Madurastatins with Imidazolidinone Rings: Natural Products or Side-Reaction Products from Extraction Solvents?

Madurastatins are a group of pentapeptides containing an oxazoline moiety, and, in a few cases, an imidazolidinone ring as an additional structural feature. In our search for new potential antiparasitic metabolites from natural sources, we studied the acetone extracts from a culture of sp. CA-135719...

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Bibliographic Details
Published in:International journal of molecular sciences 2023-12, Vol.25 (1), p.301
Main Authors: Pérez-Bonilla, Mercedes, Sánchez-Hidalgo, Marina, González, Ignacio, Oves-Costales, Daniel, Martín, Jesús, Murillo-Alba, José, Tormo, José R, Cho, Ahreum, Byun, Soo-Young, No, Joo-Hwan, Shum, David, Ioset, Jean-Robert, Genilloud, Olga, Reyes, Fernando
Format: Article
Language:English
Subjects:
Acetone
Amino acids
Chromatography
Genomes
Leishmania donovani
madurastatin
Metabolites
Natural products
neglected tropical diseases
Tropical diseases
Trypanosoma cruzi
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Summary:Madurastatins are a group of pentapeptides containing an oxazoline moiety, and, in a few cases, an imidazolidinone ring as an additional structural feature. In our search for new potential antiparasitic metabolites from natural sources, we studied the acetone extracts from a culture of sp. CA-135719. The LC/HRMS analysis of this extract identified the presence of the known madurastatins C1 ( ), D1 ( ), and D2 ( ) together with additional members of the family that were identified as the new madurastatins H2 ( ) and 33- -D1 ( ) after isolation and spectroscopic analysis. The planar structures of the new compounds were established by HRMS, ESI-qTOF-MS/MS, and 1D and 2D NMR data, and their absolute configuration was proposed using Marfey's and bioinformatic analyses of the biosynthetic gene cluster (BGC). A revision of the absolute configuration of madurastatins D1 and D2 is proposed. Additionally, madurastatins containing imidazolidinone rings are proved to be artifacts originating during acetone extraction of the bacterial cultures.
ISSN:1422-0067
1661-6596
1422-0067
DOI:10.3390/ijms25010301