Diterpene compound Lobophytumin A, Lobophytumin B, Lobophytumin C, Lobophytumin D, Lobophytumin E and Lobophytumin F, and preparation method and application thereof to preparation of medicament

A kind of technology of legumes A and diterpenoids, applied in the field of medicine, can solve the problems of difficult drug candidate compounds and the like

Inactive Publication Date: 2012-10-17
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The research on PTP1B selective inhibitors has made some progress, but most of them are limited to some peptide or non-peptide compounds, such as the inhibitor EEDE(F2PMP)M (Ki=7.2nM) designed based on the substrate sequence of PTP1B dephosphorylation ), Glu-F2PMP-F2PMP (IC 50 =40nM), although these peptide inhibitors have strong inhibitory activity and high selectivity, the fact that they are peptide phosphate compounds makes them difficult to be drug candidates

Method used

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  • Diterpene compound Lobophytumin A, Lobophytumin B, Lobophytumin C, Lobophytumin D, Lobophytumin E and Lobophytumin F, and preparation method and application thereof to preparation of medicament
  • Diterpene compound Lobophytumin A, Lobophytumin B, Lobophytumin C, Lobophytumin D, Lobophytumin E and Lobophytumin F, and preparation method and application thereof to preparation of medicament
  • Diterpene compound Lobophytumin A, Lobophytumin B, Lobophytumin C, Lobophytumin D, Lobophytumin E and Lobophytumin F, and preparation method and application thereof to preparation of medicament

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: the preparation of diterpenoid legipin, second element, third element, butyl element, pentyl element and hexanol

[0026] (1) Extraction: the South China Sea pod soft coral Lobophytum cristatum with a dry weight of 210.0g is ultrasonically extracted 3 times with acetone (3000ml), the extracts are combined and concentrated under reduced pressure to obtain a crude extract, and the gained crude extract is mixed Suspended in 500ml of water. The suspension was extracted three times with ether (1000ml), and the obtained extracts were combined and concentrated under reduced pressure to obtain 5.4g of ether extract.

[0027] (2) Separation: 5.4 g of ether extract was subjected to 200-300 mesh silica gel column chromatography, and petroleum ether / ether (100:0→95:5→90:10→80:20→50:50→20:80→ 0:100) for gradient elution, the amount of eluent for each gradient was 1000ml. Among them, 625.3 mg of petroleum ether / diethyl ether (90:10) eluent concentrate was obtained. Th...

Embodiment 2

[0036] Embodiment 2: The PTP1B inhibitory activity experiment of diterpenoid legipin A, B, C, D, Penta and Hex

[0037] Test principle: p-Nitrophenyl phosphate (pNPP) is a soluble substrate of alkaline phosphatase, under the catalysis of human protein tyrosine phosphatase 1B (hPTP1B), it removes a phosphate group, Generate yellow soluble product p-Nitrophenol (p-Nitrophenol), this product has light absorption at 410nM place, can detect alkaline phosphatase by detecting the increase of light absorption at 410nM place (specifically refer to human source protein tyrosine Phosphatase 1B (hPTP1B)) activity.

[0038]

[0039] p-Nitrophenyl Phosphate p-Nitrophenol

[0040]Standard bioassay system: 10mM Tris.Cl (Tris (hydroxymethyl) aminomethane hydrochloride, namely tris (hydroxymethyl) aminomethane hydrochloride) (pH 7.6), 10mM pNPP, 2% DMSO (dimethyl sulphoxide, namely dimethyl sulfoxide) and 100 nM hPTP1B.

[0041] Test method: The protein tyrosine phosphatase PTP1B used for...

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Abstract

The present invention relates to the field of medicine technology, and in particular relates to six novel-structured diterpene compounds of Lobophytumin A, Lobophytumin B, Lobophytumin C, Lobophytumin D, Lobophytumin E and Lobophytumin F, which are separated from Lobophytum cristatum Tixier-Durivault of Genus Lobophytum, and a preparation method and application thereof to preparation of medicament for treating type II diabetes mellitus. The structural formulas of the Lobophytumin A, Lobophytumin B, Lobophytumin C, Lobophytumin D, Lobophytumin E and Lobophytumin F are as follows. According to biological activity test, the compounds can be used as a protein tyrosine phosphatase 1B (PTP1B) inhibitor and an insulin sensitizer for preparation of medicaments for treating type II diabetes mellitus, obesity and complications thereof.

Description

technical field [0001] The present invention relates to the technical field of medicine, in particular, to a class of 6 diterpenoids with novel structures, pods A, B, C and D isolated from the pod soft coral genus Lobophytum cristatum , pentaline or hexine; the present invention also relates to the preparation method of this type of compound; The use in the medicine of disease and its complication. Background technique [0002] Diabetes mellitus is a group of clinical syndromes caused by the interaction of genetic and environmental factors. Currently, diabetes is generally divided into two types, type I diabetes (insulin-dependent diabetes mellitus, IDDM) and type II diabetes (non-insulin-dependent diabetes mellitus, NIDDM). More than 90% of diabetes is type II diabetes. [0003] Type II diabetes is characterized by resistance to the action of insulin in insulin-sensitive tissues such as skeletal muscle, liver, and adipose tissue. The role of protein tyrosine phosphatase...

Claims

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Application Information

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IPC IPC(8): C07C49/21C07C45/79C07C13/50C07C13/48C07C7/12A61K31/12A61K31/015A61P3/10A61P3/04
Inventor 郭跃伟李佳李亮盛丽周宇波
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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