Polyacetylenes from Oplopanax horridus and Panax ginseng: Relationship between Structure and PPARγ Activation.

Journal of Natural Products
Mirta ResetarVerena M Dirsch

Abstract

Oplopanax horridus and Panax ginseng are members of the plant family Araliaceae, which is rich in structurally diverse polyacetylenes. In this work, we isolated and determined structures of 23 aliphatic C17 and C18 polyacetylenes, of which five are new compounds. Polyacetylenes have a suitable scaffold for binding to PPARγ, a ligand-activated transcription factor involved in metabolic regulation. Using a reporter gene assay, their potential was investigated to activate PPARγ. The majority of the polyacetylenes showed at least some PPARγ activity, among which oplopantriol B 18-acetate (1) and oplopantriol B (2) were the most potent partial PPARγ activators. By employing in silico molecular docking and comparing the activities of structural analogues, features are described that are involved in PPARγ activation, as well as in cytotoxicity. It was found that the type of C-1 to C-2 bond, the polarity of the terminal alkyl chain, and the backbone flexibility can impact bioactivity of polyacetylenes, while diol structures with a C-1 to C-2 double bond showed enhanced cytotoxicity. Since PPARγ activators have antidiabetic and anti-inflammatory properties, the present results may help explain some of the beneficial effects observed in ...Continue Reading

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Citations

Jun 4, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lars Porskjær Christensen

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Methods Mentioned

BETA
NMR
acetylation
transfection
X-ray

Software Mentioned

ChemPLP
LigandScout
GOLD
GraphPad Prism
Omega
R

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