The results are reported from the first investigation of the secondary metabolites of the basidiomycete Hygrophorus discoxanthus (Fr.) Rea. Five new oxidized 4-oxo fatty acids (C16, C18) were isolated from the fruiting bodies and their structures established on the basis of their spectroscopic data and an ozonolysis experiment. Preliminary data indicate a moderate fungicidal activity, suggesting a possible function of these acids as chemical deterrents against mushroom parasites and predators.
This paper is Part 51 of the series “Fungal Metabolites”. Part 50: ClericuzioM, TabassoS, BiancoMA, PratesiG, BerettaG, TinelliS, ZuninoF, VidariG. (2006) Cucurbitane triterpenes from fruiting bodies and cultivated mycelia of Leucopaxillus gentianeus. Journal of Natural Products, submitted.
2.
BonM (1990) Flore Mycologique d'Europe. 1. Les Hygrophores Hygrophoraceae Lotsy. In Documents Mycologiques mémoire hors série 1. CRDP, Amiens, 1–99.
(a) LübkenT, SchmidtJ, PorzelA, ArnoldN, WessjohannL. (2004) Hygrophorones A-G: fungicidal cyclopentenones from Hygrophorus species (Basidiomycetes). Phytochemistry, 65, 1061–1071;
5.
LübkenT, ArnoldN, WessjohannL, BőttcherC, SchmidtJ. (2006) Analysis of fungal cyclopentenone derivatives from Hygrophorus spp. by liquid chromatography/electrospray-tandem mass spectrometry. Journal of Mass Spectrometry, 41, 361–371.
6.
GilardoniG, ClericuzioM, VidariG.Chry sotriones A and B from Hygrophorus chrysodon, unpublished results.
7.
BreheretS, TalouT, RapiorS, BessiereJM. (1997) Monoterpenes in the aromas of fresh wild mushrooms (Basidiomycetes). Journal of Agricultural and Food Chemistry, 45, 831–836.
8.
QuY, ZhangH, LiuJ. (2004) Isolation and structure of a new ceramide from the basidiomycete Hygrophorus eburneus. Zeitschrift fur Naturforschuns, 59B, 241–244.
9.
WoodWF, SmithJ, WaymanK, LargentDL. (2003) Indole and 3-chloroindole: the source of the disagreeable odor of Hygrophorus paupertinus. Mycologia, 95, 807–808.
10.
GillM, SteglichW. (1987) Pigments of fungi (macromycetes). In Progress in the Chemistry of Organic Natural Products. Vol 51, HerzW, GrisebachH, KirbyGW, TammCh. (Eds). Springer Verlag, Wien, New York. 1–317.
11.
(a) WilliamsonRT, CarneyJR, GerwickWH. (2000) Application of the BIRD sandwich for the rapid and accurate determination of 1H-1H NMR coupling constants in higher order spin systems. Journal of Natural Products, 63, 876–878;
12.
StamatovSD, StawinskiJ. (2000) A simple and efficient method for direct acylation of acetals with long alkyl-chain carboxylic acid anhydrides. Tetrahedron, 56, 9697–9703;
13.
VievilleC, MoulounguiZ, GasetA. (1995) Synthesis and analysis of the C1-C18 alkyl oleates. Chemistry and Physics of Lipids, 75, 101–108;
14.
RossiR, CarpitaA, QuiriciMG, VeranciniCA. (1982) Insect pheromone components. Use of carbon-13 NMR spectroscopy for assigning the configuration of carbon-carbon double bonds of monoenic or dienic pheromone components and for quantitative determination of Z/E mixtures. Tetrahedron, 38, 639–644.
15.
BaraldiPG, BarcoA, BenettiS, ManfrediniS, SimoniD. (1987) Ring cleavage of 3,5-disubstituted 2-isoxazolines by molybdenum hexacarbonyl and water to β-hydroxy ketones. Synthesis, 3, 276–278.
16.
GottsteinD, GrossD, LehmannH. (1982) Mikrobiotest mit Cladosporium cucumerinum Ell. et Arth. zum Nachweis fungitoxischer Verbidungen auf Dűnnschichtplatten. Archiv fűr Phytopatologie und Pflanzenschutz, 20, 111–116.