ANTINEOPLASTIC AGENTS .249. ISOLATION AND STRUCTURE OF THE MARINE SPONGE CELL-GROWTH INHIBITORY CYCLIC PEPTIDE PHAKELLISTATIN 1

被引:83
作者
PETTIT, GR
CICHACZ, Z
BARKOCZY, J
DORSAZ, AC
HERALD, DL
WILLIAMS, MD
DOUBEK, DL
SCHMIDT, JM
TACKETT, LP
BRUNE, DC
CERNY, RL
HOOPER, JNA
BAKUS, GJ
机构
[1] ARIZONA STATE UNIV,DEPT CHEM,TEMPE,AZ 85287
[2] UNIV NEBRASKA,DEPT CHEM,MIDWEST CTR MASS SPECTRMETRY,LINCOLN,NE 68588
[3] QUEENSLAND MUSEUM,BRISBANE,QLD 4101,AUSTRALIA
[4] UNIV SO CALIF,DEPT BIOL SCI,LOS ANGELES,CA 90089
来源
JOURNAL OF NATURAL PRODUCTS | 1993年 / 56卷 / 02期
关键词
D O I
10.1021/np50092a011
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
A new cell growth inhibitory (P-388 murine leukemia ED50 7.5 mug/ml) cycloheptapeptide designated phakellistatin 1 was isolated from two Indo-Pacific sponges, Phakellia costata and Stylotella aurantium. Structural elucidation was accomplished utilizing high field nmr, amino acid analyses, and mass spectral techniques (fab, tandem ms/ms), followed by chiral gas chromatographic procedures for absolute configuration assignments (all S-amino acid units). By these methods phakellistatin 1 [1] was found to be cyclo (Pro-Ile-Pro-Ile-Phe-Pro-Tyr), and this assignment was finally confirmed by an X-ray crystal structure determination.
引用
收藏
页码:260 / 267
页数:8
相关论文
共 41 条
[1]   OPTIMIZATION OF 2-DIMENSIONAL HOMONUCLEAR RELAYED COHERENCE TRANSFER NMR-SPECTROSCOPY [J].
BAX, A ;
DROBNY, G .
JOURNAL OF MAGNETIC RESONANCE, 1985, 61 (02) :306-320
[2]   SIR88 - A DIRECT-METHODS PROGRAM FOR THE AUTOMATIC SOLUTION OF CRYSTAL-STRUCTURES [J].
BURLA, MC ;
CAMALLI, M ;
CASCARANO, G ;
GIACOVAZZO, C ;
POLIDORI, G ;
SPAGNA, R ;
VITERBO, D .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1989, 22 :389-393
[3]  
CERNY RL, 1990, MASS SPECTROMETRY PE, P289
[4]   JASPLAKINOLIDE, A CYCLODEPSIPEPTIDE FROM THE MARINE SPONGE, JASPIS SP [J].
CREWS, P ;
MANES, LV ;
BOEHLER, M .
TETRAHEDRON LETTERS, 1986, 27 (25) :2797-2800
[5]  
EGERT E, 1986, PATSEE FRAGMENT SEAR
[6]   DEVELOPMENTS IN THE MITHRIL DIRECT METHODS PROGRAM [J].
GILMORE, CJ ;
BROWN, SR .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1988, 21 (05) :571-572
[7]   MITHRIL - AN INTEGRATED DIRECT-METHODS COMPUTER-PROGRAM [J].
GILMORE, CJ .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1984, 17 (FEB) :42-46
[8]  
GILMORE CJ, 1983, MITHRIL COMPUTER PRO
[9]  
HOOPER J N A, 1992, Invertebrate Taxonomy, V6, P261, DOI 10.1071/IT9920261
[10]  
JIMENEZ C, 1991, J ORG CHEM, V56, P3404