Bioactive sesquiterpene derivatives from mangrove endophytic fungus Phomopsis sp. SYSU-QYP-23: Structures and nitric oxide inhibitory activities

Yan Chen; Hongju Liu; Ge Zou; Wencong Yang; Lishan Zhang; Zhangyuan Yan; Yuhua Long; Zhigang She

doi:10.1016/j.bioorg.2020.104530

Bioactive sesquiterpene derivatives from mangrove endophytic fungus Phomopsis sp. SYSU-QYP-23: Structures and nitric oxide inhibitory activities

Bioorg Chem. 2021 Feb:107:104530. doi: 10.1016/j.bioorg.2020.104530. Epub 2020 Dec 3.

Authors

Yan Chen¹, Hongju Liu², Ge Zou³, Wencong Yang³, Lishan Zhang², Zhangyuan Yan⁴, Yuhua Long⁵, Zhigang She⁶

Affiliations

¹ School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, PR China; National R & D Center for Edible Fungus Processing Technology, Henan University, Kaifeng 475004, China.
² School of Pharmacy, Guangdong Medical University, Dongguan 523808, PR China.
³ School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, PR China.
⁴ School of Chemistry, South China Normal University, Guangzhou 510006, PR China.
⁵ School of Chemistry, South China Normal University, Guangzhou 510006, PR China. Electronic address: longyh@scnu.edu.cn.
⁶ School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, PR China. Electronic address: cesshzhg@mail.sysu.edu.cn.

PMID: 33323272
DOI: 10.1016/j.bioorg.2020.104530

Abstract

Eight new sesquiterpene derivatives (2, 4-6 and 10-13), along with five known analogues were isolated from the mangrove endophytic fungus Phomopsis sp. SYSU-QYP-23. Their structures of new compounds were established by spectroscopic methods, and the absolute configurations were confirmed by single-crystal X-ray diffraction analysis and comparison of the experimental ECD spectra. The absolute configuration of the side chain in 1 was first defined by modified Mosher's method. Compounds 1-7 showed potent inhibitory activities against nitric oxide (NO) production in lipopolysaccharides (LPS) induced RAW 264.7 cells with IC₅₀ values ranging from 8.6 to 14.5 μM. The molecular docking results implied that the bioactive sesquiterpenes may directly bind with targeting residues in the active cavity of iNOS protein.

Keywords: Anti-inflammatory activity; Mangrove endophytic fungus; Molecular docking; Phomopsis sp.; Sesquiterpene derivatives.

Published by Elsevier Inc.

Publication types

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

MeSH terms

Animals
Enzyme Inhibitors / chemical synthesis
Enzyme Inhibitors / isolation & purification
Enzyme Inhibitors / metabolism
Enzyme Inhibitors / pharmacology*
Humans
Hydrogen Bonding
Mice
Molecular Docking Simulation
Nitric Oxide / antagonists & inhibitors*
Nitric Oxide Synthase Type II / antagonists & inhibitors*
Nitric Oxide Synthase Type II / chemistry
Nitric Oxide Synthase Type II / metabolism
Phomopsis / chemistry*
Protein Binding
RAW 264.7 Cells
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification
Sesquiterpenes / metabolism
Sesquiterpenes / pharmacology*

Substances

Enzyme Inhibitors
Sesquiterpenes
Nitric Oxide
NOS2 protein, human
Nitric Oxide Synthase Type II
Nos2 protein, mouse