Sesquiterpenoids and Cytotoxic Lignans from the Bark of Libocedrus chevalieri

Ying-Jun Zhang,†§ Marc Litaudon,*† Hadjira Bousserouel,† Marie-Therese Martin,† Odile Thoison,† Stéphane Léonce,‡ Vincent Dumontet,† Thierry Sévenet,† and Francoise Guéritte*†
Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, 91198 Gif-sur-Yvette Cedex, France, and Institut de Recherche Servier, 125 Chemin de Ronde, 78290 Croissy-sur-Seine, France
J. Nat. Prod., 2007, 70 (8), pp 1368–1370
DOI: 10.1021/np070124q
Publication Date (Web): August 4, 2007
Copyright © 2007 American Chemical Society and American Society of Pharmacognosy
†

 Institut de Chimie des Substances Naturelles, CNRS, Gif-sur-Yvette.

,
§

 Present address:  Kunming Institute of Botany, Chinese Academy of Sciences, Heilongtan, Kunming 650204, China.

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*

 To whom correspondence should be addressed. Tel:  +33-01-522-3235. Fax:  +33-01-515-0124. E-mail:  litaudon@icsn.cnrs-gif.fr; gueritte@ icsn.cnrs-gif.fr.

,
‡

 Institut de Recherche Servier, Croissy-sur-Seine.

Abstract

Abstract Image

Investigation of an EtOAc extract of the bark of Libocedrus chevalieri led to the isolation of a new cytotoxic lignan, 5-methoxy-4-epipodophyllotoxin (1), and three known podophyllotoxin analogues, 5-methoxypodophyllotoxin, 5-methoxypodophyllotoxin-4-O-β-d-glucoside, and podophyllotoxin-4-O-β-d-glucoside. Six sesquiterpenoids and a diterpenoid were also obtained. Of these, compounds 2−4 are new sesquiterpenoids, named libocedrines A−C, and 3β-hydroxyilicic alcohol was isolated for the first time from a higher plant. Structures of the new compounds were determined on the basis of spectroscopic methods. Cytotoxicity of the isolated compounds against KB and L1210 cells and their effects on tubulin assembly were evaluated.

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History

  • Published In Issue August 24, 2007
  • Received March 22, 2007

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