Abstract
While investigating the metabolic products of Alternaria tenuis Auct, Rosett et al. (1957) observed that a fraction from the culture filtrate gave a strong orange-red ferric chloride color. The material which was very soluble in organic solvent was ketonic and acidic in nature. Its rotation in methanol was —124° Analysis of the compound indicated the molecular formula C10H15O2N. On long standing, the rotation of the product slowly became less negative, and the substance eventually crystallized. The purified crystalline substance also corresponded to the formula C10H15O2N and had very similar chemical properties to the original material. However, it was found to be dextrorotatory, [α] 22°5461 + 23°. The name of tenuazonic acid was proposed for the metabolic product and isotenuazonic acid for the isomer. Tenuazonic acid titrated sharply as a monobasic acid, contained no methoxyl group and formed a semicarbazone, m.p. 187–189° and was found to be converted into the iso-acid by boiling with aqueous alkali.
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References
Allen, D. W., and P. C. Zamecnik: The effect of puromycin on rabbit reticulocyte ribosomes. Biochim. et Biophys. Acta 55, 865 (1962).
Gitterman, C. O.: Antitumor, cytotoxic and antibacterial activities of tenuazonic acid and congeneric tetramic acids. J. Med. Chem. 8, 483 (1965).
Gitterman, C. O.. E. L. Dulaney, E. A. Kaczka, G. W. Campbell, D. Hendlin, and H. B. Woodruff: The human tumor-egg host system. III. Tumor-inhibitory properties of tenuazonic acid. Cancer Research 24, 440 (1964).
Harris, S. A., L. V. Fisher, and K. Folkers: The synthesis of tenuazonic acid and congeneric tetramic acids. J. Med. Chem. 8, 478 (1965).
Kaczka, E. A., C. O. Gitterman, E. L. Dulaney, M. C. Smith, D. Hendlin, H. B. Woodruff, and K. Folkers: Discovery of inhibitory activity of tenuazonic acid for growth of human adenocarcinoma-1. Biochem. Biophys. Research. Commun. 14, 54 (1964). LAM BERG, M. R.: The in vitro release of protein from Escherichia coli ribosomes. Biochim. et Biophys. Acta 55, 719 (1962).
Matioli, G. T., and E. H. Eylar: The biosynthesis of apoferritin by reticulocytes. Proc. Natl. Acad. Sci. U.S. 52, 508 (1964).
Miller, F. A., W. A. Rightsel, B. J. Sloan, J. Ehrlich, J. C. French, and Q. R. Bartz: Antiviral activity of tenuazonic acid. Nature 200, 1338 (1963).
Morris, A. J., and R. S. Schweet: Release of soluble protein from reticulocyte ribosomes. Biochim. et Biophys. Acta 47, 415 (1961).
Rosett, T., R. H. Sankhala, C. E. Stickings, M. E. U. Taylor, and R. Thomas: Studies in the biochemistry of micro-organisms. 103. Metabolites of Alternaria tenuis Auct.: Culture filtrate products. Biochem. J. 67, 390 (1957).
Shigeura, H. T., and C. N. Gordon: The biological activity of tenuazonic acid. Biochemistry 2, 1132 (1963).
Stickings, C. E.: Studies in the Biochemistry of Micro-organisms. 106. Metabolites of Alternaria tenuis Auct.: The structure of tenuazonic acid. Biochem. J. 72, 332 (1959).
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Shigeura, H.T. (1967). Tenuazonic Acid. In: Gottlieb, D., Shaw, P.D. (eds) Mechanism of Action. Antibiotics, vol 1. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-46051-7_24
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DOI: https://doi.org/10.1007/978-3-642-46051-7_24
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