Abstract
Cyslabdan, a new potentiator of imipenem activity against methicillin-resistant Staphylococcus aureus, was isolated from the culture broth of Streptomyces sp. K04-0144 by Diaion HP-20 and ODS column chromatographies and preparative HPLC. The structure of cyslabdan was elucidated by spectroscopic analyses including NMR. The compound has a labdane-type diterpene skeleton connecting with an N-acetylcysteine via thioether linkage.
Similar content being viewed by others
Article PDF
References
Tomasz A . Multiple-antibiotic resistant pathogenic bacteria. New England J Med 330: 1247–1251 ( 1994)
Hiramatsu K, Hanaki H, Ino T, Yabuta K, Oguri T, Tenover FC . Methicillin-resistant Staphylococcus aureus clinical strain with reduced vancomycin susceptibility. J Antimicrob Chemother 40: 135–136 ( 1997)
Centers for Disease Control and Prevention. Staphylococcus aureus with reduced susceptibility to vancomycin-United States, 1997. MMWR Morb Mortal Wkly Rep 46: 765–766 ( 1997)
Ōmura S . Antiinfective drugs into the 21st century. Nippon Saikingaku Zasshi 54: 795–813 ( 1999)
Koyama N, Nagahiro T, Yamaguchi Y, Masuma R, Tomoda H, Ōmura S . Stemphones, novel potentiators of imipenem activity against methicillin-resistant Staphylococcus aureus, produced by Aspergillus sp. FKI-2136. J Antibiot 58: 695–703 ( 2005)
Nicolson K, Evans G, O'Toole PW . Potentiation of methicillin activity against methicillin-resistant Staphylococcus aureus by diterpenes. FEMS Microbiol Lett 179: 233–239 ( 1999)
Fukumoto A, Kim YP, Hanaki H, Shiomi K, Tomoda H, Ōmura S . Cyslabdan, a new potentiator of imipenem activity against methicillin-resistant Staphylococcus aureus, produced by Streptomyces sp. K04-0144 II. Biological activities. J Antibiot 61: 7–10 ( 2008)
Shiring EB, Gottlieb D . Methods for characterization of Streptomyces species. Int J Syst Bacteriol 16: 313–340 ( 1966)
Waksman SA ( ed.) Classification, identification and description of genera and species. In: The Actinomycetes, Vol. 2. Williams & Wilkins, Baltimore, pp. 328–334 ( 1961)
Color Harmony Manual, 4th ed. Container Corporation of America, Chicago ( 1958)
Pridham TG, Gottlieb D . The utilization of carbon compounds by some Actinomycetales as an aid for species determination. J Bacteriol 56: 107–114 ( 1948)
Becker B, Lechevalier MP, Lechevalier HA . Chemical composition of cell-wall preparation from strains of various form-genera of aerobic actinomycetes. Appl Microbiol 13: 236–243 ( 1965)
Collins MD, Goodfellow M, Minnikin DE . Distribution of menaquinones in actinomycetes and corynebacteria. J Gen Microbiol 100: 221–230 ( 1977)
Tamaoka J, Katayama-Fujiwara Y, Kuraishi H . Analysis of bacterial menaquinone mixtures by high performance liquid chromatography. J Appl Bacteriol 54: 31–36 ( 1983)
Williams ST, Goodfellow M, Alderson G . Genus Streptomyces Waksman and Henrici 1943. In: Wiliams ST et al. (ed.). Bergey's Manual of Systematic Bacteriology, Vol. 4. Williams & Wilkins, Baltimore, pp. 2452–2492 ( 1989)
Ohta K, Kasahara F, Ishimaru T, Wada Y, Kanamaru T . Structures of fibrostatins, new inhibitors of prolyl hydroxylase. J Antibiot 40: 1239–1248 ( 1987)
Wolfrom ML, Lemieux RU, Olin SM . Configurational correlation of L-(levo)-glyceraldehyde with natural (dextro)-alanine by a direct chemical method. J Am Chem Soc 71: 2870–2873 ( 1949)
Birnbaum SM, Levintow L, Kingsley RB, Greenstein JP . Specificity of amino acid acylases. J Biol Chem 194: 455–470 ( 1952)
Okuhara M, Harada T . Formation of N-acetyl-L-alanine and N-acetylglycine from glucose by Candida tropicalis OH23. Biochim Biophys Acta 244: 16–18 ( 1971)
Cristina GM, Siomoes MF, Duarte A, Rodriguez B . Labdane and kauren diterpenoids from Plectranthus fruticosus. J Nat Prod 66: 491–496 ( 2003)
Bohlmann F, Fritz U . Neue diterpene und acetylenverbindungen aus Nidorella-arten. Phytochemistry 17: 1769–1772 ( 1978)
Asakawa Y, Toyota M, Takemoto T . New diterpenes from Porella perrottetiana. Phytochemistry 18: 1681–1685 ( 1979)
Hashimoto T, Shiki K, Tanaka M, Takaoka S, Asakawa Y . Chemical conversion of labdane-type diterpenoid isolated from the liverwort Porella perrottetiana into (−)-Ambrox. Heterocycles 49: 315–325 ( 1998)
Ohta K, Kasahara F, Ishimaru T, Wada Y, Kanamaru T, Okazaki H . Structures of fibrostatins, new inhibitors of prolylhydroxylase. J Antibiot 40: 1239–1248 ( 1987)
Kondo H, Naitou K, Nakajima S, Kojiri K, Suzuki H, Ouchi K, ( Banyu Pharm. Co.) Japan Pat. 94-25183 ( 1994)
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Fukumoto, A., Kim, YP., Matsumoto, A. et al. Cyslabdan, a New Potentiator of Imipenem Activity against Methicillin-resistant Staphylococcus aureus, Produced by Streptomyces sp. K04-0144. J Antibiot 61, 1–6 (2008). https://doi.org/10.1038/ja.2008.101
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1038/ja.2008.101
Keywords
This article is cited by
-
Naphthacemycins, novel circumventors of β-lactam resistance in MRSA, produced by Streptomyces sp. KB-3346-5. I. The taxonomy of the producing strain, and the fermentation, isolation and antibacterial activities
The Journal of Antibiotics (2017)
-
Naphthacemycins, novel circumventors of β-lactam resistance in MRSA, produced by Streptomyces sp. KB-3346-5. II. Structure elucidation
The Journal of Antibiotics (2017)
-
Total synthesis of (±)-naphthacemycin A9, possessing both antibacterial activity against methicillin-resistant Staphylococcus aureus and circumventing effect of β-lactam resistance
The Journal of Antibiotics (2017)
-
Biosynthesis of mercapturic acid derivative of the labdane-type diterpene, cyslabdan that potentiates imipenem activity against methicillin-resistant Staphylococcus aureus: cyslabdan is generated by mycothiol-mediated xenobiotic detoxification
Journal of Industrial Microbiology and Biotechnology (2016)
-
Streptomyces lactacystinicus sp. nov. and Streptomyces cyslabdanicus sp. nov., producing lactacystin and cyslabdan, respectively
The Journal of Antibiotics (2015)