PHLOEODICTINE-A AND PHLOEODICTINE-B - NEW ANTIBACTERIAL AND CYTOTOXIC BICYCLIC AMIDINIUM SALTS FROM THE NEW CALEDONIAN SPONGE, PHLOEODICTYON SP

被引:31
作者
KOURANYLEFOLL, E
PAIS, M
SEVENET, T
GUITTET, E
MONTAGNAC, A
FONTAINE, C
GUENARD, D
ADELINE, MT
DEBITUS, C
机构
[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE
[2] ORSTOM,NOUMEA,NEW CALEDONIA
关键词
D O I
10.1021/jo00040a022
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two new alkaloids, phloeodictine A (1) and phloeodictine B (2), possessing an unprecedented 6-hydroxy-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrimidinium skeleton have been isolated from an undescribed species of the deep sponge Phloeodictyon. The structures were determined by extensive spectroscopic analysis particularly two-dimensional NMR experiments. Both compounds exhibited in vitro antibacterial activity against Gram-positive and Gram-negative bacteria and were moderately cytotoxic against KB cells.
引用
收藏
页码:3832 / 3835
页数:4
相关论文
共 11 条
[1]   MLEV-17-BASED TWO-DIMENSIONAL HOMONUCLEAR MAGNETIZATION TRANSFER SPECTROSCOPY [J].
BAX, A ;
DAVIS, DG .
JOURNAL OF MAGNETIC RESONANCE, 1985, 65 (02) :355-360
[2]   H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR [J].
BAX, A ;
SUMMERS, MF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2093-2094
[3]   SENSITIVITY-ENHANCED TWO-DIMENSIONAL HETERONUCLEAR SHIFT CORRELATION NMR-SPECTROSCOPY [J].
BAX, A ;
SUBRAMANIAN, S .
JOURNAL OF MAGNETIC RESONANCE, 1986, 67 (03) :565-569
[4]   INVESTIGATION OF COMPLEX NETWORKS OF SPIN-SPIN COUPLING BY TWO-DIMENSIONAL NMR [J].
BAX, A ;
FREEMAN, R .
JOURNAL OF MAGNETIC RESONANCE, 1981, 44 (03) :542-561
[5]   STRUCTURE DETERMINATION OF A TETRASACCHARIDE - TRANSIENT NUCLEAR OVERHAUSER EFFECTS IN THE ROTATING FRAME [J].
BOTHNERBY, AA ;
STEPHENS, RL ;
LEE, JM ;
WARREN, CD ;
JEANLOZ, RW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (03) :811-813
[6]   ACARNIDINES, NOVEL ANTI-VIRAL AND ANTI-MICROBIAL COMPOUNDS FROM SPONGE ACARNUS-ERITHACUS-(DE LAUBENFELS) [J].
CARTER, GT ;
RINEHART, KL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (13) :4302-4304
[7]   POLYANDROCARPIDINES - ANTI-MICROBIAL AND CYTOTOXIC AGENTS FROM A MARINE TUNICATE (POLYANDROCARPA SP) FROM GULF OF CALIFORNIA [J].
CHENG, MT ;
RINEHART, KL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (23) :7409-7411
[8]  
Kalinowski H.O., 1988, CARBON 13 NMR SPECTR
[9]   SIMPLIFICATION OF NMR-SPECTRA BY FILTRATION THROUGH MULTIPLE-QUANTUM COHERENCE [J].
SHAKA, AJ ;
FREEMAN, R .
JOURNAL OF MAGNETIC RESONANCE, 1983, 51 (01) :169-173
[10]   NATURAL-PRODUCTS OF MARINE SPONGES .7. CONSTITUTION OF WEAKLY BASIC GUANIDINE COMPOUNDS, DIBROMOPHAKELLIN AND MONOBROMOPHAKELLIN [J].
SHARMA, G ;
MAGDOFFFAIRCHILD, B .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (25) :4118-4124