Starch-indolic acid derivative, preparation method and application thereof

A technology of indole acid and derivatives, applied in the field of starch-indole acid derivatives and their preparation, can solve the problems of inability to effectively reach the colon, and achieve the effects of high resistance and increased content

Active Publication Date: 2022-01-11
SHANDONG SHANWEI IMMUNOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, if these small indolic acid molecules are directly ingested orally, they are absorbed in the stomach or small intestine of the alimentary canal and cannot effectively reach the colon

Method used

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  • Starch-indolic acid derivative, preparation method and application thereof
  • Starch-indolic acid derivative, preparation method and application thereof
  • Starch-indolic acid derivative, preparation method and application thereof

Examples

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preparation example Construction

[0060] According to one aspect of the present invention, a kind of preparation method of above-mentioned starch-indole acid derivative, described preparation method comprises the following steps:

[0061] (a), dissolving starch in a solvent to obtain solution A; then adding indole acid, condensing agent and alkali to solution A for esterification reaction to obtain reaction solution A;

[0062] (b) Precipitating the starch in the reaction solution A, followed by suction filtration and drying to obtain the starch-indole acid derivative.

[0063] The preparation method of starch-indole acid derivatives provided by the invention, the preparation method first dissolves starch in a solvent to obtain solution A; then adds indole acid, condensing agent and alkali to solution A to carry out esterification reaction, A reaction solution A is obtained; then the starch in the reaction solution A is precipitated, suction filtered and dried in sequence to obtain a starch-indole acid derivat...

Embodiment 1

[0073] (1), the preparation of starch-indole acid derivatives:

[0074] (1), preparation of indole acetic acid derivatized high amylose corn starch (HAMSIAA)

[0075] Add HAMS to DMSO, stir until the solution is clear, add IAA, EDCI, and 1-methylimidazole in sequence, and continue stirring for 24 hours after the addition is complete. After the reaction, the reaction solution was added dropwise to EtOH or H 2 In O, a solid precipitated, filtered with suction, and the filter cake was washed with EtOH or H 2 O washed and dried.

[0076] (2) Preparation of indole propionic acid derivatized high amylose corn starch (HAMSIPA)

[0077] Add HAMS to DMSO, stir until the solution is clear, then add IPA, EDCI, and 1-methylimidazole in sequence, and continue stirring for 24 hours after the addition is complete. After the reaction, the reaction solution was added dropwise to EtOH or H 2 In O, a solid precipitated, filtered with suction, and the filter cake was washed with EtOH or H 2...

Embodiment 2

[0104] Example 2 Evaluation of the effect of indole acetic acid derivatized starch (HAMSIAA) colon-targeted delivery of IAA:

[0105] HAMS and HAMSIAA with different degrees of substitution were used as mouse feed at the addition ratio of 15%, and 8-week-old mice were randomly divided into 6 groups according to body weight, with 5 mice in each group: HAMS group, HAMSIAA group (group 6, DS were 0.065, 0.12, 0.19, 0.29, 0.37, 0.49), and collected mouse feces and serum.

[0106] (1) Method for determining IAA / IPA content in mouse feces, hepatic portal blood, peripheral blood and colon tissue;

[0107] High performance liquid chromatography-tandem mass spectrometry (HPLC-MS / MS) was used to detect the content of metabolite IAA / IPA in each sample. Determination of IAA / IPA content in mouse feces: add methanol to the collected feces, then vortex, ultrasonically extract, centrifuge, take the supernatant to obtain the extract, then process the obtained extract, add IAA / IPA Standard (I...

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Abstract

The invention provides a starch-indolic acid derivative, a preparation method and application thereof, and relates to the technical field of modified starch. According to the invention, the starch-indolic acid derivative is esterified starch generated by esterification reaction of starch and indolic acid under the action of a condensing agent and and alkali, has relatively high resistance, can resist degradation of the stomach and the small intestine, can release indolic acid beneficial to intestinal health through fermentation of intestinal flora after reaching the colon part, has obvious advantages compared with traditional administration modes such as intragastric administration, intraperitoneal injection and the like, and can obviously increase the content of indolic acid in colon and hepatic portal venous blood; and indoleic acid can activate an aromatic hydrocarbon receptor to play an immunoregulation role, and the indoleic acid and the regulation role of short-chain fatty acid released by fermentation of starch with intestinal flora are superposed, so that a product which synergistically plays the immunoregulation role through a plurality of immune system signal pathways is provided.

Description

technical field [0001] The invention relates to the technical field of modified starch, in particular to a starch-indole acid derivative and its preparation method and application. Background technique [0002] Indole-3-acetic acid (IAA), indole-3-propionic acid (IPA), indole-3-lactic acid (ILA), and indole-3-acrylic acid (IA) are derivatives of tryptophan The metabolites of intestinal microorganisms play an important role in regulating intestinal immune balance. The study found that IAA, IA, ILA, etc. can act as ligands of aryl hydrocarbon receptor (AhR) to regulate intestinal immune balance, and IAA inhibited the levels of pro-inflammatory cytokines in mouse macrophages and hepatocytes in an AhR-dependent manner , thereby alleviating the hepatic inflammatory response. IPA regulates intestinal barrier function in mice by acting as a ligand for the pregnane X receptor (PXR), especially in the presence of indole, and elevated serum IPA concentrations are associated with red...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B31/04A23L33/125A61P29/00A61P37/02A61P9/10A61P3/10A61P19/02
CPCC08B31/04A23L33/125A61P29/00A61P37/02A61P9/10A61P3/10A61P19/02A23V2002/00A23V2200/32A23V2200/324A23V2250/5118Y02P20/54
Inventor 查尔斯·雷伊·麦凯宋营营曲新艳王泉博
Owner SHANDONG SHANWEI IMMUNOTECH CO LTD
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