Hydroxytakakiamide and Other Constituents from a Marine Sponge-Associated Fungus MMERU23, and Antinociceptive Activity of Ergosterol Acetate, Acetylaszonalenin and Helvolic Acid.

An unreported prenylated indole derivative hydroxytakakiamide () was isolated, together with the previously described ergosterol (), ergosterol acetate (), and (3)-3-(1-indol-3-ylmethyl)-3, 4-dihydro-1-1,4-benzodiazepine-2,5-dione (), from the column fractions of the crude ethyl acetate extract of the culture of a marine sponge-associated fungus, MMERU 23. The structure of was elucidated by the interpretation of 1D and 2D NMR spectral data and high-resolution mass spectrum. The absolute configuration of the stereogenic carbon in was proposed to be the same as those of the co-occurring congeners on the basis of their biogenetic consideration and was supported by the comparison of its sign of optical rotation with those of its steroisomers.