HALICYLINDRAMIDES A-C, ANTIFUNGAL AND CYTOTOXIC DEPSIPEPTIDES FROM THE MARINE SPONGE HALICHONDRIA-CYLINDRATA

被引:58
作者
LI, HY [1 ]
MATSUNAGA, S [1 ]
FUSETANI, N [1 ]
机构
[1] UNIV TOKYO,FAC AGR,MARINE BIOCHEM LAB,BUNKYO KU,TOKYO 113,JAPAN
关键词
D O I
10.1021/jm00002a015
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Halicylindramides A-C (1-3) have been isolated from the Japanese marine sponge Halichondria cylindrata. They are tetradecapeptides with the N-terminus blocked by a formyl group and the C-terminus lactonized with a threonine residue. Their total structures including absolute stereochemistry were determined by a combination of spectral and chemical methods. Halicylindramides A-C were antifungal against Mortierella ramanniana and cytotoxic against P388 murine leukemia cells.
引用
收藏
页码:338 / 343
页数:6
相关论文
共 19 条
[1]   STRUCTURE ELUCIDATION OF THE ANTIBIOTIC DESERTOMYCIN THROUGH THE USE OF NEW TWO-DIMENSIONAL NMR TECHNIQUES [J].
BAX, A ;
ASZALOS, A ;
DINYA, Z ;
SUDO, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (25) :8056-8063
[2]   SELECTION OF COHERENCE-TRANSFER PATHWAYS IN NMR PULSE EXPERIMENTS [J].
BODENHAUSEN, G ;
KOGLER, H ;
ERNST, RR .
JOURNAL OF MAGNETIC RESONANCE, 1984, 58 (03) :370-388
[3]   MOTUPORIN, A POTENT PROTEIN PHOSPHATASE INHIBITOR ISOLATED FROM THE PAPUA-NEW-GUINEA SPONGE THEONELLA-SWINHOEI GRAY [J].
DESILVA, ED ;
WILLIAMS, DE ;
ANDERSEN, RJ ;
KLIX, H ;
HOLMES, CFB ;
ALLEN, TM .
TETRAHEDRON LETTERS, 1992, 33 (12) :1561-1564
[4]   COMPLETE PROTON AND C-13 NMR ASSIGNMENT OF THE ALKALOID GEPHYROTOXIN THROUGH THE USE OF HOMONUCLEAR HARTMANN-HAHN AND TWO-DIMENSIONAL NMR-SPECTROSCOPY [J].
EDWARDS, MW ;
BAX, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (05) :918-923
[5]   BIOACTIVE MARINE METABOLITES .33. CYCLOTHEONAMIDES, POTENT THROMBIN INHIBITORS, FROM A MARINE SPONGE THEONELLA SP [J].
FUSETANI, N ;
MATSUNAGA, S ;
MATSUMOTO, H ;
TAKEBAYASHI, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :7053-7054
[6]   BIOACTIVE SPONGE PEPTIDES [J].
FUSETANI, N ;
MATSUNAGA, S .
CHEMICAL REVIEWS, 1993, 93 (05) :1793-1806
[7]   POLYDISCAMIDE-A - A NEW BIOACTIVE DEPSIPEPTIDE FROM THE MARINE SPONGE DISCODERMIA SP [J].
GULAVITA, NK ;
GUNASEKERA, SP ;
POMPONI, SA ;
ROBINSON, EV .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1767-1772
[8]   POLYTHEONAMIDES, UNPRECEDENTED HIGHLY CYTOTOXIC POLYPEPTIDES, FROM THE MARINE SPONGE THEONELLA-SWINHOEI .1. ISOLATION AND COMPONENT AMINO-ACIDS [J].
HAMADA, T ;
SUGAWARA, T ;
MATSUNAGA, S ;
FUSETANI, N .
TETRAHEDRON LETTERS, 1994, 35 (05) :719-720
[9]   BIOACTIVE MARINE METABOLISM .56. POLYTHEONAMIDES, UNPRECEDENTED HIGHLY CYTOTOXIC POLYPEPTIDES FROM THE MARINE SPONGE THEONELLA-SWINHOEI .2. STRUCTURE ELUCIDATION [J].
HAMADA, T ;
SUGAWARA, T ;
MATSUNAGA, S ;
FUSETANI, N .
TETRAHEDRON LETTERS, 1994, 35 (04) :609-612
[10]   CYLINDRAMIDE - CYTOTOXIC TETRAMIC ACID LACTAM FROM THE MARINE SPONGE HALICHONDRIA-CYLINDRATA TANITA AND HOSHINO [J].
KANAZAWA, S ;
FUSETANI, N ;
MATSUNAGA, S .
TETRAHEDRON LETTERS, 1993, 34 (06) :1065-1068