Digalactosyldiacylglycerol and preparation method and purpose thereof

A technology of lactosyl diacylglycerol and acyl, applied in the field of preparation of digalactosyl diacylglyceride

Active Publication Date: 2017-08-01
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no literature report on the use of DGDG as

Method used

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  • Digalactosyldiacylglycerol and preparation method and purpose thereof
  • Digalactosyldiacylglycerol and preparation method and purpose thereof
  • Digalactosyldiacylglycerol and preparation method and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Extraction, preparation and structure identification of digalactosyl diacylglycerides

[0034] Take 2000 g of hijiki and extract with 10 times volume of 75% ethanol for 2 hours and repeat 3 times. The extracts were combined, filtered and concentrated until there was no alcohol taste, extracted with equal volume of ethyl acetate for 3 times, and the extracts were combined and concentrated to obtain 33.26 g of extract. The extract was dissolved in ethyl acetate, mixed with 41 g of 200-300 mesh silica gel H, and subjected to silica gel column chromatography, using dichloromethane-methanol as the solvent for gradient elution, where dichloromethane-methanol (v / v 85:15) ) The obtained components are eluted, and then subjected to Sephadex LH-20 gel column chromatography (dichloromethane-methanol 1:1) and silica gel column chromatography to obtain a mixture of digalactosyl diacylglycerides (DGDG) . Test it 1 H-NMR spectrum and 13 C-NMR spectrum (e.g. figure 1 with fi...

Embodiment 2

[0039] Example 2: The activation effect of DGDG on PPARα and PPARγ

[0040] The dual luciferase reporter gene analysis technique was used to detect the transcriptional activation of PPARα and PPARγ. Inoculate 293T cells in a 96-well plate with DMEM medium (10% FBS, without antibiotics). After 8-12 hours, the cells will grow to about 60%. Without changing the medium, transfect the plasmid directly according to lipo2000 instructions. The total amount of plasmid is 0.075g / well (0.05μg PPRE, 0.005μg internal control pRL-TK and 0.02μg PPARα / γ). The dosage of lipo2000 is 2.5 times the mass of the transfected plasmid (2.5*0.075L=0.1875μL / well). Plasmid and lipo2000 were mixed in 25μL / well optim medium. Twelve hours after transfection, a positive drug was added (the positive drug for PPARγ is rosiglitazone at a concentration of 1 μM, and the positive drug for PPARα is WY14643 at a concentration of 10 μM), and the DGDG obtained in Example 1. 24 hours after the addition of the drug, the...

Embodiment 3

[0041] Example 3: The activation effect of DD1~DD8 on PPARα and PPARγ

[0042] The dual luciferase reporter gene analysis technique was used to detect the transcriptional activation of PPARα and PPARγ, and the specific method was the same as in Example 2. The drugs added were DD1 to DD8 prepared in Example 1. The results are shown in Table 2.

[0043] Table 2 The activation effect of DD1~DD8 on PPARα / γ

[0044]

[0045] Note: Compared with the blank group, "*" P<0.05; "**" P<0.01; "***" P<0.001.

[0046] The results show that the above compounds can activate PPARα and / or PPARγ to varying degrees. In particular, DD8 (compound of formula (II)) exhibits significant PPARα / γ dual agonism.

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Abstract

The invention discloses digalactosyldiacylglycerol with a structure shown as a formula (I), a preparation method of the digalactosyldiacylglycerol and a purpose of the digalactosyldiacylglycerol for preparing a PPAR alpha agonist, or a PPAR gamma agonist and PPAR alpha/gamma double-agonists. The formula (I) is shown as the accompanying drawing, wherein R1 and R2 represent acyl fragments; the acyl fragments are straight-chain or branch-chain fatty acid containing 1 to 30 carbon atoms; in addition, 0 to 15 cis-form or trans-form double keys are contained in the acyl fragments. The agitation effect of digalactosyldiacylglycerol on PPAR alpha and PPAR gamma and the duplex agitation effect on PPAR alpha/gamma are discovered; the application value of the compound of the type to the prevention and treatment of PPARs relevant diseases is disclosed. In addition, active ingredients of alga beneficial to the cardiovascular health are discovered and separated; the medicine effect substances and functional factors are provided for developing alga medicine, health care food and food.

Description

Technical field [0001] The present invention relates to a preparation method and application of bisgalactosyl diacylglyceride, and specifically relates to a preparation method of bisgalactosyl diacylglyceride and its use as PPARα or PPARγ agonist and PPARα / γ double Use of agonists. Background technique [0002] Peroxisome proliferator-activated receptors (PPARs) are a member of the nuclear receptor superfamily, including three subtypes of PPARα, PPARβ (or PPARδ) and PPARγ. After PPARs are activated by ligands, they first form heterodimers with retinoic acid receptor X (retinoidX receptor, RXR), and then with the peroxisome proliferator response element (PPRE) upstream of the target gene promoter. In combination, it regulates important biochemical reaction processes such as lipid metabolism, adipogenesis, insulin sensitivity, inflammation, cell growth and differentiation through the transcriptional regulation of target genes. A series of metabolic syndromes are related to PPARs,...

Claims

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Application Information

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IPC IPC(8): C07H15/06C07H1/08A61K31/7032A61P3/06A61P3/04A61P9/12A61P9/10A61P3/10A61P13/12A61P37/02A61P1/16
CPCC07H1/08C07H15/06
Inventor 刘红兵王梦雪蒋盈
Owner OCEAN UNIV OF CHINA
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