Nanaomycin H: A new nanaomycin analog

Takuji Nakashima, Toru Kimura, Rei Miyano, Hirotaka Matsuo, Tomoyasu Hirose, Aoi Kimishima, Kenichi Nonaka, Masato Iwatsuki, Jun Nakanishi, Yōko Takahashi, Satoshi Ōmura

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4 Citations (Scopus)

Abstract

Physicochemical screening identified a new nanaomycin analog, nanaomycin H, which was isolated from a culture broth of Streptomyces rosa subsp. notoensis OS-3966. This microorganism is already known to produce seven nanaomycin compounds, (nanaomycin A to G). Structural elucidation of nanaomycin H showed it to be a pyranonaphthoquinone with a mycothiol moiety. A N-acetylcysteine S-conjugate of nanaomycin H, without α-glucosamine linked to myo-inositol moiety, mercapturic acid derivative, was also detected in the same culture broth. Mercapturic acid derivatives of secondary metabolites are known to be produced for xenobiotic metabolism outside microbial cells. Mycothiol acts as a detoxifier to help prevent cell damage from factors such as oxidative stress. The production of O2 [rad] generated by reduction of nanaomycin A is correlated with antibacterial activity. Mycothiol-containing nanaomycin H proved to be markedly decreased in O2 [rad] and did not express any notable antimicrobial activity. It is suggested that nanaomycin H is produced in the detoxification process.

Original languageEnglish
Pages (from-to)765-770
Number of pages6
JournalJournal of Bioscience and Bioengineering
Volume123
Issue number6
DOIs
Publication statusPublished - 2017 Jun 1
Externally publishedYes

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Keywords

  • Nanaomycin H
  • New nanaomycin analog
  • Physicochemical screening
  • Streptomyces spp.

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Applied Microbiology and Biotechnology

Cite this

Nakashima, T., Kimura, T., Miyano, R., Matsuo, H., Hirose, T., Kimishima, A., Nonaka, K., Iwatsuki, M., Nakanishi, J., Takahashi, Y., & Ōmura, S. (2017). Nanaomycin H: A new nanaomycin analog. Journal of Bioscience and Bioengineering, 123(6), 765-770. https://doi.org/10.1016/j.jbiosc.2017.01.011