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Article

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

by
Mercedes Pérez-Bonilla
1,*,
Marina Sánchez-Hidalgo
1,
Ignacio González
1,
Daniel Oves-Costales
1,
Jesús Martín
1,
José Murillo-Alba
1,
José R. Tormo
1,
Ahreum Cho
2,
Soo-Young Byun
2,
Joo-Hwan No
2,
David Shum
2,
Jean-Robert Ioset
3,
Olga Genilloud
1 and
Fernando Reyes
1,*
1
Fundación MEDINA, Avda. del Conocimiento 34, 18016 Granada, Spain
2
Institut Pasteur Korea, 16, Daewangpangyo-ro 712 beon-gil, Bundang-gu, Seongnam-si 13488, Gyeonggi-do, Republic of Korea
3
Drugs for Neglected Diseases Initiative, 15 Chemin Camille-Vidart, 1202 Geneva, Switzerland
*
Authors to whom correspondence should be addressed.
Int. J. Mol. Sci. 2024, 25(1), 301; https://doi.org/10.3390/ijms25010301
Submission received: 24 November 2023 / Revised: 21 December 2023 / Accepted: 22 December 2023 / Published: 25 December 2023
(This article belongs to the Special Issue Bioactive Natural Products: Isolation, Structural Elucidation and Biological Assays, 2nd Edition)
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Abstract

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 Actinomadura sp. CA-135719. The LC/HRMS analysis of this extract identified the presence of the known madurastatins C1 (1), D1 (4), and D2 (5) together with additional members of the family that were identified as the new madurastatins H2 (2) and 33-epi-D1 (3) 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.
Keywords: madurastatin; neglected tropical diseases; Leishmania donovani; Trypanosoma cruzi madurastatin; neglected tropical diseases; Leishmania donovani; Trypanosoma cruzi

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MDPI and ACS Style

Pérez-Bonilla, M.; Sánchez-Hidalgo, M.; González, I.; Oves-Costales, D.; Martín, J.; Murillo-Alba, J.; Tormo, J.R.; Cho, A.; Byun, S.-Y.; No, J.-H.; et al. Madurastatins with Imidazolidinone Rings: Natural Products or Side-Reaction Products from Extraction Solvents? Int. J. Mol. Sci. 2024, 25, 301. https://doi.org/10.3390/ijms25010301

AMA Style

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, et al. Madurastatins with Imidazolidinone Rings: Natural Products or Side-Reaction Products from Extraction Solvents? International Journal of Molecular Sciences. 2024; 25(1):301. https://doi.org/10.3390/ijms25010301

Chicago/Turabian Style

Pérez-Bonilla, Mercedes, Marina Sánchez-Hidalgo, Ignacio González, Daniel Oves-Costales, Jesús Martín, José Murillo-Alba, José R. Tormo, Ahreum Cho, Soo-Young Byun, Joo-Hwan No, and et al. 2024. "Madurastatins with Imidazolidinone Rings: Natural Products or Side-Reaction Products from Extraction Solvents?" International Journal of Molecular Sciences 25, no. 1: 301. https://doi.org/10.3390/ijms25010301

APA Style

Pérez-Bonilla, M., Sánchez-Hidalgo, M., González, I., Oves-Costales, D., Martín, J., Murillo-Alba, J., Tormo, J. R., Cho, A., Byun, S.-Y., No, J.-H., Shum, D., Ioset, J.-R., Genilloud, O., & Reyes, F. (2024). Madurastatins with Imidazolidinone Rings: Natural Products or Side-Reaction Products from Extraction Solvents? International Journal of Molecular Sciences, 25(1), 301. https://doi.org/10.3390/ijms25010301

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