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Sesquilignan compound as well as separation method and application thereof

A technology of lignans and separation method, which is applied in the field of sesquilignans and their separation, and can solve the problems of undisclosed application of sesquilignans and the like

Pending Publication Date: 2022-04-05
HAINAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no disclosure of the application of sesquilignans in the preparation of drugs for the prevention and / or treatment of inflammation

Method used

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  • Sesquilignan compound as well as separation method and application thereof
  • Sesquilignan compound as well as separation method and application thereof
  • Sesquilignan compound as well as separation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] The preparation of embodiment 1 sesquilignans

[0051] Include the following steps:

[0052] (1) Grind the dried noni seeds, and ultrasonically extract each kilogram of noni seeds with 4L petroleum ether and ethyl acetate solvent successively for 3 times, each extraction for 3 hours, combine the extracts, concentrate under reduced pressure to obtain the extract of ethyl acetate parts (about 110g);

[0053] (2) Take step (1) ethyl acetate part extract (about 60g), first through silica gel column chromatography, adopt sherwood oil-acetone mixed solvent to carry out gradient elution as eluent, the elution of sherwood oil-acetone mixed solvent The off-gradient is 100:1, 80:1, 20:1, 10:1, 5:1, 1:1, 1:10, 2 column volumes are collected for each gradient, and one fraction is obtained for each gradient, and a total of 7 components, namely Fr.1~Fr.7;

[0054] (3) Put Fr.5 through normal phase silica gel column chromatography first, and use the elution gradient of chloroform-m...

Embodiment 2

[0055] The preparation of embodiment 2 sesquilignans

[0056] Include the following steps:

[0057] (1) Grind the dried Noni seeds, and ultrasonically extract each kilogram of Noni seeds with 4L petroleum ether and ethyl acetate solvent sequentially for 4 times, each extraction for 2 hours, combine the extracts, concentrate under reduced pressure to obtain the extract of ethyl acetate parts (about 120g);

[0058] (2) Take step (1) ethyl acetate part extract (about 60g), first through silica gel column chromatography, adopt sherwood oil-acetone mixed solvent to carry out gradient elution as eluent, the elution of sherwood oil-acetone mixed solvent The off-gradient is 100:1, 80:1, 20:1, 10:1, 5:1, 1:1, 1:10, and each gradient collects 3 column volumes, and each gradient obtains one fraction, and a total of 7 components, namely Fr.1~Fr.7;

[0059] (3) Fr.5 was subjected to normal phase silica gel column chromatography first, and the elution gradient of chloroform-methanol mixe...

Embodiment 3

[0060] The structural identification of embodiment 3 sesquilignans

[0061] Using Spectrum ( 1 H NMR, 13 C NMR, HSQC, HMBC, NOESY) and modern structural identification techniques such as MS, determine the chemical structure of the compound III and IV obtained in embodiment 1 and embodiment 2.

[0062] The structural identification data are as follows:

[0063] Compound Ⅲ: It is a yellow oily substance, easily soluble in methanol. High resolution mass spectrometry HRESI(-)MS(m / z491.1345[M-H] - , theoretical value 491.1342) determine its molecular formula as C 27 h 24 o 9 ;according to 1 H, 13 C and two-dimensional nuclear magnetic resonance data to determine its structure, the skeleton type is sesquilignan, that is, rel-(7'β,8'α,7"β,8"α)-3,3",4",9 ',9"-Pentahydroxy-1-propenyl-7',8'-chroman-3,7":7,9'-dioxa-sequilignan, named For moricitan A, its 1 H and 13 See Table 1 for C NMR data attribution. [600MHz( 1 H), 150 MHz ( 13 C), solvent: MeOD-d 4 ].

[0064] Compo...

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Abstract

The invention discloses a lignan compound and a separation method and application thereof, and sesquilignan compounds I and II are obtained mainly through multistage separation steps of ethyl acetate extraction, reduced pressure distillation, organic solvent gradient elution, liquid chromatography separation and the like. Pharmacological activity experiments show that the compound provided by the invention has obvious anti-inflammatory activity, which shows that the compound has a good application prospect in preparation of drugs for preventing or treating inflammation.

Description

technical field [0001] The invention relates to a sesquilignan compound and its separation method and application, belonging to the technical field of phytochemistry. Background technique [0002] Morinda Citrifolia, also known as Morinda citrifolia, is an evergreen shrub or small tree of the genus Morinda in the family Rubiaceae. It is concentrated in tropical and subtropical regions. In my country, it is mainly distributed in Hainan Island, Xisha Islands and other places. "Compendium of Materia Medica" records that "Morinda officinalis" has the functions of "strengthening the body and eliminating pathogens, nourishing yin and kidney, strengthening yang, dispelling rheumatism, treating cold palace infertility, and curing impotence". [0003] Noni fruit is a polyflower fruit with unique health effects. The original juice (Noni enzyme) produced by its fermentation is a popular health drink, which has the effects of lowering blood sugar, blood pressure, blood lipids, and anti-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D407/04C07D493/04A61K31/365A61K31/357A61P29/00A61P11/08A61P11/00A61P1/04A61P1/00
CPCY02A50/30
Inventor 余章昕陈光英李小宝徐盟张斌黄莉
Owner HAINAN NORMAL UNIV
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