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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Daphniphyanoids A-C, three triterpenoids with uncommon 5/6/6/6/5-pentacyclic system from Daphniphyllum calycinum
Sha Li1, Jian-Ang Zeng2, Yao Dong1
1School of Medicine, Shanghai University, 99 Shangda Road, BaoShan District, Shanghai 200444, China.
Abstract:
Three new carbon-skeleton triterpenoids, named daphniphyanoids A-C (1-3), featuring an uncommon A-ring rearranged 5/6/6/6/5-pentacyclic nucleus, along with two biogenetically related known lupane-type triterpenoids (4 and 5), have been isolated from Daphniphyllum calycinum Benth. The determination of their structures was based on the extensive spectroscopic analysis, X-ray single crystal diffraction analysis, and chemical conversion. A plausible biosynthetic pathway for compounds 1-5 was proposed, involving a pinacol rearrangement, Wagner-Meerwein rearrangement, oxidation, and esterification. In in vitro bioassays, the methylated derivative (1a) of compound 1 exhibited preliminary selective PPAR-γ agonistic activity with an EC50 value of 5.46 μM, promoting both glucose uptake and mild lipid accumulation.
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