New anti-inflammatory sterols from a gorgonian Pinnigorgia sp

Yin-Di Su; Ching-Hsiao Cheng; Zhi-Hong Wen; Yang-Chang Wu; Ping-Jyun Sung

doi:10.1016/j.bmcl.2016.05.015

New anti-inflammatory sterols from a gorgonian Pinnigorgia sp

Bioorg Med Chem Lett. 2016 Jul 1;26(13):3060-3063. doi: 10.1016/j.bmcl.2016.05.015. Epub 2016 May 10.

Authors

Yin-Di Su¹, Ching-Hsiao Cheng², Zhi-Hong Wen³, Yang-Chang Wu⁴, Ping-Jyun Sung⁵

Affiliations

¹ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan; National Museum of Marine Biology and Aquarium, Pingtung 944, Taiwan.
² Department of Neurosurgery, Kaohsiung Chang Gung Memorial Hospital and Chang Gung University College of Medicine, Kaohsiung 833, Taiwan.
³ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan.
⁴ School of Pharmacy, College of Pharmacy, China Medical University, Taichung 404, Taiwan; Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404, Taiwan; Center for Molecular Medicine, China Medical University Hospital, Taichung 404, Taiwan; Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan. Electronic address: yachwu@mail.cmu.edu.tw.
⁵ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan; National Museum of Marine Biology and Aquarium, Pingtung 944, Taiwan; Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404, Taiwan; Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan; Graduate Institute of Marine Biology, National Dong Hwa University, Pingtung 944, Taiwan. Electronic address: pjsung@nmmba.gov.tw.

PMID: 27217003
DOI: 10.1016/j.bmcl.2016.05.015

Abstract

Chemical investigation on the EtOAc-soluble fraction from the MeOH/DCM extract of a gorgonian Pinnigorgia sp. afforded two new sterols, 11-acetoxy-24S-methyl-3β,5α,6α-trihydroxy-9,11-secocholest-7-en-9-one (1) and 5β,6β-epoxy-(22E,24R)-ergosta-8,22-diene-3β,7β-diol (2). The structures of sterols 1 and 2 were elucidated on the basis of spectroscopic analysis and by comparison of their spectroscopic data with those of related analogues. Both 1 and 2 were shown to significantly inhibit the accumulation of the pro-inflammatory iNOS and COX-2 protein in LPS-stimulated RAW264.7 macrophage cells.

Keywords: Anti-inflammatory activity; COX-2; Gorgonian; Pinnigorgia; Sterol; iNOS.

Publication types

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

MeSH terms

Animals
Anthozoa / chemistry*
Anti-Inflammatory Agents / chemistry
Anti-Inflammatory Agents / isolation & purification
Anti-Inflammatory Agents / pharmacology*
Cell Line, Tumor
Cyclooxygenase 2 / metabolism
Cyclooxygenase 2 Inhibitors / chemistry
Cyclooxygenase 2 Inhibitors / isolation & purification
Cyclooxygenase 2 Inhibitors / pharmacology
Ergosterol / analogs & derivatives*
Ergosterol / chemistry
Ergosterol / isolation & purification
Ergosterol / pharmacology
Lipopolysaccharides / pharmacology
Mice
Nitric Oxide Synthase Type II / antagonists & inhibitors
Secosteroids / chemistry
Secosteroids / isolation & purification
Secosteroids / pharmacology*
Sterols / chemistry
Sterols / isolation & purification
Sterols / pharmacology*

Substances

11-acetoxy-24-methyl-3,5,6-trihydroxy-9,11-secocholest-7-en-9-one
5,6-epoxyergosta-8,22-diene-3,7-diol
Anti-Inflammatory Agents
Cyclooxygenase 2 Inhibitors
Lipopolysaccharides
Secosteroids
Sterols
Nitric Oxide Synthase Type II
Ptgs2 protein, mouse
Cyclooxygenase 2
Ergosterol