Cytotoxic Serratane Triterpenes from Diphasiastrum complanatum with a Hydroxy Group at C-27

 

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Abstract

Four serratane-type triterpenes (1–4) were isolated from D. complanatum. Their chemical structures were elucidated as 14α,15α,20β,21β,24,27α,29-heptahydroxyserrat-3-one (1), 3β,14α,15α,20β,21β,24,27α,29-octahydroxyserratane (2), 3α,14α,20β,21β,24,27α,29-heptahydroxyserratane (3) and 3β,14α,21β,24,27α-pentahydroxyl-serratane-29-yl (E)-p-coumarate (4) by spectroscopic methods (MS, 1D and 2D NMR) and X‐ray crystallography. Interestingly, the most characteristic methylene (C-27) of the serratane ring C was oxidized to a methine. Compound 4 showed significant cytotoxic activity against the human leukemia K562/S and the doxorubicin-resistant K562/R cell lines, but the other compounds were inactive.

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Prof. Dr. Minghua Qiu

State Key Laboratory of Phytochemistry and Plant Resources in West China
Kunming Institute of Botany
The Chinese Academy of Sciences

132# Lanhei Road, Heilongtan

Kunming 650204

People's Republic of China

Phone: + 86 87 15 22 33 27

Fax: + 86 87 15 22 32 55

Email: mhchiu@mail.kib.ac.cn

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