Abstract
In our screening program for new antifungal agents from microbial secondary metabolites, we isolated two new isoflavonol glycosides, genistein 7-α-L-6-deoxy-talopyranoside (talosin A) and genistein 4′,7-di-α-L-6-deoxy-talopyranoside (talosin B), from the culture broth of Kitasatospora kifunensis MJM341. The talosins exhibited strong antifungal activity against Candida albicans, Aspergillus niger and Cryptococcus neoformans with minimal inhibitory concentrations (MIC) in the range of 3~15 μg/ml while genistein and genistein-7-glucopyranoside did not show antifungal activity at 100 μg/ml. These talosins are the first isoflavonol glycosides with a 6-deoxy-talose sugar component and they may be useful as antifungal agents with low toxicity because of no visible cytotoxicity against the human hepatic HepG2 cell.
Similar content being viewed by others
Article PDF
References
Sternberg S . The emerging fungal treatment. Science 226: 1632–1634 ( 1994)
Georgopapadakou NH, Walsh TJ . Antifungal agents: Chemotherapeutic targets and immunologic strategies. Antimicrob Agents Chemother 40: 279–291 ( 1996)
Vincente MF, Basilio A, Pelaez F . Microbial natural products as a source of antifungals. Clin Microbiol Infect 9: 15–32 ( 2003)
Iwami M, Nakayama O, Terano H, Kohsaka M, Aoki H, Imanaki H . A new immunomodulator, FR-900494: Taxonomy, fermentation, isolation, and physico-chemical and biological characteristics. J Antibiot 40: 612–622 ( 1987)
Kim WG, Yoon TM, Kwon HJ, Suh JW . Talosins A and B, new isoflavonol glycosides with potent antifungal activity from Kitasatospora kifunensis MJM341. II. Physico-chemical properties and structure determination. J Antibiot 59: 640–645 ( 2006)
Kim CJ, Lee KH, Kwon OS, Shimazu A, Yoo ID . Selective isolation of actinomycetes by physical pretreatment of soil sample. Kor J Appl Microbiol Biotechnol 22: 222–225 ( 1994)
Chun J, Goodfellow M . A phylogenetic analysis of the genus Nocardia with 16S rRNA gene sequences. Int J Syst Bacteriol 45: 240–245 ( 1995)
Thompson JD, Higgins DG, Gibson TJ . CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res 22: 4673–4680 ( 1994)
Saitou N, Nei M . The neighbor-joining method: a new method for reconstructing phylogenetic trees. Mol Biol Evol 4: 406–425 ( 1987)
Shring EB, Gottlieb D . Methods for characterization of Streptomyces species. Int J Syst Bacteriol 16: 313–340 ( 1966)
Becker B, Lechevalier MP, Gordon RE, Lechevalier HA . Rapid differentiation between Norcardia and Streptomyces by paper chromatography of whole-cell hydrolysates. Appl Microbiol 12: 421–423 ( 1964)
Kornerup A, Wanscher JH . Methuen Handbook of Colour. 3rd ed. Eyre Methuen Ltd. ( 1981)
Bolard J . How do the polyene macrolide antibiotics affect the cellular membrane properties? Brochim Biophys Acta 864: 257–304 ( 1986)
Ghannoum MA, Rice LB . Antifungal agents: mode of action, mechanism of resistance, and correlation of these mechanisms with bacterial resistance. Clin Microbiol Rev 12: 501–517 ( 1999)
Sheehan DJ, Hitchcock CA, Sibley CM . Current and emerging azole antifungal agents. Clin Microbiol Rev 12: 40–79 ( 1999)
Doco T, O’Neil MA, Pellerin P . Determination of the neutral and acidic glycosyl-residue compositions of plant polysaccharides by GC-EI-MS analysis of the trimethylsilyl methyl glycoside derivatives. Carbohydr Res 46: 249–259 ( 2001)
Knirel YA, Shashkov AS, Senchenkova SN, Merino S, Tomas JM . Structure of the O-polysaccharide of Aeromonas hydrophila O:34; a case of random O-acetylation of 6-deoxy-L-talose. Carbohydr Res 337: 1381–1386 ( 2002)
Vanhaverbeke C, Heyraund A, Achouak W, Heulin T . Structural analysis of the exopolysaccharide from Burkholderia caribensis strain MWAP71. Carbohydr Res 334: 127–133 ( 2001)
Torgov VI, Shashkov AS, Kochanowski H, Jann B, Jann K . NMR analysis of the structure of the O88 polysaccharide (O88 antigen) of Escherichia coli O88:k−:H25. Carbohydr Res 283: 223–227 ( 1996)
Maclennan AP . Composition of the cell wall of Actinomyces Bovis: the isolation of 6-deoxy-L-talose. Biochim Biophys Acta 48: 600–601 ( 1961)
Hazato T, Naganawa H, Kumagai M, Aoyagi T, Umezawa H . β-Galactosidase-inhibiting new isoflavonoids produced by actinomycetes. J Antibiot 32: 217–222 ( 1979)
Aoyagi T, Hazato T, Kumagai M, Hamada M, Takeuchi T, Umezawa H . Isoflavone rhamnosides, inhibitors of β-galactosidase produced by actinomycetes. J Antibiot 28: 1006–1008 ( 1975)
Decker H, Gaisser S, Pelzer S, Schneider P, Westrich L, Wohlleben W, Bechthold A . A general approach for cloning and characterizing dNDP-glucose dehydratase genes from actinomycetes. FEMS Microbiol Lett 141: 195–201 ( 1996)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Yoon, T., Kim, J., Kim, J. et al. Talosins A and B: New Isoflavonol Glycosides with Potent Antifungal Activity from Kitasatospora kifunensis MJM341. J Antibiot 59, 633–639 (2006). https://doi.org/10.1038/ja.2006.84
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1038/ja.2006.84
Keywords
This article is cited by
-
Bioprospecting potentials of moderately halophilic bacteria and the isolation of squalene producers from Kuwait sabkha
International Microbiology (2021)
-
A new indole glycoside from Kitasatospora sp. MG372-hF19 carrying a 6-deoxy-α-l-talopyranose moiety
The Journal of Antibiotics (2020)
-
Anti-inflammatory effects of talosin A via inhibition of NF-kappaB activation in lipopolysaccharide-stimulated RAW264.7 cells
Biotechnology Letters (2009)
-
Talosins A and B: New Isoflavonol Glycosides with Potent Antifungal Activity from Kitasatospora kifunensis MJM341
The Journal of Antibiotics (2006)