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Planta Med 2010; 76(4): 353-357
DOI: 10.1055/s-0029-1186168
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

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

Jian Yan1 , 2 , Lirong Sun3 , Wei Li4 , Lin Zhou1 , Zhongrong Li1 , Xianmin Zhang1 , Ling Yang4 , Minghua Qiu1
  • 1State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, the Chinese Academy of Sciences, Kunming, People's Republic of China
  • 2South China Botanical Garden, the Chinese Academy of Sciences, Guangzhou, People's Republic of China
  • 3School of Basic Medical Sciences, Southern Medical University, Guangzhou, People's Republic of China
  • 4Laboratory of Pharmaceutical Resources Discovery, Dalian Institute of Chemical Physics, the Chinese Academy of Sciences, Dalian, People's Republic of China
Further Information

Publication History

received July 5, 2009 revised August 20, 2009

accepted August 26, 2009

Publication Date:
28 September 2009 (online)

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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.

Key words

Lycopodiaceae - Diphasiastrum complanatum - serratane‐type - complanatumols A–D - leukemia

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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

    www.thieme-connect.de/ejournals/toc/plantamedica