CN102532211B - Lignan triglycoside compound and preparation method and application thereof - Google Patents
Lignan triglycoside compound and preparation method and application thereof Download PDFInfo
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- CN102532211B CN102532211B CN201110433164.XA CN201110433164A CN102532211B CN 102532211 B CN102532211 B CN 102532211B CN 201110433164 A CN201110433164 A CN 201110433164A CN 102532211 B CN102532211 B CN 102532211B
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Abstract
The invention discloses a lignan triglycoside compound and a preparation method and application thereof. The molecular formula of the lignan triglycoside compound is C38H56O22. The preparation method comprises the following steps of: placing crushed Castanea henryi (Skan) Rehd.et Wils husks into an organic solvent for extraction, separating to prepare the extract solution, extracting the extract solution, and preparing the extract via concentration of the extract solution; and carrying out chromatographic separation and purification of the extract to prepare the lignan triglycoside compound. The organic solvent is one or mixture of methanol, ethanol, butanol and acetone. The lignan triglycoside compound with the novel structure is prepared via extraction and separation of the Castanea henryi (Skan) Rehd.et Wils husk, has good antioxidant activity, can be applied in preparation of antioxidants, antioxidant drugs, antioxidant cosmetics or antioxidant health food, and has good development prospect.
Description
Technical field
The present invention relates to active components of plants field, relate in particular to a kind of lignanoid three glycoside compounds and its preparation method and application.
Background technology
Chinquapin (Castanea henryi (Skan) Rehd.et Wils) is Fagaceae Castanea, is the famous woody grain of south China and fruit material dual-purpose seeds, and fruit is fragrant and sweet good to eat, and local flavor is obviously better than Chinese chestnut.Chinquapin is the most concentrated in the resource distribution of Zhe Nan Mountain Area in North, and have big area artificial forest ((a) river by. river is all. Gao Xia. chinquapin new cultivation technology. Foochow: Fujian science tech publishing house, 1998.1-19. (b) Zheng Chengle. river is by. the north of Fujian Province chinquapin resource and utilize prospect. the journal .1998 of Fujian Agricultural Univeristy, 27 (3): 291-295. (c) Gong Bangchu. Chen Zenghua. the research of chinquapin farm variety resource exploration. forestry scientific research, 1997, 10 (6): 574-580. (d) Yang Zhiling, Gong Bangchu, Chen Zenghua. the quantification analysis of Economic Characters of Nut in Castanea henryi. forestry scientific research, 2001, 14 (1): 90-94.).
At present, less about the chemical constitution study of chinquapin, particularly discarded Exocarpium Castanopsis chinensis, the current utilization that is almost only limited to fertilizer.For this reason, the active skull cap components in research Exocarpium Castanopsis chinensis, can provide new approaches for the recycling of Exocarpium Castanopsis chinensis.
Summary of the invention
The invention provides a kind of lignanoid three glycoside compounds, in the shell that this compound is chinquapin, extract the natural active matter obtaining, there is anti-oxidant activity.
A kind of lignanoid three glycoside compounds, its structural formula is suc as formula shown in (I):
The preparation method who the invention provides described lignanoid's three glycoside compounds, comprises the following steps:
(1) chinquapin (Castanea henryi (Skan) Rehd.et Wils) shell after pulverizing is placed in to organic solvent lixiviate, separates and obtain vat liquor, then vat liquor is extracted, extraction liquid obtains extract after concentrated;
Wherein, described organic solvent is one or more mixtures in methyl alcohol, ethanol, propyl carbinol and acetone;
(2) extract is carried out to chromatographic separation, purification process, make described lignanoid's three glycoside compounds.
In step (1), described Exocarpium Castanopsis chinensis is pulverized to be placed in organic solvent and carry out lixiviate, be more conducive to the leaching of lignanoid's three glycoside compounds.
Described Exocarpium Castanopsis chinensis and the weight ratio of organic solvent are preferably 1: 1-1: 8.
Described lixiviate can be that cold soaking or thermal backflow are extracted.
The reagent of described extraction use can be propyl carbinol.
In step (2), preferably, described chromatographic separation is purification on normal-phase silica gel column chromatography for separation, and eluent is chloroform/methanol mixed solution; More preferably, in described purification on normal-phase silica gel column chromatography for separation: after loading, using chloroform/methanol mixed solution as eluent, within 9: 1 by volume, 5: 1,1: 1,1: 3,1: 9, carry out gradient elution, collect the cut that eluent volume ratio elutes at 5: 1 o'clock.
Described purification process can be: recrystallization, reversed-phase silica gel column chromatography separate or high performance liquid chromatography separates.By purifying, can obtain lignanoid's three glycoside compounds that purity is higher.
Preferably, the eluent that described reversed-phase silica gel column chromatography separates is methanol/water mixed solution; More preferably, during described reversed-phase silica gel column chromatography separates: after loading, using methanol/water mixed solution as eluent, within 9: 1 by volume, 5: 1,1: 1,1: 3,1: 9, carry out gradient elution.
Lignanoid's three glycoside compounds described in the present invention also provides are in the application of preparing in antioxidant.Lignanoid of the present invention three glycoside compounds can directly use as antioxidant; Or, take lignanoid of the present invention three glycoside compounds as one of main active ingredient or activeconstituents, add and make antioxidant after acceptable auxiliary material and use.
Lignanoid's three glycoside compounds described in the present invention also provides are in the application of preparing in anti-oxidation medicine.This medicine, take lignanoid of the present invention three glycoside compounds as main active ingredient, adds acceptable auxiliary material in pharmaceutics and makes, and can make preparation according to the formulation preparation method of recording in pharmaceutics.Described preparation can be injection liquid, drip liquid, powder injection, granule, tablet, electuary, powder, oral liquid, sugar coated tablet, film coated tablet, enteric coated tablet, suck agent, granule, pill, paste, sublimed preparation, sprays, pill, disintegrating agent, orally disintegrating tablet, micropill etc.
Lignanoid's three glycoside compounds described in the present invention also provides are in the application of preparing in antioxidation cosmetic product.These makeup, take lignanoid of the present invention three glycoside compounds as main active ingredient, add acceptable makeup auxiliary material and make.
Lignanoid's three glycoside compounds described in the present invention also provides are in the application of preparing in antioxidant functional food.This protective foods, take lignanoid of the present invention three glycoside compounds as main active ingredient, adds acceptable protective foods auxiliary material and makes.
The present invention extracts from Exocarpium Castanopsis chinensis, separate and obtained a kind of lignanoid's three glycoside compounds with novel structure, and the method is easy and simple to handle, extract that yield is high, product purity is high, is applicable to large-scale production.
Test by antioxidation in vitro, show that lignanoid provided by the invention three glycoside compounds have good antioxygenation, its IC
50value is 11 μ M, can be used for preparing antioxidant, anti-oxidation medicine, antioxidation cosmetic product or antioxidant functional food, has good DEVELOPMENT PROSPECT.
Accompanying drawing explanation
Fig. 1 is compound in embodiment 6
1h
1h COSY, the HMBC collection of illustrative plates of being correlated with.
Embodiment
The preparation of embodiment 1 lignanoid's three glycoside compounds
Get 5kg chinquapin (Castanea henryi (Skan) Rehd.et Wils) shell, pulverize, soak 2 weeks with methyl alcohol, soak solution is use 1L distilled water suspendible after concentrated, aqueous suspension 1L n-butanol extraction, butanol extraction liquid is through the concentrated medicinal extract that obtains; Mix sample with silica gel (100 orders, 100g), carry out purification on normal-phase silica gel column chromatography for separation (200-300 order, 1kg; Silicagel column size L 500mm,
), carry out gradient elution with the volume ratio chloroform/methanol of 9: 1,5: 1,1: 1,1: 3,1: 9 successively, each 5L; TLC detects cut, collects the wash-out ratio cut of 5: 1 and merges, then use recrystallizing methanol.
The preparation of embodiment 2 lignanoid's three glycoside compounds
Get 5kg Exocarpium Castanopsis chinensis, pulverize, use 5L alcohol reflux, extracting solution is concentrated, aqueous suspension 1L chloroform extraction, and chloroform layer discards, water layer 1L n-butanol extraction; Propyl carbinol partial concentration, mixes sample with silica gel (100 orders, 100g), carries out purification on normal-phase silica gel column chromatography for separation (200-300 order, 1kg; Silicagel column size L 500mm,
), carry out gradient elution with the volume ratio chloroform/methanol of 9: 1,5: 1,1: 1,1: 3,1: 9 successively, each 5L; TLC detects cut, collects the wash-out ratio cut of 5: 1 and merges, then use recrystallizing methanol.
The preparation of embodiment 3 lignanoid's three glycoside compounds
Get 5kg Exocarpium Castanopsis chinensis, pulverize, with the extraction of 5L methanol/ethanol mixed solution, extract is concentrated, mixes sample with 100g diatomite, and 5L propyl carbinol heat is extracted; Carry out purification on normal-phase silica gel column chromatography for separation (200-300 order, 1kg; Silicagel column size L 500mm,
), carry out gradient elution with the volume ratio chloroform/methanol mixed solution of 9: 1,5: 1,1: 1,1: 3,1: 9 successively, each 5L; TLC detects cut, collects the wash-out ratio cut of 5: 1 and merges, then use acetone/normal hexane (volume ratio 1: 1) recrystallization.
The preparation of embodiment 4 lignanoid's three glycoside compounds
Get 5kg Exocarpium Castanopsis chinensis, pulverize, with the extraction of 5L methanol/ethanol mixed solution, extract is concentrated, mixes sample with 100g diatomite, and 5L propyl carbinol heat is extracted; Carry out purification on normal-phase silica gel column chromatography for separation (200-300 order, 1kg; Silicagel column size L 500mm,
), carry out gradient elution with the volume ratio chloroform/methanol mixed solution of 9: 1,5: 1,1: 1,1: 3,1: 9 successively, each 5L; TLC detects cut, collects the wash-out ratio cut of 5: 1 and merges; Reversed-phase silica gel column chromatography for cut/high performance liquid chromatography separates, and eluent is methanol/water (9: 1-1: 9), the detection wavelength of high performance liquid chromatography is 254nm; Use recrystallizing methanol.
The preparation of embodiment 5 lignanoid's three glycoside compounds
Get 5kg Exocarpium Castanopsis chinensis, pulverize, with the extraction of 5L methanol/ethanol/acetone mixed solution, extract is concentrated into without alcohol taste, uses 5L n-butanol extraction, and extraction liquid is concentrated, upper macroporous resin after water suspendible (size L 500mm,
) except sugar; Ethanol is washed lower rear concentrated, and 100g silica gel mixed sample, carries out purification on normal-phase silica gel column chromatography for separation (200-300 order, 1kg; Silicagel column size L 500mm,
), carry out gradient elution with the volume ratio chloroform/methanol mixed solution of 9: 1,5: 1,1: 1,1: 3,1: 9 successively, each 5L; TLC detects cut, collects the wash-out ratio cut of 5: 1 and merges; Reversed-phase silica gel column chromatography for cut/high performance liquid chromatography separates, and eluent is methanol/water (9: 1-1: 9), the detection wavelength of high performance liquid chromatography is 254nm; Use recrystallizing methanol.
The Structural Identification of embodiment 6 lignanoid's three glycoside compounds
Adopt HPLC to carry out Purity to the compound making, purity is greater than 98% sample and uses mass spectrum and nuclear magnetic resonance technique to carry out Structural Identification, and nucleus magnetic resonance is measured with Bruker AVANCE DRX-500NMR Sectrometer, mark in TMS does; High resolution mass spectrum FTICRMS measures with Bruker Apex Spectrometer; Bruker Esquire 3000 for electrospray ionization mass spectrum ESI-MS
plusspectrometer measures.
According to the one-dimensional NMR analytical results (in table 1) of compound and two-dimentional NMR analytical results (seeing Fig. 1), known, this material is lignanoid's three glycoside compounds, and molecular formula is C
38h
56o
22, structure is as follows:
The NMR data of table 1 lignanoid three glycoside compounds
aRecorded?on?125MHz.
bMultiplicities?inferred?from?DEPT?and?HMQC?experiments.
cRecorded?on?500MHz.
Embodiment 7 lignanoid's three glycoside compounds anti-oxidant activities are analyzed
Get a certain amount of sample, be dissolved in dehydrated alcohol, be made into concentration 5mM solution; Successively dilute with dehydrated alcohol, dilute five times at every turn; Get 96 hollow plates, every hole adds ethanolic soln (150 μ M) the 180 μ l of DPPH; Then add successively the sample solution of 5 concentration, each concentration 4 holes, every hole adds 20 μ l; Rock a little 96 orifice plates, allow it mix; Be placed in thermostat container, 37 ℃ of standing 30min; Measure the OD value in every hole respectively at 517nm and 800nm by microplate reader; Sample concentration when obtaining DPPH clearance rate and be 50% by Bliss method, half is removed experiment.
Remove experimental result by DPPH and know, the IC of this compound
50=11 μ M, show that this compound has good antioxygenation.
Embodiment 8 is containing the preparation of lignanoid's three glycoside compounds dropping pill formulations
Get 0.5g lignanoid three glycoside compounds and mix with 10.5g PEG-4000, heating and melting, moves to after material in dripping pill drip irrigation, and liquid drops in 6～8 ℃ of whiterusss, and oil removing makes 300 of dripping pills.
Embodiment 9 is containing the preparation of lignanoid's three glycoside compounds lyophilized injectable powders
Get the three glycoside compounds 0.5g of lignanoid, glucose 4.5g, Sulfothiorine 0.9g and distilled water 1000ml, after said components mixes, lyophilize, 400 of packing, to obtain final product.
Claims (7)
1. lignanoid's three glycoside compounds, its structural formula is suc as formula shown in (I):
2. the preparation method of lignanoid as claimed in claim 1 three glycoside compounds, is characterized in that, comprises the following steps:
(1) chinquapin (Castanea henryi (Skan) Rehd.et Wils) shell after pulverizing is placed in to organic solvent lixiviate, separates and obtain vat liquor, then vat liquor is extracted, extraction liquid obtains extract after concentrated;
Wherein, described organic solvent is one or more mixtures in methyl alcohol, ethanol, propyl carbinol and acetone;
(2) extract is carried out to chromatographic separation, purification process, make lignanoid claimed in claim 1 three glycoside compounds.
3. preparation method according to claim 2, is characterized in that, in step (1), described Exocarpium Castanopsis chinensis and the weight ratio of organic solvent are 1: 1-1: 8.
4. preparation method according to claim 2, is characterized in that, in step (2), described chromatographic separation is purification on normal-phase silica gel column chromatography for separation, and eluent is chloroform/methanol mixed solution.
5. preparation method according to claim 2, is characterized in that, in step (2), described purification process is: recrystallization, reversed-phase silica gel column chromatography separate or high performance liquid chromatography separates.
6. preparation method according to claim 5, is characterized in that, the eluent that described reversed-phase silica gel column chromatography separates is methanol/water mixed solution.
7. lignanoid as claimed in claim 1 three glycoside compounds are in the application of preparing in antioxidant, anti-oxidation medicine, antioxidation cosmetic product or antioxidant functional food.
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| YOUNG-WON CHIN et al..Lignans and Other Constituents of the Fruits of Euterpe oleracea (Aç |
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