Lecanora rupicola

Lichen xanthonee. Compounds found in numerous lichens that are mostly derived from norlichexanthone (occurring, e. g., in Lecanora straminea). The occurrence of mono-, di-, tri-, and tetrachloroxanthones such as, e.g., thuringione (from Lecidella carpathica) or thiophanic acid (from Lecanora rupicola and numerous other lichens) is remarkable. 

Fligh photobiont diversity associated with the euryoecious lichen-forming ascomycete Lecanora rupicola (Lecanoraceae, Ascomycota). Biological Journal of the Linnean Society S3, 283-293. 

Lichen acid from Lecanora rupicola. Needles (MeOH). Mp 296° dec. 

Lecanora rupicola Atranorin Chloroatranorin Roccellic acid Sordidone Thiophanic acid Eugenitin Eugenitol Roccellic acid Sordidone Fox and Huneck (1969)... 

Lactone carboxylic acid from Lecanora rupicola (Lactoncarbonsaure aus Lecanora rupicola)... 

Deriv Diacetyleugenitol, mp 200-202 °C, by acetylation of eugenitol with AC2O-H2SO4 StL Mycobiont of Lecanora rupicola (L.) Zahlbr. 

MS, m/z 402 (M%2%), 400 (12), 398 (50), 396 (100), 394 (75), 361 (10), 360 (6), 359 (8), 331 (5) Deriv Tri-O-methylthiophanic acid, cream-coloured needles (CHjClj-MeOH), mp 215-216 °C, from thiophanic acid with CHjNj at room temperature in 3 days. Triacetylthio-phanic acid, cream-coloured needles (CHjClj-MeOH), mp 261-262 °C, from thiophanic acid with AC2O-H2SO4 StL Lecanora rupicola (L.) Zahlbr. 

Foo LY, Gwyn SA (1978) The identification of norlobariol, a new lichen constituent from Xanthoparmelia scabrosa (Tayl.) Hale. Experientia 34 970-971 Fox CH, Huneck S (1969) The formation of roccellic acid, eugenitol, eugenitin, and rupicolon by the mycobiont Lecanora rupicola. Phytochemistry 8 1301-1304... 

Huneck S, Santesson J (1969) 64. Mitteilung iiber Flechteninhaltsstoffe. Uber die Inhaltsstoffe von Lecanora rupicola (L.) Zahlbr. und Lecanora carpinea (L.) Ach. em. Vain, und die Strukturaufklarung sowie Synthese von 8-Chlor-5,7-dihydroxy-2,6-dimethylchromon. Z Naturforsch 24b 750-756 Huneck S, Sargent MV (1976) Depsidone synthesis. V. The chemistry of psoromic acid. Aust J Chem 29 1059-1067... 

Sordidone, a chromone occurring in the lichen Lecanora rupicola (5,99), has been synthesized by Huneck and Santesson (185) by the chlorination of eugenitol. More recently a total synthesis of sordidone has been reported 4), which incorporates the above-mentioned chlorination (Scheme 13). Thus treatment of methylphloroacetophenone with acetic anhydride-sodium acetate yielded a 1 1 mixture of the isomeric chromones (117) and (118). Alkaline hydrolysis and separation of the isomers by fractional crystalization yielded eugenitol (119), and this compound was subsequently chlorinated to give sordidone (120). 

Fox, C. H., and Huneck, S. (1969). The formation of rocellic acid, eugenitol, eugenitin, and rupicolin by the mycobiont of Lecanora rupicola. Phytochem. 8, 1301. 

Lecanora reptans, 346 Lecanora rubina, 167, 192, 319, 360, 506 Lecanora nigosella, 431 Lecanora rupicola, 501, 519 Lecanora rupicola var. sorediata, 108 Lecanora ruteri, 503 Lecanora soralifera, 108 Lecanora stramineum, 503 Lecanora subcamea var. sorediata, 108 Lecanora subfusca, 100, 110, 128, 129, 136, 137, 141, 142... 

Also obtained by alkaline hydrolysis of sordidone dimethyl ether (8-chloro-5,7-dimelhoxy-2,6-di-methylchromone) [3209,3210] with refluxing 5% aqueous potassium hydroxide under nitrogen (83%) [3209]. Sordidone is a metabolite isolated from the lichen Lecanora rupicola (L) Zahlbr. (syn. Lecanora sordida Th. Fr.) [3209]. 

Two y-lactonic acids of unknown stereochemistry were found in Lecanora rupicola 174) resp. Cladonia impexa 173). 25 from the former and 26 from the latter species. 

Lecanora Analysis of the Lecanora rupicola group in Europe (507)... 

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