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Tri- and Bicyclic Taxoids from the Taiwanese Yew Taxus sumatrana

✍ Scribed by Lon-Je Luh; Mohamed H. Abd El-Razek; Chia-Ching Liaw; Chen-Tung Arthur Chen; Yun-Sheng Lin; Yao-Haur Kuo; Ching-Te Chien; Ya-Ching Shen

Publisher
John Wiley and Sons
Year
2009
Tongue
German
Weight
197 KB
Volume
92
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Five new taxoids, including a new 2(3→20)‐abeo‐taxane with a 6/10/6‐membered ring system and four 3,8‐seco‐taxanes having a 6/12‐membered ring system, were isolated from an acetone extract of the leaves and twigs of the Taiwanese yew (Taxus sumatrana, Taxaceae). The structures were established as 2__α__,7__β__,10__α__‐triacetoxy‐5__α__‐hydroxy‐2(3→20)‐abeo‐taxa‐4(20),11‐dien‐9,13‐dione (1), (3__E__,8__E__)‐2__α__,9,10__β__, 13__α__,20‐pentaacetoxy‐7__β__‐hydroxy‐3,8‐secotaxa‐3,8,11‐trien‐5‐one (2), (3__E__,8__E__)‐2__α__,9,10__β__,13__α__,20‐pentaacetoxy‐5__α__,7__β__‐dihydroxy‐3,8‐secotaxa‐3,8,11‐triene (3), (3__E__,8__E__)‐9,10__β__,13__α__‐triacetoxy‐2__α__,7__β__,20‐trihydroxy‐5__α__‐[(2__E__)‐cinnamoyloxy]‐3,8‐secotaxa‐3,8,11‐triene (4), and (3__E__,8__E__)‐2__α__,5__α__,7__β__,9,10__β__,13__α__‐hexaacetoxy‐20‐hydroxy‐3,8‐secotaxa‐3,8,11‐triene (5), respectively, on the basis 1D‐ and 2D‐NMR spectral analyses. The in vitro cytotoxic activity of compounds 1–5 against four human tumor cell lines, including HeLa (cervical epitheloid), WiDr (colon), Daoy (medulloblastoma), and Hep2 (liver carcinoma) tumor cells was evaluated. Whereas compounds 1–3 were inactive, the novel taxanes 4 and 5 showed significant cytotoxicity.

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