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Nocardamin glucuronide, a new member of the ferrioxamine siderophores isolated from the ascamycin-producing strain Streptomyces sp. 80H647

The Journal of Antibiotics volume 72, pages 991–995 (2019)Cite this article

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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.

In search for new bioactive compounds, the Streptomyces sp. 80H647 strain was subjected to the one strain-many compounds (OSMAC) method [1]. This strain is a producer of the nucleoside antibiotic, ascamycin [2], and we hypothesized that the production of more structurally interesting metabolites will be stimulated under different culture conditions [1].

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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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  1. RIKEN Center for Sustainable Resource Science, Chemical Biology Research Group, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan

    Julius Adam V. Lopez, Toshihiko Nogawa, Yushi Futamura, Takeshi Shimizu & Hiroyuki Osada

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  1. Julius Adam V. Lopez
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  2. Toshihiko Nogawa
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Correspondence to Hiroyuki Osada.

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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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