Abstract
Fifteen days-old surface cultures ofPenicillium fennelliae Stolk grown on a modified Czapek medium were analyzed for the production of metabolites. The presence of orsellinic acid, orcinol and penicillic acid was proved by means of chromatographic and physicochemical methods.
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Alsberg, C. L. andBlack, O. F. 1913. Contributions to the study of maize deterioration; biochemical and toxicological investigations ofPenicillium puberulum andPenicillium sloloniferum. - U. S. Dept. Agric. Bureau Plant Ind. Bull. No. 270, 1–47.
Bentley, R. andKeil, J. 1961. The role of acetate and malonate in the biosynthesis of penicillic acid. - Proc. Chem. Soc.1961: 111–112.
Bentley, R. andKeil, J. G. 1962. Tetronic acid biosynthesis in molds. II. Formation of penicillic acid inPenicillium cyclopium. - J. Biol. Chem.237: 867–873.
Bentley, R. andCampbell, I. M. 1968. Secondary metabolism of fungi, p. 415–489.In: M. Florkin and E. H. Stotz, [eds.], Comprehensive Biochemistry, Vol. 20. Metabolism of cyclic compounds. - Elsevier, Amsterdam.
Birkinshaw, J. H., Oxford, A. E. andRaistrick, H. 1936. Penicillic acid, a metabolic product ofPenicillium puberulum Bainier andP. cyclopium Westling. - Biochem. J.30: 394–411.
Birkinshaw, J. H. andGowlland, A. 1964. Production and biosynthesis of orsellinic acid byPenicillium madriti G. Smith. - Biochem. J.84: 342–347.
Curtis, R. F., Harries, P. C., Hassall, C. H. andLevi, J. D. 1964. The biosynthesis of phenols. 5. The relationship of some phenolic metabolites of mutants ofAspergillus terreus Thom I. M. I. 16043. - Biochem. J.90: 43–51.
Feigl, F. 1966. Spot tests in organic analysis, 7th English ed., p. 425. - Elsevier, Amsterdam.
Ford, J. H., Johnson, A. R. andHinman, J. W. 1950. The structure of penicillic acid. - J. Am. Chem. Soc.72: 4529–4531.
Grove, J. F. 1952. Infra-red spectroscopy and structural chemistry. Part III. Gladiolic acid. - J. Chem. Soc.1952: 3345–3354.
Mosbach, K. 1959. Das Vorkommen von Orsellinsäure inChaetomium cochliodes. - Z. Naturforsch.14b: 69–70.
Mosbach, K. 1960. Die Biosynthese der Orsellinsäure und Penicillinsäure. - Acta Chem. Scand.14: 457–464.
Packter, N. M. 1965. Studies on the biosynthesis of quinones in fungi. Incorporation of 6-methylsalicylic acid into fumigatin and related compounds inAspergillus fumigatus I. M. I. 89.353. - Biochem. J.97: 321–332.
Packter, N. M. andSteward, M. W. 1967. Studies on the biosynthesis of phenols in fungi. Biosynthesis of 3, 4 dimethoxy, 6- methyltoluquinol and gliorosein inGliocladium roseum. I. M. I. 93.065. - Biochem. J.102: 122–132.
Pettersson, G. 1965. An orsellinic acid decarboxylase isolated fromGliocladium roseum. - Acta Chem. Scand.19: 2013–2021.
Raphael, R. A. 1947. Compounds related to penicillic acid. Part II. Synthesis of dihydropenicillic acid. - J. Chem. Soc.1947: 805–808.
Reio, L. 1959. A method for the paper-chromatographic separation and identification of phenol derivatives, mould metabolites and related compounds of biochemical interest, using a “reference system”. - Chromatog. Rev.1:39–74.
Shibata, S., Natori, S. andUdagawa, S. 1964. List of fungal products, p. 17. - Charles C. Thomas, Springfield, U.S.A.
Stolk, A. C. 1969. Four new species ofPenicillium. - Antonie van Leeuwenhoek35: 261–274.
Wachmeister, C. A. 1958. Studies on the chemistry of lichens. XI. Structure of picrolichenic acid. - Acta Chem. Scand.12: 147–164.
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The author is indebted to Mr. J. A. Weber and Dr. M. J. A. de Bie of the Laboratory of Organic Chemistry, University of Utrecht for measuring the UV and 60 Mc NMR spectra and to Mrs. G.E.E. Snijders-Woldringh, Miss L. Veldstra and Miss H. G. M. Stolwijk of the Institute for Organic Chemistry TNO, Utrecht for running the IR and 100 Mc NMR spectra and for performing the microanalysis.
The mass spectra were determined by Mr. W. Heerma of the Analytical Laboratory, University of Utrecht, whom we wish to thank for helpful discussions on the interpretation of the results.
The skillful technical assistance of Miss M. van Rietschote is gratefully acknowledged.
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van Eijk, G.W. Isolation and identification of orsellinic acid and penicillic acid produced byPenicillium fennelliae Stolk. Antonie van Leeuwenhoek 35, 497–504 (1969). https://doi.org/10.1007/BF02219167
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DOI: https://doi.org/10.1007/BF02219167