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N-Acetyl-α-hydroxy-β-oxotryptamine, a racemic natural product isolated from Streptomyces sp. 80H647

The Journal of Antibiotics volume 74, pages 477–479 (2021)Cite this article

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Abstract

N-acetyl-α-hydroxy-β-oxotryptamine (1) along with N-acetyl-β-oxotryptamine (2) and pimprinine (3) were isolated from the culture broth of Streptomyces sp. 80H647. Compound 1 was found to be a racemate via X-ray diffraction analysis and the enantiomers were successfully purified by chiral-phase HPLC. The absolute configuration was assigned by comparison of the calculated and experimental ECD spectra. The α-hydroxy moiety of 1 was vital for cytotoxicity against different cancer cell lines.

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Acknowledgements

We thank Dr. T. Kawamura for the ROS assay. The computer calculation using Gaussian 16 was performed using the HOKUSAI supercomputer at RIKEN.

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Authors and Affiliations

  1. RIKEN Center for Sustainable Resource Science, Chemical Biology Research Group, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan

    Julius Adam V. Lopez, Toshihiko Nogawa, Yushi Futamura, Harumi Aono & Hiroyuki Osada

  2. RIKEN Center for Emergent Matter Science, Materials Characterization Support Team, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan

    Daisuke Hashizume

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  1. Julius Adam V. Lopez
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  2. Toshihiko Nogawa
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  3. Yushi Futamura
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  4. Harumi Aono
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  6. Hiroyuki Osada
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Correspondence to Hiroyuki Osada.

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Lopez, J.A.V., Nogawa, T., Futamura, Y. et al. N-Acetyl-α-hydroxy-β-oxotryptamine, a racemic natural product isolated from Streptomyces sp. 80H647. J Antibiot 74, 477–479 (2021). https://doi.org/10.1038/s41429-021-00420-7

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  • DOI: https://doi.org/10.1038/s41429-021-00420-7

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