Tasumatrols P – T, Five New Taxoids from Taxus sumatrana

✍ Scribed by Ya-Ching Shen; Yun-Sheng Lin; Shaw-Man Hsu; Ashraf Taha Khalil; Shih-Sheng Wang; Ching-Te Chien; Yao-Haur Kuo; Chang-Hung Chou

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: German
• Weight: 146 KB
• Volume: 90
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200790133

✦ Synopsis

Abstract

The phytochemical investigation of the more polar fractions from the leaves and twigs of Taxus sumatrana (Taxaceae) afforded five new taxane diterpene esters, tasumatrols P–T (1–5) possessing an 11(15→1),11(10→9)‐diabeotaxane skeleton. Compounds 1, 4, and 5 contain an α‐hydroxy group at C(14), while 3 has no OH group at either C(13) or C(14). Compound 2 is a natural 4,5‐acetonide derivative, while 4 has an unusual spiro‐connected 2‐hydroxy‐2‐phenyl‐1,3‐dioxolane ring. Ten known taxoids, were also isolated in the course of the chromatographic fractionation. Five additional new O‐acetyl derivatives 3a, 4a, 4b, 5a, and 5b were prepared from the taxanes 3–5. The structures of all new compounds were established on the basis of their spectroscopic analyses. Compound 1 showed mild cytotoxic activity against human Hela and Daoy tumor cells.