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Studies on Diterpenoid Constituents from Taxus sumatrana in TaiwanJhuang, Chuan-fu 13 February 2008 (has links)
Taxol is a complex polyoxygenated diterpene isolated from Pacific yew (Taxus brevifolia). The structures of Taxoids are diversified with species, season and growth environment and the clinical effectiveness of Taxol as a microtubule-stabilizing therapeutic agent for treatment of several malignancies has motivated many scientists to isolate new taxoids and investigate their anti-tumor activities.
In this continuing search for new and bioactive natural taxoids, reinvestigation of the acetone extract of the twigs, needles and branches of Taxus sumatrana (Taxaceae) afforded thirty-seven taxane diterpenes esters, including sumataxins sumataxin A (1)¡Bsumataxin B (2)¡Bsumataxin C (3)¡Bsumataxin D (4)¡Btaxuyunnanine C (5)¡B5a,7B,9a,10B,13a-petaacetoxy-4(20),11-taxadiene (6)¡B2a,5a,9a,10B,14B-pentaacetoxytaxa-4(20),11-taxadiene (7)¡B14B-hydroxytaxusin (8)¡B2a-deacetoxytaxinine J (9)¡Btaxa-4-(20),11-diene-2a,5a,7B,9a,10B,13a-hexaol hexaacetate (10)¡B1-dehydroxy baccatin VI (11)¡B7B,9a,10B,13a,20-pentaacetoxy-2a-benzoyloxy-4a,5a-dihydroxytax-11-ene (12)¡Btaxacin (13)¡Bbaccatin VI (14)¡Btaxuspinanane J (15)¡B2-deacetoxy-5-decinnamoyltaxinine J (16)¡BN-Methyl taxol C (17)¡B10-deacetyl yunnanaxane (18)¡Btaxumairol B (19)¡Btaxinine M (20)¡Bbaccatin III (21)¡Btaxuspinanane I (22)¡Btaxumairol K (23)¡Bwallifoliol (24)¡B13-oxo-baccatin III (25)¡Btaxol (26)¡B7-epi-10-deacetyl taxol (27)¡B10-deacetyl-13-oxo-baccatin III (28)¡B19-hydroxybaccatin III (29)¡B10-deacetyl taxol (30)¡B10-deacetyl-baccatin III (31)¡B13-acetyl-13-decinamoyltaxachinin B (32)¡B5-deacetyltaxachitriene B (33)¡B5-epicanadensene (34)¡Btaxezopidine F (35)¡B13a,7B-diacetoxy-2a,5a,10B-trihydroxy-9-keto-2(3¡÷20)abeotaxane (36)¡B2-deacetyl taxine B (37). The structures of new compounds were established on the basis of their spectroscopic analyses. Among them, compounds 1, 2, 3 and 4 are new compounds from natural source, 2a-deacetoxytaxinine J (9)¡Btaxuspinanane J (15) had effects on PBMC (Peripheral Blood Mononuclear Cells) proliferation, and sumataxin A¡BD (1¡B4) had light exhibitedactivity of HSV-1.
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Studies on Diterpenoid Constituents from Formosan Taxus sumatranaHsu, Shiao-Man 08 February 2006 (has links)
Abstract
In recent years, Taxus species have attracted a great interest because Paclitaxel, an anticancer agent, was isolated from T.brevifolia. Since the discovery of Paclitaxel many new taxane diterpenes from various Taxus species were isolated. In order to discover new taxoids, twigs and leaves of Taxus sumatrana (Miq.) de Laub. Growing in Taiwan were employed. Chromatographic separation of acetone extract of the leaves and twigs of the plant has yielded four taxane diterpenes and one derivative, designated tasumatrol M (1), tasumatrol N (2), tasumatrol O (3) and 7-deacetyl-canadensene (4). All structures were established primarily on the basis of 1D and 2D NMR techniques, including DEPT, COSY, HMBC and NOESY experiments. Compound 1, 2 and 3 were inactive as tested against human KB, Hepa59T, Hela, DLD-1 and WiDr tumor cell lines. Compounds 1 and 2, possessing a bicyclic skeleton, together with compounds 3 were new compounds from natural source. The possible biosynthetic pathway of compounds 1 and 2 were derived from
geranylgeranyl pyrophosphate and verticillene.
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