Penicillium stipitatum

Triacetic acid lactone (1) is one of the simplest polyketides, and its formation from acetyl-CoA and malonyl-CoA has been proved (68JBC5471). Biogenetic formation of triacetic acid lactone has been considered a derailment from fatty acid biosynthesis promoted by the absence of the reductant NADPH (69MII). Pyrone 1 has been isolated from microorganisms (67JA676) and is transformed into tropolone derivatives by Penicillium stipitatum (67JA681). 

StipHatic add (6-hydroxytropolone-4-carboxylic acid). CgHfiOs, Mr 182.13, yellow plates, mp. 302-304 °C (decomp.). A metabolite of Penicillium stipitatum. 

Among the tropolone compounds found in nature are four tropolone-carboxylic acids,obtained from mold cultures.Two ofthese,stipitatonicadd(CXIV,R = COOH) and stipitatic acid (CXIV, R = H) have been obtained from Penicillium stipitatum (Bentley and Thiessen, 1963). Puberulonic add (CXV, R = COOH) and puberulic acid (CXV, R = H) were obtained from P. aurantio-virens, P. puberulum and P.johan-nioli as well as from strains of the P. cyclopium-viridicatum series (sources quoted in this paper). The infrared spectrum of the sodium salt of the anhydride of stipitatonic... 

Kuhr, I., J. Fuska, P. Sedmera, M. Podojil, J. VokoUN, and Z. Van6k An Antitumor Antibiotic Produced by Penicillium stipitatum its Identity with Duclauxin. J. Antibiotics 26, 535 (1973). 

Stipitatonic Acid (75). The mechanism for the oxidative cleavage of 3-methyl-orsellinic acid (74) to afford the tropolone stipitatonic acid (75) in Penicillium stipitatum was very elegantly demonstrated with labelling. Two pathways were considered, the dioxygenase recyclization route. Scheme 20, and the mono-oxygenase ring-expansion route, Scheme 21. 

Paecilomyces victoria Parmelia birulae Peltophorum interme Penicillium brevicompactum Penicillium canescens Penicillium citreo-viride Penicillium citrinum Penicillium cyclopium Penicillium duclauxi Penicillium herquei Penicillium stipitatum Penicillium thomii Penicillium viridicatum Peniophora sanguinea Periconia macrospinosa Pestalotia ramula Pseudomonas yoshitomiensis Pyricularia oryzae... 

Bentley, R. Biosynthesis of tropolones in Penicillium stipitatum II. The degradation of C -labeled stipitatonic and stipitatic acids. J. Biol. Chem. 238, 1889 (1963 a). 

Bentley, R., J. A. Ghaphery, and J. G. Keil Effect of ethionine on tropolone biosynthesis in Penicillium stipitatum. Arch. Biochem. Biophys. Ill, 80 (1965). 

Birkinshaw, J. H., A. R. Chambers, and H. Raistrick Studies in the biochemistry of microorganisms. 70. Stipitatic acid CgHgOg a metabolic product of Penicillium stipitatum Thom. Biochem. J. 36, 242 (1942). ... 

Tanenbaum, S. W., E. W. Bassett, and M. Kaplan Environmental factors relating to tropolone formation by Penicillium stipitatum. Arch. Biochem. Biophys. 81, 169 (1958a). 

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