Circumdatin H Explained

Circumdatin H is an alkaloid. It was isolated, along with related compounds, from the fungus Aspergillus ochraceus.^[1]

Circumdatin C, and circumdatin F are prototypical members, while other members such as circumdatin D, circumdatin E and circumdatin H have an additional tetrahydropyrrole ring.

The compounds of this group are considered to be useful chemotaxonomic markers. Among these circumdatin H and circumdatin E are able to inhibit the mitochondrial respiratory chain in submitochondrial particles from beef heart, presumable by interfering with NADH oxidase activity (IC₅₀ 1.5 μM and 2.5 μM, respectively).

First total synthesis of circumdatin H was reported starting from anthranilic acid.^[2]

Notes and References

1. López-Gresa. M Pilar. González, M Carmen . Primo, Jaime . Moya, Pilar . Romero, Vanessa . Estornell, Ernesto . Circumdatin H, a New Inhibitor of Mitochondrial NADH Oxidase, from Aspergillus ochraceus. The Journal of Antibiotics. 1 June 2005. 58. 6. 416–419. 10.1038/ja.2005.54. 16156520. free.
2. 10.1055/s-0029-1218606. First Total Synthesis of (-)-Circumdatin H, a Novel Mitochondrial NADH Oxidase Inhibitor. Synthesis. 2010. 4. 643. 2009. Bose. D.. Chary. M..