Klyflaccisteroids K-M, bioactive steroidal derivatives from a soft coral Klyxum flaccidum

Yi-Ying Tsai; Chiung-Yao Huang; Wan-Ru Tseng; Pei-Lun Chiang; Tsong-Long Hwang; Jui-Hsin Su; Ping-Jyun Sung; Chang-Feng Dai; Jyh-Horng Sheu

doi:10.1016/j.bmcl.2017.01.060

Klyflaccisteroids K-M, bioactive steroidal derivatives from a soft coral Klyxum flaccidum

Bioorg Med Chem Lett. 2017 Mar 1;27(5):1220-1224. doi: 10.1016/j.bmcl.2017.01.060. Epub 2017 Jan 21.

Authors

Yi-Ying Tsai¹, Chiung-Yao Huang¹, Wan-Ru Tseng¹, Pei-Lun Chiang², Tsong-Long Hwang³, Jui-Hsin Su⁴, Ping-Jyun Sung⁴, Chang-Feng Dai⁵, Jyh-Horng Sheu⁶

Affiliations

¹ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan.
² Department of Biochemistry, University of Toronto, Toronto M5G2R3, Canada.
³ Graduate Institute of Natural Products, School of Traditional Medicine, College of Medicine, and Chinese Herbal Medicine Research Team, Healthy Aging Research Center, Chang Gung University, Taoyuan 333, Taiwan; Department of Cosmetic Science and Research Center for Industry of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 333, Taiwan.
⁴ National Museum of Marine Biology & Aquarium, Pingtung 944, Taiwan.
⁵ Institute of Oceanography, National Taiwan University, Taipei 112, Taiwan.
⁶ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan; Department of Medical Research, China Medical University Hospital, China Medical University, Taichung 404, Taiwan; Graduate Institute of Natural Products, School of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan; Frontier Center for Ocean Science and Technology, National Sun Yat-sen University, Kaohsiung 804, Taiwan; Doctoral Degree Program in Marine Biotechnology, National Sun Yat-sen University, Kaohsiung 804, Taiwan. Electronic address: sheu@mail.nsysu.edu.tw.

PMID: 28159416
DOI: 10.1016/j.bmcl.2017.01.060

Abstract

New steroids, klyflaccisteroids K-M (1-3), were isolated from a soft coral Klyxum flaccidum. Their structures were elucidated on the basis of extensive spectroscopic analysis. Klyflaccisteroid K (1) is the unique 9,11-secosteroid with a 5,8-epidioxy-9-ene functional group. Klyflaccisteroid L (2) has an unusual 11-norsteroid skeleton and is the first example of 11-oxasteroid isolated from natural sources. Cytotoxicity assay showed that 1 and 3 possessed moderate to weak cytotoxicity against these cancer cells. Compound 1 was also found to display significant anti-inflammatory activity of suppressing superoxide anion generation (O₂^-) and elastase release, and compound 3 was found to show notable anti-inflammatory activity toward inhibition of elasstase release, too.

Keywords: Anti-inflammatory activity; Cytotoxicity; Klyflaccisteroid; Klyxum flaccidum; Steroid.

Publication types

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

MeSH terms

Animals
Anthozoa / chemistry*
Anti-Inflammatory Agents / chemistry
Anti-Inflammatory Agents / pharmacology*
Cell Line, Tumor
Cell Survival / drug effects
Humans
Inhibitory Concentration 50
Neutrophils / drug effects*
Steroids / chemistry*
Steroids / pharmacology
Superoxides / antagonists & inhibitors

Substances

Anti-Inflammatory Agents
Steroids
klyflaccisteroid K
klyflaccisteroid L
Superoxides