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Preparation method and application of monogalactosyl-based monooleoyl glycerol

A technology based on monoacylglycerol and galactose, which is applied in the field of preparation of monogalactosyl monoacylglycerides, and can solve the problems of no MGMG and other problems

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 are no literature reports on the use of MGMG as a PPARα or PPARγ agonist, especially a PPARα / γ dual agonist

Method used

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  • Preparation method and application of monogalactosyl-based monooleoyl glycerol
  • Preparation method and application of monogalactosyl-based monooleoyl glycerol
  • Preparation method and application of monogalactosyl-based monooleoyl glycerol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: Extraction preparation and structure identification of monogalactosyl monoacylglyceride

[0036]Take 2000g of Hijiki, extract with 10 times the volume of 75% ethanol under reflux for 2h, repeat 3 times. Combine the extracts, filter and concentrate until there is no alcohol smell, extract 3 times with an equal volume of ethyl acetate, combine the extracts, concentrate to obtain 33.26 g of extract. The extract was dissolved in ethyl acetate, mixed with 41g 200-300 mesh silica gel H, and subjected to silica gel column chromatography, using dichloromethane-methanol as solvent for gradient elution, wherein dichloromethane-methanol (v / v 90:10 ) to elute the resulting components, and then through Sephadex LH-20 gel column chromatography (dichloromethane-methanol 1:1) and silica gel column chromatography to obtain a mixture of monogalactosyl monoacylglycerides (MGMG) , measure its 1 H-NMR spectrum and 13 C-NMR spectrum (such as figure 1 with 2 shown).

[0037] ...

Embodiment 2

[0041] Example 2: Activation of PPARα and PPARγ by MGMG

[0042] Transcriptional activation of PPARα and PPARγ was detected using a dual-luciferase reporter gene assay. 293T cells were inoculated in 96-well plates with DMEM medium (10% FBS, without antibiotics). After 8-12 hours, the cells grew to about 60%. Without changing the medium, the plasmid was directly transfected according to the instructions of lipo2000. The total amount of plasmid was 0.075 g / well (0.05 μg PPRE, 0.005 μg internal control pRL-TK and 0.02 μg PPARα / γ). The amount of lipo2000 used was 2.5 times the mass of the transfected plasmid (2.5*0.075L=0.1875 μL / well). The plasmid and lipo2000 were mixed in 25 μL / well optim medium in advance. After 12 hours of transfection, the positive drug (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 MGMG obtained in Example 1 were added. 24 hours after adding the dru...

Embodiment 3

[0043] Example 3: Activation of MM1-MM7 on PPARα and PPARγ

[0044] The transcriptional activation of PPARα and PPARγ was detected by dual-luciferase reporter gene analysis technology, and the specific method was the same as that in Example 2. Added drugs are MM1-MM7 prepared in Example 1. The results are shown in Table 2.

[0045] Table 2 The activation effect of MM1~MM7 on PPARα / γ

[0046]

[0047] Note: Compared with the blank group, "*", P<0.05; "**", P<0.01; "***", P<0.001.

[0048] The results showed that the above compounds could activate PPARα and / or PPARγ to varying degrees. In particular, MM5 (compound of formula (II)) and MM6 (compound of formula (III)) exhibited significant PPARα / γ dual agonism.

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Abstract

The invention discloses a preparation method of monogalactosyl-based monooleoyl glycerol with a structure as shown in a formula (I) and application in preparing a PPARalpha agonist or a PPARgamma agonist and a PPARalpha / gamma dual-agonist. According to the formula (I) as shown in the description, R1 and R2 represent acyl fragments; the acyl fragments are straight-chain or branched-chain fatty acid containing 1 to 30 carbon atoms; the acyl fragments contain 0 to 15 maleinoid form or anti-form double bonds. An agonistic action of the monogalactosyl-based monooleoyl glycerol on PPARalpha and PPARgamma, and a dual-agonistic action of the monogalactosyl-based monooleoyl glycerol on PPARalpha / gamma are discovered, and an application value of the compound in preventing PPARs related diseases is disclosed. In addition, active ingredients of seaweed beneficial for cardiovascular health are discovered and separated, and pharmacodynamic materials and functional factors are provided for developing seaweed medicines, health food and food.

Description

technical field [0001] The present invention relates to a preparation method and use of monogalactosyl monoacylglycerides, in particular to a preparation method of monogalactosyl monoacylglycerides and its use as a PPARα or PPARγ agonist and a PPARα / γ dual Agonist use. Background technique [0002] Peroxisome proliferator-activated receptors (PPARs for short) is a member of the nuclear receptor superfamily, including three subtypes of PPARα, PPARβ (or PPARδ) and PPARγ. After being activated by ligand, PPARs first form a heterodimer with retinoid X receptor (RXR), and then with the peroxisome proliferator response element (PPRE) upstream of the target gene promoter. Combined with transcriptional regulation of target genes to regulate important biochemical processes such as lipid metabolism, lipogenesis, insulin sensitivity, inflammatory response, cell growth and differentiation. A series of metabolic syndromes are associated with PPARs, including insulin resistance, impaire...

Claims

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Application Information

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Patent Type & Authority Applications(China)
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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