Abstract
The marine actinomycete strain OPMA02852, identified as the genus Streptomyces, was found to produce anti-mycobacterial compounds against Mycobacterium avium complex (MAC). One new compound, designated as steffimycin E (1), was isolated together with three known steffimycins (steffimycin (2), 10-dihydrosteffimycin (3), and 8-demethoxysteffimycin (4)) from the culture broth of this producing microorganism by solvent extraction, ODS column chromatography, and preparative HPLC. Compound 1 has a tetracyclic quinone structure with a sugar moiety. Compound 1 exhibited anti-mycobacterial activity against M. intracellulare, M. bovis BCG, and M. smegmatis.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 12 print issues and online access
$259.00 per year
only $21.58 per issue
Buy this article
- Purchase on Springer Link
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
References
Namkoong H, Kurashima A, Morimoto K, Hoshino Y, Hasegawa N, Ato M, et al. Epidemiology of pulmonary nontuberculous mycobacterial disease, Japan. Emerg Infect Dis. 2016;22:1116–7.
Adjemian J, Olivier NC, Seitz EA, Holland MS, Prevots RD. Prevalence of nontuberculous mycobacterial lung disease in U.S. medicare beneficiaries. Am J Respir Crit Care Med. 2012;185:881–6.
Bergy EM, Reusser FA. new antibacterial agent (U20,661) isolated from a streptomycete strain. Experientia. 1967;23:254–5.
Wiley PF, Elrod DW, Slavicek JM, Marshall VP. Microbial conversion of steffimycin and steffimycin B to 10-dihydrosteffimycin and 10-dihydrosteffimycin B. J Antibiot. 1980;33:819–23.
Kunnari T, Tuikkanen J, Hautala A, Hakala J, Ylihonko K, Mäntsälä P. Isolation and characterization of 8-demethoxy steffimycins and generation of 2,8-demethoxy steffimycins in Streptomyces steffisburgensis by the nogalamycin biosynthesis genes. J Antibiot. 1997;50:496–501.
Gullón S, Olano C, Abdelfattah MS, Braña AF, Rohr J, Méndez C, et al. Isolation, characterization, and heterologous expression of the biosynthesis gene cluster for the antitumor anthracycline steffimycin. Appl Environ Microbiol. 2006;72:4172–83.
Kelly CR, Schletter I, Koert MJ, MacKellar AF, Wiley FW. Structures of steffimycin and steffimycin B1. J Org Chem. 1977;22:3591–6.
Koyama N, Kojima S, Nonaka K, Masuma R, Matsumoto M, Omura S, et al. Calpinactam, a new anti-mycobacterial agent, produced by Mortierella alpina FKI-4905. J Antibiot. 2010;63:183–6.
Kaneko M, Matsuda D, Ohtawa M, Fukuda T, Nagamitsu T, Yamori T, et al. Potentiation of bleomycin in jurkat cells by fungal pycnidione. Biol Pharm Bull. 2012;35:18–28.
Acknowledgements
We express our thanks to Ms Noriko Sato and Dr Kenichiro Nagai, School of Pharmacy, Kitasato University for the measurements of NMR spectra and MS data, respectively. This work was supported by JSPS KAKENHI grant numbers 26253009 (HT) and 15K07867 (NK) from the Ministry of Education, Culture, Sport, Science, and Technology, Japan.
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Additional information
Dedicated to Professor William Fenical in recognition of his contributions to marine-derived secondary metabolites.
Publisher’s note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary information
Rights and permissions
About this article
Cite this article
Koyama, N., Shigeno, S., Kanamoto, A. et al. Steffimycin E, a new anti-mycobacterial agent against Mycobacterium avium complex, produced by Streptomyces sp. OPMA02852. J Antibiot 73, 581–584 (2020). https://doi.org/10.1038/s41429-020-0290-9
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1038/s41429-020-0290-9
This article is cited by
-
New polycyclic tetramate macrolactams with antimycobacterial activity produced by marine-derived Streptomyces sp. KKMA-0239
The Journal of Antibiotics (2024)