Tripartilactam, a Cyclobutane-Bearing Tricyclic Lactam from a <i>Streptomyces</i> sp. in a Dung Beetle’s Brood Ball

Tripartilactam, a structurally unprecedented cyclobutane-bearing tricyclic lactam metabolite, was discovered from <i>Streptomyces</i> sp. isolated from a brood ball of the dung beetle, <i>Copris tripartitus</i>. The structure of this compound was elucidated by the combination of NMR, MS, UV, and IR spectroscopy and multistep chemical derivatization. Tripartilactam was evaluated as a Na⁺/K⁺ ATPase inhibitor (IC₅₀ = 16.6 μg/mL)

Coprisamides A and B, New Branched Cyclic Peptides from a Gut Bacterium of the Dung Beetle <i>Copris tripartitus</i>

Coprisamides A and B (<b>1</b> and <b>2</b>) were isolated from a bacterium in the gut of the dung beetle <i>Copris tripartitus</i>. Spectroscopic analysis revealed that the planar structures of <b>1</b> and <b>2</b> are novel cyclic heptapeptides bearing unusual units, such as β-methylaspartic acid and 2,3-diaminopropanoic acid branched to valine and 2-heptatrienyl cinnamic acid. Absolute configurations were established by chemical derivatization and chiroptical spectroscopy. The coprisamides displayed significant activity for induction of quinone reductase

Tripartin, a Histone Demethylase Inhibitor from a Bacterium Associated with a Dung Beetle Larva

Tripartin (<b>1</b>), a new dichlorinated indanone, was isolated from the culture broth of the <i>Streptomyces</i> sp. associated with a larva of the dung beetle <i>Copris tripartitus</i> Waterhouse. The planar structure of tripartin (<b>1</b>) was identified by the spectroscopic analyses of NMR, mass, UV, and IR data. The structure was confirmed, and the absolute configuration of <b>1</b> was determined by X-ray crystallography. Tripartin displayed specific activity as an inhibitor of the histone H3 lysine 9 demethylase KDM4 in HeLa cells

Naphthoquinone–Oxindole Alkaloids, Coprisidins A and B, from a Gut-Associated Bacterium in the Dung Beetle, <i>Copris tripartitus</i>

Coprisidins A and B (<b>1</b> and <b>2</b>) were isolated from a gut-associated <i>Streptomyces</i> sp. in the dung beetle <i>Copris tripartitus</i>. Using a combination of spectroscopic techniques, the structures of the compounds were determined to be the first examples of natural naphthoquinone–oxindole alkaloids. Coprisidin A was found to inhibit the action of Na⁺/K⁺-ATPase, and coprisidin B showed activity for the induction of NAD­(P)­H:quinone oxidoreductase 1