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Four new 5-hydroxyanthranilic acid related compounds, named anthocidins A⁻D ( 1 ⁻ 4 ), two known analogues n -lauryl 5-hydroxyanthranilate ( 5 ) and isolauryl 5-hydroxyanthranilate ( 6 ), together with benzamide ( 7 ), 3-hydroxy-4-methoxycinnamamide ( 8 ), and (3 S - cis )-hexahydro-3-[(3,4-dihydroxyphenyl)methyl]pyrrolo[1,2- a ]pyrazine-1,4-dione ( 9 ), were isolated from the fermentation broth of the marine-derived actinomycete, Streptomyces sp. HDa1, which was isolated from the gut of a sea urchin, Anthocidaris crassispina , collected from Hainan Island, China. The structures of these secondary metabolites were elucidated on the basis of their 1D and 2D-NMR and mass spectroscopic data, and anthocidin A was confirmed by single-crystal X-ray diffraction with Cu Kα radiation. Anthocidins A⁻D ( 1 ⁻ 4 ) feature an acetyl group substitution at the amino group and varying alkyl side chains at the carboxyl group of 5-hydroxyanthranilic acid, and compound 5 was isolated as a natural product for the first time. The cytotoxic and antibacterial activity of compounds 1 ⁻ 9 were evaluated.

Anthocidins A–D, New 5-Hydroxyanthranilic Acid Related Metabolites from the Sea Urchin-Associated Actinobacterium, Streptomyces sp. HDa1