CYTOTOXIC DITERPENOIDS FROM THE BROWN ALGA DILOPHUS-LIGULATUS

被引:16
作者
BOUAICHA, N [1 ]
PESANDO, D [1 ]
PUEL, D [1 ]
机构
[1] UNIV CATANIA,DIPARTIMENTO SCI CHIM,I-95125 CATANIA,ITALY
来源
JOURNAL OF NATURAL PRODUCTS | 1993年 / 56卷 / 10期
关键词
D O I
10.1021/np50100a013
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
A new xenicane-type diterpene, dilopholide [5], and four known diterpenoids, acetoxycrenulide [1), acetylcoriacenone [2), and its epimer isoacetylcoriacenone [3], and hydroxyacetyldictyolal [4], have been isolated from the brown alga Dilophus ligulatus [syn. spiralis (Montagne) Hamell. The structure of dilopholide [5] was elucidated by spectroscopic methods, including the concerted application of a number of 2D nmr techniques, including H-1-H-1 COSY, heteronuclear proton-carbon chemical shift correlation (HETCOSY), and long-range HETCOSY. The cytotoxic activity of compounds 1-5 has been examined against several types of mammalian cells: human nasopharynx carcinoma cells (KB), human lung carcinoma cells (NSCLC-N6), murine leukemia cells (P-388), and murine leukemia cells expressing the multi-drug-resistance gene, mdr (P-388/DOX).
引用
收藏
页码:1747 / 1752
页数:6
相关论文
共 12 条
  • [1] BLOUNT JF, 1982, AUST J CHEM, V34, P145
  • [2] BOUAICHA N, 1993, PLANTA MED, V9, P195
  • [3] STRUCTURES AND CONFORMATIONS OF NEW 9-MEMBERED RING DITERPENOIDS FROM THE MARINE ALGA DICTYOTA-DICHOTOMA
    ENOKI, N
    ISHIDA, R
    MATSUMOTO, T
    [J]. CHEMISTRY LETTERS, 1982, (11) : 1749 - 1752
  • [4] FINER J, 1979, J ORG CHEM, V44, P2047
  • [5] NOVEL DITERPENES WITH A CYCLOBUTENONE MOIETY FROM THE BROWN ALGA PACHYDICTYON-CORIACEUM
    ISHITSUKA, M
    KUSUMI, T
    KAKISAWA, H
    KAWAKAMI, Y
    NAGAI, Y
    SATO, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (11) : 1937 - 1938
  • [6] STRUCTURE OF PACHYALDEHYDE, A NOVEL NORDITERPENE FROM THE BROWN ALGA, PACHYDICTYON-CORIACEUM
    ISHITSUKA, M
    KUSUMI, T
    KAKISAWA, H
    NAGAI, Y
    KAWAKAMI, Y
    SATO, T
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (14) : 906 - 908
  • [7] ANTITUMOR XENICANE AND NORXENICANE LACTONES FROM THE BROWN ALGA DICTYOTA-DICHOTOMA
    ISHITSUKA, MO
    KUSUMI, T
    KAKISAWA, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) : 5010 - 5013
  • [8] ANTIFUNGAL AND ANTIBACTERIAL SCREENING OF DICTYOTALES FROM THE FRENCH MEDITERRANEAN COAST
    MOREAU, J
    PESANDO, D
    CARAM, B
    [J]. HYDROBIOLOGIA, 1984, 116 (SEP) : 521 - 524
  • [9] NEW XENICANE DITERPENES FROM THE BROWN-ALGAE OF DICTYOTACEAE
    NORTE, M
    GONZALEZ, AG
    ARROYO, P
    ZARRAGA, M
    PEREZ, C
    RODRIGUEZ, ML
    RUIZPEREZ, C
    DORTA, L
    [J]. TETRAHEDRON, 1990, 46 (17) : 6125 - 6132
  • [10] ABSOLUTE-CONFIGURATIONS OF MARINE DITERPENES POSSESSING A XENICANE SKELETON - AN APPLICATION OF AN ADVANCED MOSHER METHOD
    OHTANI, I
    KUSUMI, T
    ISHITSUKA, MO
    KAKISAWA, H
    [J]. TETRAHEDRON LETTERS, 1989, 30 (24) : 3147 - 3150