CN107903233A - A kind of method of extraction separation myricetin and dihydromyricetin from HERBA SHUTERIAE - Google Patents
A kind of method of extraction separation myricetin and dihydromyricetin from HERBA SHUTERIAE Download PDFInfo
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- CN107903233A CN107903233A CN201810016141.0A CN201810016141A CN107903233A CN 107903233 A CN107903233 A CN 107903233A CN 201810016141 A CN201810016141 A CN 201810016141A CN 107903233 A CN107903233 A CN 107903233A
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- CN
- China
- Prior art keywords
- dihydromyricetin
- myricetin
- ethyl acetate
- extraction
- herba shuteriae
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a kind of new method of extraction separation myricetin and dihydromyricetin from HERBA SHUTERIAE.Its main feature is that using cheap HERBA SHUTERIAE as raw material, ethyl acetate is extracted by ethanol medicinal extract is obtained by extraction, obtained medicinal extract DIRECT GEL chromatographic isolation obtains myricetin and dihydromyricetin.This method is easy to operate, and sample loss is small, and recovery rate is high, is adapted to industrialized production.
Description
Technical field
The invention belongs to pharmaceutical technology field, specifically provides one kind and prepares myricetin and two by raw material extraction of HERBA SHUTERIAE
The new method of hydrogen myricetin.
Background technology
Myricetin and dihydromyricetin have extensive pharmacological action, have great utility value.Pharmacological activity is previously
Research confirms myricetin and dihydromyricetin has anti-oxidant, antitumor, anti-inflammatory, Antialcoholic liver-protecting, resisting pathogenic microbes and adjusts blood
(Hou little Long, Wang Wenqing, apply spring sun-light, wait dihydromyricetin Advance on Pharmacological Activities for many pharmacological actions such as fat
[J] Chinese herbal medicines, 2015,46 (4): 603-609.) .
HERBA SHUTERIAE is pulse family Shuteria vegetable hair place bud beansShuteria pampaninianaHand.-Mazz. dry
Band base of leaf rattan,《Chinese medicine resource will will》Recording hair place bud beans has purging liver-heat, except steaming peaceful cough effect, for deficiency of Yin hectic fever,
Tuberculosis cough, acute mastitis.Research shows that myricetin and dihydromyricetin are its active ingredient.At present domestic literature report to shuteria pampaniniana
Myricetin and dihydromyricetin separation method mainly use decocting, polyamide column separation, the method complex process, extraction in rattan
The bad processing of liquid, material consumption is big, yield is low（Cao Yanhuai, Huang expedition, fourth found flavone component [J] China in raw HERBA SHUTERIAEs
J Chinese, 2000,25 (5): 290-291）.
The content of the invention
It is an object of the invention to provide a kind of method of extraction separation myricetin and dihydromyricetin from HERBA SHUTERIAE.
The technical solution used for：Include the following steps：
（1）HERBA SHUTERIAE powder is taken, adds 70-95% ethanol heating and refluxing extraction 1-5 times, adds distilled water after ethanol extract is concentrated
It is allowed to scattered, then is extracted with ethyl acetate 1-5 times, ethyl acetate extract layer is concentrated to give HERBA SHUTERIAE ethyl acetate extract medicinal extract；
（2）The directly upper gel column chromatography of ethyl acetate extract medicinal extract dissolving, the elution of 50-100% methanol, collects eluent 15-30 altogether
Part, you can extraction separating dihydromyricetin and myricetin.
Further, the step（1) in, the alcohol reflux for adding 80-90% extracts 2-3 times, when extraction 2~5 is small every time.
Further, the step（2) in, gel column chromatography is Sephadex LH-20 column chromatographys, the use of eluant, eluent is 90-
100% methanol.
The present invention extracts isolated myricetin and dihydromyricetin from HERBA SHUTERIAE, and gained dihydromyricetin purity reaches
92%, myricetin purity reaches 97%.The method of the present invention using cheap HERBA SHUTERIAE as raw material, can be greatly lowered bulk pharmaceutical chemicals into
This, provides new extraction source for myricetin and dihydromyricetin, is also compound myricetin and dihydromyricetin standard items
Preparation provide new method.
Brief description of the drawings
The structure chart of Fig. 1 myricetins and dihydromyricetin；
Fig. 2 is dihydromyricetin prepared by the embodiment of the present invention 1H-NMR spectrograms；
Fig. 3 is dihydromyricetin prepared by the embodiment of the present invention13C-NMR spectrograms；
Fig. 4 prepares myricetin for the embodiment of the present invention 1H-NMR spectrograms；
Fig. 5 prepares myricetin for the embodiment of the present invention13C-NMR spectrograms.
Embodiment
The present invention is further described with reference to embodiment and attached drawing, but the present invention is not limited only to following embodiments, can be with
Those skilled in the art are predicted in the case where combining the prior art, there may be many variations for performance.
Embodiment 1
（1）100 g of HERBA SHUTERIAE powder is taken, adds 80% ethanol heating and refluxing extraction 3 times, after ethanol extract concentration plus distilled water makes
It is scattered, it is extracted with ethyl acetate 2 times, ethyl acetate extract layer is concentrated to give 12 g of HERBA SHUTERIAE ethyl acetate extract medicinal extract.
（2）Ethyl acetate extract medicinal extract is dissolved with methanol, upper Sephadex LH-20 gel filtration chromatographies, the elution of 90% methanol,
30 parts of eluent is collected altogether.
（3）Cut 13 is dihydromyricetin, and 25 be myricetin.
Embodiment 2
（1）500 g of HERBA SHUTERIAE disk powder is taken, adds 90% ethanol heating and refluxing extraction 2 times, adds distilled water after ethanol extract concentration
It is allowed to scattered, is extracted with ethyl acetate 2 times, ethyl acetate extract layer is concentrated to give 54 g of HERBA SHUTERIAE ethyl acetate extract medicinal extract.
（2）Ethyl acetate extract medicinal extract methanol dissolves, upper Sephadex LH-20 gel filtration chromatographies, the elution of 100% methanol,
30 parts of eluent is collected altogether.
（3）Cut 12 is dihydromyricetin, and 23 be myricetin.
The Structural Identification of compound
The present invention extracts isolated myricetin and dihydromyricetin by systematic solvent extraction and gel chromatography technology from HERBA SHUTERIAE
Element, through physics and chemistry constant measuring and spectrum analysis, identification obtains their structure, such as attached drawing 1- attached drawings 5.
Dihydromyricetin：White powder, ESI-MSm/z:321 [M+H]+。1H-NMR (400 MHz, DMSO-d 6)δ: 11.9 (1H, s, 5-OH), 6.39 (2H, s, H-2', 6'), 5.90, 5.86 (each 1H, br. s, H-
6, 8), 5.76 (1H, d, J = 6.0 Hz, 3- OH), 4.90 (1H, d, J = 10.8 Hz, H-2), 4.41
(1H, dd, J= 10.8, 6.0 Hz, H-3)；13C-NMR (100 MHz, DMSO-d 6) δ: 83.2 (C-2), 71.6
(C-3), 197.7 (C-4), 163.3 (C-5), 95.9 (C-6), 166.8 (C-7), 95.0 (C-8), 162.5
(C-9), 100.5 (C-10), 127.1 (C-1'), 106.9 (C-2', 6'), 145.7 (C-3', 5'), 133.4
(C-4')。
Myricetin：Yellow powder, ESI-MSm/z:319 [M+H]+。1H-NMR (400 MHz, DMSO-d 6) δ:
12.5 (1H, s, 5-OH), 7.24 (2H, s, H-2', 6'), 6.37 (1H, d, J = 1.9 Hz, H-8),
6.18 (1H, d, J= 1.9 Hz, H-6)；13C-NMR (100 MHz, DMSO-d 6) δ: 146.8 (C-2), 135.9
(C-3), 175.8 (C-4), 160.7 (C-5), 98.2 (C-6), 163.9 (C-7), 93.2 (C-8), 156.1
(C-9), 103.0 (C-10), 120.8 (C-1'), 107.2 (C-2', 6'), 145.7 (C-3', 5'), 135.9
(C-4')。
The present invention is using cheap HERBA SHUTERIAE as raw material, and by extraction, gel chromatography separation obtains the poplar of high-purity
Syphilis and dihydromyricetin, are greatly lowered the separation and Extraction cost of compound, are carried for the preparation of myricetin and dihydromyricetin
New method is supplied.
Claims (3)
- A kind of 1. method of extraction separation myricetin and dihydromyricetin from HERBA SHUTERIAE, it is characterised in that include the following steps：（1）HERBA SHUTERIAE powder is taken, adds 70-95% ethanol heating and refluxing extraction 1-5 times, adds distilled water after ethanol extract is concentrated It is allowed to scattered, then is extracted with ethyl acetate 1-5 times, ethyl acetate extract layer is concentrated to give HERBA SHUTERIAE ethyl acetate extract medicinal extract；（2）The directly upper gel column chromatography of ethyl acetate extract medicinal extract dissolving, the elution of 50-100% methanol, collects eluent 15-30 altogether Part, you can obtain extracting separated dihydromyricetin and myricetin.
- 2. method as claimed in claim 1, it is characterised in that the step（1) in, the alcohol reflux extraction of 80-90% is added 2-3 times, when extraction 2~5 is small every time.
- 3. method as claimed in claim 1, it is characterised in that the step（2) in, gel column chromatography is Sephadex LH- 20 column chromatographys, are 90-100% methanol using eluant, eluent.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810016141.0A CN107903233A (en) | 2018-01-08 | 2018-01-08 | A kind of method of extraction separation myricetin and dihydromyricetin from HERBA SHUTERIAE |
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| CN201810016141.0A CN107903233A (en) | 2018-01-08 | 2018-01-08 | A kind of method of extraction separation myricetin and dihydromyricetin from HERBA SHUTERIAE |
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| CN201810016141.0A Pending CN107903233A (en) | 2018-01-08 | 2018-01-08 | A kind of method of extraction separation myricetin and dihydromyricetin from HERBA SHUTERIAE |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101336978A (en) * | 2008-08-12 | 2009-01-07 | 西北农林科技大学 | Extraction method of total flavone of Hovenia dulcisThunb |
-
2018
- 2018-01-08 CN CN201810016141.0A patent/CN107903233A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101336978A (en) * | 2008-08-12 | 2009-01-07 | 西北农林科技大学 | Extraction method of total flavone of Hovenia dulcisThunb |
Non-Patent Citations (2)
| Title |
|---|
| 张梅等: "川产中药材草红藤质量标准研究", 《成都中医药大学学报》 * |
| 曹延怀等: "草红藤中的黄酮成分", 《中国中药杂志》 * |
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