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Caffeoyl group-containing tannin derivative, and preparation technology and application thereof

A technology of caffeoyl group and preparation process, which is applied in the field of secondary metabolic active components and their utilization, can solve the problems of little research on secondary metabolic chemical components of Yangbi walnut leaves, and achieves simple and standardized operation method, low preparation cost and high yield high effect

Inactive Publication Date: 2015-10-07
TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the research on the chemical constituents of Yangbi walnut tree has mainly focused on its walnut kernel, walnut kernel shell, fruit green bark, trunk bark and other parts, and the compounds extracted and separated from the above parts are mainly hydrolyzed tannins, condensed unit Nings and α-tetralones, but there are few studies on the chemical constituents of the secondary metabolism of walnut leaves (Liu et al, Helvetica Chimica Acta, 2010, 93(2), 265-271; Si et al, Chemistry of Natural Compounds, 2011, 47(3), 442~445; Si et al, Biochemical Systematics and Ecology, 2011, 39(3), 225~227)

Method used

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  • Caffeoyl group-containing tannin derivative, and preparation technology and application thereof
  • Caffeoyl group-containing tannin derivative, and preparation technology and application thereof
  • Caffeoyl group-containing tannin derivative, and preparation technology and application thereof

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Experimental program
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Effect test

Embodiment 1

[0020] Preparation of 1,3-di-O-galloyl-6-O-caffeoyl-β-D-glucopyranose

[0021] (1) Take pulverized Yangbi walnut leaves, add 60% acetone aqueous solution at a mass ratio of 1:4, extract at room temperature for 3 times, each time for 72 hours, filter, and concentrate the filtrate under reduced pressure to 4% of the original volume. %, get crude extract;

[0022] (2) adding water with 3 times the mass of the crude extract, stirring, adding n-hexane with 2 times the mass of the crude extract to extract 4 times, separating the n-hexane layer, and concentrating the n-hexane layer under reduced pressure to obtain the n-hexane extract phase;

[0023] (3) The n-hexane extraction phase was prepared by silica gel column chromatography to obtain 1,3-di-O-galloyl-6-O-caffeoyl-β-D-glucopyranose.

[0024] The structural identification of the compound:

[0025] The m / z[M+Na] of the compound can be known from the positive fast atom bombardment mass spectrum (Positive FAB-MS) + is 669, and ...

Embodiment 2

[0029] (1) Take pulverized Yangbi walnut leaves, add 70% acetone aqueous solution at a mass ratio of 1:5, microwave-assisted extraction for 4 times, each time for 1.5 hours, filter, and concentrate the filtrate under reduced pressure to the original volume 5%, get the crude extract;

[0030] (2) adding water with 2 times the mass of the crude extract, stirring, adding n-hexane with 3 times the mass of the crude extract to extract 3 times, separating the n-hexane layer, and concentrating the n-hexane layer under reduced pressure to obtain the n-hexane extract phase;

[0031] (3) The n-hexane extract phase was prepared by gel column chromatography to obtain 1,3-di-O-galloyl-6-O-caffeoyl-β-D-glucopyranose.

Embodiment 3

[0033] (1) Take pulverized Yangbi walnut leaves, add 80% acetone aqueous solution with a volume percentage concentration of 1:6 by mass ratio, ultrasonically assisted extraction 2 times, each time for 2 hours, filter, and the filtrate is concentrated under reduced pressure to the original volume. 8%, get the crude extract;

[0034] (2) adding water with 1.5 times the mass of the crude extract, stirring, adding n-hexane with 2 times the mass of the crude extract to extract twice, separating the n-hexane layer, and concentrating the n-hexane layer under reduced pressure to obtain the n-hexane extract phase;

[0035] (3) The n-hexane extraction phase was prepared by silica gel column chromatography and gel column chromatography to obtain 1,3-di-O-galloyl-6-O-caffeoyl-β-D-glucopyranose.

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Abstract

The invention belongs to the field of preparation and utilization of secondary metabolism active components of forestry processing residues, and concretely relates to a technology for preparing a caffeoyl group-containing tannin derivative 1,3-di-O-galloyl-6-O-caffeoyl-beta-D-glucopyranose from Juglandaceae Juglans Juglans sigillata tree leaves, and an application of the derivative in the preparation of anti-oxidation products. The technology has the advantages of standardized extracting and separating preparation process, high yield, low cost and simple operation.

Description

technical field [0001] The invention belongs to the technical field of secondary metabolic active components of forestry processing residues and their utilization, and in particular relates to a new caffeoyl-containing tannin derivative 1,3-di-O-galloyl-6-O-caffeoyl -β-D-glucopyranose (1,3-di-O-galloyl-6-O-caffeoyl-β-D-glucoside) and its preparation process and application. Background technique [0002] Yangbi walnut (Juglans sigillata Doda) is a deciduous tree of the family Juglandanceae (Juglandanceae), mainly distributed in the hillsides and valleys of Yunnan, Tibet, Sichuan and Guizhou in southwest my country (Wu&Raven, Flora of China, Vol.4 , Science Press, Beijing, 1999, 283-284). The tree height of Yangbi walnut tree can reach more than 30 meters. The surface of the core is obviously wrinkled and not smooth. Yangbi walnuts have deep roots and well-developed taproots. Yangbi walnut is light-loving, resistant to heat and humidity, but not resistant to dry and cold (Zh...

Claims

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Application Information

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IPC IPC(8): C07H13/08C07H1/08A61P39/06A23L1/09A61Q19/00
Inventor 司传领陈志永安亮亮
Owner TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY
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