ANTINEOPLASTIC AGENTS .285. ISOLATION AND STRUCTURES OF CEPHALOSTATIN-14 AND CEPHALOSTATIN-15

被引:37
作者
PETTIT, GR
XU, JP
ICHIHARA, Y
WILLIAMS, MD
BOYD, MR
机构
[1] ARIZONA STATE UNIV,DEPT CHEM,TEMPE,AZ 85287
[2] NCI,FREDERICK CANC RES & DEV CTR,DIV CANC TREATMENT,DRUG DISCOVERY RES & DEV LAB,FREDERICK,MD 21702
来源
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1994年 / 72卷 / 11期
关键词
D O I
10.1139/v94-288
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The tube-inhabiting marine worm, Cephalodiscus gilchristi has been found to produce a series of cytotoxic and antineoplastic disteroidal alkaloids. A substantial study concerned with discovery of new cell growth inhibitory constituents of this marine animal has led to isolation of cephalostatins 14 (5a) and 15 (5b). The structures were determined by interpretation of spectral data, principally high-field (400 and 500 MHz) NMR and HRFABMS combined with NMR spectral relationships to cephalostatin 1 (4) where the structure was previously assigned by X-ray crystal structure analysis. The stereochemical assignments were established employing the ROESY NMR technique. Both new cephalostatins significantly inhibited growth of the P388 lymphocytic leukemia and a selection of human cancer cell lines. The two new cephalostatins further enhance knowledge of structure-activity parameters for these potentially important steroidal alkaloids.
引用
收藏
页码:2260 / 2267
页数:8
相关论文
共 29 条
  • [1] ARENE EO, 1987, LLOYDIA, V41, P186
  • [2] BOYD MR, 1992, ANTITUMOR DRUG DISCO, P11
  • [3] BOYD MR, 1989, CANC PRINCIPLES PRAC, P1
  • [4] PSAMMAPLYSIN-C - A NEW CYTOTOXIC DIBROMOTYROSINE-DERIVED METABOLITE FROM THE MARINE SPONGE DRUINELLA (=PSAMMAPLYSILLA) PURPUREA
    COPP, BR
    IRELAND, CM
    BARROWS, LR
    [J]. JOURNAL OF NATURAL PRODUCTS, 1992, 55 (06): : 822 - 823
  • [5] AGELASINE-G, A NEW ANTILEUKEMIC ALKALOID FROM THE OKINAWAN MARINE SPONGE AGELAS SP
    ISHIDA, K
    ISHIBASHI, M
    SHIGEMORI, H
    SASAKI, T
    KOBAYASHI, J
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 1992, 40 (03) : 766 - 767
  • [6] SEPARATION OF CROSS-RELAXATION AND J-CROSS-PEAKS IN 2D ROTATING-FRAME NMR-SPECTROSCOPY
    KESSLER, H
    GRIESINGER, C
    KERSSEBAUM, R
    WAGNER, K
    ERNST, RR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (02) : 607 - 609
  • [7] CYSTODYTINS D-I, NEW CYTOTOXIC TETRACYCLIC AROMATIC ALKALOIDS FROM THE OKINAWAN MARINE TUNICATE CYSTODYTES-DELLECHIAJEI
    KOBAYASHI, J
    TSUDA, M
    TANABE, A
    ISHIBASHI, M
    CHENG, JF
    YAMAMURA, S
    SASAKI, T
    [J]. JOURNAL OF NATURAL PRODUCTS, 1991, 54 (06): : 1634 - 1638
  • [8] MATSUNAGA S, 1992, CHEM PHARM BULL, V40, P766
  • [9] MONKS A, 1989, J NATL CANCER I, V84, P757
  • [10] DISPLAY AND ANALYSIS OF PATTERNS OF DIFFERENTIAL ACTIVITY OF DRUGS AGAINST HUMAN-TUMOR CELL-LINES - DEVELOPMENT OF MEAN GRAPH AND COMPARE ALGORITHM
    PAULL, KD
    SHOEMAKER, RH
    HODES, L
    MONKS, A
    SCUDIERO, DA
    RUBINSTEIN, L
    PLOWMAN, J
    BOYD, MR
    [J]. JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1989, 81 (14) : 1088 - 1092