Ningpoensines A–C: unusual zwitterionic alkaloids from Scrophularia ningpoensis

[Display omitted] 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 abso...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 56; no. 40; pp. 5453 - 5456
Main Authors Zhang, Jun, Ip, Fanny C.F., Tong, Estella P.S., Chan, Kim Wan, Li, Liang-Chun, Ng, Yu Pong, Ip, Nancy Y.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.09.2015
Elsevier
Subjects
Chemistry
Chemistry, Organic
Ningpoensines A–C
Physical Sciences
Science & Technology
Scrophularia ningpoensis
Wound closure
Zwitterionic alkaloids
Zwitterionic alkaloids
Scrophularia ningpoensis
Wound closure
Ningpoensines A–C
Ningpoensines A-C
IRIDOIDS
PHENYLPROPANOID GLYCOSIDES
HARPAGOSIDE
Online AccessGet full text

Cover

More Information
Summary:[Display omitted] 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.08.021