CN104529985B - Method for simultaneous preparation of rhamnocitrin and rhamnazin chemical reference substances - Google Patents
Method for simultaneous preparation of rhamnocitrin and rhamnazin chemical reference substances Download PDFInfo
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- CN104529985B CN104529985B CN201410327623.XA CN201410327623A CN104529985B CN 104529985 B CN104529985 B CN 104529985B CN 201410327623 A CN201410327623 A CN 201410327623A CN 104529985 B CN104529985 B CN 104529985B
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- ethyl acetate
- rhamnocitrin
- petroleum ether
- rhammazin
- extract
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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
- C07D311/40—Separation, e.g. from natural material; Purification
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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
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Abstract
A stiff paste-like ethyl acetate extract is obtained by extracting nervilia fordii with petroleum ether through heating reflux, extracting residues with ethyl acetate through heating reflux, and recovering ethyl acetate. The ethyl acetate extract is separated by silica gel column chromatography or polyamide chromatography; components of rhamnocitrin and rhamnazin are collected and combined by silica gel thin layer chromatography or a hydrochloric acid-magnesium powder chemical identification method; after solvent recovery, a crude product (yellow powder) of a mixture of rhamnocitrin and rhamnazin is obtained; the crude product is separated by reversed-phase high performance liquid chromatography to obtain two chemical reference substances of rhamnocitrin and rhamnazin with purity of more than 98%. The method of the invention is simple in process step, high in purity, good in product color, and large in preparation capacity.
Description
First, technical field
The present invention relates to one kind two kinds of chemical references of rhamnocitrin and rhammazin are prepared from Chinese medicine ford nervilia leaf simultaneously
The method of product.Category modern Chinese traditional medicine field.Mainly include ford nervilia leaf through petroleum ether degreasing, ethyl acetate extraction, silica gel column chromatography
Or polyamide column chromatography is separated, RP-HPLC preparative chromatography refines four steps, so as to obtain rhamnocitrin and sandlwood
Two kinds of chemical reference substances of Qin Su.The structure of two kinds of reference substances is as follows：
2nd, background technology
Ford nervilia leaf is from the underground stem tuber of orchid Nervilia fordii NerviliaFordii (Hance) Schltr and complete
Grass, is distributed mainly on the provinces and regions such as Guangdong, Guangxi, Sichuan, Yunnan, Guizhou, is China's traditional Chinese medicine.Ford nervilia leaf is cold in nature sweet, returns
The heart, lung, Liver Channel.Can moisten the lung and relieve the cough, clearing heat and detoxicating, scattered silt analgesic.Ford nervilia leaf have antitussive and antiasthmatic, antitumor and Immune-enhancing effect and
Antibiosis and antiviral functions, clinical practice is in treatment asthma, chronic asthmatic bronchitis, COPD, radioactivity
Pneumonia, acute bartholinitis, acpuei pharyngitis, acute episode of chronic pharyngitis etc. have significant curative effect.In view of ford nervilia leaf is to lung
Disease has significant curative effect and can be antiviral, and Feng Chonglian is applied to and prevents and treats SARS (SARS), and effect is significant is (in China
Doctor's acute disease, 2005,13 (6)：339-341).
Ford nervilia leaf is always in short supply and economic worth Chinese medicine higher for a long time, but current ford nervilia leaf medicinal material standard is also
Remain at low levels, it is rarely seen to be embodied in《Guangxi Zhuang Autonomous Region prepared slices of Chinese crude drugs concocted specification》(version in 2007) and《Guangdong Province
Chinese medicine standard》In (version in 2004).The standard inspection project that the former includes is only limitted to the medicinal material profile proterties in terms of pharmacognosy
Inspection, the latter introduces indentification by TLC project in medicinal material standard, by the way of comparing with control medicinal material come
Differentiated.Lack the detection of ford nervilia leaf specificity composition or pharmacological activity index components in two kinds of standards, it is difficult to accurate control
Its inherent quality is made, causing in the market to circulate has the adulterant of various ford nervilia leafs.Common adulterant have asarum, sweet potato leaves, centella,
Babysbreath, RHIZOMA TYPHONII FLAGELLIFORMIS leaf, Herba Plantaginis extract and colter point leaf etc., wherein adulterant asarum is slightly poisonous.
It is beautiful wait report rhamnocitrin and rhammazin be flavone compound main in ford nervilia leaf (Acta Pharmaceutica Sinica,
2011,46 (10)：1237-1240), acted on antibacterial, anti-inflammatory, lipoid peroxidization resistant, antitumor etc., be ford nervilia leaf
Pharmacological activity index components.But so far, not yet there are rhamnocitrin and rhammazin chemical reference substance, reference substance city in country
Also the supply of rhamnocitrin and rhammazin reference substance is had no on field.Therefore prepare rhamnocitrin and rhammazin chemistry is right
According to product, the adulterant for the multi-objective control and discrimination ford nervilia leaf of ford nervilia leaf medicinal material and related compound is significant.
The present invention with ford nervilia leaf as raw material, through petroleum ether degreasing, ethyl acetate extract, silica gel column chromatography or polyamide column layer
Analysis is separated, RP-HPLC preparative chromatography is refined, and can obtain rhamnocitrin simultaneously in batches and two chemistry of rhammazin are right
According to product.
3rd, the content of the invention
The present invention is intended to provide a kind of while obtaining the preparation work of two chemical reference substances of rhamnocitrin and rhammazin
Skill.Present invention process step is simple, and purity is high, and color and luster is good, and preparation amount is big.
To achieve the above object, the technical solution adopted by the present invention is as follows：
It is a kind of while preparing two kinds of methods of chemical reference substance of rhamnocitrin and rhammazin.Ford nervilia leaf is de- through petroleum ether
Fat, ethyl acetate are extracted, silica gel column chromatography or polyamide column chromatography separation, refined four of RP-HPLC preparative chromatography are walked
Suddenly, the two kinds of chemical reference substances of rhamnocitrin and rhammazin of purity more than 98% are obtained.It is comprised the following steps that：
(1) petroleum ether degreasing：Ford nervilia leaf is ground into meal, the 6-10 times of 60- for measuring is added according to mass volume ratio kg/L
90 DEG C of petroleum ether is heated to reflux 5-7 times, each 1h.Filtering, ford nervilia leaf residue volatilizes petroleum ether.
(2) ethyl acetate is extracted：Ford nervilia leaf residue after degreasing, the 4-8 times of second measured is added according to mass volume ratio kg/L
Acetoacetic ester is heated to reflux 6-8 times, each 1h.Combined ethyl acetate extract solution, recycling design obtains the ethyl acetate extract of ford nervilia leaf
Medicinal extract, 60-80 DEG C of vacuum constant temperature of medicinal extract dries 12-24h.
(3) column chromatography for separation：Dried ethyl acetate extract medicinal extract is separated or with polyamide chromatogram with silica gel column chromatography
Separate.
1. silica gel column chromatography separate when, ethyl acetate extract medicinal extract with 1-3 times of anhydrous alcohol solution, in 1: 1-1: 2 ratios
Mixed thoroughly with 100-200 mesh column chromatography silica gels and mixed, 50 DEG C of constant-temperature vacuums dry 12h. and take the 10-20 times of fresh silica gel for mixing mixed silica gel
Dress post, then with petroleum ether-acetone (30: 1-4: 1) or petroleum ether-ethyl acetate (30: 1-4: 1) gradient elution.Petroleum ether-acetone
During gradient elution, 12: 1-8: 1 flow point is collected；When petroleum ether-ethyl acetate is eluted, 9: 1-5: 1 flow point is collected.It is recovered under reduced pressure molten
Agent, obtains final product the mixture (yellow) of rhamnocitrin and rhammazin.
2. during polyamide chromatographic isolation, ethyl acetate extract medicinal extract with 1-3 times of anhydrous alcohol solution, in 1: 1-1: 2 ratios
Mixed thoroughly with 100-200 mesh polyamide and mixed, 50 DEG C of constant-temperature vacuums dry 12h.Take the 20-30 times of polyamide dress of preprocessed mistake
Post, is eluted with water, 10% ethanol water, 30% ethanol water and 50% ethanol water successively, and every kind of solvent has been washed till
Little material washed under when change under a kind of solvent.By hydrochloric acid magnesium powder identification, determine whether eluate contains flavonoids
Material.50% eluent is collected, solvent is recovered under reduced pressure, obtain final product the mixture (yellow) of rhamnocitrin and rhammazin.
(4) RP-HPLC preparative chromatography is refined：The mixture of rhamnocitrin and rhammazin is with 60% methanol-water
Solution dissolve, be made into concentration be 20-30mg/ml sample solution, filtering with microporous membrane, chromatographic column be ODS-C18 (250mm ×
20mm, 15 μm), sampling volume is 1-4ml, and it is 60% methanol aqueous solution isocratic elution to use mobile phase, and flow velocity is 10-15ml/
Min, is detected with 368nm, and retention time is respectively two main colors of 11.5min and 12.4min in collection preparative chromatography respectively
Spectral peak, is recovered under reduced pressure solvent, and 50 DEG C of constant-temperature vacuums dry 24h, obtains final product two chemical reference substances of rhamnocitrin and rhammazin.
Its purity using reversed phase high performance liquid facies analysis chromatography, purity reaches more than 98%.
With the present invention, separation prepares two chemical reference substances of rhamnocitrin and rhammazin from ford nervilia leaf, with as follows
Advantage and progress：
1. the present invention prepares two chemical reference substances of rhamnocitrin and rhammazin first.
2. present invention process is simple, and ford nervilia leaf is through petroleum ether degreasing, ethyl acetate extraction, silica gel column chromatography or polyamide column
Chromatography, RP-HPLC preparative chromatography refine four steps, you can while obtaining sandlwood lemon of the purity more than 98%
Element and two chemical reference substances of rhammazin, are conducive to maximum resource utilization.
3. separation costs of the present invention are low, the equal recoverable of agents useful for same.
4th, illustrate
Fig. 1 is RP-HPLC preparative chromatography figure (368nm)；
Fig. 2 analyzes collection of illustrative plates (368nm) for the HPLC of rhamnocitrin；
Fig. 3 analyzes collection of illustrative plates (368nm) for the HPLC of rhammazin；
5th, specific embodiment
The present invention is described in further details in conjunction with embodiment and accompanying drawing.Embodiment is only limitted to the explanation present invention, and
Non- limitation of the present invention.
Embodiment 1
(1) petroleum ether degreasing：10kg ford nervilia leafs are ground into meal, are heated to reflux with 6 times 60-90 DEG C of amount of petroleum ether
7 times, each 1h.Filtering, ford nervilia leaf residue volatilizes petroleum ether.
(2) ethyl acetate is extracted：Ford nervilia leaf residue after degreasing, adds the ethyl acetate of 5 times of amounts to be heated to reflux 6 times, often
Secondary 1h.Combined ethyl acetate extract solution, recycling design, 60 DEG C of vacuum constant temperatures dry 24h, obtain medicinal extract 96.1g.
(3) silica gel column chromatography is separated：Dried ethyl acetate extract medicinal extract is separated with silica gel column chromatography.Take 60g acetic acid
Ethyl ester position medicinal extract is mixed thoroughly with 100-200 mesh column chromatography silica gels in 1: 2 ratio and mixed with 2 times of anhydrous alcohol solutions, 50 DEG C of constant temperature
Vacuum drying 12h. takes the fresh silica gel dress posts of 900g, then with petroleum ether-acetone (30: 1-4: 1) gradient elution, collects 12: 1-8: 1
Flow point, is recovered under reduced pressure solvent, obtains final product the mixture 0.9g (yellow) of rhamnocitrin and rhammazin.
(4) RP-HPLC preparative chromatography is refined：The mixture of 0.9g rhamnocitrins and rhammazin is with 60% first
Alcohol solution dissolves, and is made into the sample solution that concentration is 30mg/ml, filtering with microporous membrane, Shimadzu permaphase ODS-C18 (250mm
× 20mm, 15 μm), sampling volume is 3ml, and it is 60% methanol aqueous solution isocratic elution to use mobile phase, and flow velocity is 10ml/min,
Detection wavelength 368nm, retention time is respectively two main chromatograms of 11.5min and 12.4min in collection preparative chromatography respectively
Peak, is recovered under reduced pressure solvent, and 50 DEG C of constant-temperature vacuums dry 24h, obtains final product two chemical reference substances of rhamnocitrin and rhammazin.Mouse
Lee's citrin reference substance weight 0.48g, HPLC purity analysis is 98.5%；Rhammazin reference substance weight 0.33g, HPLC purity analysis
It is 99.0%.
Embodiment 2
(1) petroleum ether degreasing：10kg ford nervilia leafs are ground into meal, are heated to reflux with 8 times 60-90 DEG C of amount of petroleum ether
6 times, each 1h.Filtering, ford nervilia leaf residue volatilizes petroleum ether.
(2) ethyl acetate is extracted：Ford nervilia leaf residue after degreasing, adds the ethyl acetate of 6 times of amounts to be heated to reflux 6 times, often
Secondary 1h.Combined ethyl acetate extract solution, recycling design, 60 DEG C of vacuum constant temperatures dry 24h, obtain medicinal extract 100g.
(3) silica gel column chromatography is separated：Dried ethyl acetate extract medicinal extract is separated with silica gel column chromatography.Take 60g acetic acid
Ethyl ester position medicinal extract is mixed thoroughly with 200-300 mesh column chromatography silica gels in 1: 2 ratio and mixed with 2 times of anhydrous alcohol solutions, 50 DEG C of constant temperature
Vacuum drying 12h. takes the fresh silica gel dress posts of 900g, then with petroleum ether-ethyl acetate (30: 1-4: 1) gradient elution, collects 9: 1-
5: 1 flow points.Solvent is recovered under reduced pressure, the mixture 0.82g (yellow) of rhamnocitrin and rhammazin is obtained final product.
(4) RP-HPLC preparative chromatography is refined：The mixture of 0.82g rhamnocitrins and rhammazin is with 60% first
Alcohol solution dissolves, and is made into the sample solution that concentration is 25mg/ml, filtering with microporous membrane, Shimadzu permaphase ODS-C18 (250mm
× mm, 15 μm), sampling volume is 3.5ml, and it is 60% methanol aqueous solution isocratic elution to use mobile phase, and flow velocity is 15ml/min,
Detection wavelength 368nm, retention time is respectively two main chromatograms of 11.5min and 12.4min in collection preparative chromatography respectively
Peak, is recovered under reduced pressure solvent, and 50 DEG C of constant-temperature vacuums dry 24h, obtains final product two chemical reference substances of rhamnocitrin and rhammazin.Mouse
Lee's citrin reference substance weight 0.40g, HPLC purity analysis is 98.3%；Rhammazin reference substance weight 0.26g, HPLC purity analysis
It is 98.7%.
Embodiment 3
(1) petroleum ether degreasing：10kg ford nervilia leafs are ground into meal, are heated to reflux with 6 times 60-90 DEG C of amount of petroleum ether
8 times, each 1h.Filtering, ford nervilia leaf residue volatilizes petroleum ether.
(2) ethyl acetate is extracted：Ford nervilia leaf residue after degreasing, adds the ethyl acetate of 7 times of amounts to be heated to reflux 6 times, often
Secondary 1h.Combined ethyl acetate extract solution, recycling design, 60 DEG C of vacuum constant temperatures dry 24h, obtain medicinal extract 98.1g.
(3) polyamide chromatographic isolation：Dried ethyl acetate extract medicinal extract is separated with polyamide column chromatography.Take 60g second
Acetoacetic ester position medicinal extract is mixed thoroughly with 100-200 mesh polyamide in 1: 1.5 ratio and mixed with 2 times of anhydrous alcohol solutions, 50 DEG C of constant temperature
Vacuum drying 12h. takes the polyamide dress post of the preprocessed mistakes of 1500g, successively with water, 10% ethanol water, 30% ethanol water
Solution and 50% ethanol water are eluted, a kind of solvent under being changed when every kind of solvent has been washed till under little material is washed.By salt
Sour magnesium powder identification, determines whether eluate contains Flavonoid substances.50% eluent is collected, solvent is recovered under reduced pressure, dried,
Obtain final product the mixture 1.2g (yellow) of rhamnocitrin and rhammazin.
(4) RP-HPLC preparative chromatography is refined：The mixture of 1.2g rhamnocitrins and rhammazin is with 60% first
Alcohol solution dissolves, and is made into the sample solution that concentration is 30mg/ml, filtering with microporous membrane, Shimadzu permaphase ODS-C18 (250mm
× mm, 15 μm), sampling volume is 3ml, and it is 60% methanol aqueous solution isocratic elution to use mobile phase, and flow velocity is 12ml/min, inspection
Wavelength 368nm is surveyed, retention time is respectively two main chromatographic peaks of 11.5min and 12.4min in collection preparative chromatography respectively,
Solvent is recovered under reduced pressure, 50 DEG C of constant-temperature vacuums dry 24h, obtains final product two chemical reference substances of rhamnocitrin and rhammazin.Sandlwood
Citrin reference substance weight 0.62g, HPLC purity analysis is 99.1%；Rhammazin reference substance weighs 0.42g, and HPLC purity analysis is
98.6%.
Claims (7)
1. a kind of while preparing two kinds of methods of chemical reference substance of rhamnocitrin and rhammazin, it is characterised in that by following step
Suddenly carry out：
(1) petroleum ether degreasing：Ford nervilia leaf is ground into meal, is heated to reflux carrying out degreasing with 60-90 DEG C of petroleum ether；
(2) ethyl acetate is extracted：Ford nervilia leaf residue after degreasing, with ethyl acetate heating and refluxing extraction, combined ethyl acetate is carried
Liquid is taken, recycling design obtains the ethyl acetate extract medicinal extract of ford nervilia leaf, and 60-80 DEG C of vacuum constant temperature of medicinal extract dries 24h；
(3) column chromatography for separation：Dried ethyl acetate extract medicinal extract is separated or with polyamide chromatographic isolation with silica gel column chromatography；
When silica gel column chromatography is separated, with 30: 1-4: 1 petroleum ether-acetone or 30: 1-4: 1 petroleum ether-ethyl acetate gradient elution；
During petroleum ether-acetone gradient elution, 12: 1-8: 1 flow point is collected；When petroleum ether-ethyl acetate is eluted, 9: 1-5: 1 flow point is collected；
During polyamide chromatographic isolation, eluted with water, 10% ethanol water, 30% ethanol water and 50% ethanol water successively,
Collect 50% ethanol water；Solvent is recovered under reduced pressure, the mixture of rhamnocitrin and rhammazin is obtained final product, outward appearance is yellow；
(4) RP-HPLC preparative chromatography is refined：Yellow mixture powder is dissolved with methanol-water solution, filtering with microporous membrane,
Separated with RP-HPLC preparative chromatograph, methanol-water solution is elution system, preparative chromatography is collected in 368nm detections respectively
In two main chromatographic peaks, solvent is recovered under reduced pressure, 50 DEG C of constant-temperature vacuums dry 24h, obtain final product rhamnocitrin and rhammazin
Two chemical reference substances.
2. method according to claim 1, it is characterised in that：The consumption of 60-90 DEG C of petroleum ether is the blue sky in step (1)
6-10 times of certain herbaceous plants with big flowers medicinal material is measured, and the heating and refluxing extraction time is 1-2h, and extraction time is 4-6 times.
3. method according to claim 1, it is characterised in that：The consumption of ethyl acetate is 4-8 times of medicinal material in step (2)
Amount, the heating and refluxing extraction time is 1-2h, and extraction time is 6-8 times；Combined ethyl acetate extract solution, recycling design obtains the blue sky
The ethyl acetate extract medicinal extract of certain herbaceous plants with big flowers.
4. method according to claim 1, it is characterised in that：The mixing of rhamnocitrin and rhammazin in step (4)
Thing is dissolved with 60% methyl alcohol, and sample concentration is 20-30mg/ml.
5. method according to claim 1, it is characterised in that：In step (4), RP-HPLC prepares the filling material of post
Expect to be C18,15 μm of granularity；Prepare column length 250mm, diameter 20mm.
6. method according to claim 1, it is characterised in that：In step (4), reversed phase high efficiency prepares liquid phase sampling volume and is
1-4ml, flow velocity is 10-15ml/min, the mobile phase for using for 60% methanol aqueous solution.
7. method according to claim 1, it is characterised in that：In step (4), collect retention time and be respectively 11.5min
With the flow point of 12.4min, solvent is recovered under reduced pressure, dries, obtain final product two kinds of reference substances of rhamnocitrin and rhammazin.
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| CN1872282A (en) * | 2006-01-13 | 2006-12-06 | 广州中医药大学 | Active extractive of Foliumnerviliae, preparation method and application |
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| CN101891729A (en) * | 2010-07-02 | 2010-11-24 | 广西医科大学 | Method for extracting high-purity rhamnazin from ford nervilia leaf |
| CN102887928A (en) * | 2012-03-21 | 2013-01-23 | 广西壮族自治区药用植物园 | Flavonoids from nervilia fordii and preparation method and use thereof |
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| WO2009035987A1 (en) * | 2007-09-13 | 2009-03-19 | Gateway Health Alliances, Inc. | METHODS AND RELATED COMPOSITIONS USING SPECIFIC FLAVONOIDS AND INDANES TO REDUCE WEIGHT AND INHIBIT LIPASE. α-AMYLASE AND α-GLUCOSIDASE ACTIVITY IN MAMMALS |
| CN101891729A (en) * | 2010-07-02 | 2010-11-24 | 广西医科大学 | Method for extracting high-purity rhamnazin from ford nervilia leaf |
| CN102887928A (en) * | 2012-03-21 | 2013-01-23 | 广西壮族自治区药用植物园 | Flavonoids from nervilia fordii and preparation method and use thereof |
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