Brassinosteroid analogues from the fruiting bodies of Laetiporus sulphureus and their anti-inflammatory activity

Qosimjon Khalilov; Liya Li; Yushuang Liu; Wei Liu; Sodik Numonov; Haji Akber Aisa; Tao Yuan

doi:10.1016/j.steroids.2019.108468

Brassinosteroid analogues from the fruiting bodies of Laetiporus sulphureus and their anti-inflammatory activity

Steroids. 2019 Nov:151:108468. doi: 10.1016/j.steroids.2019.108468. Epub 2019 Aug 7.

Authors

Qosimjon Khalilov¹, Liya Li², Yushuang Liu¹, Wei Liu¹, Sodik Numonov³, Haji Akber Aisa⁴, Tao Yuan⁵

Affiliations

¹ The Key Laboratory of Plant Resources and Chemistry of Arid Zone, and State Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China; University of Chinese Academy of Sciences, Beijing 10009, China.
² Institute of Microbial Pharmaceuticals, College of Life and Health Sciences, Northeastern University, Shenyang 110819, China.
³ The Key Laboratory of Plant Resources and Chemistry of Arid Zone, and State Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China; Chinese Tajik Innovation Center for Natural Products, Dushanbe 734063, Tajikistan.
⁴ The Key Laboratory of Plant Resources and Chemistry of Arid Zone, and State Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China. Electronic address: haji@ms.xjb.ac.cn.
⁵ The Key Laboratory of Plant Resources and Chemistry of Arid Zone, and State Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China. Electronic address: yuantao@ms.xjb.ac.cn.

PMID: 31400389
DOI: 10.1016/j.steroids.2019.108468

Abstract

Three new brassinosteroid analogues, named sulphurenolide A, sulphurenolide B and sulphurenolide C, were isolated from the methanolic extract of fruiting bodies of Laetiporus sulphureus. Their structures were established on the basis of extensive spectroscopic analysis (1D, 2D NMR, and HRESIMS) and ECD calculation. Sulphurenolides A and B are a pair of C-20 epimer, and sulphurenolide B represents the first naturally occurring 20R-brassinosteroid. Moreover, sulphurenolides A-C are firstly reported 5-hydroxylation and homo-6-oxa derivatives of brassinosteroids from natural sources. Anti-inflammatory assay revealed that sulphurenolides B and C exhibited significant inhibitory effects on NO production in lipopolysaccharide-induced RAW264.7 cells, and sulphurenolide C showed stronger inhibition than that of positive control, minocycline.

Keywords: Anti-inflammatory; Brassinosteroid; Laetiporus sulphureus; Polyporaceae; RAW264.7.

Publication types

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

MeSH terms

Animals
Anti-Inflammatory Agents / chemistry*
Anti-Inflammatory Agents / pharmacology*
Brassinosteroids / chemistry*
Brassinosteroids / pharmacology*
Fruiting Bodies, Fungal / chemistry*
Mice
Models, Molecular
Molecular Conformation
Nitric Oxide / biosynthesis
Polyporales / chemistry*
RAW 264.7 Cells

Substances

Anti-Inflammatory Agents
Brassinosteroids
Nitric Oxide