CN104003999A - Method for preparing cinnamtannin B1 - Google Patents

Method for preparing cinnamtannin B1 Download PDF

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Publication number
CN104003999A
CN104003999A CN201410204144.9A CN201410204144A CN104003999A CN 104003999 A CN104003999 A CN 104003999A CN 201410204144 A CN201410204144 A CN 201410204144A CN 104003999 A CN104003999 A CN 104003999A
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Prior art keywords
methyl alcohol
cinnamtannin
lychee leaf
ethyl acetate
methanol
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CN201410204144.9A
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CN104003999B (en
Inventor
杨宝
蒋跃明
温玲蓉
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South China Botanical Garden of CAS
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South China Botanical Garden of CAS
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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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

The invention discloses a method for preparing cinnamtannin B1. The structural formula of cinnamtannin B1 is as shown in formula (I). According to the invention, a lot of cinnamtannin B1 is prepared and separated from lichee leaves, and the yield is 51-196 mg/kg (the purity is 85-95%). The method of the invention has important significance on promoting lichee deep processing and utilization, increasing the added value lichee products, and promoting the sustainable development of the industry.

Description

A kind of method of preparing cinnamtannin B1
Technical field
The invention belongs to natural product field, be specifically related to a kind of method that obtains cinnamtannin B1 that separates of preparing from Lychee leaf.
Background of invention
Lichee belongs to Sapindaceae, have the title of " south of the Five Ridges fruit king ", is one of Guangdong four your name fruits.Lichee is fragrant and sweet good to eat, and nutritive value and nourishing function are higher, is traditional protective foods, is deeply subject to liking of consumers in general.China is the country of cultivating the earliest in the world lichee, with a long history; Also be the country of Yield of Litchi maximum in the world, various in style.Lychee leaf is the branches and leaves of litchi, and can adopt the whole year, aboundresources.Research is found, in Semen Litchi and Litchi exocarp, is rich in flavonoid compound, has the biological activitys such as anti-oxidant, anticancer, hypoglycemic, but outer very limited about the research of Lychee leaf activeconstituents at present, Active substance composition still requires study.
Cinnamtannin B1, its structural formula is as shown in formula I:
Summary of the invention
The object of this invention is to provide the method for the cinnamtannin of preparation B1 a kind of.
The method of preparing cinnamtannin B1 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, to after vat liquor concentrated removal methyl alcohol or ethanol, use water dissolution, successively use respectively again sherwood oil, ethyl acetate extraction, ethyl acetate is concentrated to obtain to medicinal extract mutually, medicinal extract is through silica gel column chromatography, taking chloroform/methanol as eluent, from volume ratio 100/0～60/40 gradient elution, collecting chloroform/methanol volume ratio is the cut of 75/25 wash-out, this cut is again through reversed phase column chromatography, taking methanol/water as eluent, from volume ratio 5/95～45/55 gradient elution, collecting methanol/water volume ratio is the cut of 10/90 wash-out, this cut passes through Sephadex LH-20 column chromatography again, methyl alcohol is as eluting solvent, can obtain cinnamtannin B1.
Described Lychee leaf is preferably Lychee leaf powder, after further preferably fresh Lychee leaf being dried or dried, 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 will use water dissolution after vat liquor concentrated removal methyl alcohol or ethanol, preferably removes methyl alcohol or ethanol by concentrated at 40～80 DEG C vat liquor, then adds the water dissolution of 1～3 times of volume.
Described priority with sherwood oil, ethyl acetate extraction, is preferably first used petroleum ether extraction 3～12 times, then is extracted with ethyl acetate 3～12 times respectively.
The present invention also provides the application of Lychee leaf in preparation cinnamtannin B1.
The present invention prepares separation and has obtained cinnamtannin B1 from Lychee leaf, and its productive rate is 51～196mg/kg (purity is 85～95%).The present invention, for the deep processing and utilization that promotes lichee, promotes lichee added value of product, promotes the Sustainable development of the sector to have great importance.Simultaneously also for the preparation of cinnamtannin B1 provides a kind of new method.
Embodiment:
Following examples are to further illustrate of the present invention, instead of limitation of the present invention.
Embodiment 1:cinnamtannin B1 preparation separates and Structural Identification.
One, the preparation of cinnamtannin B1 separates
1) select materials: select fresh lichee leaf, clear water washing;
2) drying and crushing: Lychee leaf is dried or dried, adopt pulverizer to be ground into powder, cross 20 mesh sieves, obtain Lychee leaf powder;
3) lixiviate: Lychee leaf powder is added in the methanol aqueous solution of volume fraction 40% of 5 times of volumes (being 5mL/g Lychee leaf powder), 80 DEG C of lixiviates 4 hours, filter, collect filtered liquid;
4) organic solvent classification: remove methyl alcohol by concentrated at 40 DEG C above-mentioned filtered liquid, add the water of its 1 times of volume, successively extract respectively 3 times by isopyknic sherwood oil, ethyl acetate respectively; Select ethyl acetate phase extraction liquid concentrated that medicinal extract is used for subsequent purification.
5) get the medicinal extract (200g) of ethyl acetate phase extraction liquid, adopt silicagel column (100～200 order) chromatography, taking chloroform/methanol as eluting solvent, from volume ratio 100/0～60/40 gradient elution, collecting chloroform/methanol volume ratio is the component of 75/25 wash-out, again through C18 reversed phase column chromatography, taking methanol/water as eluent, from volume ratio 5/95～45/55 gradient elution, collecting methanol/water volume ratio is the cut of 10/90 wash-out, this cut is through Sephadex LH-20 column chromatography, methyl alcohol is as eluting solvent, finally collect component at 60 DEG C of evaporating, concentrating and dryings, can obtain compound 1 (cinnamtannin B1).
The cinnamtannin B1 productive rate that adopts the method to obtain is 51～95mg/kg, and purity is 85～95%.
Two, the Structural Identification of compound cinnamtannin B1
Compound 1 (cinnamtannin B1) is yellow powder, dissolves in methyl alcohol, and ESI-MS mass spectrum result shows that this compound molecular weight is 864.This compound 1h NMR (500MHz, CD 3oD) and 13c NMR (125MHz, CD 3oD) in table 1:
Table 1. compound 1 (Cinnamtannin B1) 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: cinnamtannin B1, this compound is soluble in methyl alcohol.
Embodiment 2:
1) select materials: select fresh lichee leaf, clear water washing;
2) drying and crushing: Lychee leaf is dried or dried, adopt pulverizer to be ground into powder, cross 120 mesh sieves, obtain Lychee leaf powder;
3) lixiviate: it is 90% methanol aqueous solution that Lychee leaf powder is added to the volume fraction of 20 times of volumes (20mL/g Lychee leaf powder), room temperature lixiviate 35 hours, filters, and collects filtered solution;
4) organic solvent classification: above-mentioned filtered solution is concentrated and removes methyl alcohol at 60 DEG C, add the water of its 3 times of volumes, successively extract respectively 12 times by isopyknic sherwood oil, ethyl acetate respectively; After selecting ethyl acetate phase extraction liquid concentrated, obtain medicinal extract for subsequent purification.
Subsequent purification step is identical with embodiment 1, obtains thus compound and is accredited as cinnamtannin B1.
The cinnamtannin B1 productive rate that adopts the method to obtain is 150～196mg/kg, and purity is 85～95%.
Embodiment 3:
1) select materials: select fresh lichee leaf, clear water washing;
2) drying and crushing: Lychee leaf is dried or dried, adopt pulverizer to be ground into powder, cross 60 mesh sieves, obtain Lychee leaf powder;
3) lixiviate: it is 40% aqueous ethanolic solution that Lychee leaf powder is added to the volume fraction of 10 times of volumes (10mL/g Lychee leaf powder), 50 DEG C of lixiviates 20 hours, filters, and collects filtered solution;
4) organic solvent classification: above-mentioned filtered solution is concentrated and removes ethanol at 60 DEG C, add the water of its 2 times of volumes, successively extract respectively 6 times by isopyknic sherwood oil, ethyl acetate respectively; After selecting ethyl acetate phase extraction liquid concentrated, obtain medicinal extract for subsequent purification.
Subsequent purification step is identical with embodiment 1, obtains compound and is accredited as cinnamtannin B1.
Adopting the productive rate of the cinnamtannin B1 of the method acquisition is 90～142mg/kg, and purity is 85～95%.
Embodiment 4:
1) select materials: select fresh lichee leaf, clear water washing;
2) drying and crushing: Lychee leaf is dried or dried, adopt pulverizer to be ground into powder, cross 60 mesh sieves, obtain Lychee leaf powder;
3) lixiviate: Lychee leaf powder is added to volume fraction 100% ethanolic soln of 10 times of volumes (10mL/g Lychee leaf powder), 25 DEG C of lixiviates 15 hours, filter, collect filtered solution;
4) organic solvent classification: above-mentioned filtered solution is concentrated and removes ethanol at 70 DEG C, add the water of 1 times of volume, successively extract respectively 6 times with isopyknic sherwood oil, ethyl acetate, propyl carbinol respectively; After selecting ethyl acetate phase extraction liquid concentrated, obtain medicinal extract for subsequent purification.
Subsequent purification step is identical with embodiment 1, obtains compound and is accredited as cinnamtannin B1.
Adopting the productive rate of the cinnamtannin B1 of the method acquisition is 82～129mg/kg, and purity is 85～95%.

Claims (6)

1. prepare the method for cinnamtannin B1 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, to after vat liquor concentrated removal methyl alcohol or ethanol, use water dissolution, successively use respectively again sherwood oil, ethyl acetate extraction, ethyl acetate is concentrated to obtain to medicinal extract mutually, medicinal extract is through silica gel column chromatography, taking chloroform/methanol as eluent, from volume ratio 100/0～60/40 gradient elution, collecting chloroform/methanol volume ratio is the cut of 75/25 wash-out, this cut is again through reversed phase column chromatography, taking methanol/water as eluent, from volume ratio 5/95～45/55 gradient elution, collecting methanol/water volume ratio is the cut of 10/90 wash-out, this cut passes through Sephadex LH-20 column chromatography again, methyl alcohol is as eluting solvent, can obtain cinnamtannin B1.
2. method according to claim 1, is characterized in that, described Lychee leaf is Lychee leaf powder, and it is after fresh Lychee leaf is dried or dried, and pulverizes the Lychee leaf powder of 20～120 mesh sieves.
3. method according to claim 1, it is characterized in that, 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, the temperature of lixiviate is 25～80 DEG C, and extraction time is 4～35 hours.
4. method according to claim 1, is characterized in that, described will use water dissolution after vat liquor concentrated removal methyl alcohol or ethanol, is to remove methyl alcohol or ethanol by concentrated at 40～80 DEG C vat liquor, then adds the water dissolution of 1～3 times of volume.
5. method according to claim 1, is characterized in that, described priority with sherwood oil, ethyl acetate extraction, is first to use petroleum ether extraction 3～12 times, then is extracted with ethyl acetate 3～12 times respectively.
6. the application of Lychee leaf in preparation cinnamtannin B1.
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Cited By (1)

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US10842774B2 (en) * 2017-09-13 2020-11-24 In Ingredients, Inc. Inhibited expression of PD-L1 and enhanced expression of PD-1

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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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LIANG LIU等: "Oxidation of (-)-epicatechin is a precursor of litchi pericarp enzymatic browning", 《FOOD CHEMISTRY》, vol. 118, no. 3, 31 December 2009 (2009-12-31), pages 508 - 511, XP026563862, DOI: doi:10.1016/j.foodchem.2009.05.019 *
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10842774B2 (en) * 2017-09-13 2020-11-24 In Ingredients, Inc. Inhibited expression of PD-L1 and enhanced expression of PD-1

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