Madurastatins with imidazolidinone rings: Natural products or side-reaction products from extraction solvents?

By Pérez-Bonilla M, Sánchez-Hidalgo M, González I, Oves-Costales D, Martín J, Murillo-Alba J, Tormo JR, Cho A, Byun S-Y, No J-H, David S, Ioset J-R, Genilloud O, Reyes F. International Journal of Molecular Sciences 2023, 25(1): 301. doi: 10.3390/ijms25010301

Summary: Madurastatins are a group of pentapeptides containing an oxazoline moiety, and, in a few cases, an imidazolidinone ring as an additional structural feature. As part of their search for new potential antiparasitic metabolites from natural sources, the authors studied acetone extracts from a culture of Actinomadura sp. CA-135719. Analysis identified the presence of three known and two new madurastatins. Four of these compounds, containing 4-imidazolidinone rings, were shown to be artifacts formed during the acetone extraction of the culture broths, meaning that only one madurastatin (C1) is produced in significant titers by the strain Actinomadura sp. CA-135719. The authors also revised and corrected the absolute stereochemistry of two previously reported madurastatins.

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