CN101613384A - A kind of dihydroxyphenyl ethanol glycoside compound and preparation method thereof - Google Patents
A kind of dihydroxyphenyl ethanol glycoside compound and preparation method thereof Download PDFInfo
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- CN101613384A CN101613384A CN200810012006A CN200810012006A CN101613384A CN 101613384 A CN101613384 A CN 101613384A CN 200810012006 A CN200810012006 A CN 200810012006A CN 200810012006 A CN200810012006 A CN 200810012006A CN 101613384 A CN101613384 A CN 101613384A
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Abstract
The invention discloses and a kind ofly prepare the method for dihydroxyphenyl ethanol glycoside new compound, this system of compounds called after 1-(2, the 5-dihydroxyl) styroyl-β-D-glucopyanoside from the traditional Chinese medicine capsule of weeping forsythia by acid-alkali treatment and chromatographic separation technology.Its main technique step is that the Chinese medicine capsule of weeping forsythia is pulverized, water boiling and extraction, and the ethanol alcohol precipitation adds a certain amount of sodium bicarbonate or yellow soda ash again, and reaction transfers to the pH value and is 2-3, and rotary evaporation obtains medicinal extract; Medicinal extract further separation obtains this compound.The present invention is the preparation method of a kind of purity height, favorable reproducibility, short (2, the 5-dihydroxyl) phenylethyl alcohol glycoside new compound of cycle.Being used for preparation of phenylethyl alcohol glycoside compound standard substance and pharmacologically active further studies.
Description
Technical field
The present invention relates to the phenylethyl alcohol glycoside compound, specifically a kind of dihydroxyphenyl ethanol glycoside new compound and preparation and separation method, it is a kind ofly to prepare the new compound of separating by acid-alkali treatment and chromatographic separation technology from the traditional Chinese medicine capsule of weeping forsythia.
Background technology
The phenylethyl alcohol glycoside compound have effects such as anti-inflammatory, antibiotic, antiviral, anti-oxidant, hypermnesis (quiet can the grade. the time treasure traditional Chinese medical science traditional Chinese medicines .2006,17 (3): 440; Piao Jinghua etc. Chinese Pharmacological circular .2001,17 (6): 625; Hooke outstanding person etc. Chinese Chinese materia medica research .2001,8 (2): 89).
Wang milli equal to separate in the Tibet picrorhiza rhizome root and identified six phenylethyl alcohol glycoside compounds (Wang's milli etc. Chinese medicine impurity .2004,29 (6): 531); Zheng Xiaoke equal in the Herba Corallodisci Flabellati successively to separate and identified nine phenylethyl alcohol glycoside compounds (Zheng Xiaoke etc. Acta Pharmaceutica Sinica .2003,38 (2): 116; Zheng Xiaoke etc. herbal medicine .2002,33 (10): 881); Wang Manyuan equal in the red medicine to separate and identified five phenylethyl alcohol glycoside compounds (Wang Manyuan etc. Chinese medicine impurity .2005,30 (24): 1921).Above phenylethyl alcohol glycoside compound is 3, the phenylethyl alcohol glycoside compound of 4-dihydroxyl (or corresponding hydroxyl replaces the back); Document reports that in addition 4-hydroxylphenylethyl alcohol glycoside compound is (as rhodioloside in addition.Li Jianxin etc. herbal medicine .1998,29 (10): 659; Chen Jijun etc. Yunnan plant research .1999,21 (4): 525).So far do not see about 2 the report of 5-dihydroxyphenyl ethanol glycoside compound.
Summary of the invention
The purpose of this invention is to provide a kind of phenylethyl alcohol glycoside compound, the systematic naming method of this compound is 1-(2, the 5-dihydroxyl)-styroyl-β-D-glucopyanoside; Satisfying phenylethyl alcohol glycoside compound standard substance preparations, pharmacologically active is further studied and the needs of industrial application; It is a kind of new compound with Oleaceae plant capsule of weeping forsythia preparation (2, the 5-dihydroxyl)-phenylethyl alcohol glycoside; Its preparation product purity height, favorable reproducibility, with short production cycle.
For achieving the above object, the technical solution used in the present invention is:
1) preparation of capsule of weeping forsythia aqueous extract: capsule of weeping forsythia crude drug is pulverized, quantitatively taken by weighing, decoct and extract 2-4 time, decocting time 1-3 hour at every turn, add the water boil of capsule of weeping forsythia 8-12 times weight at every turn, united extraction liquid is concentrated into the medicinal extract that relative density is 1.01-1.20g/ml;
2) preparation of capsule of weeping forsythia alcohol precipitation component: medicinal extract is with the water suspendible of 2-5 times of volume and add ethanol and make alcohol concn reach 50%-70%, and room temperature left standstill 12-24 hour, filtered, and filtrate is concentrated into does not have the alcohol flavor, obtains capsule of weeping forsythia alcohol precipitation component;
3) preparation of medicinal extract behind the capsule of weeping forsythia acid-alkali treatment: capsule of weeping forsythia alcohol precipitation component adds sodium bicarbonate or yellow soda ash reaction, saturated being metered in the aqueous solution by sodium bicarbonate or yellow soda ash, place, transferring to the pH value with acid is 2-4, rotary evaporation is to doing, use the 80-95% dissolve with ethanol again, the supernatant liquor rotary evaporation obtains the extractum A of relative density 1.20-1.35g/ml;
4) preparation of capsule of weeping forsythia macroporous resin component: extractum A goes up macroporous resin column after adding water dissolution, solution is through macroporous resin ethanol water gradient elution, the volumetric concentration of alcohol changes from 15% to 95% in the elutriant, and the volumetric concentration of collecting alcohol is that 15% o'clock target elutriant rotary evaporation gets macroporous resin component one;
5) industrial chromatography of dihydroxyphenyl ethanol glycoside compound separates: macroporous resin component one concentrates the back and adopts C18 reverse chromatograms post sample introduction to separate, moving phase is the methanol-water gradient elution, the volumetric concentration of alcohol changes from 5% to 45% in the elutriant, ultraviolet detection is by the time Fractional Collections, once or once above sample introduction, merge the elutriant under same period, mass spectrometric detection, the target components that contains dihydroxyphenyl ethanol glycoside compound concentrate component two;
6) purifying of dihydroxyphenyl ethanol glycoside compound: component two is concentrated back C18 reverse chromatograms post sample introduction purifying, moving phase acetonitrile water gradient elution, the volumetric concentration of acetonitrile changes from 3% to 25% in the elutriant, mass spectrometric detection is collected target components, obtains dihydroxyphenyl ethanol glycoside new compound.
Described acid is hydrochloric acid, sulfuric acid or nitric acid; The also available silica gel column chromatography of described C18 reverse chromatograms post is replaced.
The present invention has the following advantages:
1. sample message is abundant, and the present invention adopts acid-alkali treatment capsule of weeping forsythia aqueous extract, and the Compound I that obtains be a new compound through Beilstein and SCI Finder verification, and former aqueous extract does not detect this compound.
2 favorable reproducibility adopt industrial chromatography to separate preparation system with purification plant, and anti-phase C18 is a column packing, and processability is stable, favorable reproducibility.
3 sample purity height, the present invention adopts industrial chromatography and purification plant separation and preparation technology, and separating power is strong, the dihydroxyphenyl ethanol glycoside new compound purity height that obtains.
Description of drawings
Fig. 1 be The compounds of this invention 13C-NMR (D2O, 400MHz).
Fig. 2 be The compounds of this invention 1H-NMR (D2O, 400MHz).
Embodiment
Now in conjunction with example, the present invention will be further described.Example only limits to illustrate the present invention, but not limitation of the invention.
Embodiment 1
Capsule of weeping forsythia crude drug is pulverized, and takes by weighing 1 kilogram, places 50 liters of extractors, adds 10 premium on currency and decocts 2 hours, filters, and the filtrate preservation is standby, adds 10 premium on currency in the filter residue again and decocts 2 hours, filter, and filtrate and merging for the first time, filter residue discards.With the filtrate rotary evaporation, get medicinal extract 190ml (relative density 1.05).Medicinal extract is dissolved in equal-volume water, adds 653 milliliter of 95% ethanol, stirs, and leaves standstill 24 hours, filters, and filter residue discards, and filtrate is concentrated into does not have the alcohol flavor, obtains 142 milliliters of capsule of weeping forsythia alcohol precipitation components.
Capsule of weeping forsythia alcohol precipitation component water is settled to 200 milliliters, adds 28.4 gram sodium bicarbonates again, stirs, and reacts 3 hours, and placement is spent the night.Progressively add 56.8 milliliters of 1: 1 hydrochloric acid, 1.4 milliliters of 1: 2 hydrochloric acid (this moment, pH was about 2).Rotary evaporation is used 95% dissolve with ethanol again to doing, and the supernatant liquor rotary evaporation obtains 55 milliliters of medicinal extract (relative density 1.27) behind the capsule of weeping forsythia acid-alkali treatment.
Medicinal extract dissolves with 2.1 premium on currency behind the capsule of weeping forsythia acid-alkali treatment, and supernatant liquor is collected 15% ethanol eluate rotary evaporation and got one 2.8 milliliters of macroporous resin components through NKA-II macroporous resin ethanol water gradient elution (the pH value transfers to 3 with hydrochloric acid), solid content 1.8 grams.
Capsule of weeping forsythia macroporous resin component one is used industrial chromatographic separation.400 millimeters of industrial chromatography post column lengths, 80 millimeters of internal diameters, chromatograph packing material are the C18 bonded stationary phase of 10-20 micron, and it is 15000 column plate/rice that post is imitated, setting the ultraviolet detection wavelength is 270nm, gradient elution, and repeatedly sample introduction is collected, the mass spectrometric detection target components merges, and rotary evaporation is concentrated into 10 milliliters.
Said mixture is further purified with purification plant.The purification plant chromatographic column be X-Tera Prep MSC18 OBD preparative column (19 * 100mm, i.d., 50um).The setting negative ion mass spectrum detects, gradient elution, and repeatedly sample introduction is collected target components, merges, and SPE concentrates, and 30 ℃ of rotary evaporations obtain 5.2 milligrams of this compounds.This compd E SI--TOF accurate molecular weight 315.1078, molecular formula C
14H
19O
8(PPM-0.6).
Determine that according to nuclear magnetic data this compound structure is as follows,
13C-NMR data such as table 1.
Table 1 13C-NMR (D2O, 400MHz)
1H-NMR data such as table 2.
Table 2 1H-NMR (D2O, 400MHz)
Embodiment 2
Capsule of weeping forsythia crude drug is pulverized, and takes by weighing 3 kilograms, places 100 liters of extractors, adds 30 premium on currency and decocts 2 hours, filters, and the filtrate preservation is standby, adds 30 premium on currency in the filter residue again and decocts 2 hours, filter, and filtrate and merging for the first time, filter residue discards.With the filtrate rotary evaporation, get medicinal extract 570ml (relative density 1.05).Medicinal extract is dissolved in equal-volume water, adds 1959 milliliter of 95% ethanol, stirs, and leaves standstill 24 hours, filters, and filter residue discards, and filtrate is concentrated into does not have the alcohol flavor, obtains 426 milliliters of capsule of weeping forsythia alcohol precipitation components.
Capsule of weeping forsythia alcohol precipitation component water is settled to 600 milliliters, adds 85.2 gram sodium bicarbonates, stirs, and reacts 3 hours, and placement is spent the night.Progressively add 170.4 milliliters of 1: 1 hydrochloric acid, 4.1 milliliters of 1: 2 hydrochloric acid (this moment, pH was about 2).Rotary evaporation is used 95% dissolve with ethanol again to doing, and the supernatant liquor rotary evaporation obtains 165 milliliters of medicinal extract (relative density 1.27) behind the capsule of weeping forsythia acid-alkali treatment.
Medicinal extract dissolves with 6.3 premium on currency behind the capsule of weeping forsythia acid-alkali treatment, and supernatant liquor is collected 15% ethanol eluate rotary evaporation and got one 8.4 milliliters of macroporous resin components through NKA-II macroporous resin ethanol water gradient elution (the pH value transfers to 3 with hydrochloric acid), solid content 5.4 grams.
Capsule of weeping forsythia macroporous resin component one is used industrial chromatographic separation.400 millimeters of industrial chromatography post column lengths, 80 millimeters of internal diameters, chromatograph packing material are the C18 bonded stationary phase of 10-20 micron, and it is 15000 column plate/rice that post is imitated, setting the ultraviolet detection wavelength is 270nm, gradient elution, and repeatedly sample introduction is collected, the mass spectrometric detection target components merges, and rotary evaporation is concentrated into 30 milliliters.
Said mixture is further purified with purification plant.The purification plant chromatographic column be X-Tera Prep MSC18 OBD preparative column (19 * 100mm, i.d., 50um).The setting negative ion mass spectrum detects, gradient elution, and repeatedly sample introduction is collected target components, merges, and SPE concentrates, and 30 ℃ of rotary evaporations obtain 15.6 milligrams of Compound I.
Embodiment 3
Capsule of weeping forsythia crude drug is pulverized, and takes by weighing 6.8 kilograms, places 100 liters of extractors, adds 68 premium on currency and decocts 2 hours, filters, and the filtrate preservation is standby, adds 68 premium on currency in the filter residue again and decocts 2 hours, filter, and filtrate and merging for the first time, filter residue discards.The filtrate rotary evaporation gets medicinal extract 1292ml (relative density 1.05).Medicinal extract is dissolved in equal-volume water, adds 4.44 liter of 95% ethanol, and stirring was left standstill 24 hours, filters, and filter residue discards, and filtrate is concentrated into does not have the alcohol flavor, gets 966 milliliters of capsule of weeping forsythia alcohol precipitation components.
Capsule of weeping forsythia alcohol precipitation component water is settled to 1.36 liters, adds 193 gram sodium bicarbonates, stirs, and reacts 3 hours, and placement is spent the night.Progressively add 386 milliliters of 1: 1 hydrochloric acid, 9.3 milliliters of 1: 2 hydrochloric acid (this moment, pH was about 2).Rotary evaporation is used 95% dissolve with ethanol to doing, and the supernatant liquor rotary evaporation obtains 374 milliliters of medicinal extract (relative density 1.27) behind the capsule of weeping forsythia acid-alkali treatment.
Medicinal extract 14.3 premium on currency behind the capsule of weeping forsythia acid-alkali treatment, dissolving, supernatant liquor is collected 15% ethanol eluate rotary evaporation and is got one 19 milliliters of macroporous resin components through NKA-II macroporous resin ethanol water gradient elution (the pH value transfers to 3 with hydrochloric acid), solid content 12.2 grams.
Capsule of weeping forsythia macroporous resin component one is used industrial chromatographic separation.400 millimeters of industrial chromatography post column lengths, 80 millimeters of internal diameters, chromatograph packing material are the C18 bonded stationary phase of 10-20 micron, and it is 15000 column plate/rice that post is imitated, setting the ultraviolet detection wavelength is 270nm, gradient elution, and repeatedly sample introduction is collected, the mass spectrometric detection target components merges, and rotary evaporation is concentrated into 68 milliliters.
This mixture is further purified with purification plant.The purification plant chromatographic column be X-Tera Prep MSC18 OBD preparative column (19 * 100mm, i.d., 50um).The setting negative ion mass spectrum detects, gradient elution, and repeatedly sample introduction is collected target components, merges, and SPE concentrates, and 30 ℃ of rotary evaporations obtain 36 milligrams of Compound I.
Embodiment 4
Capsule of weeping forsythia crude drug is pulverized, and takes by weighing 8 kilograms, places 100 liters of extractors, adds 80 premium on currency and decocts 2 hours, filters, and the filtrate preservation is standby, adds 80 premium on currency in the filter residue again and decocts 2 hours, filter, and filtrate and merging for the first time, filter residue discards.With the filtrate rotary evaporation, get medicinal extract 1520ml (relative density 1.05).Medicinal extract is dissolved in equal-volume water, adds 5224 milliliter of 95% ethanol, stirs, and leaves standstill 24 hours, filters, and filter residue discards, and filtrate is concentrated into does not have the alcohol flavor, obtains 1136 milliliters of capsule of weeping forsythia alcohol precipitation components.
Capsule of weeping forsythia alcohol precipitation component is settled to 1600 milliliters with water, adds 227 gram sodium bicarbonates again, stirs, and reacts 3 hours, and placement is spent the night.Progressively add 454.4 milliliters of 1: 1 hydrochloric acid, 10.9 milliliters of 1: 2 hydrochloric acid (this moment, pH was about 2).Rotary evaporation is used 95% dissolve with ethanol again to doing, and the supernatant liquor rotary evaporation obtains 440 milliliters of medicinal extract (relative density 1.27) behind the capsule of weeping forsythia acid-alkali treatment.
Medicinal extract adds 16.8 premium on currency behind the capsule of weeping forsythia acid-alkali treatment, dissolving, and supernatant liquor is collected 15% ethanol eluate rotary evaporation and is got one 22.4 milliliters of macroporous resin components through NKA-II macroporous resin ethanol water gradient elution (the pH value transfers to 3 with hydrochloric acid), solid content 14.4 grams.
Capsule of weeping forsythia macroporous resin component one is used industrial chromatographic separation.400 millimeters of industrial chromatography post column lengths, 80 millimeters of internal diameters, chromatograph packing material are the C18 bonded stationary phase of 10-20 micron, and it is 15000 column plate/rice that post is imitated, setting the ultraviolet detection wavelength is 270nm, gradient elution, and repeatedly sample introduction is collected, the mass spectrometric detection target components merges, and rotary evaporation is concentrated into 80 milliliters.
This mixture is further purified with purification plant.The purification plant chromatographic column be X-Tera Prep MSC18 OBD preparative column (19 * 100mm, i.d., 50um).The setting negative ion mass spectrum detects, and gradient elution is collected target components, merges, and SPE concentrates, and 30 ℃ of rotary evaporations obtain 41.6 milligrams of Compound I.
This compound has anti-oxidant, anti-aging effects can be used for cosmetics additive.
This compound has antiviral, antitumor action, mass production can be used as pharmaceutical preparation.
Claims (4)
1. dihydroxyphenyl ethanol glycoside compound, it is characterized in that: described structural formula of compound is as follows,
Its systematic naming method is 1-(2, the 5-dihydroxyl) styroyl-β-D-glucopyanoside.
2. according to the preparation method of the described compound of claim 1, it is characterized in that: it is specially for the product behind the Chinese medicine Fructus Forsythiae extract acid and alkali hydrolysis,
1) preparation of capsule of weeping forsythia aqueous extract: capsule of weeping forsythia crude drug is pulverized, quantitatively taken by weighing, decoct and extract 2-4 time, decocting time 1-3 hour at every turn, add the water boil of capsule of weeping forsythia 8-12 times weight at every turn, united extraction liquid is concentrated into the medicinal extract that relative density is 1.01-1.20g/ml;
2) preparation of capsule of weeping forsythia alcohol precipitation component: medicinal extract is with the water suspendible of 2-5 times of volume and add ethanol and make alcohol concn reach 50%-70%, and room temperature left standstill 12-24 hour, filtered, and filtrate is concentrated into does not have the alcohol flavor, obtains capsule of weeping forsythia alcohol precipitation component;
3) preparation of medicinal extract behind the capsule of weeping forsythia acid-alkali treatment: capsule of weeping forsythia alcohol precipitation component adds sodium bicarbonate or yellow soda ash reaction, saturated being metered in the aqueous solution by sodium bicarbonate or yellow soda ash, place, transferring to the pH value with acid is 2-4, rotary evaporation is to doing, use the 80-95% dissolve with ethanol again, the supernatant liquor rotary evaporation obtains the extractum A of relative density 1.20-1.35g/ml;
4) preparation of capsule of weeping forsythia macroporous resin component: extractum A goes up macroporous resin column after adding water dissolution, solution is through macroporous resin ethanol water gradient elution, the volumetric concentration of alcohol changes from 15% to 95% in the elutriant, and the volumetric concentration of collecting alcohol is that 15% o'clock target elutriant rotary evaporation gets macroporous resin component one;
5) industrial chromatography of dihydroxyphenyl ethanol glycoside compound separates: macroporous resin component one concentrates the back and adopts C18 reverse chromatograms post sample introduction to separate, moving phase is the methanol-water gradient elution, the volumetric concentration of alcohol changes from 5% to 45% in the elutriant, ultraviolet detection is by the time Fractional Collections, once or once above sample introduction, merge the elutriant under same period, mass spectrometric detection, the target components that contains dihydroxyphenyl ethanol glycoside compound concentrate component two;
6) purifying of dihydroxyphenyl ethanol glycoside compound: component two is concentrated back C18 reverse chromatograms post sample introduction purifying, moving phase acetonitrile water gradient elution, the volumetric concentration of acetonitrile changes from 3% to 25% in the elutriant, negative ion mass spectrum detects collects target components, obtains dihydroxyphenyl ethanol glycoside new compound.
3. according to the described preparation method of claim 2, it is characterized in that: described acid is hydrochloric acid, sulfuric acid or nitric acid.
4. according to the described preparation method of claim 2, it is characterized in that: the also available silica gel column chromatography of described C18 reverse chromatograms post is replaced.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103808749A (en) * | 2013-01-30 | 2014-05-21 | 河南省科高植物天然产物开发工程技术有限公司 | Method for identifying forsythia suspensa derivatives |
| CN112300230A (en) * | 2020-11-20 | 2021-02-02 | 河南大学 | Method for separating and extracting phenolic glycoside compounds from seeds of Nigella sativa |
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2008
- 2008-06-25 CN CN2008100120065A patent/CN101613384B/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103808749A (en) * | 2013-01-30 | 2014-05-21 | 河南省科高植物天然产物开发工程技术有限公司 | Method for identifying forsythia suspensa derivatives |
| CN112300230A (en) * | 2020-11-20 | 2021-02-02 | 河南大学 | Method for separating and extracting phenolic glycoside compounds from seeds of Nigella sativa |
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