Original Article | Published:

Valgamicin C, a novel cyclic depsipeptide containing the unusual amino acid cleonine, and related valgamicins A, T and V produced by Amycolatopsis sp. ML1-hF4

The Journal of Antibiotics volume 71, pages 129134 (2018) | Download Citation

Abstract

In the course of optimizing pargamicin A production in Amycolatopsis sp. ML1-hF4, we discovered novel cyclic depsipeptide compounds in the broth and designated them valgamicins A, C, T and V. The structures of these molecules were determined by spectroscopic studies, advanced Marfey’s method and X-ray crystal structural analysis. Valgamicin C contains the extremely rare amino acid cleonine. To our knowledge, this is the first report of a cleonine-containing metabolite from a naturally isolated microorganism without any breeding or mutation treatment. None of the valgamicins showed potent antibacterial activity against either Gram-positive or -negative bacteria. Valgamicins A, C and T exhibited moderate cytotoxicity against human tumor cell lines.

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Acknowledgements

The authors are grateful to the following researchers working at the Institute of Microbial Chemistry (BIKAKEN): Ms Yumiko Kubota for the measurement of NMR spectra; Ms Yuko Shibuya for the measurement of MICs; Ms Shigeko Harada for her technical assistance; Ms Miho Nagayoshi for the measurement of cytotoxicity; and Dr Yoshio Nishimura and Dr Hayamitsu Adachi for valuable discussions. This work was supported by the Japan Society for the Promotion of Science KAKENHI, grant number 16K08338.

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  1. Institute of Microbial Chemistry (BIKAKEN), Tokyo, Japan

    • Hideki Hashizume
    • , Kiyoko Iijima
    • , Kazuma Yamashita
    • , Tomoyuki Kimura
    • , Shun-ichi Wada
    • , Ryuichi Sawa
    •  & Masayuki Igarashi

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The authors declare no conflict of interest.

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Correspondence to Hideki Hashizume.

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https://doi.org/10.1038/ja.2017.135

Supplementary Information accompanies the paper on The Journal of Antibiotics website (http://www.nature.com/ja)