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A new indole glycoside from Kitasatospora sp. MG372-hF19 carrying a 6-deoxy-α-l-talopyranose moiety

The Journal of Antibiotics volume 73, pages 167–170 (2020)Cite this article

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Abstract

Small cell lung cancer (SCLC) is a severe malignancy with early and widespread metastasis, and novel therapeutic drugs are needed. To identify cytotoxic natural compounds against SCLC, we screened libraries of microbial fermentation broths using several lung cancer cell lines. We found that the actinomycete strain MG372-hF19 produces a compound that has not been isolated from natural sources but previously chemically synthesized, 6-chloro-1H-indole-3-carboxaldehyde (1), and an entirely new compound, named 6-deoxy-α-L-talopyranose 1-(6-chloro-1H-indole-3-carboxylate) (2), together with leptomycins. The molecular formulas of the compounds were established as C9H6ClNO and C15H16ClNO6, respectively, via high-resolution electrospray ionization mass spectrometry, and their structures were determined using detailed NMR. Absolute configurational analysis of the sugar unit of compound 2 revealed that the compound incorporates the rare deoxyhexose 6-deoxy-α-L-talopyranose. Both compounds exhibited weak growth-inhibiting activities against human lung cancer cell lines.

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Acknowledgements

We thank Ms Tamami Yoshida, Ms Satomi Unno, and Ms Rina Ando for their technical assistance. We also thank the members of the Institute of Microbial Chemistry, Numazu for helpful discussion. This work was supported in part by grants from JSPS KAKENHI Grant Number 17K08777. We thank Joe Barber, Jr., PhD, from Edanz Group (www.edanzediting.com/ac) for editing a draft of this manuscript.

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Authors and Affiliations

  1. Institute of Microbial Chemistry (BIKAKEN), Numazu, 18-24 Miyamoto, Numazu-shi, Shizuoka, 410-0301, Japan

    Yasuko Kohda, Shuichi Sakamoto, Yasunari Otsuka, Masatomi Iijima & Manabu Kawada

  2. Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo, 141-0021, Japan

    Ryuichi Sawa, Yumiko Kubota, Masayuki Igarashi, Hideyuki Muramatsu & Manabu Kawada

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  1. Yasuko Kohda
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  2. Shuichi Sakamoto
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  3. Yasunari Otsuka
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Correspondence to Shuichi Sakamoto.

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Kohda, Y., Sakamoto, S., Otsuka, Y. et al. A new indole glycoside from Kitasatospora sp. MG372-hF19 carrying a 6-deoxy-α-l-talopyranose moiety. J Antibiot 73, 167–170 (2020). https://doi.org/10.1038/s41429-019-0258-9

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  • DOI: https://doi.org/10.1038/s41429-019-0258-9

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