Abstract

A chemical investigation of secondary metabolites from the sponge Aiolochroia crassa has been performed and five bromotyrosine derivatives ( 1–5) were identified. Their structures have been assigned on the basis of spectroscopic analysis, of which araplysillin III ( 2) and hexadellin C ( 3) possess new structures. The absolute configurations of dibromotyrosine moieties of 2 were determined by HPLC analysis of derivatized constituent amino acids obtained from acid hydrolysis. The stereochemistry of the spirocyclohexadienylisoxazoline moiety of compounds 1–3 was deduced from spectroscopic comparison of the same moiety of aerothionin, of which the absolute configuration was previously assigned by X-ray and CD analysis. Five bromotyrosine derivatives from the sponge Aiolochroia crassa have been identified. The structures including stereochemistry are reported for the new compounds ( 1) and ( 2). [Display omitted]

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