CN104003854B - One prepares the method for guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol - Google Patents
One prepares the method for guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol Download PDFInfo
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- CN104003854B CN104003854B CN201410203163.XA CN201410203163A CN104003854B CN 104003854 B CN104003854 B CN 104003854B CN 201410203163 A CN201410203163 A CN 201410203163A CN 104003854 B CN104003854 B CN 104003854B
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- guaiacyl glycerol
- methyl alcohol
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
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Abstract
The invention discloses the method that one prepares guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol.Guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol structures formula is as shown in formula I.The present invention's preparative separation from Lychee leaf obtains a large amount of guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol, and its productive rate is 10 ~ 56mg/kg (purity is 85 ~ 95%).The present invention, for the deep processing and utilization promoting lichee, promotes lichee added value of product, promotes that the Sustainable development of the sector has great importance.
Description
Technical field
The invention belongs to natural product field, be specifically related to a kind of from Lychee leaf preparative separation obtain the method for guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol.
Background of invention
Lichee belongs to Sapindaceae, and have the title of " south of the Five Ridges fruit king ", is one of Guangdong four your name fruit.Lichee is fragrant and sweet good to eat, nutritive value and nourishing function higher, be traditional protective foods, dark liking by consumers in general.China is the country of cultivating lichee in the world the earliest, with a long history; Also be the country that Yield of Litchi is maximum in the world, various in style.Lychee leaf is the branches and leaves of litchi, and the whole year can adopt, aboundresources.Research finds, is rich in flavonoid compound, has the biological activitys such as anti-oxidant, anticancer, hypoglycemic in Semen Litchi and Litchi exocarp, but outer very limited about the research of Lychee leaf activeconstituents at present, and Active substance composition still requires study.
Guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol, its structural formula is as shown in formula I:
Summary of the invention
The object of this invention is to provide the method that one prepares guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol.
The method preparing guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol of the present invention, it is characterized in that, comprise the following steps: with volume fraction 40 ~ 100% methyl alcohol or aqueous ethanolic solution lixiviate Lychee leaf, water dissolution is used by after vat liquor concentrated removal methyl alcohol or ethanol, successively use sherwood oil respectively again, extraction into ethyl acetate, ethyl acetate is concentrated to obtain medicinal extract mutually, medicinal extract is through silica gel column chromatography, take chloroform/methanol as eluent, from volume ratio 100/0 ~ 60/40 gradient elution, collect the cut that chloroform/methanol volume ratio is 85/15 wash-out, this cut is again through SephadexLH-20 column chromatography, methyl alcohol is as eluting solvent, collect component and utilize high-efficient liquid phase chromatogram purification, with methanol-water from volume ratio 5/95 ~ 15/85 gradient elution, collect the component that methanol/water volume ratio is 15/85 wash-out, guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol can be obtained.
Described Lychee leaf is preferably Lychee leaf powder, after preferably fresh Lychee leaf being dried or dried further, pulverizes the Lychee leaf powder of 20 ~ 120 mesh sieves.
Described use volume fraction 40 ~ 100% methyl alcohol or aqueous ethanolic solution lixiviate Lychee leaf, the consumption of methyl alcohol or aqueous ethanolic solution is 5 ~ 20mL/g Lychee leaf, and the temperature of lixiviate is preferably 25 ~ 80 DEG C, and extraction time is 4 ~ 35 hours.
Described uses water dissolution by after vat liquor concentrated removal methyl alcohol or ethanol, preferably by vat liquor concentrated removing methyl alcohol or ethanol at 40 ~ 80 DEG C, then adds the water dissolution of 1 ~ 3 times of volume.
Described priority uses sherwood oil, extraction into ethyl acetate respectively, preferably first uses petroleum ether extraction 3 ~ 12 times, then be extracted with ethyl acetate 3 ~ 12 times.
Present invention also offers Lychee leaf and prepare the application in guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol.
The present invention's preparative separation from Lychee leaf obtains guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol, and its productive rate is 10 ~ 56mg/kg (purity is 85 ~ 95%).The present invention, for the deep processing and utilization promoting lichee, promotes lichee added value of product, promotes that the Sustainable development of the sector has great importance.Simultaneously also for the preparation of guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol provides a kind of new method.
Embodiment:
Following examples further illustrate of the present invention, instead of limitation of the present invention.
Embodiment 1: guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol preparative separation and Structural Identification.
The preparative separation of one, guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol
1) select materials: select fresh lichee leaf, clear water washs;
2) drying and crushing: dried by Lychee leaf or dry, adopts pulverizer to be ground into powder, crosses 20 mesh sieves, obtain Lychee leaf powder;
3) lixiviate: added by Lychee leaf powder in the methanol aqueous solution of the volume fraction 40% of 5 times of volumes (i.e. 5mL/g Lychee leaf powder), 80 DEG C of lixiviates 4 hours, filters, collects filtered liquid;
4) organic solvent classification: by above-mentioned filtered liquid concentrated removing methyl alcohol at 40 DEG C, add the water of its 1 times of volume, successively extract 3 times respectively by isopyknic sherwood oil, ethyl acetate; Selection ethyl acetate phase extraction liquid is concentrated that medicinal extract is used for subsequent purification.
5) medicinal extract (200g) of ethyl acetate phase extraction liquid is got, adopt silicagel column (100 ~ 200 order) chromatography, take chloroform/methanol as eluting solvent, from volume ratio 100/0 ~ 60/40 gradient elution, collect the cut that chloroform/methanol volume ratio is 85/15 wash-out, this cut is again through SephadexLH-20 column chromatography, methyl alcohol is as eluting solvent, collecting main ingredient utilizes high performance liquid chromatography through C18 column purification, methanol-water (5:95 ~ 15:85) gradient elution, collect the component that methanol/water volume ratio is 15/85 wash-out, at 60 DEG C of evaporating, concentrating and dryings, compound 1 (guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol can be obtained).
The guaiacyl glycerol adopting the method to obtain-(8-O-4 ')-guaiacyl glycerol productive rate is 10 ~ 29mg/kg, and purity is 85 ~ 95%.
Two, compound 1 (guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol) Structural Identification
Compound 1 (guaiacyl glycerol-(and 8-O-4 ')-guaiacyl glycerol) dissolve in methyl alcohol, mass spectral results shows that this compound molecular weight is 410.This compound
1h NMR (500MHz, CD
3oD) and
13c NMR (125MHz, CD
3oD) in table 1:
Table 1. guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol
13c with
1h composes chemical shift
| 1H | 13C | |
| C1 | 133.9 | |
| C2 | 7.02(d,2.0) | 111.8 |
| C3 | 148.9 | |
| 3-OCH3 | 3.82(s) | 56.5 |
| C4 | 147.2 | |
| C5 | 6.76(d,8.5) | 116.0 |
| C6 | 6.86(dd,2.0,8.5) | 120.8 |
| C7 | 4.89(d,6.0) | 73.9 |
| C8 | 4.28(dd,5.0,9.5) | 87.3 |
| C9 | 3.48,3.75(dd,12,4.5) | 62.0 |
| C1’ | 137.9 | |
| C2’ | 7.07(d,2.0) | 112.3 |
| C3’ | 151.6 | |
| 3’-OCH3 | 3.87(s) | 56.6 |
| C4’ | 149.0 | |
| C5’ | 7.02(d,8.5) | 118.7 |
| C6’ | 6.86(dd,2.0,8.5) | 120.8 |
| C7’ | 4.58(d,5.5) | 75.2 |
| C8’ | 3.67(m) | 77.6 |
| C9’ | 3.38,3.52(dd,11.0,6.0) | 64.3 |
In sum, identify that the structural formula of this compound is as shown in formula I, name is called: guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol, this compound is soluble in methyl alcohol.
Embodiment 2:
1) select materials: select fresh lichee leaf, clear water washs;
2) drying and crushing: dried by Lychee leaf or dry, adopts pulverizer to be ground into powder, crosses 120 mesh sieves, obtain Lychee leaf powder;
3) lixiviate: volume fraction Lychee leaf powder being added 20 times of volumes (i.e. 20mL/g Lychee leaf powder) is 90% methanol solution, room temperature lixiviate 35 hours, filters, collects filtered solution;
4) organic solvent classification: by above-mentioned filtered solution at 60 DEG C of concentrated removing methyl alcohol, add the water of its 3 times of volumes, successively extract 12 times respectively by isopyknic sherwood oil, ethyl acetate; Obtain medicinal extract after selecting ethyl acetate phase extraction liquid concentrated and be used for subsequent purification.
Following purification steps is identical with embodiment 1, obtains compound thus and is accredited as guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol.
The guaiacyl glycerol adopting the method to obtain-(8-O-4 ')-guaiacyl glycerol productive rate is 32 ~ 56mg/kg, and purity is 85 ~ 95%.
Embodiment 3:
1) select materials: select fresh lichee leaf, clear water washs;
2) drying and crushing: dried by Lychee leaf or dry, adopts pulverizer to be ground into powder, crosses 60 mesh sieves, obtain Lychee leaf powder;
3) lixiviate: volume fraction Lychee leaf powder being added 10 times of volumes (i.e. 10mL/g Lychee leaf powder) is 40% aqueous ethanolic solution, 50 DEG C of lixiviates 20 hours, filters, collects filtered solution;
4) organic solvent classification: by above-mentioned filtered solution at 60 DEG C of concentrated removing ethanol, add the water of its 2 times of volumes, successively extract 6 times respectively by isopyknic sherwood oil, ethyl acetate; Obtain medicinal extract after selecting ethyl acetate phase extraction liquid concentrated and be used for subsequent purification.
Following purification steps is identical with embodiment 1, obtains compound and is accredited as guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol.
The productive rate of the guaiacyl glycerol adopting the method to obtain-(8-O-4 ')-guaiacyl glycerol is 26 ~ 42mg/kg, and purity is 85 ~ 95%.
Embodiment 4:
1) select materials: select fresh lichee leaf, clear water washs;
2) drying and crushing: dried by Lychee leaf or dry, adopts pulverizer to be ground into powder, crosses 60 mesh sieves, obtain Lychee leaf powder;
3) lixiviate: volume fraction 100% ethanolic soln Lychee leaf powder being added 10 times of volumes (i.e. 10mL/g Lychee leaf powder), 25 DEG C of lixiviates 15 hours, filters, collects filtered solution;
4) organic solvent classification: by above-mentioned filtered solution at 70 DEG C of concentrated removing ethanol, add the water of 1 times of volume, successively extract 6 times respectively with isopyknic sherwood oil, ethyl acetate, propyl carbinol; Obtain medicinal extract after selecting ethyl acetate phase extraction liquid concentrated and be used for subsequent purification.
Following purification steps is identical with embodiment 1, obtains compound and is accredited as guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol.
The productive rate of the guaiacyl glycerol adopting the method to obtain-(8-O-4 ')-guaiacyl glycerol is 22 ~ 39mg/kg, and purity is 85 ~ 95%.
Claims (5)
1. prepare the method for guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol for one kind, it is characterized in that, comprise the following steps: with volume fraction 40 ~ 100% methyl alcohol or aqueous ethanolic solution lixiviate Lychee leaf, water dissolution is used by after vat liquor concentrated removal methyl alcohol or ethanol, successively use sherwood oil respectively again, extraction into ethyl acetate, ethyl acetate is concentrated to obtain medicinal extract mutually, medicinal extract is through silica gel column chromatography, take chloroform/methanol as eluent, from volume ratio 100/0 ~ 60/40 gradient elution, collect the cut that chloroform/methanol volume ratio is 85/15 wash-out, this cut is again through SephadexLH-20 column chromatography, methyl alcohol is as eluting solvent, collect component and utilize high-efficient liquid phase chromatogram purification, with methanol-water from volume ratio 5/95 ~ 15/85 gradient elution, collect the component that methanol/water volume ratio is 15/85 wash-out, guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol can be obtained,
Described use volume fraction 40 ~ 100% methyl alcohol or aqueous ethanolic solution lixiviate Lychee leaf, the consumption of methyl alcohol or aqueous ethanolic solution is 5 ~ 20mL/g Lychee leaf, and the temperature of lixiviate is 25 ~ 80 DEG C, and extraction time is 4 ~ 35 hours.
2. method according to claim 1, is characterized in that, described Lychee leaf is Lychee leaf powder, and it, after fresh Lychee leaf is dried or dried, pulverized the Lychee leaf powder of 20 ~ 120 mesh sieves.
3. method according to claim 1, is characterized in that, described uses water dissolution by after vat liquor concentrated removal methyl alcohol or ethanol, is by vat liquor concentrated removing methyl alcohol or ethanol at 40 ~ 80 DEG C, then adds the water dissolution of 1 ~ 3 times of volume.
4. method according to claim 1, is characterized in that, described priority uses sherwood oil, extraction into ethyl acetate respectively, is first to use petroleum ether extraction 3 ~ 12 times, then is extracted with ethyl acetate 3 ~ 12 times.
5. Lychee leaf is preparing the application in guaiacyl glycerol-(8-O-4 ')-guaiacyl glycerol.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102718650A (en) * | 2012-06-11 | 2012-10-10 | 中国科学院华南植物园 | 2-(2- hydroxyl-5-(methoxycarbonyl) phenoxyl) benzoic acid as well as preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102718650A (en) * | 2012-06-11 | 2012-10-10 | 中国科学院华南植物园 | 2-(2- hydroxyl-5-(methoxycarbonyl) phenoxyl) benzoic acid as well as preparation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| Conformation-Specific Spectroscopy and Populations of Diastereomers of a Model Monolignol Derivative: Chiral Effects in a Triol Chain;Jacob C. Dean et al.;《The Journal of Physical Chemistry A》;20110714;第115卷;8464–8478 * |
| 荔枝叶的化学成分研究;黄绍军 等;《中草药》;20070930;第38卷(第9期);1313-1315 * |
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