Brominated polyunsaturated lipids and their stereochemistry from the Chinese marine sponge Xestospongia testudinaria

被引:23
作者
Jiang, Wei [1 ]
Liu, Dong [1 ]
Deng, Zhiwei [2 ]
de Voogd, Nicole J. [3 ]
Proksch, Peter [4 ]
Lin, Wenhan [1 ]
机构
[1] Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
[2] Beijing Normal Univ, Analyt & Testing Ctr, Beijing 100075, Peoples R China
[3] Natl Museum Nat Hist, NL-2300 RA Leiden, Netherlands
[4] Univ Dusseldorf, Inst Pharmaceut Biol & Biotechnol, D-40225 Dusseldorf, Germany
关键词
Marine sponge; Xestospongia testudinaria; Brominated polyunsaturated lipids; Structural elucidation; Mosher reaction; ACETYLENIC FATTY-ACIDS; CONFIGURATION; INHIBITORS; ALKALOIDS; LACTONES; ALCOHOLS; POSITION; MUTA; NMR;
D O I
10.1016/j.tet.2010.11.045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chemical examination of the Chinese marine sponge Xestospongia testudinaria led to the isolation of 39 new brominated polyunsaturated compounds, which were designated with the trivial names xestospongienes A-Z and Z(1)-Z(13). The structures of these compounds were elucidated by analyzing extensive spectroscopic (IR. MS, 1D, and 2D NMR) data and the results from CD spectral assignment, chemical conversion, and Mosher reaction. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:58 / 68
页数:11
相关论文
共 32 条
[1]   CARDUUSYNES (A-E) - ACETYLENIC ACIDS FROM A GREAT-AUSTRALIAN-BIGHT MARINE SPONGE PHAKELLIA-CARDUUS [J].
BARROW, RA ;
CAPON, RJ .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (10) :1901-1918
[2]   BIOACTIVE BROMOPOLYACETYLENES FROM THE MARINE SPONGE XESTOSPONGIA-TESTUDINARIA [J].
BOURGUETKONDRACKI, ML ;
RAKOTOARISOA, MT ;
MARTIN, MT ;
GUYOT, M .
TETRAHEDRON LETTERS, 1992, 33 (02) :225-226
[3]   BROMINATED ACETYLENIC FATTY-ACIDS FROM XESTOSPONGIA SP, A MARINE SPONGE-BACTERIA ASSOCIATION [J].
BRANTLEY, SE ;
MOLINSKI, TF ;
PRESTON, CM ;
DELONG, EF .
TETRAHEDRON, 1995, 51 (28) :7667-7672
[4]   Novel alkaloids of the aaptamine class from an Indonesian marine sponge of the genus Xestopongia [J].
Calcul, L ;
Longeon, A ;
Al Mourabit, A ;
Guyot, M ;
Bourguet-Kondracki, ML .
TETRAHEDRON, 2003, 59 (34) :6539-6544
[5]   WIEDENDIOL-A AND WIEDENDIOL-B, CHOLESTERYL ESTER TRANSFER PROTEIN INHIBITORS FROM THE MARINE SPONGE XESTOSPONGLIA-WIEDENMAYERI [J].
COVAL, SJ ;
CONOVER, MA ;
MIERZWA, R ;
KING, A ;
PUAR, MS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (06) :605-610
[6]   ANTIFUNGAL BROMINATED C-18 ACETYLENIC ACIDS FROM THE MARINE SPONGE, PETROSIA-VOLCANO HOSHINO [J].
FUSETANI, N ;
LI, HY ;
TAMURA, K ;
MATSUNAGA, S .
TETRAHEDRON, 1993, 49 (06) :1203-1210
[7]   Sterol composition and chemotaxonomic considerations in relation to sponges of the genus Xestospongia [J].
Gauvin, A ;
Smadja, J ;
Aknin, M ;
Gaydou, EM .
BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 2004, 32 (05) :469-476
[8]   Calculation of Electronic Circular Dichroism Spectra with Time-Dependent Double-Hybrid Density Functional Theory [J].
Goerigk, Lars ;
Grimme, Stefan .
JOURNAL OF PHYSICAL CHEMISTRY A, 2009, 113 (04) :767-776
[9]   2 EPIMERIC ALIPHATIC AMINO-ALCOHOLS FROM A SPONGE, XESTOSPONGIA SP [J].
GULAVITA, NK ;
SCHEUER, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (02) :366-369
[10]   BROMINATED UNSATURATED-ACIDS FROM THE MARINE SPONGE XESTOSPONGIA SP [J].
HIRSH, S ;
CARMELY, S ;
KASHMAN, Y .
TETRAHEDRON, 1987, 43 (14) :3257-3261