61(P-39) Ianthella属海綿より得られた新規Na,K-ATPase阻害物質iantheran類およびianthesine類(ポスター発表の部)

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During the course of our search for biologically active metabolites in marine invertebrates, we have found that the organic extract of an Australian sponge of the genus Ianthella (order Verongida) showed potent inhibitory activity against Na, K-ATPase. From the EtOAc soluble portion six novel metabolites, named iantherans A and B (1 and 2) and ianthesines A-D (3-6), were isolated as active components. The structural determination of these compounds was accomplished by spectroscopic analyses and chemical derivatizations. The symmetrical molecule iantheran A(1) comprises a quite rare structure of a 1,4-disubstituted 2,3-bis(sulfooxy)-1,3-butadiene and two brominated benzofurans. Iantheran B (2) is the geometric isomer of 1 containing a (Z,E)-1,3-butadiene moiety. Ianthesines are all dibromotyrosine-derived metabolites with a spirocyclohexadienylisoxazoline moiety. Ianthesines A, B, and D (3, 4 and 6) are derived from two bromotyrosines, and ianthesine C (5) is a tetramer possessing eight bromine atoms and the molecular weight of 1606. The absolute stereochemistry of ianthesines were partially determined by degradation and CD spectroscopic method. The inhibitory activity of 1-6 and two derivatives of 1 against the dog kidney Na, K-ATPase was evaluated by a convenient HPLC-assisted assay method. The most active 1 inhibits the enzyme at IC_<50>=4μM.
天然有機化合物討論会の論文
2000-10-01