76(P61) 海洋付着生物幼生の着生誘起および阻害物質(ポスター発表の部)

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As a part of our study on larval settlement (attachment and metamorphosis) of sessile marine invertebrates, we are searching the settlement inducing and inhibiting substances from various marine organisms. Here we present our new findings on the metamorphosis inducing compounds on ascidian Halocynthia roretzi larvae and the antifoulants against barnacle Balanus amphitrite larvae. Metamorphisis of ascidian larvae has been thought to be induced by some chemical cues. a) We found the conditioned medium with the ascidian H. roretzi larvae induced the larval metamorphosis of the conspecies. The metamorphosis-inducer has been isolated, and the strucutre was identified as lumichrome (1). b) From various marine organisms, we have isolated almost 40 compounds including 24 new ones as the metamorphosis-inducers on the ascidian. For example, from a marine sponge Callyspongia sp. (to be), ten acyclic polyacetylene derivatives were obtained (e.g. 2 and 3). A marine sponge Stelletta sp. afforded a norsesequiterpenamide with two guanidium moieties, stellettadine A (4), the absolute stereochemistry of which was determined by degradation into 2-methylglutaric acid. From the marine sponge Anthosigmella aff. raromicrosclera, two pipecolate derivatives (5 and 6) were obtained. On MeOH extracts of more than 300 marine invertebrates, we have performed antifouling screening against barnacle larvae (B. amphitrite). Following the screening result, we attempted the isolation and structure determination of antifoulants to afford more than 60 compounds including almost 30 new ones. a) From the marine sponge Acanthella cavernosa, 26 antifoulants were obtained. Kalihinane-type compounds with isocyano, formamino, and/or isothiocyano group(s) showed prominent antifouling activities, some of which were stronger than that of cupric sulfate. Steroids with epidioxy group (e.g. 7) delayed the timing of larval settlement. b) Nudibranchs of the family Phillidiidae afforded 11 sesquiterpenoid antifoulants (e.g. 8). c) From the marine sponge Pseudoceratina purpurea, seven antifoulants (9 - 15) including a unique cyanoformamide derivative (14) were obtained. d) The marine sponge Agelas mauritiana afforded oroidin and its unique dimer (16). e) From a marine sponge Axinyssa sp., three new sesquiterpenoids with dichloromethyleneamino group (17-19) were obtained. f) A soft coral Dendronephthya sp. afforded four new D-seco-steroids (e.g. 20). These research results will become important on understanding the more concise mechanism of larval settlement and for development of commercial antifouling agents.
天然有機化合物討論会の論文
1996-09-02

76(P61) 海洋付着生物幼生の着生誘起および阻害物質(ポスター発表の部)

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