CN1629175A - Process for preparing kaempferol derivatives - Google Patents
Process for preparing kaempferol derivatives Download PDFInfo
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- CN1629175A CN1629175A CN 200410054147 CN200410054147A CN1629175A CN 1629175 A CN1629175 A CN 1629175A CN 200410054147 CN200410054147 CN 200410054147 CN 200410054147 A CN200410054147 A CN 200410054147A CN 1629175 A CN1629175 A CN 1629175A
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- kaempferol
- glucoside
- rutinoside
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Abstract
The invention provides a novel process for preparing Kacmpferol derivative, i.e. Kacmpferol-3-0-rutinose glycoside and Kacmpferol-3-0-glucose glycoside monomer or their mixture by using the white flowers or light-yellow flowers of Carthamus tinctorius L. as raw material, extracting with water or water-containing ethanol, and isolating and purifying through microporous resin and silica gel column chromatography.
Description
Technical field
The present invention relates to medical technical field, particularly a kind of novel method for preparing kaempferol derivative, said here kaempferol derivative is meant kaempferol-3-O-rutinoside, kaempferol-3-O-glucoside.
Background technology
Kaempferol derivative kaempferol-3-O-rutinoside, kaempferol-3-O-glucoside are the effective constituent of control cardiovascular and cerebrovascular diseases, it is reported, kaempferol derivative also has analgesia, promotes cutaneous pigmentation, antianaphylaxis isoreactivity.Existing preparation method is raw materials used to meet the Hefei safflower that pharmacopeia stipulates (see application number for details be 02137548.8 patent of invention) for the medicinal material appearance character, but the content of kaempferol in this raw material-3-O-rutinoside, kaempferol-3-O-glucoside is on the low side, the total yield of the two all is no more than 0.5%, thereby production cost is higher.Stipulate according to pharmacopeia, flos carthami " being the dried floral of feverfew safflower Carthamus tinctorius L.; plucked when red by xanthochromia summer; dry in the shade or dry " (seeing the version Pharmacopoeia of the People's Republic of China in 2000 for details), as seen, pattern is the flower of white or lurid feverfew safflower, not being taken as flos carthami uses, in fact, up to the present, do not see the report that they is extracted kaempferol derivative as raw material yet.
Summary of the invention
The invention provides a kind of novel method for preparing kaempferol-3-O-rutinoside and/or kaempferol-3-O-glucoside.Key of the present invention is that to select pattern for use be that white or the flower of lurid feverfew safflower Carthamus tinctorius L. are raw material, its advantage is to spend the content height of middle kaempferol-3-O-rutinose, kaempferol-3-O-glucoside, both total yields can reach more than 5%, at more than 10 times of usually said flos carthami content.And this feverfew is easy to cultivation, sufficient raw.The present invention has enlarged plant resources utilization, has reduced production cost.
The method that the present invention prepares kaempferol derivative is: the flower that with the pattern is white or lurid feverfew safflower Carthamus tinctorius L. is a raw material, extract through aqueous ethanol, then with step separation and purification such as macroporous resin or dextrane gel, silica gel or polyamide column chromatographies, just can obtain kaempferol derivative kaempferol-3-O-rutinose and/or kaempferol-3-O-glucoside, preparation process sees embodiment for details.
Embodiment
Now in conjunction with the embodiments the present invention is described in detail.
Embodiment 1 usefulness white flowers prepares kaempferol derivative kaempferol-3-O-glucoside and/or kaempferol-3-O-rutinoside.
Get the dry white flowers 1.8kg of feverfew safflower,, collect 30 times of amount percolates, be extracting solution with 70% ethanol 9L infiltration diacolation extraction after 12 hours; Extracting solution is the upper prop sample liquid after using rotating thin film concentrating instrument decompression recycling ethanol; Sample liquid is equipped with in the chromatographic column of macroporous resin (SIP-905 type, Shanghai Institute of Pharmaceutical Industry) by 0.3 times of column volume applied sample amount feeding, uses 30% ethanol of the water of 8 times of amounts, 6 times of amounts, 95% ethanol elution of 10 times of amounts successively; Collect 30% ethanol elution part; 30% ethanol eluate is evaporated to does not have the alcohol flavor, leaves standstill 12 hours, filters, and gets light-yellow precipitate, and dry weight is 182.6g, and yield is 10.1%, and this is the mixture of kaempferol-3-O-glucoside and kaempferol-3-O-rutinoside.With the light-yellow precipitate dissolve with methanol, with silica gel H (60 types, Qingdao Haiyang Chemical Industry Group Corp.) mixes sample, last silica gel H chromatography column, with chloroform-methanol (10: 1-1: 1) solvent systems wash-out, the elutriant of collect chloroform-methanol respectively 7: 1 and 3: 1, and concentrate respectively, be placed in the refrigerator respectively after the concentrated solution cooling and leave standstill, then separate out kaempferol-3-O-glucoside respectively, the needle of kaempferol-3-O-rutinoside, to weigh after the needle drying, the weight of these 2 compounds is respectively: kaempferol-3-O-glucoside 42.1g, kaempferol-3-O-rutinoside 71.9g.Respectively divided by the white flowers dry weight, yield is respectively 2.3% and 4.0% with resulting two monomeric compounds.These two kinds of compounds are identified through structure, and are accurate.Below be the structure appraising datum of these 2 compounds:
The structure appraising datum of kaempferol-3-O-glucoside: yellow needle.MP：192-193℃。EI-MS:m/z 286 sloughs fragment peak behind the glucose for compound.Determine that its molecular weight is 448, molecular formula is: C21H20O11.Its 13C-NMR spectrum shows that this compound has 21 carbon signals, and the DEPT spectrum shows 1 methylene radical, and 11 methynes and 9 quaternary carbon signals determine that it is flavonoid glycoside compound.1H-NMR (DMSO-d6) δ H:12.63,10.88,10.19 is that female ring is gone up hydroxyl hydrogen signal, 8.06 (2H, d, J=9Hz, H-2 ', 6 '), 6.91 (2H, d, J=9Hz, H-3 ', 5 '), 6.46 (1H, d, J=3Hz, H-8), 6.24 (1H, d, J=2Hz, H-6), (5.41 1H, the terminal hydrogen of m sugar), 3.0-5.0 (m, the H signal on the sugar).1H-NMR, 13C-NMR is consistent with bibliographical information with EI-MS, determines that this compound is kaempferol-3-O-glucoside.
The structure appraising datum of kaempferol-3-O-rutinoside: yellow needle.MP：190-192℃。FAB-MS (m/z) 617[M+Na]+determine that molecular weight is 594.Its 13C-NMR spectrum shows that this compound has 27 carbon signals, and the DEPT spectrum shows 1 methyl, and 1 methylene radical, 16 methynes and 9 quaternary carbon signals determine that it is flavonoid glycoside compound.1H-NMR (DMSO-d
6) δ ppm:12.58,10.93,10.20 is the hydroxyl hydrogen signal, 7.99 (2H, d, H-2 ' H-6 '), 6.88 (2H, d, H-3 ' and H-5 '), 6.43 (1H, d, H-8), 6.22 (1H, d, H-6), 5.32 (1H, d, J=7.2Hz, H-1 "; Glc-1), 5.13 (1H, m, H-1 " Rha-1), 3.0-5.0 be that sugar is gone up hydrogen signal, 0.98 (3H, d, Rha-6).13C-NMR(DMSO-d6)δppm：133.30(C-3)，101.41(C-1-glc)，100.85(C-1-rha)。1H-NMR, 13C-NMR spectrum, MS compose consistent with bibliographical information, determine that this compound is kaempferol-3-O-rutinoside.
Symbolic representation among the above embodiment is as follows:
MP---point, EI-MS---electron impact mass spectra, 13C-NMR---nuclear magnetic resonance spectrum, 1H-NMR---hydrogen nuclear magnetic resonance spectrum.
The light yellow flower preparation kaempferol-3-O-rutinoside of embodiment 2 usefulness and/or kaempferol-3-O-glucoside.
Get the dry light yellow colored 2.0kg of feverfew safflower,, filter after 3 hours with 70% ethanol 20L heating extraction, collect filtrate, residual residue adds 70% ethanol 20L heating again to be extracted, and filtrate is collected in filtration; Merge 2 times filtrate, be extracting solution; After extracting solution is used rotating thin film concentrating instrument decompression recycling ethanol, be the upper prop sample liquid, sample liquid is equipped with Silon (30-60 order by 0.3 times of column volume applied sample amount feeding, the biochemical plastic molding and processing plant of Tai Zhou city road and bridge tetramethyl) in the chromatographic column, uses 50% ethanol of 5% ethanol of the water of 10 times of amounts, 20 times of amounts, 15 times of amounts, 95% ethanol elution of 10 times of amounts successively.Collect 50% ethanol eluate of 20 times 5% ethanol eluate, 15 times of amounts respectively, concentrate, left standstill 12 hours, then separate out kaempferol-3-O-rutinoside light-yellow precipitate, kaempferol-3-O-glucoside yellow-white precipitation respectively, weigh respectively after the drying, the weight of these 2 compounds is respectively: kaempferol-3-O-rutinoside 66.8g, kaempferol-3-O-glucoside 37.5g.Respectively divided by light yellow colored dry weight, yield is respectively 3.3% and 1.9% with resulting two monomeric compounds.
The above results shows, the present invention's pattern is that the flower of white or lurid feverfew safflower is a raw material, the yield of its preparation kaempferol-3-O-rutinoside and/or kaempferol-3-O-glucoside is higher more than 10 times than used usually flos carthami yield, thereby greatly reduce production cost, enlarged the utilization of plant resources.
Claims (1)
1, a kind of method for preparing kaempferol derivative, comprise with feverfew safflower Carthamus tinctorius L. being that raw material water or aqueous ethanol extract, extracting solution separates purification step through macroporous resin with silica gel column chromatography etc., it is characterized in that said kaempferol derivative is meant kaempferol-3-O-rutinoside and/or kaempferol-3-O-glucoside, used raw material is that pattern is white in color or the flower of lurid feverfew safflower Carthamus tinctorius L..
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| CNB2004100541475A CN100340569C (en) | 2004-08-31 | 2004-08-31 | Process for preparing kaempferol derivatives |
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| CNB2004100541475A CN100340569C (en) | 2004-08-31 | 2004-08-31 | Process for preparing kaempferol derivatives |
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| CN1629175A true CN1629175A (en) | 2005-06-22 |
| CN100340569C CN100340569C (en) | 2007-10-03 |
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| CNB2004100541475A Expired - Fee Related CN100340569C (en) | 2004-08-31 | 2004-08-31 | Process for preparing kaempferol derivatives |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101921301A (en) * | 2010-09-17 | 2010-12-22 | 福州大学 | Method for extracting and separating astragalin from plant Mesona chinensis Benth |
| CN103113436A (en) * | 2012-10-23 | 2013-05-22 | 北京华润高科天然药物有限公司 | Method for preparing kaempferol-3-O-rutinoside from ginkgo leaf extract |
| CN103989732A (en) * | 2012-12-30 | 2014-08-20 | 中国人民解放军第二军医大学 | Beggarweed extract, total flavonoids and kaempferitrin separated therefrom, and medicinal uses of beggarweed extract, total flavonoids and kaempferitrin |
| CN105463044A (en) * | 2016-01-15 | 2016-04-06 | 扬州大学 | Method for enzymatically synthesizing astragalin |
| CN105924479A (en) * | 2016-06-22 | 2016-09-07 | 浙江大学 | Indian kalimeris herb active component and compounds as well as preparation and application |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1231222C (en) * | 2001-10-22 | 2005-12-14 | 中国人民解放军第二军医大学 | Application of Funaosu in preventing and treating cadiovascular and cerebrovascular diseases |
| CN1197567C (en) * | 2002-10-21 | 2005-04-20 | 中国人民解放军第二军医大学 | Application of kaempferol and its derivative in preparing medicine for cardiac and cerebral vascular diseases |
-
2004
- 2004-08-31 CN CNB2004100541475A patent/CN100340569C/en not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101921301A (en) * | 2010-09-17 | 2010-12-22 | 福州大学 | Method for extracting and separating astragalin from plant Mesona chinensis Benth |
| CN101921301B (en) * | 2010-09-17 | 2012-12-05 | 福州大学 | Method for extracting and separating astragalin from plant Mesona chinensis Benth |
| CN103113436A (en) * | 2012-10-23 | 2013-05-22 | 北京华润高科天然药物有限公司 | Method for preparing kaempferol-3-O-rutinoside from ginkgo leaf extract |
| CN103113436B (en) * | 2012-10-23 | 2015-09-23 | 北京华润高科天然药物有限公司 | A kind of method preparing FNS from Folium Ginkgo extract |
| CN103989732A (en) * | 2012-12-30 | 2014-08-20 | 中国人民解放军第二军医大学 | Beggarweed extract, total flavonoids and kaempferitrin separated therefrom, and medicinal uses of beggarweed extract, total flavonoids and kaempferitrin |
| CN105463044A (en) * | 2016-01-15 | 2016-04-06 | 扬州大学 | Method for enzymatically synthesizing astragalin |
| CN105924479A (en) * | 2016-06-22 | 2016-09-07 | 浙江大学 | Indian kalimeris herb active component and compounds as well as preparation and application |
| CN105924479B (en) * | 2016-06-22 | 2019-01-11 | 浙江大学 | Kalimeris active component and compound and preparation and application |
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| CN100340569C (en) | 2007-10-03 |
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