CN101328114A - Method for extracting walnuts ketone from walnut green husk - Google Patents
Method for extracting walnuts ketone from walnut green husk Download PDFInfo
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- CN101328114A CN101328114A CNA2007100182353A CN200710018235A CN101328114A CN 101328114 A CN101328114 A CN 101328114A CN A2007100182353 A CNA2007100182353 A CN A2007100182353A CN 200710018235 A CN200710018235 A CN 200710018235A CN 101328114 A CN101328114 A CN 101328114A
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- ethyl acetate
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- nucin
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Abstract
The invention discloses a method for extracting walnut ketone from walnut green peel. The walnut green peel is taken as a raw material, is subjected to raw material collect and processing, solvent extraction, common silicagel column chromatography and separation, crystallization and recrystallization and so on, and the walnut ketone is obtained. Pharmacology experiments show that the walnut ketone has certain anticancer activity, and can be a medicine for preventing and treating tumour and cancer. The method adopts the walnut green peel to prepare the walnut ketone through extraction and separation, has simple process, reliability, high yield and low cost; moreover, the walnut peel has rich resources and can be utilized as waste.
Description
Technical field
The present invention relates to a kind of method of from green peel of walnut, extracting nucin.
Background technology
Juglandaceae Juglans (Juglans L.) plant, about 18 kinds of the whole world mainly is distributed in the north temperate zone.China has 5 kinds, and its branch, leaf, exocarp, root skin, nut kernel and kernel can be used as medicine.Walnut is very high to curative effect of disease such as urinary system calculus, chronic tracheitis, dermatitis, eczema and dysentery.The Tang Dynasty well-known doctor numerous in the Meng is set forth the effect that walnut has " qualcomm meridian, profit blood vessels, the fine and smooth smoothness of informal dress kindred "; The big physician's LI Shi-Zhen of the Ming Dynasty is to be summarised as " benefiting qi and nourishing blood, moistening the lung and resolving the phlegm, the beneficial gate of vitality, sharp three warmers, the warm lung ease constipation " of the pharmaceutical value of walnut kernel.The effect that immature fruit of walnut and Juglans mandshurica or exocarp (Exocarpium Juglandis Immaturum) have heat-clearing, detoxifcation, end dysentery, make eye bright; The root skin of Juglans mandshurica is treated cancer in Korea S as folk medicine; In India and Africa, the extract at each position of walnut used a lot of years as folk medicine.The chemical ingredients of Juglans plant mainly contains naphthoquinones, flavones, polyphenol, diaryl heptane, terpene and above all kinds of glycosides compound.That this platymiscium generally has is antibiotic, antitumor, analgesia and remove pharmacologically active such as free radical.
Studies show that both at home and abroad to separate from the Juglans plant so far to obtain more than 50 kind of compound, wherein naphthoquinones and glycoside thereof, diaryl heptane and glycosides compound thereof have stronger anticancer and anti-oxidant activity.At present, both at home and abroad from the meta-bolites (Chem.Pharm.Bull. of Penicillium notatum Penicillium diversum var.aureum, 34:4,1986,1497-1500), branch skin (the Phytochemistry of walnut Juglans regia L, 27:12,1988,3929-3932), rice blast mould (Pyricularia oryzae) (Khim.Prir.Soedin., 4,1991,471-475), rye grass brown streak bacterium Scolecotrichum graminis Fuckel (Biosci.Biotechnol.Biochem., 58:11,1994,1956-1959), Diplogelasinospora grovesiiCailleux (Chem.Pharm.Bull., 46:3,1998,423-429), Microsphaeropsis species (J.Nat.Prod., 62:1,1999,114-118), the mould Humicola grisea of grey humic (Tetrahedron, 58:45,2002,9163-9168), the root of Juglans mandshurica Juglans mandshurica Maximowicz, fruit and bark (Chem.Pharm.Bull., 51:3,2003,262-264; Chem.Pharm.Bull., 53:8,2005,934-937), root (Planta Med., 71:2,2005 of yellow Qi Engelhardia roxburghiana Wall, 171-175) etc. extraction separation obtains nucin (Regiolone) in meta-bolites of multiple microorganism or the plant materials, but the extraction separation nucin does not have bibliographical information at present in the green peel of walnut of walnut industry.
Summary of the invention
The object of the present invention is to provide a kind of method of from green peel of walnut, extracting nucin (Regio1one).
The present invention is raw material with the green peel of walnut, by feedstock capture processing, and solvent extraction, the ordinary silicon plastic column chromatography separates, and steps such as crystallization and reclosing crystalline substance obtain nucin.
A kind of method of extracting nucin from green peel of walnut is characterized in that this method comprises that feedstock capture processing, medicinal extract extract, three steps of separation and purification:
A, feedstock capture processing: gather green peel of walnut, drying is pulverized;
B, medicinal extract extraction step: adopt ethanol to raw material cold soaking or reflux heat carry total medicinal extract;
C, separation and purification:
Total medicinal extract water suspendible is used sherwood oil successively, ethyl acetate, and propyl carbinol carries out liquid liquid and distributes extraction to obtain F
A, F
B, F
CThree components; F
BWith the mixed solvent of forming of different volumes ratio, by polarity from small to large, gradient elution carries out common silica gel column chromatography and separates component with petrol ether/ethyl acetate or acetone, collects polarity scope petrol ether/ethyl acetate or acetone at 6: 1 to 2: 1 component F
B3.F
B3The mixed solvent of forming in 4: 1 by volume with petrol ether/ethyl acetate or acetone carries out the column chromatography separation again, be collected under the ultraviolet lamp 254nm displaing yellow fluorescence partly the nucin crude product, the mixed solvent recrystallization of forming in 2: 1 by volume with sherwood oil and ethyl acetate obtains nucin.
For purification procedures, we also can take following measure to realize:
Total medicinal extract is directly used silica gel mixed sample, mix the solvent of forming with petrol ether/ethyl acetate or acetone with the different volumes ratio, by polarity from small to large, gradient elution, carry out common silica gel column chromatography and separate, collect polarity scope petrol ether/ethyl acetate or acetone at 6: 1 to 2: 1 component F
B3F
B3The mixed solvent of forming in 4: 1 by volume with petrol ether/ethyl acetate or acetone carries out the column chromatography separation again, be collected under the ultraviolet lamp 254nm displaing yellow fluorescence partly the nucin crude product, the mixed solvent recrystallization of forming in 2: 1 by volume with sherwood oil and ethyl acetate obtains nucin.
Have application in antitumor and the cancer chemoprevention drugs with function by the invention provides the separating obtained nucin of preparation method (Regiolone) in preparation, it is characterized in that this compound has antitumour activity.
The invention has the advantages that:
1, utilize green peel of walnut to extract nucin for raw material, aboundresources can utilization of waste material.
2, first from green peel of walnut extraction separation to compound nucin (Regiolone) with antitumour activity;
3, by preparation method provided by the invention, extraction separation prepares that nucin technology is simple, and method is reliable, the productive rate height, and compound purity is good.
The present invention relates to compound nucin (Regiolone) and belong to-naphthoquinone compound, have C
10H
10O
3Molecular formula and the chemical structural formula shown in the formula I.Its chemical structure process
1HNMR,
13CNMR data and reference (Phytochemistry, 27:12,1988, the experiment to single crystal X diffraction when 3929-3932) is determined and is had a following physicochemical constant, spectroscopy data and crystal parameter: colourless crystallization (ethyl acetate), fusing point: 73-74 ℃, []
± 0 ° (c 1.3, CH
2Cl
2);
1H-NMR (400MHz, CDCl
3,
Ppm): 12.4 (1H, s, OH-8), 7.46 (1H, t, J=8.4,7.6Hz, H-6), 6.99 (1H, d, J=7.6Hz, H-5), 6.89 (1H, d, J=8.4Hz, H-7), 4.88 (1H, dd, J=7.2Hz, 4.0), 2.97 (1H, ddd, J=18.0,8.4,4.8Hz, H-2a), 2.62 (1H, ddd, J=18.0Hz, 8.4,4.8, H-2b), 2.31 (1H, m, H-3a), 2.16 (1H, m, H-3b);
13C NMR (100MHz,
Ppm): 204.4 (C-1), 162.4 (C-8), 145.8 (C-9), 136.9 (C-6), 117.5 (C-5), 117.4 (C-7), 115.1 (C-10), 67.5 (C-4), 34.5 (C-2), 31.1 (C-3).The crystal data of nucin: molecular formula: C
10H
10O
3, molecular weight: Mr=178.18, crystallographic system: Monoclinic, spacer: P2 (1)/c, unit cell parameters: a=12.4859 (3)
, b=16.6010 (5)
, c=8.7947 (2)
,=109.4270 (10) °, V=1719.16 (8)
, molecule number: Z=8 in the structure cell, crystalline density: D
x=1.377Mg m
-3, diffraction light sources: MoKa radiation, input angle :=0.71073
, point diffraction: Cell parameters from 1898reflections, scanning angle :=2.45-21.92 °, μ=0.102mm
-1, temperature: T=294K, crystal habit: column colourless crystallization, unit cell volume: 0.25 * 0.20 * 0.19mm.
Formula I
Description of drawings
Fig. 1 is a formula I compound nucin
1H NMR figure.
Fig. 2 is a formula I compound nucin
13C NMR figure.
Fig. 3 is the DEPT figure of formula I compound nucin.
Fig. 4 is the X-Ray crystalline structure of formula I compound nucin.
Fig. 5 is the structure cell accumulation graph of formula I compound nucin.
Embodiment
For a more clear understanding of the present invention, the present invention is further illustrated below in conjunction with embodiment, but the invention is not restricted to following examples.
Embodiment 1: the extraction separation of nucin in the green peel of walnut
A, feedstock capture procedure of processing: it is an amount of to gather green peel of walnut, dries in the shade, and suitably pulverizes.
B, medicinal extract extraction step: get green peel of walnut 5Kg, add 8 times of amount 95% ethanol, cold soaking (7d * 3) filters, and decompression and solvent recovery gets total medicinal extract 200g.
C, separating step: 200g medicinal extract is suspended in the 1000mL water,, reclaims solvent and get medicinal extract F with 300mL sherwood oil (60-90 ℃) extraction 3 times
A20g, residuum 300mL ethyl acetate extraction 3 times are reclaimed solvent and are got medicinal extract F
B30g, residuum gets medicinal extract F 3 times with the 300mL n-butanol extraction
C40g.With ethyl acetate part medicinal extract F
BMix sample with 35g silica gel (100-200 order), 600g silica gel (200-300 order) is gone up the simple glass chromatography column, sherwood oil (60-90 ℃)/ethyl acetate (10: 1-2: 1) carry out gradient elution, 500mL is first-class part, reclaim solvent, differentiate down at ultraviolet lamp (UV) with thin-layer chromatography, merge same composition, get F
B1(3.5g, 10: 1), F
B2(4g, 8: 1), F
B3(10g, 6: 1-2: 1) three components.Component F
B3Mix sample with 12g silica gel (100-200 order), 120g silica gel (200-300 order) is gone up the simple glass chromatography column, sherwood oil (60-90 ℃)/ethyl acetate (4: 1) wash-out, differentiate down at ultraviolet lamp (UV) with thin-layer chromatography, merge same composition and get nucin 200mg crude product, get nucin with the mixed solvent recrystallization of sherwood oil (60-90 ℃)/ethyl acetate (4: 1).
Embodiment 2: the extraction separation of nucin in the green peel of walnut
A, feedstock capture procedure of processing: it is an amount of to gather green peel of walnut, dries in the shade, and suitably pulverizes.
B, medicinal extract extraction step: get green peel of walnut 5Kg, add 10 times of amount 95% ethanol, reflux heat is carried (2h * 3), filters, and decompression and solvent recovery gets total medicinal extract 250g.
C, separating step: 250g medicinal extract is suspended in the 1000mL water,, reclaims solvent and get medicinal extract F with 300mL sherwood oil (60-90 ℃) extraction 3 times
A25g, residuum 300mL ethyl acetate extraction 3 times are reclaimed solvent and are got medicinal extract F
B35g, residuum gets medicinal extract F 3 times with the 300mL n-butanol extraction
C50g.With ethyl acetate part medicinal extract F
BMix sample with 35g silica gel (100-200 order), 600g silica gel (200-300 order) is gone up simple glass chromatography column, sherwood oil (60-90 ℃)/acetone (10: 1-2: 1) carry out gradient elution, 500mL is first-class part, reclaims solvent, differentiates down at ultraviolet lamp (UV) with thin-layer chromatography, merge same composition, get F
B1(3.5g, 10: 1), F
B2(4g, 8: 1), F
B3(10g, 6: 1-2: 1) three components.Component F
B3Mix sample with 12g silica gel (100-200 order), 120g silica gel (200-300 order) is gone up the simple glass chromatography column, sherwood oil (60-90 ℃)/acetone (4: 1) wash-out, differentiate down at ultraviolet lamp (UV) with thin-layer chromatography, merge same composition and get nucin 200mg crude product, get nucin with the mixed solvent recrystallization of sherwood oil (60-90 ℃)/acetone (4: 1).
Embodiment 3: the extraction separation of nucin in the green peel of walnut
A, feedstock capture procedure of processing: it is an amount of to gather the walnut branches and leaves, dries in the shade, and suitably pulverizes.
B, medicinal extract extraction step: get Walnut Leaves 5Kg, add 8 times of water gagings, refluxing extraction (2h * 2) is filtered decompression and solvent recovery 100g.
C, separating step: with 100g medicinal extract simple glass chromatography column on the 150g silica gel mixed sample, (10: 1-2: 1) carry out gradient elution, 500mL is first-class part to sherwood oil (60-90 ℃)/acetone, reclaim solvent, in ultraviolet lamp (UV) appreciation down, merge same composition with thin-layer chromatography, get F
A(10g, 10: 1), F
B1(10g, 9: 1), F
B2(14g, 8: 1), F
B3(18g, 6: 1-2: 1), F
C(20g, 1: 1) four components.Component F
B3Mix sample with 20g silica gel (100-200 order), 200g silica gel (200-300 order) is gone up the simple glass chromatography column, sherwood oil (60-90 ℃)/ethyl acetate (4: 1) wash-out, differentiate down at ultraviolet lamp (UV) with thin-layer chromatography, merge same composition and get nucin 200mg crude product, get nucin with the mixed solvent recrystallization of sherwood oil (60-90 ℃)/ethyl acetate (4: 1).
Embodiment 4: nucin is to liver cancer cell HepG
2The cell in vitro toxic action
A, preparation human hepatoma cell strain HepG
2Suspension: 0.25% tryptic digestion is made into 8 * 10 with nutrient solution
4Individual cell/mL cell suspension; Inoculating cell: every hole 100L is inoculated in 96 orifice plates;
B, the pre-cultivation: 37 ℃, 5%CO
2And cultivate 24h under the saturated humidity;
C, with medicine nucin and positive control cis-platinum: by 0.2,0.4,0.6,1.2,1.6, the dosing of 2.0mol/mL concentration, every hole 100L, each concentration is established three multiple holes.37 ℃, 5%CO
2And 24h is cultivated in continuation under the saturated humidity;
Behind D, the 24h, take out culture plate, every hole adds trichoroacetic acid(TCA) (TCA) the 50L fixed cell of 50% (mass/volume), and the final concentration of TCA is 10%, is added on the liquid level of every hole, places 1h in 4 ℃ of refrigerators; Deionized water wash 5 times of each hole of culture plate, remove TCA, behind air drying, every hole adds 0.4% SRB100L, place 10～30min under the room temperature, discard in each hole and wash 5 times with 1% acetate behind the liquid, remove unconjugated dyestuff, be 10.5 with pH behind the air drying, the dissolving of 10mmol/L tri methylol amino methane, 5min vibrates on oscillator plate, under enzyme-linked immunosorbent assay instrument 490nm wavelength, measure the OD value, with the blank zeroing, obtaining growth of tumour cell inhibiting rate is defined as the extracorporeal inhibiting rate of medicine to tumour cell, measure IC with the medicine nucin
50For: 1.16mol/mL (cis-platinum: 0.67mol/mL).
Claims (2)
1, a kind of method of extracting nucin from green peel of walnut is characterized in that this method comprises that feedstock capture processing, medicinal extract extract, three steps of separation and purification:
A, feedstock capture processing: gather green peel of walnut, drying is pulverized;
B, medicinal extract extraction step: adopt ethanol to raw material cold soaking or reflux heat carry total medicinal extract;
C, separation and purification:
Total medicinal extract water suspendible is used sherwood oil successively, ethyl acetate, and propyl carbinol carries out liquid liquid and distributes extraction to obtain F
A, F
B, F
CThree components; F
BWith the mixed solvent of forming of different volumes ratio, by polarity from small to large, gradient elution carries out common silica gel column chromatography and separates component with petrol ether/ethyl acetate or acetone, collects polarity scope petrol ether/ethyl acetate or acetone at 6: 1 to 2: 1 component F
B3.F
B3The mixed solvent of forming in 4: 1 by volume with petrol ether/ethyl acetate or acetone carries out the column chromatography separation again, be collected under the ultraviolet lamp 254nm displaing yellow fluorescence partly the nucin crude product, the mixed solvent recrystallization of forming in 2: 1 by volume with sherwood oil and ethyl acetate obtains nucin.
2, method according to claim 1 is characterized in that purification procedures is:
Total medicinal extract is directly used silica gel mixed sample, mix the solvent of forming with petrol ether/ethyl acetate or acetone with the different volumes ratio, by polarity from small to large, gradient elution, carry out common silica gel column chromatography and separate, collect polarity scope petrol ether/ethyl acetate or acetone at 6: 1 to 2: 1 component F
B3F
B3The mixed solvent of forming in 4: 1 by volume with petrol ether/ethyl acetate or acetone carries out the column chromatography separation again, be collected under the ultraviolet lamp 254nm displaing yellow fluorescence partly the nucin crude product, the mixed solvent recrystallization of forming in 2: 1 by volume with sherwood oil and ethyl acetate obtains nucin.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102219664A (en) * | 2011-04-26 | 2011-10-19 | 安徽农业大学 | Method for extracting walnut ketones from epicarps of carya cathayensis Sarg and preparing walnut ketone standard product |
| CN102784195A (en) * | 2011-05-20 | 2012-11-21 | 中国科学院兰州化学物理研究所 | Method for extracting anti-tumor active component from traditional Chinese medicine pericarpium juglantis |
| CN105037122A (en) * | 2015-06-30 | 2015-11-11 | 兰州大学 | Compound obtained from extraction and separation from pericarpium juglans and application of compound |
| CN105037121A (en) * | 2015-06-30 | 2015-11-11 | 兰州大学 | Method for extracting and separating NEO-Z (4,8-dimethylenenaphthalene-1,5(4H,8H)-dione) from pericarpium juglans |
| CN105136916A (en) * | 2015-07-22 | 2015-12-09 | 黑龙江省中医药科学院 | Method of promoting hydrolysis of juglan regia ketone glucoside in immature juglans mandshurica skin into juglan regia ketone, and content measurement method of juglone and juglan regia ketone |
| CN113499361A (en) * | 2021-07-28 | 2021-10-15 | 西北农林科技大学 | Method for extracting terpenoid substances in walnut green seedcase |
| CN114752585A (en) * | 2022-05-20 | 2022-07-15 | 山西大学 | Walnut green husk anti-tumor active protein and preparation method and application thereof |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102219664A (en) * | 2011-04-26 | 2011-10-19 | 安徽农业大学 | Method for extracting walnut ketones from epicarps of carya cathayensis Sarg and preparing walnut ketone standard product |
| CN102219664B (en) * | 2011-04-26 | 2013-11-20 | 安徽农业大学 | Method for extracting walnut ketones from epicarps of carya cathayensis Sarg and preparing walnut ketone standard product |
| CN102784195A (en) * | 2011-05-20 | 2012-11-21 | 中国科学院兰州化学物理研究所 | Method for extracting anti-tumor active component from traditional Chinese medicine pericarpium juglantis |
| CN105037122A (en) * | 2015-06-30 | 2015-11-11 | 兰州大学 | Compound obtained from extraction and separation from pericarpium juglans and application of compound |
| CN105037121A (en) * | 2015-06-30 | 2015-11-11 | 兰州大学 | Method for extracting and separating NEO-Z (4,8-dimethylenenaphthalene-1,5(4H,8H)-dione) from pericarpium juglans |
| CN105136916A (en) * | 2015-07-22 | 2015-12-09 | 黑龙江省中医药科学院 | Method of promoting hydrolysis of juglan regia ketone glucoside in immature juglans mandshurica skin into juglan regia ketone, and content measurement method of juglone and juglan regia ketone |
| CN113499361A (en) * | 2021-07-28 | 2021-10-15 | 西北农林科技大学 | Method for extracting terpenoid substances in walnut green seedcase |
| CN114752585A (en) * | 2022-05-20 | 2022-07-15 | 山西大学 | Walnut green husk anti-tumor active protein and preparation method and application thereof |
| CN114752585B (en) * | 2022-05-20 | 2023-07-18 | 山西大学 | Walnut green seedcase antitumor active protein and preparation method and application thereof |
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Effective date of registration: 20190617 Address after: 748100 South of Chang'an Road, Wenfeng Town, Longxi County, Dingxi City, Gansu Province (No. 2 Yaochang Road, Traditional Chinese Medicine Industrial Park) Patentee after: Gansu Sandi Plant Chemistry Co., Ltd. Address before: 730000 Tianshui Middle Road, Chengguan District, Lanzhou City, Gansu Province, No. 18 Patentee before: Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences |
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