abeo-taxane diterpenoids from the Taiwanese yew Taxus sumatrana
Journal
Chemistry and Biodiversity
Journal Volume
6
Journal Issue
12
Pages
2255-2262
Date Issued
2009
Author(s)
Abstract
Chemical investigation of the acetonic extract of the leaves and twigs of Taxus sumatrana (Taxaceae) led to the isolation of four new taxane diterpene esters, taiwantaxins A-D (1-4, resp.). Their structures were determined primarily on the basis of 1D- and 2D-NMR techniques as well as MS. Compound 1 is a rearranged taxane diterpenoid possessing an opened oxetane ring moiety containing C(4), C(5), and C(20). The metabolites 2 and 3 belong to a 5/6/6 taxene system having a rare five-membered g-lactone ring comprising C(8), C(9), C(10), and C(19). Compound 4 is an example of a taxane diterpene containing a 6/8/6 ring system with a tetrahydrofuran ring comprising C(2), C(3), C(4), and C(20). The 11(15→1)abeo-taxane diterpenoids, taiwantaxins A-C (1-3, resp.) are lacking an O-bearing functionality at either C(13) or C(14). Compound 2 showed significant cytotoxic activity against human PC-3 tumor cells. ? 2009 Verlag Helvetica Chimica Acta AG.
Other Subjects
abeo taxane diterpenoid derivative; diterpenoid; gamma lactone derivative; herbaceous agent; oxetane derivative; taiwantaxin a; taiwantaxin b; taiwantaxin c; taiwantaxin d; tetrahydrofuran; unclassified drug; article; cancer cell culture; carbon nuclear magnetic resonance; chemical structure; controlled study; cytotoxicity; human; mass spectrometry; metabolite; nonhuman; prostate cancer; proton nuclear magnetic resonance; Taxus; Taxus sumatrana; tumor cell; Antineoplastic Agents, Phytogenic; Bridged Compounds; Cell Line, Tumor; Diterpenes; Humans; Magnetic Resonance Spectroscopy; Molecular Conformation; Plant Leaves; Plant Stems; Taiwan; Taxoids; Taxus; Taxaceae; Taxus; Taxus sumatrana
Type
journal article