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TMKS8A, an antibacterial and cytotoxic chlorinated α-lapachone, from a sea slug-derived actinomycete of the genus Streptomyces

The Journal of Antibiotics volume 74, pages 464–469 (2021)Cite this article

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Abstract

TMKS8A (1), a new chlorinated α-lapachone derivative, along with five known related metabolites, A80915 C (2), SF2415B1 (3), chlorinated dihydroquinone 3 (4), SF2415B3 (5), and A80915 C (6), were identified from the culture extract of Streptomyces sp. TMKS8, which was isolated from a sea slug, Paromoionchis tumidus. The structure of 1 was determined by the analysis of NMR and MS spectral data, assisted by NMR chemical shift prediction using DFT-based calculation. The absolute configuration was determined to be R by comparison of experimental and calculated ECD spectra. Compound 1 displayed antimicrobial activity against Gram-positive bacteria with MIC values ranging from 6.25 to 12.5 μg ml−1 and cytotoxicity against murine leukemia P388 cells with IC50 9.8 μM.

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Acknowledgements

P388 cells were obtained from JCRB Cell Bank under an accession code JCRB0017 (Lot. 06252002). We thank Mr. Tatsuya Matsui and Mr. Yiwei Ge at Toyama Prefectural University for cytotoxicity assay.

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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

    Zhiwei Zhang, Akiho Kai, Keisuke Fukaya, Daisuke Urabe & Yasuhiro Igarashi

  2. Department of Marine Science, Faculty of Fisheries and Marine Science, Diponegoro University, Semarang, Central Java, 50275, Indonesia

    Mada Triandala Sibero

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  1. Zhiwei Zhang
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  3. Akiho Kai
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Correspondence to Yasuhiro Igarashi.

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Zhang, Z., Sibero, M.T., Kai, A. et al. TMKS8A, an antibacterial and cytotoxic chlorinated α-lapachone, from a sea slug-derived actinomycete of the genus Streptomyces. J Antibiot 74, 464–469 (2021). https://doi.org/10.1038/s41429-021-00415-4

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  • DOI: https://doi.org/10.1038/s41429-021-00415-4

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