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2-Epi-anthracimycin, a new cytotoxic agent from the marine-derived actinomycete Streptomyces sp. OPMA00631

The Journal of Antibiotics volume 73, pages 548–553 (2020)Cite this article

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Abstract

A new cytotoxic agent designated as 2-epi-anthracimycin (1) was isolated along with anthracimycin and anthracimycin B (2-demethylanthracimycin) from the culture broth of the marine-derived actinomycete Streptomyces sp. OPMA00631. The structure of 1 was elucidated based on spectroscopic analyses (1D and 2D NMR data and ROESY correlations). Compound 1 exhibited cytotoxicity against Jurkat cells with an IC50 value of 50.5 μM in 20 h. The effect of 1 on the cell cycle distribution of Jurkat cells was investigated. Compound 1 (7.80 μM) increased G1 phase cells from 51.1 to 62.0% and conversely, decreased G2 and M phase cells from 30.7 to 19.3 % in 20 h. At a higher concentration, 1 (250 μM) markedly increased subG1 phase cells (1.9% at 0 h to 16.5% at 20 h), while the proportion of G1 phase cells was maintained (62.3%). These results suggest that 1 exhibits cytotoxicity against Jurkat cells by arresting the cell cycle at the G1 phase.

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Acknowledgements

We wish to thank Mr Yuto Akamada, Ms Ikumi Katayose, and Yuichi Naganuma for their excellent assistance with this work, and Ms Noriko Sato (School of Pharmaceutical Sciences, Kitasato University) for measuring NMR spectra. This work was supported by JSPS KAKENHI Grant Number 19K05855 (TF) and the Front and Grant for Scientific Research from the Faculty of Agriculture, Kindai University.

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Authors and Affiliations

  1. Department of Fisheries, Faculty of Agriculture and Agricultural Technology and Innovation Research Institute, Kindai University, 3327-204 Nakamachi, Nara, 631-8505, Japan

    Takashi Fukuda

  2. Microbial Chemistry and Medicinal Research Laboratories, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan

    Takashi Fukuda, Kenichiro Nagai & Hiroshi Tomoda

  3. OP BIO FACTORY Co., Ltd., 5 Uruma Sandpit, Okinawa, 904-2234, Japan

    Akihiko Kanamoto

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  1. Takashi Fukuda
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Correspondence to Takashi Fukuda or Hiroshi Tomoda.

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Dedication: This paper is dedicated to Professor William Fenical, an inspirational mentor, in recognition of his pioneering work on marine microorganisms and marine natural products.

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Fukuda, T., Nagai, K., Kanamoto, A. et al. 2-Epi-anthracimycin, a new cytotoxic agent from the marine-derived actinomycete Streptomyces sp. OPMA00631. J Antibiot 73, 548–553 (2020). https://doi.org/10.1038/s41429-020-0309-2

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