Ningpoensines A–C: unusual zwitterionic alkaloids from Scrophularia ningpoensis. Issue 40 (30th September 2015)

• Record Type: Journal Article
• Authors: Zhang, Jun; Ip, Fanny C.F.; Tong, Estella P.S.; Chan, Kim Wan; Li, Liang-Chun; Ng, Yu Pong; Ip, Nancy Y.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 40(2015)
• Page Start: 5453
• Page End: 5456
• Publication Date: 2015-09-30
• Subjects: Zwitterionic alkaloids -- Scrophularia ningpoensis -- Ningpoensines A–C -- Wound closure; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.08.021
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Three novel zwitterionic alkaloids—ningpoensine A (1 ) and a pair of epimers, ningpoensines B/C (2a /2b )—with unprecedented molecular skeletons were isolated from the root of Scrophularia ningpoensis . Their structures were established by extensive spectroscopic analyses, and the absolute configuration of ningpoensine A was determined by quantum chemical calculations. A biosynthetic pathway leading to ningpoensines A–C from harpagide and natural amino acids is proposed. Ningpoensines B/C tended to promote wound closure in human embryonic keratinocytes.