The results of the first investigation of secondary metabolites occurring in intact and damaged fruiting bodies of the European mushrooms Lactarius aurantiacus, L. subdulcis, and Russula sanguinaria are reported. The pattern of sesquiterpenes in injured R. sanguinaria is dramatically different from that of Lactarius. The structure of the new furanolactarane 4, isolated from L. aurantiacus, was established on the basis of spectral data.
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(a) ClericuzioM., CassinoC., CoranaF., VidariG. (2012) Terpenoids from Russula, Lepida and R. amarissma (Basidiomycota, Russulaceae). Phytochemistry, 84, 154–159; (b) Sterner O, Bergman R, Kihlberg J, Wickberg B. (1985) The sesquiterpenes of Lactarius vellereus and their role in a proposed chemical defence system. Journal of Natural Products, 48, 279–288; (c) Yaoita Y, Hirao M, Kikuchi M, Machida K. (2012) Three new lactarane sesquiterpenoids from the mushroom Russula sanguinea. Natural Product Communications, 9, 1133–1135.
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(a) DaniewskiW.M., KocorM. (1971) Constituents of higher fungi. II. Structure of lactarorufin A. Bulletin de l'Academie Polonaise des Sciences. Serie des sciences chimiques, 19, 553–561; (b) Froborg J, Magnusson G. (1978) Fungal e xtractives. 12. Construction of the vellerane skeleton with total syntheses of racemic velleral, vellerolactone, and pyrovellerolactone. Revised structures. Journal of the American Chemical Society, 100, 6728–6733; (c) De Bernardi M, Fronza G, Mellerio G, Vidari G, Vita-Finzi P. (1980) Stereochemistry of blennin A and blennin D from Lactarius blennius. Phytochemistry, 19, 99–101; (d) Vidari G, De Bernardi M, Vita-Finzi P, Fronza G. (1976) Sesquiterpenes from Lactarius blennius. Phytochemistry, 15, 1953–1955; (e) Sterner O, Bergman R, Franzén C, Wickberg B. (1985) New sesquiterpenes in a proposed Russulaceae chemical defense system. Tetrahedron Letters, 26, 3163–3166; (f) Magnusson G, Thorén S, Dahmèn J, Leander K (1974) Fungal extractives. VIII. Two sesquiterpene furans from Lactarius. Acta Chemica Scandinavica B, 28, 841–846; (g) Widén KG, Seppa EL. (1979) 15-Hydroxyblennin A, a new lactarane-type sesquiterpene lactone isolated from Lactarius torminosus. Phytochemistry, 18, 1226–1227.
10.
The names of 15-hydroxyblennin A and 14-hydroxyblennin A, reported in references [5c] and [9g], must, therefore, be corrected to 14-hydroxy-blennin A and 15-hydroxyblennin A, respectively.
11.
SternerO., BergmanR., KihlbergJ., OluwadiyaJ., WickbergB., VidariG., De BernardiM., De MarchiF., FronzaG., Vita-FinziP. (1985) Basidiomycetes sesquiterpenes: the silica gel induced degradation of velutinal derivatives. The Journal of Organic Chemistry, 50, 950–953.
