Novel highly oxygenated and B-ring-seco-ent-diterpene glucosides from the seeds of Prinsepia utilis. Issue 50 (16th December 2015)

• Record Type: Journal Article
• Authors: Zhang, Qiao; Liu, Hong-Xin; Tan, Hai-Bo; Qiu, Sheng-Xiang
• Is Part Of: Tetrahedron. Volume 71:Issue 50(2015)
• Page Start: 9415
• Page End: 9419
• Publication Date: 2015-12-16
• Subjects: Rosaceae -- Prinsepia utilis -- Diterpene glucoside -- Prinsosides A, B and C; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.10.055
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Two novel highly oxygenated and one rare B-ring cleave ent -kaurane diterpene glucosides, named prinsoside A (1 ), B (2 ) and C (3 ), respectively, were isolated from an ethanolic extract of the seeds of Prinsepia utilis . To our knowledge, prinsoside B (2 ) was the most highly oxygenated ent -kaurane diterpene glucoside discovered in nature. Their structures were elucidated by various spectroscopic methods including 1D, 2D NMR and HR-ESI-MS analyses, with the absolute configurations clarified by CD measurements on their corresponding diterpenoid aglycones obtained by enzymatic hydrolysis with β-glucosidase. Compounds1 –3 exhibited weak α-glucosidase inhibitory activities. Graphical abstract: