Novel Taxa-4(20),12-diene and 2(3→20)<i>Abeo</i>taxane from Needles of<i>Taxus canadensis</i>

Ni, Zhi Yu; Wu, Yi Bing; Zhang, Man Li; Wang, Yu Fang; Dong, Ming; Sauriol, Françoise; Huo, Chang Hong; Shi, Qing; Gu, Yu‐Cheng; Kiyota, Hiromasa; Cong, Bin

doi:10.1271/bbb.110223

Cited by 3 publications

(1 citation statement)

References 14 publications

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“…Comparison of these data with those in the literature suggests the structure of 6 to be a 11(15→1) abeo -taxa-4(20)-ene-type taxoid, as evident from the 13 C NMR chemical shifts of an oxygenated quaternary carbon (C-15; δ C 88.6) and a quaternary carbon (C-1; δ C 61.3) . The characteristic olefinic signals at δ 5.50 (brs, H-13) and 126.9 (C-13) and the 1 H– 1 H COSY correlations (bold lines) between an olefinic proton H-13 and CH 2 -14 suggested the presence of an unusual double bond at C-12(13) in ring A, which was confirmed by the HMBC correlations between H-13/C-10 and H-13/C-11. The HMBC correlation between the H-10 oxymethine proton and quaternary oxygenated carbon at δ C 88.6 (C-15) indicated the presence of a C-10(15)-oxido bridge in 6 .…”

Section: Resultssupporting

confidence: 94%

α-Glucosidase Inhibitory and Cytotoxic Taxane Diterpenoids from the Stem Bark of Taxus wallichiana

et al. 2017

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From a CHCl extract of the bark of Taxus wallichiana, six new taxoids, wallitaxanes A-F (1-6), were isolated, together with 29 known compounds. The structures of the new compounds were elucidated on the basis of spectroscopic data interpretation. Wallitaxane D (4) was identified as an opened oxetane-type taxoid having the first naturally occurring C(H)-20 acetal group, while wallitaxanes E (5) and F (6) are representative of the rare abeo-taxoid class. The isolated compounds were evaluated for their α-glucosidase inhibitory activity and for cytotoxicity against the HeLa human cervical cancer cell line. In the present work, taxanes were found to exhibit α-glucosidase inhibitory activity for the first time, and wallitaxane A (1) showed the most potent effect, with an IC value of 3.6 μM. In turn, 7-epi-taxol (16) and 7-epi-10-deacetyltaxol (17) showed IC values of 0.05 and 0.085 nM, respectively, against HeLa cells.

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Section: Resultssupporting

confidence: 94%

α-Glucosidase Inhibitory and Cytotoxic Taxane Diterpenoids from the Stem Bark of Taxus wallichiana

et al. 2017

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Chemical Studies on Taxus canadensis

Qin

Wang

et al. 2013

Chemistry & Biodiversity

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A series of new taxanes, 1-93, have been isolated, together with 37 known taxoids including Taxol(®) (paclitaxel) and cephalomannine, from the Canadian yew, Taxus canadensis (Taxaceae) in the past 30 years. These new taxoids possess various skeletons containing 5/7/6, 6/10/6, 6/5/5/6, 6/8/6, and 6/12 ring systems and six new taxanes with four novel skeletons, i.e., a taxane with a 6/6/8/6 ring system, a taxane with a [3.3.3] propellane skeleton, three taxanes with [3.3.3] [3.4.5] dipropellane sytems, as well as a novel taxane with a unique 5/5/4/6/6/6 hexacyclic skeleton, containing a unique [3.3.2] propellane, were isolated for the first time from natural sources. It should be emphasized that 13-acetyl-9-dihydrobaccatin III, a very useful starting material for the semisynthesis of Taxol(®) and Taxotere(®) , represents the most abundant taxane in the needles of this yew tree. These findings establish the above mentioned yew tree as significantly different from the remaining species. On the other hand, some chemical modifications on the taxanes isolated from this plant were carried out.

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Diterpenoids of terrestrial origin

Hanson

2012

Nat. Prod. Rep.

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Novel Taxa-4(20),12-diene and 2(3→20)Abeotaxane from Needles ofTaxus canadensis

Cited by 3 publications

References 14 publications

α-Glucosidase Inhibitory and Cytotoxic Taxane Diterpenoids from the Stem Bark of Taxus wallichiana

α-Glucosidase Inhibitory and Cytotoxic Taxane Diterpenoids from the Stem Bark of Taxus wallichiana

Chemical Studies on Taxus canadensis

Diterpenoids of terrestrial origin

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