Nanaomycin I and J: New nanaomycins generated by mycothiol-mediated compounds from “Streptomyces rosa subsp. notoensis” OS-3966

Hirotaka Matsuo, Yoshihiko Noguchi, Akira Také, Jun Nakanishi, Katsumi Shigemura, Toshiaki Sunazuka, Yōko Takahashi, Satoshi Ōmura, Takuji Nakashima

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Two new nanaomycin analogs, nanaomycin I and J, were isolated from a cultured broth of an actinomycete strain, “Streptomyces rosa subsp. notoensis” OS-3966. In our previous study, we have confirmed the occurrence of nanaomycin I (m/z = 482 [M + H]+) that lacks a pseudo-disaccharide from the mycothiol of nanaomycin H under same culture condition. In this study, to confirm the structure of nanaomycin I, the strain “S. rosa subsp. notoensis” OS-3966 was re-cultured and the target compound with m/z = 482 [M + H]+ was isolated. Furthermore, we discovered another new analog, designated as nanaomycin J in isolating nanaomycin I. The NMR analyses revealed that the structures of nanaomycin I and J are N-acetylcysteine S-conjugates without a pseudo-disaccharide and N-acetylcysteine S-conjugates without a myo-inositol of nanaomycin H, respectively. The relative configurations of the tetrahydropyrane moiety of nanaomycin I and J were determined by rotating-frame overhauser effect spectroscopy (ROESY) analysis. Absolute configurations of the N-acetylcysteine moiety of nanaomycin I and J were determined by advanced Marfey's analyses for acid hydrolysis of de-sulfurized nanaomycin I and J with Raney nickel. Nanaomycin I and J showed moderate cytotoxicity against several human tumor cell lines.

Original languageEnglish
JournalJournal of Bioscience and Bioengineering
DOIs
Publication statusAccepted/In press - 2018 Jan 1
Externally publishedYes

Fingerprint

Acetylcysteine
Streptomyces
Disaccharides
Actinobacteria
Inositol
Cytotoxicity
Tumor Cell Line
Nickel
Tumors
Hydrolysis
Spectrum Analysis
Cells
Nuclear magnetic resonance
Spectroscopy
Acids
mycothiol

Keywords

  • Actinomycete
  • Metabolite
  • Mycothiol
  • Nanaomycin I
  • Nanaomycin J
  • Streptomyces

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Applied Microbiology and Biotechnology

Cite this

Nanaomycin I and J : New nanaomycins generated by mycothiol-mediated compounds from “Streptomyces rosa subsp. notoensis” OS-3966. / Matsuo, Hirotaka; Noguchi, Yoshihiko; Také, Akira; Nakanishi, Jun; Shigemura, Katsumi; Sunazuka, Toshiaki; Takahashi, Yōko; Ōmura, Satoshi; Nakashima, Takuji.

In: Journal of Bioscience and Bioengineering, 01.01.2018.

Research output: Contribution to journalArticle

Matsuo, Hirotaka ; Noguchi, Yoshihiko ; Také, Akira ; Nakanishi, Jun ; Shigemura, Katsumi ; Sunazuka, Toshiaki ; Takahashi, Yōko ; Ōmura, Satoshi ; Nakashima, Takuji. / Nanaomycin I and J : New nanaomycins generated by mycothiol-mediated compounds from “Streptomyces rosa subsp. notoensis” OS-3966. In: Journal of Bioscience and Bioengineering. 2018.
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