Letharia vulpina

Vulpinic acid (phenolic) Letharia vulpina (lichen) Uncoupler (<5)... 

A further family of aromatic compounds produced by lichens is derived from shikimic add via phenylalanine and is exemplified by vulpinic acid (7.55), which was isolated from Letharia vulpina. Vulpinic acid has been synthesized by the lead tetra-acetate oxidation of polyporic acid. Lichens also produce some alkylated citric acid derivatives such as lichesterinic acid (7.56) and some sterols. 

C15H14O5, Mr 322.32, yellow cryst., mp. 148-149°C (other reports 145-146 °C), soluble in chloroform. A typical lichen acid, e. g., in Letharia vulpina. V. a. also occurs in some mushrooms of the order Boletales. Saponification of V. a. affords pulvinic acid (see also gomphidic acid, xerocomic acid). V. a. has antibacterial as well as antiviral activities and inhibits the growth of plants. V. a. is used in some countries as a natural dye for wool. ... 

Usnea sp. Parmotrema sp. Peltigera sp. Cladonia sp. Lentinula sp. Ganoderma sp. Pleurotus sp. Flavoparmelia sp. Punctelia sp. Cladonia sp. Vulpicida canadensis Parmelia sulcata Letharia vulpina... 

Dauriac H, Rondon Y (1976) Quelques aspects des pro-prietes d un lichen, le Letharia vulpina (L.) Hue, en biologie vegetale experimentale. I. Action sur la germination du ble et de developpment de Tail. Bull Soc Bot Fr 123 235-241... 

Stephenson NL, Rundel PW (1979) Quantitative variation and the ecological role of vulpinic acid and atranorin in the thallus of Letharia vulpina, Biochem Syst Ecol 7 263-267... 

Tabacchi R, Tsoupras G (1987) The chemical composition of Letharia vulpina (L.) Hue. Bibl Lichenol 25 475-480... 

Scandinavia Possibly used to poison wolves along with Letharia vulpina (Smith... 

Schade A (1954) Uber Letharia vulpina (L.) Vain, und ihre Vorkommen in der Alten Welt. 

The lowest temperatures at which lichens have assimilated are shown in Table II. Photosynthesis at these temperatures is surprisingly efficient. For example, Lange (1965) found that in Letharia vulpina, an alpine lichen, carbon dioxide uptake was maximal at 7°C, only slightly depressed at 0°C, and still half the optimum at — 5 C. However, at temperatures between —5" and -10°C, Atanasiu (1969) found that photosynthesis of lichens collected during winter months in Bucharest, Rumania was very low, about 2 mg CO2/ 100 gm fresh weight of lichen. As the temperature rose above — 5°C at the end of February, photosynthesis increased noticeably. 

Ramalina maciformis Parmelia melanothrix Parmelia tinctorum Usnea pseudocyphellata Cladonia alcicornis Stereocaulon alpinum Letharia vulpina Xanthoria mawsoni Neuropogon acromelanus Lecanora melanophthalma... 

Vulpinic acid has been separated from an extract of Letharia vulpina by droplet counter-current chromatography using methanol acetone n-heptane 4 1 5 (V/V/V) (775). 

Demethylleprapinic acid (542), 4-hydroxyvulpinic acid (543), 2-hydroxypulvinic acid dilactone (544) and methylcalycin (545) have been isolated from Himalayan Lepraria species and from Letharia vulpina respectively (14, 685). The structure of vulpinic acid (546) has been confirmed by an X-ray analysis (41). More than twenty years ago Pattenden (573) reviewed naturally occurring 4-ylidenebutenolides in vol. 38 of this series. Since then numerous new synthetic ways to pulvinones have been developed (see Schemes 165-168). 

Phytol and manool have been isolated from Letharia vulpina ((555), rimuene was isolated from Evernia prunastri 561) and (—)-sandara-copimaric acid from Ramalina hierrensis 330). 

Lichen cultures of Cetraria Jmiperina, Hypogymnia physodes and Letharia vulpina tyrosinase 368)... 

Solberg Y, Remedios G (1978) Studies on the Chemistry of Lichens, XVIII. Chemical Investigations of the Species Letharia vulpina (L.) Hue and New Derivatives of Vulpinic Acid. Z Naturforsch 33c 449... 

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