Antifouling steroids from the South China Sea gorgonian coral Subergorgia suberosa

Jun Zhang; Yan Liang; Kai-Ling Wang; Xiao-Jian Liao; Zhou Deng; Shi-Hai Xu

doi:10.1016/j.steroids.2013.10.007

Antifouling steroids from the South China Sea gorgonian coral Subergorgia suberosa

Steroids. 2014 Jan:79:1-6. doi: 10.1016/j.steroids.2013.10.007. Epub 2013 Oct 31.

Authors

Jun Zhang¹, Yan Liang², Kai-Ling Wang³, Xiao-Jian Liao⁴, Zhou Deng⁴, Shi-Hai Xu⁵

Affiliations

¹ College of Pharmacy, Jinan University, Guangzhou 510632, PR China.
² Division of Life Science, School of Science, The Hong Kong University of Science and Technology, Hong Kong Special Administrative Region, PR China.
³ Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, PR China.
⁴ Department of Chemistry, Jinan University, Guangzhou 510632, PR China.
⁵ College of Pharmacy, Jinan University, Guangzhou 510632, PR China; Department of Chemistry, Jinan University, Guangzhou 510632, PR China. Electronic address: txush@jnu.edu.cn.

PMID: 24184487
DOI: 10.1016/j.steroids.2013.10.007

Abstract

Two new unusual cholestane derivatives, pentacyclic steroid 16,22-epoxy-20β,23S-dihydroxycholest-1-ene-3-one (1) and 20β,23S-dihydroxycholest-1-ene-3,22-dione (2), along with two new pregnane derivatives, 15β,17α-dihydroxypregna-4,6-diene-3,20-dione (3) and 11α-hydroxypregna-4-ene-3,6,20-trione (4), were isolated from the South China Sea gorgonian coral Subergorgia suberosa. Their structures were established based on the extensive analyses of 2D NMR, IR, and HRMS. Antifouling tests against Balanus amphitrite larvae settlement indicated that 1 and 2 exhibited inhibitory effect with EC50 values of 5.3, and 14.5 μg/mL, respectively.

Keywords: 20β,23S-Dihydroxycholest; Antifouing; Gorgonian coral; Pentacyclic steroid; Subergorgia suberosa.

Publication types

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

MeSH terms

Animals
Anthozoa / chemistry*
Biofouling / prevention & control*
Cholestanes / chemistry
Cholestanes / pharmacology
Cholestenones / chemistry
Cholestenones / pharmacology
Dose-Response Relationship, Drug
Larva / drug effects
Larva / growth & development
Magnetic Resonance Spectroscopy / methods
Mass Spectrometry
Molecular Structure
Oceans and Seas
Prednisone / analogs & derivatives
Prednisone / chemistry
Prednisone / pharmacology
Pregnadienediols / chemistry
Pregnadienediols / pharmacology
Pregnanes / chemistry
Pregnanes / pharmacology
Spectrophotometry
Stereoisomerism
Steroids / chemistry*
Steroids / pharmacology*
Thoracica / drug effects
Thoracica / growth & development

Substances

11-hydroxypregna-4-ene-3,6,20-trione
15,17-dihydroxypregna-4,6-diene-3,20-dione
16,22-epoxy-20,23-dihydroxycholest-1-ene-3-one
20,23-dihydroxycholest-1-ene-3,22-dione
Cholestanes
Cholestenones
Pregnadienediols
Pregnanes
Steroids
Prednisone