Two ring opened oxetane taxoids containing a C-20 benzoyloxy group from the roots of Taxus wallichiana Zucc. Issue 40 (4th October 2017)

• Record Type: Journal Article
• Authors: Dang, Phu H.; Nguyen, Hanh H.T.; Truong, Hien T.T.; Do, Truong N.V.; Nguyen, Hai X.; Nguyen, Mai T.T.; Abe, Manabu; Takagi, Ryukichi; Nguyen, Nhan T.
• Is Part Of: Tetrahedron letters. Volume 58:Issue 40(2017)
• Page Start: 3897
• Page End: 3900
• Publication Date: 2017-10-04
• Subjects: Taxus wallichiana -- Taxaceae -- Opened-oxetane ring -- C-20 benzoyloxy -- α-Glucosidase; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.08.073
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Based on spectroscopic analysis, the structures of two new taxanes were elucidated. The α -glucosidase inhibitory activities of isolated compounds were evaluated. The oxetane ring-opening process with the benzoyl migration were proposed. Abstract: Two new taxanes, named wallitaxane G (1 ) and H (2 ), were isolated from the roots of Taxus wallichiana (Taxaceae), together with nine known compounds (3 −11 ). Their structures were elucidated on the basis of NMR spectroscopic analysis and the relative configurations of1 and2 were determined based on NOESY data. Wallitaxane H (2 ) showed the most potent α-glucosidase inhibitory activity, with an IC50 value of 16.1 μM. Plausible biosynthetic pathways for the formation of1 and2 were proposed based on oxetane ring-opening and benzoyl migration.