Abstract
Two new antibiotics, designated virantmycin B (1) and C (2), were isolated from the cultured broth of Streptomyces sp. AM-2504. Compounds 1 and 2 were purified by Diaion HP-20, silica gel, and octadecylsilane chromatography, followed by high-performance liquid chromatography. The chemical structures of the new compounds, 1 and 2, were determined by nuclear magnetic resonance and mass spectrometry, as containing a terahydroquinoline and an indoline, respectively, each also containing a hydroxy cyclopentenone moiety. Both compounds demonstrated weak antimicrobial (both antibacterial and antifungal) activity and compound 1 also showed antiviral activity against the dengue virus, whereas compound 2 exhibited no antiviral properties.
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References
Nakashima T, Takahashi Y, Ōmura S. Search for new compounds from Kitasato microbial library by physicochemical screening. Biochem Pharmacol. 2017;15:42–55.
Takahashi Y, Nakashima T. Actinomycetes, an inexhaustible source of naturally occurring. Antibiotics (Basel). 2018;7:E45.
Takahashi Y, Nakashima T. Microorganisms are an inexhaustible gold mine of new natural compounds. Jpn J Antibiot. 2018;71:99–112.
Ōmura S, et al. A new antibiotic, AM-2504. Agric Biol Chem. 1977;41:1827–8.
Teshima T, et al. The structure of an antibiotic, dityromycin. Tetrahedron Lett. 1988;29:1963–6.
Ōmura S, et al. Virantmycin, a potent antiviral antibiotic produced by a strain of Streptomyces. J Antibiot. 1980;33:1395–6.
Nakagawa A, et al. Virantmycin, a new antiviral antibiotic produced by a strain of Streptomyces. J Antibiot. 1981;34:1408–15.
Ōmura S, Nakagawa A. Structure of virantmycin, a novel antiviral antibiotic. Tetrahedron Lett. 1981;22:2199–202.
Kim WG, Kim JP, Yoo ID. Benzastatins A, B, C, and D: new free radical scavengers from Streptomyces nitrosporeus 30643, II. Structural determination. J Antibiot. 1996;49:26–30.
Kim WG, et al. Benzastatins E, F, and G: new indoline alkaloids with neuronal cell protecting activity from Streptomyces nitrosporeus. Tetrahedron. 1997;53:4309–16.
Motohashi K, Nagai A, Takagi M, Shin-ya K. Two novel benzastatin derivatives, JBIR-67 and JBIR-73, isolated from Streptomyces sp. RI18. J Antibiot. 2011;64:281–3.
Hirota-Takahata Y, et al. Studies on novel HIF activators, A-503451s. I. Producing organism, fermentation, isolation and structural elucidation. J Antibiot. 2016;69:747–53.
Acknowledgements
This study was supported by funding from the Institute for Fermentation, Osaka (IFO), Japan. We are grateful to Dr Kenichiro Nagai and Ms Noriko Sato, School of Pharmacy, Kitasato University, for measurements of MS spectra and NMR spectral data.
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Kimura, T., Suga, T., Kameoka, M. et al. New tetrahydroquinoline and indoline compounds containing a hydroxy cyclopentenone, virantmycin B and C, produced by Streptomyces sp. AM-2504. J Antibiot 72, 169–173 (2019). https://doi.org/10.1038/s41429-018-0117-0
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DOI: https://doi.org/10.1038/s41429-018-0117-0
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