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Fucoxanthin derivatives with anti-inflammatory effect and preparation method thereof

A technology for fucoxanthin and anti-inflammatory effects, which can be used in medical preparations containing active ingredients, anti-inflammatory agents, drug combinations, etc., and can solve the problems of high-value development and application of fucoxanthin series derivative products.

Active Publication Date: 2021-01-29
THIRD INST OF OCEANOGRAPHY MINIST OF NATURAL RESOURCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are no reports on the batch preparation of fucoxanthin series derivatives at home and abroad, and the high-value development and application of fucoxanthin series derivatives cannot be carried out. Therefore, it is necessary to invent a high-purity fucoxanthin series derivatives To study the biological activity of a series of fucoxanthin derivatives, and provide an important basis for the development and application of functional products of series derivatives

Method used

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  • Fucoxanthin derivatives with anti-inflammatory effect and preparation method thereof
  • Fucoxanthin derivatives with anti-inflammatory effect and preparation method thereof
  • Fucoxanthin derivatives with anti-inflammatory effect and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0059] 1) Preparation of fucoxanthin derivative mixture: take 500 mg of fucoxanthin (purity: 99%) (prepared according to ZL2012105643395 method), dissolve in 200 mL of methanol, add 100 mg of lithium aluminum hydride, and react at 37 ° C for 10 h, There are multiple fucoxanthin derivative chromatographic peaks detected by liquid chromatography (see figure 1 ), concentrated to nearly dry, and set aside;

[0060] 2) Preliminary separation of fucoxanthin fucoxanthin: From the chromatogram of fucoxanthin derivatives, it can be seen that the derivative components need to be preliminarily separated, and then separated and purified by high performance liquid chromatography. In this study, a decompression reversed-phase chromatography column was used for separation, and 70%-75%-80%-85%-90%-100% methanol water was used for gradient elution, and the eluents were collected separately and concentrated under reduced pressure for detection. The high performance liquid chromatogram of its p...

Embodiment 2

[0067] 1. Anti-inflammatory drug activity screening of fucoxanthin and its derivatives

[0068] Mouse macrophages (RAW264.7) were used to detect the inhibitory effect of compounds on NO production. When immune cells are stimulated by microbial endotoxins, inflammatory mediators, etc., they will generate a large amount of induced NO synthase (induced NOsynthase, iNOS) to generate NO for immune response. Inhibition of NO production is therefore a direct indicator of the anti-inflammatory activity of a compound. This model directly evaluates the NO production inhibitory activity of the compound at the cellular level, which in turn reflects its anti-inflammatory activity.

[0069] 2. Screening method:

[0070] Instrument: microplate reader (Molecular Device 384plus)

[0071] Materials: RAW264.7 cells, NO detection kit (Thermo Fisher)

[0072] Process: Cells were first stimulated with drugs for one hour and then induced with lipopolysaccharide (LPS, 1 μg / ml) for 24 hours. Coll...

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Abstract

The invention relates to nine kinds of fucoxanthin derivatives. The preparation method of a derivative includes taking fucoxanthin as a raw material; adding a reducing agent, and obtaining a fucoxanthin derivative crude extract through concentration after reaction; performing preliminary separation on the fucoxanthin derivative crude extract through silica gel column chromatography to divide intodifferent components; and performing separating and purifying through semi-preparative / preparative high-performance liquid chromatography. The prepared fucoxanthin derivative has strong anti-inflammatory activity and good clinic application prospects.

Description

technical field [0001] The present invention relates to a compound and a preparation method thereof, in particular to a fucoxanthin derivative and its preparation method and application, in particular to a fucoxanthin derivative and its application in the preparation of anti-inflammatory drugs. Background technique [0002] Fucoxanthin, also known as fucoxanthin, is a natural carotenoid extracted from edible brown algae, such as Undaria pinnatifida and Laminaria japonica Aresch. The two ends of the all-trans long chain have a chemically active 5,6-epoxy unsaturated allene bond structure, which is different from other carotenoid molecules and has strong biological activity. In recent years, its multiple biological activities have been confirmed, and some potential activities are being actively explored by scientists, and it has become one of the main hot spots in the research and development of marine drugs. [0003] Traditional Chinese medicine or natural medicine shows div...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D303/48C07C45/78C07C49/242C07C67/48C07C69/21A61K31/336A61K31/12A61K31/22A61P29/00A61P19/02A61P25/28A61P1/04A61P1/06A61P3/10A61P9/10A61P1/16A61P13/12A61P25/00
CPCA61P1/04A61P1/06A61P1/16A61P3/10A61P9/10A61P13/12A61P19/02A61P25/00A61P25/28A61P29/00C07C49/242C07C69/21C07D303/48
Inventor 张怡评洪专杨隆河晋文慧陈伟珠陈晖
Owner THIRD INST OF OCEANOGRAPHY MINIST OF NATURAL RESOURCES
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