CN110698521A - Cis-ferulic acid glucoside in walnut green seedcase and preparation method thereof - Google Patents

Cis-ferulic acid glucoside in walnut green seedcase and preparation method thereof Download PDF

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CN110698521A
CN110698521A CN201911014885.XA CN201911014885A CN110698521A CN 110698521 A CN110698521 A CN 110698521A CN 201911014885 A CN201911014885 A CN 201911014885A CN 110698521 A CN110698521 A CN 110698521A
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beta
cis
feruloyl
glucopyranoside
walnut
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司传领
刘华玉
韩笑
刘坤
刘慰
徐蕊
段亚欣
王慧
杨佳鑫
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Tianjin University of Science and Technology
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    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • C07H1/08—Separation; Purification from natural products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
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    • C07—ORGANIC CHEMISTRY
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Abstract

The invention belongs to the field of comprehensive utilization of high value-added chemical components in residue resources of agricultural and forestry product processing, and particularly relates to cis-ferulic acid glucoside (namely 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside (corresponding English name is 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside) which is never reported in the prior literature and a preparation method thereof. The walnut green seedcase is prepared by taking walnut green husks of trees of juglans of juglandaceae as raw materials and performing extraction, separation and other means. The preparation method provided by the invention has the characteristics of high efficiency of preparation process, simple and convenient operation, mild process conditions, high product purity, high yield and the like.

Description

Cis-ferulic acid glucoside in walnut green seedcase and preparation method thereof
Technical Field
The invention belongs to the field of comprehensive utilization of high value-added chemical components in residue resources in agriculture and forestry product processing, and particularly relates to cis-ferulic acid glucoside (2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside) which is never reported in the prior literature and a preparation method thereof. The walnut green seedcase is prepared by taking walnut green husks of trees of juglans of juglandaceae as raw materials and performing extraction, separation and other means.
Background
The walnut green husk is the residue of immature green peel left after processing walnuts, and is a valuable reusable resource (Xiaowangcheng, et al, Chinese livestock veterinarian, 2019, 46 (08): 2431-2437; Liudi, et al, grain and oil, 2019, 32 (01): 89-92). China is a big walnut producing country, a large amount of walnut green husks can be harvested every year, but the walnut green husks are not fully developed and utilized. At present, the method for treating the waste walnut green husks in China is mainly incineration, a large amount of smoke is generated by the method, and the combustion is not thorough. The method not only wastes walnut green husk resources, but also seriously damages the ecological environment (Wangyiyuan, et al, seed science and technology, 2019, 37 (03): 117-119).
At present, the walnut green seedcase has more and more attention on the anti-inflammatory and antibacterial activity at home and abroad, and a great deal of research shows that the walnut green case has better antibacterial effect (Cao Wen Li, etc., brewed in China, 2019, 38 (01): 149-153). For example, the polyphenol compound with higher content in the walnut green husk has stronger functions of analgesia, anti-inflammation, bacteriostasis and the like (Zhao Li Hua, etc., food industry, 2019, 40 (06): 148-152). The extract of exocarpium Juglandis Immaturus contains various active substances, such as macromolecular compounds such as polysaccharide, has effects of clearing heat and detoxicating, improving eyesight and resisting tumor, and can effectively treat diarrhea, skin pruritus and pain (Korean Xiaoyun, et al, green technology, 2019 (14): 218-220). The study on the walnut green husk polysaccharide finds that the polysaccharide has stronger antioxidant activity. The research can provide a certain theoretical basis for further research, development and utilization of walnut green husk wastes (Xidongxue, et al, food science, 2019, 40 (18): 281-286). As a precious recyclable resource, the walnut green seedcase is not comprehensively researched at home and abroad, and has great potential for developing and utilizing the resource. Therefore, the chemical components, the pharmacological activity and the like of the walnut green seedcase are further and deeply researched, so that the walnut green seedcase is widely applied to various research fields, and a new direction can be pointed for the development of the walnut green seedcase. Meanwhile, the development and application of the walnut green seedcase can also promote the application of the walnut green seedcase in the actual industry, so that the income level of farmers can be improved, the cyclic recycling of the walnut green seedcase can be realized, the resources are utilized to the maximum extent, and the ecological environment is protected.
The invention prepares a cis-ferulic acid glucoside, namely 2-O-cis feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside, which is not reported in the literature from a walnut green husk raw material by extraction and extraction technologies and a column chromatographic separation means.
Disclosure of Invention
One of the objects of the present invention is to provide a cis-ferulic acid glycoside, i.e. 2-O-cis-feruloyl-3-O- β -D-glucopyranosyl- β -D-glucopyranoside (the compound corresponds to the english name 2-O-cis-feruloyl-3-O- β -D-glucopyranosyl- β -D-glucopyranoside), which has not been reported in the literature.
Another object of the present invention is to provide a method for preparing 2-O-cis-feruloyl-3-O- β -D-glucopyranosyl- β -D-glucopyranoside from a plant material of green husk of Juglans regia of Juglans of Juglandaceae.
The technical scheme of the invention is summarized as follows:
a compound of the formula:
Figure BSA0000193006880000021
the method for preparing 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside from walnut green husk comprises the following characteristic steps:
step 1: taking walnut green husks which are cleaned and dried in the shade, crushing and sieving the walnut green husks by a 40-mesh sieve, adding a methanol water solution with the volume percentage concentration of 60-80% according to the mass ratio of 1: 1-1: 5, extracting at normal temperature or by heating or ultrasonic-assisted extraction for 1-5 times, each time for 0.5-96 hours, filtering, and concentrating the filtrate under reduced pressure to 3-10% of the original volume to obtain a crude extract;
step 2: adding water with the mass of 1-5 times of that of the crude extract, stirring, adding petroleum ether with the mass of 2-6 times of that of the crude extract, extracting for 1-6 times, separating out a petroleum ether layer, adding ethyl acetate with the mass of 2-6 times of that of the crude extract into the residual water layer, extracting for 1-6 times, separating out an ethyl acetate layer, and concentrating the ethyl acetate layer under reduced pressure to obtain an ethyl acetate extract phase;
and step 3: performing ODS vacuum column chromatography and/or macroporous resin D101 on the ethyl acetate extract phase, and performing Sephadex LH-20 column chromatography to obtain 2-O-cis-feruloyl-3-O-beta-D-glucopyranose-beta-D-glucopyranoside crude fraction;
and 4, step 4: and refining the crude component of the 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside by HPLC to obtain the 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside.
The raw material of the walnut green husk used in the above process can be walnut green husk of any walnut tree in Juglandaceae Juglans.
The compound prepared in the invention is white powder, and the melting point of the compound is 163-165 ℃ and the optical rotation is measured
Figure BSA0000193006880000022
Figure BSA0000193006880000023
FAB-MS in positive mode showed its M/z [ M + H ]]+519, M/z [ M + Na ]]+Is 541, M/z [ M + K]+557, revealing a molecular weight of 518. The results of the experiments combined speculate that the compound prepared in the invention has the molecular formula C22H30O14The chemical name of the compound is 2-O-cis feruloyl-3-O-beta-D-glucopyranose-beta-D-glucopyranoside, and the English name of the compound is 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside.
The preparation method provided by the invention has the characteristics of high product purity, high efficiency of preparation process, high product yield, easily available raw materials, simple and convenient operation, mild process conditions and the like.
TABLE 1 preparation of 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside1H (400MHz) and13c Nuclear magnetic (100MHz) data (MeOH-d)4)
Figure BSA0000193006880000031
Detailed Description
The invention will be more fully and more readily understood by reference to the following examples, which are given to illustrate the invention more clearly, and are not intended to limit the invention in any way.
Example 1: preparation of 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside from green peel of walnuts of Yangbi walnut
Step 1: taking walnut green peel of a cleaned and dried Yangbi walnut tree (Juglans sigillata, namely three-walnut-soaked in the shade, tea-soaked walnut, deep-grained soaked walnut, walnut kernel and the like), crushing, sieving with a 40-mesh sieve, adding 70% methanol aqueous solution according to the mass ratio of 1: 2, extracting for 3 times at normal temperature for 72 hours each time, filtering, and concentrating the filtrate under reduced pressure to 4% of the original volume to obtain a crude extract;
step 2: adding water with the mass 3 times of that of the crude extract, stirring, adding petroleum ether with the mass 3 times of that of the crude extract, extracting for 4 times, separating a petroleum ether layer, adding ethyl acetate with the mass 3 times of that of the crude extract into the residual water layer, extracting for 4 times, separating an ethyl acetate layer, and concentrating the ethyl acetate layer under reduced pressure to obtain an ethyl acetate extract phase;
and step 3: performing ODS vacuum column chromatography on the ethyl acetate extract phase and Sephadex LH-20 column chromatography to obtain a crude component of 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside;
and 4, step 4: and refining the crude component of the 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside by HPLC to obtain the 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside.
Structural characterization of the compounds of the invention:
the compound is whiteA powder having a melting point of 163 to 165 ℃ and an optical rotation of
Figure BSA0000193006880000041
In Thin Layer Chromatography (TLC) development test, R of the compound is developed by a solvent system of tert-butyl alcohol-glacial acetic acid-water with a volume ratio of 3: 1fA value of about 0.25, R of the compound when developed in a solvent system having a glacial acetic acid-water volume ratio of 6: 94fThe value is about 0.56. The compound is tested by fast atom bombardment (positive mode) experiment to obtain M/z [ M + H ]]+、[M+Na]+And [ M + K]+519, 541 and 557, respectively, and it is found that the molecular weight of this compound is 518. The molecular formula of the compound is C by combining the nuclear magnetic resonance spectrum data of the compound22H30O14. The infrared spectrum of the compound is 3405cm-1The strong absorption peak is attributed to the hydroxyl group. A1% ferric trichloride ethanol solution (mass percent) is sprayed to form dark green color, and the compound contains phenolic hydroxyl groups in the molecule (Si C.L., et al, Wood Science and Technology, 2016, 50: 645-659).
One-dimensional NMR spectrum signal of the compound (13C and1H) the compound is shown to contain two beta-D-glucopyranosides: one is [1 terminal proton (. delta.) ]H4.45, 1H, d, J ═ 7.7Hz, H-1') and δC96.37(C-1′)、6″-CH2(δH3.86&3.79, 1H and δ respectivelyC62.68)]The other beta-D-glucopyranoside is [1 terminal proton (. delta.) ]H4.75, 1H, d, J ═ 8.5Hz, H-1 ″) and δC105.82(C-1″)、6″-CH2(δH3.68&3.96, 1H and Δ eachC62.60)]。
Checking proton map shows that the compound contains one ABX type proton resonance peak deltaH7.25(1H，d，J＝1.9Hz，H-2)、δH6.76(1H, d, J ═ 8.0Hz, H-5) and δH7.29(1H，dd，J＝1.9&8.0Hz，H-6)]An AB type proton resonance peak [ delta ]H7.75(1H，d，J＝12.0Hz，H-7)、δH6.42(1H，d，J＝12.0Hz，H-8)]And deltaH3.80(3H，s，10-OCH3) Uncovering deviceThe compound contains a cis-feruloyl (Luo Y., et al, chemistry Natural Compounds, 2018, 54 (4): 642-645).
Examining two-dimensional HMBC spectra, the methoxy proton delta of this compoundH3.80(3H, s, H-10) and δC150.18(C-3) remote correlation, the H-2' proton delta of the first β -D-glucopyranoseH4.95 and cis-feruloyl C-9 position deltaC168.02 remote dependence of the terminal proton delta of the second beta-D-glucopyranoseH4.75(1H, D, J ═ 8.5, H-1 ″) to the C-3' position δ of the first β -D-glucopyranoseC85.05 remote correlation.
By combining the experimental data, the chemical structural formula of the compound is determined to be 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside. After retrieval, the compound obtained by the preparation is a novel cis-ferulic acid glucoside compound.
Example 2: preparation of 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside from green walnut peel of wild walnut
Step 1: taking walnut green peel of a cleaned and dried wild walnut tree (Juglans cathayensis Dode, alias hickory, pecan and the like), crushing, sieving with a 40-mesh sieve, adding 75% methanol aqueous solution by volume percentage concentration according to the mass ratio of 1: 3, performing ultrasonic-assisted extraction for 2 times, each time for 1 hour, filtering, and concentrating the filtrate under reduced pressure to 6% of the original volume to obtain a crude extract;
step 2: adding water with the mass 2 times of that of the crude extract, stirring, adding petroleum ether with the mass 4 times of that of the crude extract, extracting for 3 times, separating a petroleum ether layer, adding ethyl acetate with the mass 4 times of that of the crude extract into the residual water layer, extracting for 2 times, separating an ethyl acetate layer, and concentrating the ethyl acetate layer under reduced pressure to obtain an ethyl acetate extract phase;
and step 3: the ethyl acetate extract phase is subjected to macroporous resin D101 and Sephadex LH-20 column chromatography to prepare a crude component of 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside;
and 4, step 4: and refining the crude component of the 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside by HPLC to obtain the 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside.
Example 3: preparation of 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside from green walnut peel of walnut
Step 1: taking walnut green peel of a cleaned and dried walnut tree (Juglans regia, also known as Chinese walnut, common walnut and the like), crushing, sieving with a 40-mesh sieve, adding a methanol water solution with the volume percentage concentration of 65% according to the mass ratio of 1: 2.5, heating and extracting for 4 times, each time for 12 hours, filtering, and concentrating the filtrate under reduced pressure to 5% of the original volume to obtain a crude extract;
step 2: adding water with the mass 2 times of that of the crude extract, stirring, adding petroleum ether with the mass 3 times of that of the crude extract, extracting for 2 times, separating a petroleum ether layer, adding ethyl acetate with the mass 3 times of that of the crude extract into the residual water layer, extracting for 2 times, separating an ethyl acetate layer, and concentrating the ethyl acetate layer under reduced pressure to obtain an ethyl acetate extract phase;
and step 3: performing ODS vacuum column chromatography and macroporous resin D101 on the ethyl acetate extract phase, and performing Sephadex LH-20 column chromatography to obtain a crude 2-O-cis-feruloyl-3-O-beta-D-glucopyranose-beta-D-glucopyranoside fraction;
and 4, step 4: and refining the crude component of the 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside by HPLC to obtain the 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside.

Claims (2)

1. A preparation method of cis-ferulic acid glucoside, namely 2-O-cis-feruloyl-3-O-beta-D-glucopyranose-beta-D-glucopyranoside, is characterized by comprising the following steps in sequence:
step 1: taking walnut green husks which are cleaned and dried in the shade, crushing and sieving the walnut green husks by a 40-mesh sieve, adding a methanol water solution with the volume percentage concentration of 60-80% according to the mass ratio of 1: 1-1: 5, extracting at normal temperature or by heating or ultrasonic-assisted extraction for 1-5 times, each time for 0.5-96 hours, filtering, and concentrating the filtrate under reduced pressure to 3-10% of the original volume to obtain a crude extract;
step 2: adding water with the mass of 1-5 times of that of the crude extract, stirring, adding petroleum ether with the mass of 2-6 times of that of the crude extract, extracting for 1-6 times, separating out a petroleum ether layer, adding ethyl acetate with the mass of 2-6 times of that of the crude extract into the residual water layer, extracting for 1-6 times, separating out an ethyl acetate layer, and concentrating the ethyl acetate layer under reduced pressure to obtain an ethyl acetate extract phase;
and step 3: performing ODS vacuum column chromatography and/or macroporous resin D101 on the ethyl acetate extract phase, and performing SephadexLH-20 column chromatography to obtain crude 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside;
and 4, step 4: and refining the crude component of the 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside by HPLC to obtain the 2-O-cis-feruloyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside.
2. The method as claimed in claim 1, wherein the green walnut peel is a green walnut peel of any one of walnut trees belonging to the genus Juglans of the family Juglandaceae.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07238088A (en) * 1994-02-25 1995-09-12 Pola Chem Ind Inc Acylated oligosaccharide and composition containing the same
CN105646621A (en) * 2016-02-16 2016-06-08 天津科技大学 Isoflavone glycoside in green Juglans sigillata Dode peel as well as preparation method and anti-inflammation application of isoflavone glycoside
CN106589019A (en) * 2016-12-02 2017-04-26 天津科技大学 Walnut green peel isoflavone glycoside and clean and efficient preparation technology thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07238088A (en) * 1994-02-25 1995-09-12 Pola Chem Ind Inc Acylated oligosaccharide and composition containing the same
CN105646621A (en) * 2016-02-16 2016-06-08 天津科技大学 Isoflavone glycoside in green Juglans sigillata Dode peel as well as preparation method and anti-inflammation application of isoflavone glycoside
CN106589019A (en) * 2016-12-02 2017-04-26 天津科技大学 Walnut green peel isoflavone glycoside and clean and efficient preparation technology thereof

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