Effect of the azetidine and azocine rings of okaramine B on insecticidal activity

被引:37
作者
Shiono, Y [1 ]
Akiyama, K [1 ]
Hayashi, H [1 ]
机构
[1] Univ Osaka Prefecture, Coll Agr, Dept Appl Biol Chem, Osaka 5998531, Japan
关键词
Penicillium simplicissimum; okaramines; insecticidal compound;
D O I
10.1271/bbb.64.1519
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
Four degraded okaramine B (2) products, 4',5'-dihydrookaramine B (3), two azetidine ring-opened compounds (4 and 5) and 1',2',4',5'-tetrahydrookaramine B (6), were prepared and their insecticidal activity was examined. Neither compounds 4 nor 5 showed such activity against silkworms, indicating that the azetidine ring moiety played an important role in the insecticidal activity. Moreover, both compounds 3 and 6 exhibited lower activity than 2, which means that the azocine ring moiety was indispensable to form the active conformation.
引用
收藏
页码:1519 / 1521
页数:3
相关论文
共 7 条
  • [1] Okaramine G, a new okaramine congener from Penicillium simplicissimum ATCC 90288
    Hayashi, H
    Sakaguchi, A
    [J]. BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1998, 62 (04) : 804 - 806
  • [2] OKARAMINE-C, A NEW INSECTICIDAL INDOLE ALKALOID FROM PENICILLIUM-SIMPLICISSIMUM
    HAYASHI, H
    FUJIWARA, T
    MURAO, S
    ARAI, M
    [J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1991, 55 (12): : 3143 - 3145
  • [3] STRUCTURE AND INSECTICIDAL ACTIVITY OF NEW INDOLE ALKALOIDS, OKARAMINE-A AND OKARAMIN-B FROM PENICILLIUM-SIMPLICISSIMUM AK-40
    HAYASHI, H
    TAKIUCHI, K
    MURAO, S
    ARAI, M
    [J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1989, 53 (02): : 461 - 469
  • [4] Okaramines H and I, new okaramine congeners, from Aspergillus aculeatus
    Hayashi, H
    Furutsuka, K
    Shiono, Y
    [J]. JOURNAL OF NATURAL PRODUCTS, 1999, 62 (02): : 315 - 317
  • [5] NEW OKARAMINE CONGENERS, OKARAMINE-D, OKARAMINE-E, AND OKARAMNE-F, FROM PENICILLIUM-SIMPLICISSIMUM ATCC-90288
    HAYASHI, H
    ASABU, Y
    MURAO, S
    ARAI, M
    [J]. BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1995, 59 (02) : 246 - 250
  • [6] New okaramine congeners, okamines J, K, L, M and related compounds, from Penicillium simplicissimum ATCC 90288
    Shiono, Y
    Akiyama, K
    Hayashi, H
    [J]. BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1999, 63 (11) : 1910 - 1920
  • [7] Okaramines N, O, P, Q and R, new okaramine congeners, from Penicillium simplicissimum ATCC 90288
    Shiono, Y
    Akiyama, K
    Hayashi, H
    [J]. BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2000, 64 (01) : 103 - 110