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Bisprenyl naphthoquinone and chlorinated calcimycin congener bearing thiazole ring from an actinomycete of the genus Phytohabitans

The Journal of Antibiotics volume 75, pages 542–551 (2022)Cite this article

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Abstract

A bisprenyl naphthoquinone, phytohabinone (1), and a calcimycin congener with unusual modifications, phytohabimicin (2), were isolated from the culture extract of Phytohabitans sp. RD003013. The structures of 1 and 2 were determined by NMR and MS analyses, and the absolute configuration of 2 was established by using electronic circular dichroism (ECD) calculation. The prenylation pattern of 1 was unprecedented among the known prenylated naphthoquinones. Compound 2 represents a spiroacetal core of polyketide origin substituted with a thiazole carboxylic acid and a dichrolopyrrole moiety, which is an unprecedented modification pattern in the known calcimycin family natural products. Remarkably, 2 showed moderate antimicrobial activity against a Gram-negative bacterium Ralstonia solanacearum while calcimycin was inactive. Additionally, 2 inhibits the migration of EC17 cancer cells at noncytotoxic concentrations.

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Acknowledgements

P388 cells were obtained from JCRB Cell Bank under accession code JCRB0017 (Lot. 06252002). This research was supported by JSPS KAKENHI grant no. JP19K05848 to Y. I.

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Authors and Affiliations

  1. Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama, 939-0398, Japan

    Enjuro Harunari, Shunsuke Mae, Keisuke Fukaya, Daisuke Urabe & Yasuhiro Igarashi

  2. Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo, 194-8543, Japan

    Etsu Tashiro

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  1. Enjuro Harunari
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Correspondence to Yasuhiro Igarashi.

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Harunari, E., Mae, S., Fukaya, K. et al. Bisprenyl naphthoquinone and chlorinated calcimycin congener bearing thiazole ring from an actinomycete of the genus Phytohabitans. J Antibiot 75, 542–551 (2022). https://doi.org/10.1038/s41429-022-00559-x

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