Bioactive polyhydroxylated sterols from the marine sponge Haliclona crassiloba

被引:32
作者
Cheng, Zhong-Bin [1 ]
Xiao, Han [1 ]
Fan, Cheng-Qi [2 ]
Lu, Ya-Nan [2 ]
Zhang, Ge [1 ]
Yin, Sheng [1 ]
机构
[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China
[2] Chinese Acad Fishery Sci, East China Sea Fisheries Res Inst, Shanghai 200090, Peoples R China
基金
中国国家自然科学基金;
关键词
Polyhydroxylated sterols; Structure elucidation; Antibacterial activity; Haliclona crassiloba; CORAL SINULARIA-MAYI; SOFT CORAL; SARCOPHYTON SP; SARCOSTEROL; BOND;
D O I
10.1016/j.steroids.2013.10.004
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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 32 mu g/mL. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1353 / 1358
页数:6
相关论文
共 21 条
[1]   Steroids from sponges: Recent reports [J].
Aiello, A ;
Fattorusso, E ;
Menna, M .
STEROIDS, 1999, 64 (10) :687-714
[2]  
Appeltans W., 2012, World Register of Marine Species
[3]   Steroids from the gorgonian Isis hippuris [J].
Chao, CH ;
Huang, LF ;
Wu, SL ;
Su, JH ;
Huang, HC ;
Sheu, JH .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (09) :1366-1370
[4]   C-13 NUCLEAR MAGNETIC-RESONANCE SPECTRA OF HYDROXY STEROIDS [J].
EGGERT, H ;
VANANTWERP, CL ;
BHACCA, NS ;
DJERASSI, C .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (01) :71-78
[5]   Densanins A and B, New Macrocyclic Pyrrole Alkaloids Isolated from the Marine Sponge Haliclona densaspicula [J].
Hwang, Buyng Su ;
Oh, Jung Soon ;
Jeong, Eun Ju ;
Sim, Chung J. ;
Rho, Jung-Rae .
ORGANIC LETTERS, 2012, 14 (24) :6154-6157
[6]   CONTACT ELECTRON-SPIN COUPLING OF NUCLEAR MAGNETIC MOMENTS [J].
KARPLUS, M .
JOURNAL OF CHEMICAL PHYSICS, 1959, 30 (01) :11-15
[7]   MARINE STEROLS [J].
KERR, RG ;
BAKER, BJ .
NATURAL PRODUCT REPORTS, 1991, 8 (05) :465-497
[8]   MARINE STEROLS .8. ISOLATION AND STRUCTURE OF SARCOSTEROL, A NEW STEROL WITH A DELTA-17(20) DOUBLE BOND FROM THE SOFT CORAL SARCOPHYTON-GLAUCUM [J].
KOBAYASHI, M ;
TOMIOKA, A ;
MITSUHASHI, H .
STEROIDS, 1979, 34 (03) :273-284
[9]  
KOBAYASHI M, 1991, CHEM PHARM BULL, V39, P297
[10]  
KOBAYASHI M, 1994, J CHEM RES-S, P44