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Paper | Regular issue | Vol 65, No. 4, 2005, pp.809-822
Published online, 10th February, 2005
DOI: 10.3987/COM-05-10327
New Labdane-Type Diterpenoids from Croton oblongifolius and Their Cytotoxic Activity

Chaiyo Chaichantipyuth,* Amorn Petsom, Pagorn Taweechotipatr, Nongnuj Muangsin, Narongsak Chaichit, Songchan Puthong, Sophon Roengsumran, Masatoshi Kawahata, Toshiko Watanabe, and Tsutomu Ishikawa

*Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan


Eight new labdane-type diterpenoids (1-3) and (5-9) and hardwickiic acid (4), a clerodane, were isolated from the stem bark of Croton oblongifolius. Their structures were established to be 3-oxygenated ent-manoyl oxide derivatives with a 8,13-epoxytricyclic ring system and hydroxylabdandienes on the basis of spectroscopic and X-Ray crystallographic analysis. The absolute stereochemistry of the core labdane skeleton was deduced to be (5S,8S,9S,10R,13S) from the X-Ray crystallographic analysis of the p-bromobenzoate of ent-3α-hydroxymanoyl oxide (3) and mutual chemical correlation. Cytotoxicity of these compounds was tested against a panel of human tumor cell lines.