TY - JOUR
T1 - Nocardamin glucuronide, a new member of the ferrioxamine siderophores isolated from the ascamycin-producing strain Streptomyces sp. 80H647
AU - Lopez, Julius Adam V.
AU - Nogawa, Toshihiko
AU - Futamura, Yushi
AU - Shimizu, Takeshi
AU - Osada, Hiroyuki
N1 - Funding Information:
Acknowledgements This work was supported in part by JSPS KAKENHI Grant Numbers JP16H06276, JP17H06412, and JP18H03945. We would like to thank Ms Harumi Aono, Ms Akiko Okano, Dr Rachael Uson-Lopez, Ms Emiko Sanada, and Dr Motoko Uchida for technical support.
Publisher Copyright:
© 2019, The Author(s), under exclusive licence to the Japan Antibiotics Research Association.
PY - 2019/12/1
Y1 - 2019/12/1
N2 - A new siderophore glucuronide, nocardamin glucuronide (1), was isolated together with nocardamin (2) by applying the one strain-many compounds (OSMAC) approach to the ascamycin-producing strain, Streptomyces sp. 80H647, and performing multivariate analysis using mass spectral data. Structure elucidation was accomplished by a combination of NMR and MS analyses. The absolute configuration of the glucuronic acid moiety was found to be β-D-GlcA by hydrolysis using β-glucuronidase, subsequent derivatization of the hydrolysate, and comparison with standards. The siderophore activity of 1 was evaluated through the chrome azurol S assay and was comparable to that of 2 and deferoxamine (IC50 13.4, 9.5, and 6.3 μM, respectively). Nocardamin glucuronide (1) is the first example of a siderophore glucuronide.
AB - A new siderophore glucuronide, nocardamin glucuronide (1), was isolated together with nocardamin (2) by applying the one strain-many compounds (OSMAC) approach to the ascamycin-producing strain, Streptomyces sp. 80H647, and performing multivariate analysis using mass spectral data. Structure elucidation was accomplished by a combination of NMR and MS analyses. The absolute configuration of the glucuronic acid moiety was found to be β-D-GlcA by hydrolysis using β-glucuronidase, subsequent derivatization of the hydrolysate, and comparison with standards. The siderophore activity of 1 was evaluated through the chrome azurol S assay and was comparable to that of 2 and deferoxamine (IC50 13.4, 9.5, and 6.3 μM, respectively). Nocardamin glucuronide (1) is the first example of a siderophore glucuronide.
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U2 - 10.1038/s41429-019-0217-5
DO - 10.1038/s41429-019-0217-5
M3 - Article
C2 - 31395970
AN - SCOPUS:85070868842
SN - 0021-8820
VL - 72
SP - 991
EP - 995
JO - Journal of Antibiotics
JF - Journal of Antibiotics
IS - 12
ER -