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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
Journal of bioscience and bioengineering 2019 v.127 no.5 pp. 549-553
Streptomyces rosa, acetylcysteine, acid hydrolysis, cytotoxicity, human cell lines, humans, moieties, myo-inositol, neoplasm cells, nickel, nuclear magnetic resonance spectroscopy
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.