Bioactive polyhydroxylated sterols from the marine sponge Haliclona crassiloba

• Published in: Steroids Vol. 78; no. 14; pp. 1353 - 1358
• Main Authors: Cheng, Zhong-Bin, Xiao, Han, Fan, Cheng-Qi, Lu, Ya-Nan, Zhang, Ge, Yin, Sheng
• Format: Journal Article
• Language: English
• Published: NEW YORK Elsevier Inc 20.12.2013; Elsevier
• Subjects: Animals; Anti-Infective Agents - chemistry; Anti-Infective Agents - isolation & purification; Anti-Infective Agents - pharmacology; anti-infective properties; Antibacterial activity; Bacillus - drug effects; Bacillus - growth & development; Bacillus subtilis - drug effects; Bacillus subtilis - growth & development; Biochemistry & Molecular Biology; Candida - drug effects; Candida - growth & development; Endocrinology & Metabolism; Enterococcus faecalis - drug effects; Enterococcus faecalis - growth & development; fungi; Haliclona - chemistry; Haliclona - metabolism; Haliclona crassiloba; Hydroxylation; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Molecular Structure; Polyhydroxylated sterols; Porifera; Science & Technology; spectroscopy; Staphylococcus aureus - drug effects; Staphylococcus aureus - growth & development; sterols; Sterols - chemistry; Sterols - isolation & purification; Sterols - pharmacology; Structure elucidation; Polyhydroxylated sterols; Antibacterial activity; Structure elucidation; Haliclona crassiloba; CORAL SINULARIA-MAYI; SARCOPHYTON SP; SOFT CORAL; BOND; SARCOSTEROL
• ISSN: 0039-128X; 1878-5867; 1878-5867
• DOI: 10.1016/j.steroids.2013.10.004

[Display omitted] •Four new polyhydroxylated sterols were isolated from the sponge Haliclona crassiloba.•This is the first report of a steroid profile for this species.•Compounds 1 and 2 represented rare examples of Δ17(20) steroids.•Structures were established by spectroscopic methods and comparisons with literature values.•Two compounds showed moderate activity against some of the Gram-positive strains. Four new polyhydroxylated sterols, named halicrasterols A–D (1–4), together with six known analogs (5–10) were isolated from the marine sponge Haliclona crassiloba. Compounds 1 and 2 represented rare examples of steroids featuring 17(20)E-double bonds. The structures of 1–10 were elucidated by spectroscopic analysis and comparison with reported data. This is the first report of a steroid profile for this species. The antimicrobial activities of 1–10 were evaluated against a panel of bacterial and fungal strains in vitro, and compounds 4 and 9 showed moderate activity against some of the Gram-positive strains with MICs ranging from 4 to 32μg/mL.