica gel method as claimed in claim 1 extracts germacrone from thymeleaf rhododendron herb leaf, it is characterised in that：Murraya paniculataJack Rhododendron leaves are ground into powder for 40~60 mesh.
- 3. the technique that silica gel method as claimed in claim 1 extracts germacrone from thymeleaf rhododendron herb leaf, it is characterised in that：It is described to wash The volume ratio of de- liquid petroleum ether and ethyl acetate in the mixed solvent, petroleum ether and ethyl acetate is 200:1~50:1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510719269.XA CN105237377B (en) | 2015-10-30 | 2015-10-30 | The technique that silica gel method extracts germacrone from thymeleaf rhododendron herb leaf |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510719269.XA CN105237377B (en) | 2015-10-30 | 2015-10-30 | The technique that silica gel method extracts germacrone from thymeleaf rhododendron herb leaf |
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| Publication Number | Publication Date |
|---|---|
| CN105237377A CN105237377A (en) | 2016-01-13 |
| CN105237377B true CN105237377B (en) | 2017-10-13 |
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| CN201510719269.XA Expired - Fee Related CN105237377B (en) | 2015-10-30 | 2015-10-30 | The technique that silica gel method extracts germacrone from thymeleaf rhododendron herb leaf |
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Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101973861A (en) * | 2010-07-26 | 2011-02-16 | 南京泽朗医药科技有限公司 | Method for preparing germacrone |
| RU2436771C1 (en) * | 2010-08-06 | 2011-12-20 | Государственное образовательное учреждение высшего профессионального образования "Белгородский государственный университет" | Method of extracting xanthophylls from plant material |
| CN103330700A (en) * | 2013-06-26 | 2013-10-02 | 深圳海王药业有限公司 | Application of germacrone in preparing HSV (Herpes Simplex Virus) resisting medicine |
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2015
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| CN105237377A (en) | 2016-01-13 |
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Inventor after: Liang Junyu Inventor after: Kong Weibao Inventor after: Zhang Lijuan Inventor after: Zhang Xinxin Inventor after: Zhu Jieni Inventor after: Zhou Jiaxin Inventor after: Wang Mengzhen Inventor after: Yu Jinyan Inventor after: Li Lingyan Inventor after: Wang Junlong Inventor before: Liang Junyu Inventor before: Wang Wenting Inventor before: Zheng Yanfei Inventor before: Qin Juan Inventor before: Ma Yingxiong Inventor before: Zhang Ji Inventor before: Wang Junlong Inventor before: Kong Weibao |
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