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 language | English |
|---|---|
| Pages (from-to) | 765-770 |
| Number of pages | 6 |
| Journal | Journal of Bioscience and Bioengineering |
| Volume | 123 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - 2017 Jun 1 |
| Externally published | Yes |
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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
Nanaomycin H : A new nanaomycin analog. / Nakashima, Takuji; Kimura, Toru; Miyano, Rei; Matsuo, Hirotaka; Hirose, Tomoyasu; Kimishima, Aoi; Nonaka, Kenichi; Iwatsuki, Masato; Nakanishi, Jun; Takahashi, Yōko; Ōmura, Satoshi.
In: Journal of Bioscience and Bioengineering, Vol. 123, No. 6, 01.06.2017, p. 765-770.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Nanaomycin H
T2 - A new nanaomycin analog
AU - Nakashima, Takuji
AU - Kimura, Toru
AU - Miyano, Rei
AU - Matsuo, Hirotaka
AU - Hirose, Tomoyasu
AU - Kimishima, Aoi
AU - Nonaka, Kenichi
AU - Iwatsuki, Masato
AU - Nakanishi, Jun
AU - Takahashi, Yōko
AU - Ōmura, Satoshi
PY - 2017/6/1
Y1 - 2017/6/1
N2 - 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.
AB - 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.
KW - Nanaomycin H
KW - New nanaomycin analog
KW - Physicochemical screening
KW - Streptomyces spp.
UR - http://www.scopus.com/inward/record.url?scp=85012025937&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85012025937&partnerID=8YFLogxK
U2 - 10.1016/j.jbiosc.2017.01.011
DO - 10.1016/j.jbiosc.2017.01.011
M3 - Article
C2 - 28202308
AN - SCOPUS:85012025937
VL - 123
SP - 765
EP - 770
JO - Journal of Bioscience and Bioengineering
JF - Journal of Bioscience and Bioengineering
SN - 1389-1723
IS - 6
ER -