Sesquineolignan and neolignan enantiomers from Triadica sebifera

Min Yu; Yong-Li Zhang; Jin-Long Liu; Su-Juan Wang; Gui-Jie Zhang

doi:10.1016/j.bioorg.2020.104147

Sesquineolignan and neolignan enantiomers from Triadica sebifera

Bioorg Chem. 2020 Oct:103:104147. doi: 10.1016/j.bioorg.2020.104147. Epub 2020 Jul 28.

Authors

Min Yu¹, Yong-Li Zhang¹, Jin-Long Liu¹, Su-Juan Wang¹, Gui-Jie Zhang²

Affiliations

¹ College of Pharmacy, Guilin Medical University, Guilin 541199, People's Republic of China.
² College of Pharmacy, Guilin Medical University, Guilin 541199, People's Republic of China. Electronic address: zhangguijie001@126.com.

PMID: 32763522
DOI: 10.1016/j.bioorg.2020.104147

Abstract

Two pairs of new sesquineolignan enantiomers (1a/1b and 1c/1d), two pair of new 4',7-epoxy-8,3'-neolignan enantiomers (2a/2b and 3a/3b), and a pair of new 3',7-epoxy-8,4'-oxyneolignan enantiomers (4a/4b), along with two pairs of known 4',7-epoxy-8,3'-neolignan enantiomers (5a/5b and 6a/6b), were obtained from the stems and leaves of Triadica sebifera. The structures of the enantiomers were elucidated by spectroscopic analyses, and their absolute configurations were assigned by the experimental ECD spectra. Among them, compounds 5b, 6a and 6b showed inhibitory activities against NO production in activated microglial BV-2 cells, with IC₅₀ values of 14.3, 23.2 and 33.3 μM, respectively.

Keywords: NO inhibitors; Neolignan enantiomers; Sesquineolignan ennatiomers; Triadica sebifera.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Euphorbiaceae / chemistry*
Lignans / chemistry*
Molecular Structure
Stereoisomerism
Structure-Activity Relationship

Substances

Lignans