Synthesis and anti-barnacle activities of novel 3-isocyanotheonellin analogues.
An antifouling active natural compound, 3-isocyanotheonellin, and its analogues were synthesized and evaluated for antifouling activity against the larvae of the barnacle Balanus amphirite in order to explore structure-activity relationships. The anti-barnacle effect of the 3-isocyanotheonellin analogues was in the EC50 range 0.18-7.20 micrograms ml-1. Some synthesized analogues exhibited potent antifouling activity as high as 3-isocyanothoenllin, and none of the synthesized isocyano compounds showed significant toxicity. The results of the present study suggest that an isocyano group and a hydrophobic site at a suitable position are important for potent antifouling activity without toxicity.
Kitano
Yoshikazu
Y
Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan. kitayo@cc.tuat.ac.jp
Yokoyama
Atsuko
A
Nogata
Yasuyuki
Y
Shinshima
Kyouji
K
Yoshimura
Erina
E
Chiba
Kazuhiro
K
Tada
Masahiro
M
Sakaguchi
Isamu
I
D000818:Animals; D003486:Cyanides / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*; D003510:Cyclohexanes / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*; D020128:Inhibitory Concentration 50; D007814:Larva / Q000187:drug effects / Q000502:physiology; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000633:toxicity*; D001468:Thoracica / Q000187:drug effects* / Q000502:physiology
C480378:3-isocyanotheonellin; D003486:Cyanides; D003510:Cyclohexanes; D012717:Sesquiterpenes