New acetylenic metabolites from the marine sponge Pellina triangculata

被引:37
作者
Fu, X
Abbas, SA
Schmitz, FJ
Vidavsky, I
Gross, ML
Laney, M
Schatzman, RC
Cabuslay, RD
机构
[1] UNIV OKLAHOMA, DEPT CHEM & BIOCHEM, NORMAN, OK 73019 USA
[2] WASHINGTON UNIV, DEPT CHEM, ST LOUIS, MO 63130 USA
[3] SYNTEX INC, DISCOVERY RES, INST BIOCHEM & CELL BIOL, PALO ALTO, CA 94304 USA
基金
美国国家卫生研究院; 美国国家科学基金会;
关键词
D O I
10.1016/S0040-4020(96)01037-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Six new acetylenic compounds, 1, 7-11, were isolated from the marine sponge Pellina triangulata. Structures were established using NMR spectroscopy and chemical degradation. Collisional activation decomposition (CAD) tandem mass spectrometry of the lithium adducts of the acetylenic compounds was applied to ascertain if charge-remote fragmentation would yield definitive information regarding the site of internal unsaturation in these polyfunctional compounds. Pellynic acid (1) inhibited inosine monophosphate dehydrogenase (IMPDH) in vitro. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:799 / 814
页数:16
相关论文
共 30 条
[1]   ENERGY-REQUIREMENTS FOR REMOTE CHARGE SITE ION DECOMPOSITIONS AND STRUCTURAL INFORMATION FROM COLLISIONAL ACTIVATION OF ALKALI-METAL CATIONIZED FATTY ALCOHOLS [J].
ADAMS, J ;
GROSS, ML .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) :6915-6921
[2]   PHOSPHOLIPID STUDIES OF MARINE ORGANISMS - .5. NEW ALPHA-METHOXY ACIDS FROM HIGGINSIA-TETHYOIDES [J].
AYANOGLU, E ;
POPOV, S ;
KORNPROBST, JM ;
ABOUDBICHARA, A ;
DJERASSI, C .
LIPIDS, 1983, 18 (11) :830-836
[3]   BIOACTIVE BROMOPOLYACETYLENES FROM THE MARINE SPONGE XESTOSPONGIA-TESTUDINARIA [J].
BOURGUETKONDRACKI, ML ;
RAKOTOARISOA, MT ;
MARTIN, MT ;
GUYOT, M .
TETRAHEDRON LETTERS, 1992, 33 (02) :225-226
[4]   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
[5]  
BROOK MA, 1983, SYNTHESIS-STUTTGART, P201
[6]   1,3-DIPOLAR CYCLOADDITION REACTIONS OF TRANSITION-METAL CARBENE COMPLEXES AND THE FORMAL [3 + 2 + 1] PYRIDINANNULATION OF THE CYCLOADDUCTS [J].
CHAN, KS ;
WULFF, WD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (17) :5229-5236
[7]   MINOR BIOACTIVE POLYACETYLENES FROM PETROSIA-FICIFORMIS [J].
CIMINO, G ;
DEGIULIO, A ;
DEROSA, S ;
DIMARZO, V .
JOURNAL OF NATURAL PRODUCTS, 1990, 53 (02) :345-353
[8]   Triangulynes A-H and triangulynic acid, new cytotoxic polyacetylenes from the marine sponge Pellina triangulata [J].
Dai, JR ;
Hallock, YF ;
Cardellina, JH ;
Gray, GN ;
Boyd, MR .
JOURNAL OF NATURAL PRODUCTS, 1996, 59 (09) :860-865
[9]   ENZYME-INHIBITORS - NEW AND KNOWN POLYBROMINATED PHENOLS AND DIPHENYL ETHERS FROM 4 INDO-PACIFIC DYSIDEA SPONGES [J].
FU, XO ;
SCHMITZ, EJ ;
GOVINDAN, M ;
ABBAS, SA ;
HANSON, KM ;
HORTON, PA ;
CREWS, P .
JOURNAL OF NATURAL PRODUCTS, 1995, 58 (09) :1384-1391
[10]   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