CN104003999B - A kind of method preparing cinnamtannin B1 - Google Patents
A kind of method preparing cinnamtannin B1 Download PDFInfo
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- CN104003999B CN104003999B CN201410204144.9A CN201410204144A CN104003999B CN 104003999 B CN104003999 B CN 104003999B CN 201410204144 A CN201410204144 A CN 201410204144A CN 104003999 B CN104003999 B CN 104003999B
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- methyl alcohol
- lychee leaf
- ethyl acetate
- methanol
- lychee
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/18—Bridged systems
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- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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Abstract
The invention discloses one and prepare cinnamtannin? the method of B1.Cinnamtannin? B1 structural formula is as shown in formula I.Does the present invention's preparative separation from Lychee leaf obtain a large amount of cinnamtannin? B1, its productive rate is 51 ~ 196mg/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 cinnamtanninB1.
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.
CinnamtanninB1, its structural formula is as shown in formula I:
Summary of the invention
The object of this invention is to provide a kind of method preparing cinnamtanninB1.
The method preparing cinnamtanninB1 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 75/25 wash-out, this cut is again through reversed phase column chromatography, take methanol/water as eluent, from volume ratio 5/95 ~ 45/55 gradient elution, collect the cut that methanol/water volume ratio is 10/90 wash-out, this cut is again through SephadexLH-20 column chromatography, methyl alcohol is as eluting solvent, cinnamtanninB1 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 the application of Lychee leaf in preparation cinnamtanninB1.
The present invention's preparative separation from Lychee leaf obtains cinnamtanninB1, and its productive rate is 51 ~ 196mg/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 cinnamtanninB1 provides a kind of new method.
Embodiment:
Following examples further illustrate of the present invention, instead of limitation of the present invention.
Embodiment 1:cinnamtanninB1 preparative separation and Structural Identification.
One, the preparative separation of cinnamtanninB1
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 respectively; 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 component that chloroform/methanol volume ratio is 75/25 wash-out, again through C18 reversed phase column chromatography, take methanol/water as eluent, from volume ratio 5/95 ~ 45/55 gradient elution, collect the cut that methanol/water volume ratio is 10/90 wash-out, this cut is through SephadexLH-20 column chromatography, methyl alcohol is as eluting solvent, finally collect component at 60 DEG C of evaporating, concentrating and dryings, compound 1 (cinnamtanninB1) can be obtained.
The cinnamtanninB1 productive rate adopting the method to obtain is 51 ~ 95mg/kg, and purity is 85 ~ 95%.
Two, the Structural Identification of compound cinnamtanninB1
Compound 1 (cinnamtanninB1) is yellow powder, dissolves in methyl alcohol, and ESI-MS mass spectral results shows that this compound molecular weight is 864.This compound
1hNMR (500MHz, CD
3oD) and
13cNMR (125MHz, CD
3oD) in table 1:
Table 1. compound 1 (CinnamtanninB1)
13c with
1h composes chemical shift
In sum, identify that the structural formula of this compound 1 is as shown in formula I, name is called: cinnamtanninB1, and 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 (20mL/g Lychee leaf powder) is 90% methanol aqueous 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 respectively; 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 cinnamtanninB1.
The cinnamtanninB1 productive rate adopting the method to obtain is 150 ~ 196mg/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 (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 respectively; 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 cinnamtanninB1.
The productive rate of the cinnamtanninB1 adopting the method to obtain is 90 ~ 142mg/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 (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 respectively; 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 cinnamtanninB1.
The productive rate of the cinnamtanninB1 adopting the method to obtain is 82 ~ 129mg/kg, and purity is 85 ~ 95%.
Claims (2)
1. prepare the method for cinnamtanninB1 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 75/25 wash-out, this cut is again through reversed phase column chromatography, take methanol/water as eluent, from volume ratio 5/95 ~ 45/55 gradient elution, collect the cut that methanol/water volume ratio is 10/90 wash-out, this cut is again through SephadexLH-20 column chromatography, methyl alcohol is as eluting solvent, cinnamtanninB1 can be obtained,
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;
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;
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;
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.
2. the application of Lychee leaf in preparation cinnamtanninB1.
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WO1990004968A1 (en) * | 1988-10-31 | 1990-05-17 | University Of North Carolina At Chapel Hill | Inhibition of human retroviruses |
CN102796070A (en) * | 2012-08-29 | 2012-11-28 | 西南林业大学 | Preparation method of oligomeric proanthocyanidins |
CN103467477A (en) * | 2013-07-24 | 2013-12-25 | 中国科学院华南植物园 | Procyanidin A2, and preparation method and application thereof |
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A-type procyanidins from Litchi chinensis pericarp with antioxidant activity;Liang Liu等;《Food Chemistry》;20150731;第105卷(第4期);第1446–1451页 * |
Oxidation of (-)-epicatechin is a precursor of litchi pericarp enzymatic browning;Liang Liu等;《Food Chemistry》;20091231;第118卷(第3期);第508–511页 * |
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