Sesquiterpenes from the Hainan sponge Dysidea septosa

被引:40
作者
Huang, Xiao-Chun [1 ]
Li, Jia [1 ]
Li, Zhen-Yu [1 ]
Shi, Lei [1 ]
Guo, Yue-Wei [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
来源
JOURNAL OF NATURAL PRODUCTS | 2008年 / 71卷 / 08期
关键词
D O I
10.1021/np8002035
中图分类号
Q94 [植物学];
学科分类号
071001 [植物学];
摘要
Five new sesquiterpenes. named lingshuiolides A (1) and B (2), lingshuiperoxide (6), isodysetherin (10), and spirolingshuiolide (12), along with several known related analogues (7-9, 11 and 13-15), were isolated from the Hainan marine sponge Dysidea septosa. The structures of new compounds 1, 2, 6 10, and 12 were determined by detailed analysis of 1D and 2D NMR spectra and by comparison with related model compounds. The absolute configuration of lingshuiolide B (2) was established by using the modified Mosher's method. Spirolingshuiolide (12) represents the first example of a sesquiterpene with a rearranged drimane skeleton. Compounds 7-9 and 15 exhibited significant inhibitory activity against human protein tyrosine phosphatase 1B (hPTP1B), an enzyme involved in the regulation of insulin signaling. In particular, 15 showed the most potent effect, with ail IC(50) value of 1.9 mu g/mL.
引用
收藏
页码:1399 / 1403
页数:5
相关论文
共 20 条
[1]
Protein-tyrosine phosphatase-1B acts as a negative regulator of insulin signal transduction [J].
Byon, JCH ;
Kusari, AB ;
Kusari, J .
MOLECULAR AND CELLULAR BIOCHEMISTRY, 1998, 182 (1-2) :101-108
[2]
New sesquiterpene and brominated metabolites from the tropical marine sponge Dysidea sp. [J].
Cameron, GM ;
Stapleton, BL ;
Simonsen, SM ;
Brecknell, DJ ;
Garson, MJ .
TETRAHEDRON, 2000, 56 (29) :5247-5252
[3]
METABOLITES OF THE NUDIBRANCH CHROMODORIS-FUNEREA AND THE SINGLET OXYGEN OXIDATION-PRODUCTS OF FURODYSIN AND FURODYSININ [J].
CARTE, B ;
KERNAN, MR ;
BARRABEE, EB ;
FAULKNER, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (18) :3528-3532
[4]
CIMINO G, 1975, TETRAHEDRON LETT, V43, P3723
[5]
A new cacospongionolide derivative from the sponge Fasciospongia cavernosa [J].
De Rosa, S ;
Crispino, A ;
De Giulio, A ;
Iodice, C ;
Amodeo, P ;
Tancredi, T .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (09) :1316-1318
[6]
New terpenoid metabolites from the skin extracts, an egg mass, and dietary sponges of the Northeastern Pacific dorid nudibranch Cadlina luteomarginata [J].
Dumdei, EJ ;
Kubanek, J ;
Coleman, JE ;
Pika, J ;
Andersen, RJ ;
Steiner, JR ;
Clardy, J .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1997, 75 (06) :773-789
[7]
Vanillic acid derivatives from the green algae Cladophora socialis as potent protein tyrosine phosphatase 1B inhibitors [J].
Feng, Yunjiang ;
Carroll, Anthony R. ;
Addepalli, Rama ;
Fechner, Gregory A. ;
Avery, Vicky M. ;
Quinn, Ronald J. .
JOURNAL OF NATURAL PRODUCTS, 2007, 70 (11) :1790-1792
[8]
Pelseneeriol-1 and -2:: new furanosesquiterpene alcohols from porostome nudibranch Doriopsilla pelseneeri [J].
Gaspar, H ;
Gavagnin, M ;
Calado, G ;
Castelluccio, F ;
Mollo, E ;
Cimino, G .
TETRAHEDRON, 2005, 61 (46) :11032-11037
[9]
SESQUITERPENES FROM THE SPONGE DYSIDEA-ETHERIA AND THE NUDIBRANCH HYPSELODORIS-ZEBRA [J].
GRODE, SH ;
CARDELLINA, JH .
JOURNAL OF NATURAL PRODUCTS, 1984, 47 (01) :76-83
[10]
Biscembranoids and their probable biogenetic precursor from the hainan soft coral Sarcophyton tortuosum [J].
Jia, Rui ;
Guo, Yue-Wei ;
Chen, Ping ;
Yang, Yi-Ming ;
Mollo, Ernesto ;
Gavagnin, Margherita ;
Cimino, Guido .
JOURNAL OF NATURAL PRODUCTS, 2007, 70 (07) :1158-1166