Taxuspines U, V, and W, new taxane and related diterpenoids from the Japanese yew Taxus cuspidata

Hosoyama, Hirokazu; Inubushi, Akiko; Katsui, Takie; Shigemori, Hideyuki; Kobayashi, Jun’ichi

doi:10.1016/0040-4020(96)00777-6

Cited by 39 publications

(27 citation statements)

References 11 publications

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“…Table 1. Structural and biological properties of taxanes (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) and epothilones (15,16,(18)(19)(20)(21) used in this study location of paclitaxel binding site in the β subunit but lacked the resolution to exactly define the whole ligand conformation. As a consequence, not all the amino acid residues were well solved and paclitaxel was replaced by the X-ray structure of docetaxel.…”

Section: Resultsmentioning

confidence: 99%

“…One of the most interesting taxanes fitted into our pseudoreceptor has been taxuspine U, 15 which seemed to adopt a paclitaxel-like bioactive conformation when docked into the binding pocket. Taxuspine U (22) and X 16 (23) were found in methanolic extract of stems of genus Taxus and are constituted by the A ring of paclitaxel condensed with a 12-membered ring macrocycle ( Figure 5).…”

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confidence: 99%

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A pharmacophore modeling approach to design new taxol® mimics: towards the synthesis of potential anticancer and MDR-reversing agent

Renzulli¹,

Rocheblave²,

Avramova³

et al. 2006

Arkivoc

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The remarkable therapeutic importance of taxane diterpenoids as anticancer drugs and their challenging structural complexity have stimulated worldwide enormous efforts. Our group developed a theoretic quantitative model describing the relationship between structure and biological activity of microtubules-stabilizing anticancer agents (MSAAs) aimed at gaining an insight into the specific structural features required for the ligand-receptor binding. The model was demonstrated to be able to estimate/predict the microtubule-stabilising activity for a series of taxanes and provided further details about the influence of each pharmacophore point on the ligand binding affinity. Molecular modeling studies from our group revealed that modified Taxuspines U and X could adopt a conformation similar to the bioactive conformation of paclitaxel and can be well accommodated within the pseudoreceptor model. Following the suggestions coming from the model we rationally designed and synthesized new simplified taxuspine U analogues. In particular, we developed a new methodology for the synthesis of such compounds involving a macrocyclisation reaction via RCM in presence of different functional groups.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

A pharmacophore modeling approach to design new taxol® mimics: towards the synthesis of potential anticancer and MDR-reversing agent

Renzulli¹,

Rocheblave²,

Avramova³

et al. 2006

Arkivoc

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“…3,8-Secotaxanes were first reported simultaneously in 1995 from Chinese yew, T. chinensis [98], and Canadian yew, T. canadensis [99], independently. Later, this class of taxanes is also isolated from T. mairei [100] and T. cuspidata [28]. So far, five bicyclic taxanes (154 -158) are isolated from T. cuspidata.…”

Section: 144mentioning

confidence: 96%

Chemical Studies on Taxus cuspidata

Dong

Zhang

et al. 2010

Chemistry & Biodiversity

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“…2). Taxuspines J (9), M (12), O (14), and Y (24) were also assigned as 11(15!1)-abeo-taxanes on the basis of 2D NMR data. Taxuspines J (9) and M (12) were 10-debenzoyl-10-acetyltaxuspine A and 10-debenzoyltaxuspine A, respectively, while taxuspines O (14) and Y (24) contained a carbonyl group at C-13.…”

Section: Introductionmentioning

confidence: 99%

Bioactive taxoids from the Japanese yew Taxus cuspidata

Kobayashi

Shigemori

2002

Medicinal Research Reviews

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A series of new taxoids, named taxuspines A-H and J-Z (1-25) and taxezopidines A-H and J-L (26-36), have been isolated together with 37 known taxoids (37-73) including paclitaxel (53) from the Japanese yew, Taxus cuspidata Sieb. et Zucc. (Taxaceae). These new taxoids possess various skeletons containing 5/7/6, 6/10/6, 6/5/5/6, 6/8/6, or 6/12-membered ring systems. Among the new taxoids, some non-taxol-type compounds remarkably reduced CaCl(2)-induced depolymerization of microtubules, or increased cellular accumulation of vincristine in multidrug-resistant tumor cells as potent as verapamil. On the other hand, chemical derivatization of taxinine (37), one of major taxoids obtained from this yew, led to the discovery of unusual reactions of taxinine derivatives. Here we describe our recent results on the isolation, structure elucidation, and bioactivity of these new and known taxoids and the formation of unexpected products of the unusual reactions of taxinine.

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Taxuspines U, V, and W, new taxane and related diterpenoids from the Japanese yew Taxus cuspidata

Cited by 39 publications

References 11 publications

A pharmacophore modeling approach to design new taxol® mimics: towards the synthesis of potential anticancer and MDR-reversing agent

A pharmacophore modeling approach to design new taxol® mimics: towards the synthesis of potential anticancer and MDR-reversing agent

Chemical Studies on Taxus cuspidata

Bioactive taxoids from the Japanese yew Taxus cuspidata

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