Tridemethylisovelleral, a potent cytotoxic agent

被引:17
作者
Aujard, I
Röme, D
Arzel, E
Johansson, M
de Vos, D
Sterner, O
机构
[1] Lund Univ, Dept Organ Chem, S-22100 Lund, Sweden
[2] Pharmachemie BV, Dept Med, NL-2003 RN Haarlem, Netherlands
关键词
tridemethylisovelleral; isovelleral; unsaturated dialdehydes; cytotoxicity;
D O I
10.1016/j.bmc.2005.06.035
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The synthesis and in vitro cytotoxicity toward various tumor cell lines of (+/-)-tridemethylisovelleral, an analogue of the bioactive fungal sesquiterpene (+)-isovelleral retaining the bicyclo[4,1,0]hept-2-en-1,2-dicarbaidehyde system but lacking the three methyl groups, is reported. The cytotoxicity of tridemethylisovelleral toward several tumor cell lines was found to be comparable with those of established antitumor drugs, and significantly higher than that of isovelleral. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6145 / 6150
页数:6
相关论文
共 20 条
  • [1] COMPARISON OF THE ANTIMICROBIAL AND CYTOTOXIC ACTIVITIES OF 20 UNSATURATED SESQUITERPENE DIALDEHYDES FROM PLANTS AND MUSHROOMS
    ANKE, H
    STERNER, O
    [J]. PLANTA MEDICA, 1991, 57 (04) : 344 - 346
  • [2] ENANTIOSPECIFIC PREPARATION OF [(2R, 6S)-ENDO]-5-AZA-1,10,10-TRIMETHYL-3-OXATRICYCLO[5.2.1.0(2,6)]DECAN-4-ONE BY A NITRENE-MEDIATED ROUTE FROM [(1S)-ENDO]-(-)-BORNEOL AND ITS UTILITY AS A CHIRAL AUXILIARY IN SOME ASYMMETRIC TRANSFORMATIONS
    BANKS, MR
    BLAKE, AJ
    CADOGAN, JIG
    DAWSON, IM
    GOSNEY, I
    GRANT, KJ
    GAUR, S
    HODGSON, PKG
    KNIGHT, KS
    SMITH, GW
    STEVENSON, DE
    [J]. TETRAHEDRON, 1992, 48 (37) : 7979 - 8006
  • [3] Reduction by dissolving metals. Part I.
    Birch, AJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1944, : 430 - 436
  • [4] PALLADIUM-CATALYZED CARBONYLATION OF ENOL TRIFLATES - A NOVEL METHOD FOR ONE-CARBON HOMOLOGATION OF KETONES TO ALPHA,BETA-UNSATURATED CARBOXYLIC-ACID DERIVATIVES
    CACCHI, S
    MORERA, E
    ORTAR, G
    [J]. TETRAHEDRON LETTERS, 1985, 26 (08) : 1109 - 1112
  • [5] DIMETHYLOXOSULFONIUM METHYLIDE ((CH3)2SOCH2) AND DIMETHYLSULFONIUM METHYLIDE ((CH3)2SCH2) FORMATION AND APPLICATION TO ORGANIC SYNTHESIS
    COREY, EJ
    CHAYKOVSKY, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) : 1353 - +
  • [6] REACTION OF POLYGODIAL WITH PRIMARY AMINES - AN ALTERNATIVE EXPLANATION TO THE ANTIFEEDANT ACTIVITY
    DISCHIA, M
    PROTA, G
    SODANO, G
    [J]. TETRAHEDRON LETTERS, 1982, 23 (32) : 3295 - 3298
  • [7] The reactivity of the antibiotic sesquiterpene isovelleral towards primary amines
    Gustafsson, J
    Jonassohn, M
    Kahnberg, P
    Anke, H
    Sterner, O
    [J]. NATURAL PRODUCT LETTERS, 1997, 9 (04): : 253 - 258
  • [8] SYNTHESIS OF ANALOGS OF THE MUTAGENIC SESQUITERPENES ISOVELLERAL AND MERULIDIAL VIA STEREOSELECTIVE CYCLOPROPANATION OF CYCLOHEXENECARBALDEHYDES
    GUSTAFSSON, J
    STERNER, O
    [J]. TETRAHEDRON, 1995, 51 (13) : 3865 - 3872
  • [9] STUDIES OF THE CONVERSIONS OF SESQUITERPENES IN INJURED FRUIT BODIES OF LACTARIUS-VELLEREUS - A BIOMIMETIC TRANSFORMATION OF STEAROYLVELUTINAL TO ISOVELLERAL
    HANSSON, T
    STERNER, O
    [J]. TETRAHEDRON LETTERS, 1991, 32 (22) : 2541 - 2544
  • [10] The preparation and bioactivities of (-)-isovelleral
    Jonassohn, M
    Hjertberg, R
    Anke, H
    Dekermendjian, K
    Szallasi, A
    Thines, E
    Witt, R
    Sterner, O
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1997, 5 (07) : 1363 - 1367