New taxane diterpenoids from the leaves and twigs of Taxus sumatrana.
Two new taxoids, taxumairol Q (1) and 13-O-acetyl wallifoliol (2), have been isolated from the leaves and twigs of Taxus sumatrana. Taxuspine F and wallifoliol (10) have been isolated for the first time from the yew T. sumatrana. Seventeen known taxoid diterpenoids have also been isolated. The new derivatives, 9,13-diacetyltaxumairol W (3), 10,13-dibenzoyltaxacustin (4), 7,13-diacetylwallifoliol (5), 7,13-dibenzoylwallifoliol (6), and 7,9-dibenzoyltaxumairol P (7), have been prepared by acylation of a crude mixture of taxoids. All structures were established primarily on the basis of 1D and 2D NMR techniques, including DEPT, COSY, and HMBC experiments, as well as chemical correlation with known compounds. Wallifoliol (10) exhibited significant cytotoxicities against both Hepa 59 T/VGH (human liver carcinoma) and KB (human oral epidermoid carcinoma) tumor cells. Taxuspine F and compound 5 possessed moderate activity against Hepa cells only, while 3, 6, 7, and 10-deacetylbaccatin III showed only marginal activity against Hepa cells.
Shen
Ya-Ching
YC
Institute of Marine Resources, National Sun Yat-sen University, 70 Lien Hai Road, Kaohsiung, Taiwan 80424, Republic of China. ycshen@mail.nsysu.edu.tw
Wang
Shih-Sheng
SS
Pan
Yu-Ling
YL
Lo
Kuang-Liang
KL
Chakraborty
Rupak
R
Chien
Ching-Te
CT
Kuo
Yao-Haur
YH
Lin
Yu-Chi
YC
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001952:Bridged-Ring Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007624:KB Cells; D015394:Molecular Structure; D018515:Plant Leaves / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D043823:Taxoids; D020946:Taxus / Q000737:chemistry*; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000972:Antineoplastic Agents, Phytogenic; D001952:Bridged-Ring Compounds; D004224:Diterpenes; D043823:Taxoids; C080625:taxane