Abstract
A new siderophore glucuronide, nocardamin glucuronide (1), was isolated together with nocardamin (2) by applying the one strain-many compounds (OSMAC) approach to the ascamycin-producing strain, Streptomyces sp. 80H647, and performing multivariate analysis using mass spectral data. Structure elucidation was accomplished by a combination of NMR and MS analyses. The absolute configuration of the glucuronic acid moiety was found to be β-D-GlcA by hydrolysis using β-glucuronidase, subsequent derivatization of the hydrolysate, and comparison with standards. The siderophore activity of 1 was evaluated through the chrome azurol S assay and was comparable to that of 2 and deferoxamine (IC50 13.4, 9.5, and 6.3 μM, respectively). Nocardamin glucuronide (1) is the first example of a siderophore glucuronide.
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Acknowledgements
This work was supported in part by JSPS KAKENHI Grant Numbers JP16H06276, JP17H06412, and JP18H03945. We would like to thank Ms Harumi Aono, Ms Akiko Okano, Dr Rachael Uson-Lopez, Ms Emiko Sanada, and Dr Motoko Uchida for technical support.
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This article is dedicated to Dr Kiyoshi Isono with respect and admiration for his achievements in antibiotics research.
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Nocardamin glucuronide, a new member of the ferrioxamine siderophores isolated from the ascamycin-producing strain Streptomyces sp. 80H647
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Lopez, J.A.V., Nogawa, T., Futamura, Y. et al. Nocardamin glucuronide, a new member of the ferrioxamine siderophores isolated from the ascamycin-producing strain Streptomyces sp. 80H647. J Antibiot 72, 991–995 (2019). https://doi.org/10.1038/s41429-019-0217-5
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DOI: https://doi.org/10.1038/s41429-019-0217-5
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