Lichen acids atranorin acid

Slansky, F., 1979. Effect of lichen chemicals atranorin and vulpinic acid upon feeding and growth of larvae of the yellow-striped armyworm, Spodoptera ornithogalli. Env. Entomol. 8, 865-868. 

CH2OH R = H, CHj. Most D. are didepsides, such as, e.g., atranorin, chloroatranorin, gyrophoric acid, and lecanoric acid. In some D. (e. g., alectorialic acid and barbatolic acid) the acid part (S) is linked with a benzylic hydroxy group of the A part. The structures of about 100 D. isolated from lichens have been elucidated by hydrolysis and alcoholysis to the corresponding carboxylic acids or esters (S part) and to the phenols (A part), respectively. 

Lichen acids and fumaric acid are available from Chemotechnique, and usnic acid and Atranorin from Trolab and Chemotechnique these can be used to screen fo rlichen allergy. Oak-moss absolute, one of eight components of the perfume mix in the standard series, is also derived from a lichen... 

Lichen acid mix (atranorin, evernic acid, usnic acid) 0.3% pet. ... 

Norstictic acid, physodic acid, evemic acid, usnic acid, salazinic acid, fumar-protocetraric acid, protocetraric acid, atranorin and zeorin isolated from different lichen species are relatively strong antioxidant, antimicrobial and anticancer agents (Kosanic et al. 2010, 2013, 2014 Manojlovic et al. 2012 Rankovic et al. 2014). 

Yamamoto Y, Kinoshita Y, Matsubara H et al (1998) Screening of biological activities and isolation of biological-active compounds from lichens. Recent Res Dev Phytochem 2 23-34 Yilmaz M, Tiirk AO, Tay T et al (2004) The antimicrobial activity of extracts of the lichen Cladonia foliacea and its (—)-usnic acid, atranorin, and fumarprotocetraric acid constituents. Z Naturforsch C 59 249-254... 

Depsides, tridepsides, and tetradepsides consist of two, three, and four hydroxybenzoic acid residues linked by ester groups. These are the most numerous classes of secondary metabolites in lichens. More than one hundred Uchen compounds are depsidones, which have an additional ether bond between aromatic rings. Depsidones in Uchen are believed to arise by oxidative cycUzation of depsides. It has been found that depsidone and depside compounds such as atranorin, divaricatic acid, lecanoric acid, evemic acid, salazinic acid, physodic acid, and stictic acid possess important antimicrobial activity (Manojlovic et al. 2012 Kosanic et al. 2013, 2014a Rankovic et al. 2014). 

Jayaprakasha and Rao (2000) extracted with benzene and acetone the lichen Parmotrema stuppeum in order to investigate its antioxidant effect. Both the extracts were fractionated on 1 % oxalic acid impregnated silica gel column to obtain methyl orsenillate, orsellinic acid, atranorin and lecanoric acid, respectively. Antioxidant activities of benzene extract, acetone extract and isolated compounds were evaluated in a carotene-linoleate model system. The obtained results showed that the pure compounds and extracts have moderate antioxidant activity. 

Antioxidant activities of major lichen metabolites in Hypogymnia physodes lichen (physodic acids, atranorin and usnic acid) were studied by Rankovic et al. (2014b). An physodic acid was found to be the most effective antioxidant in free radical and superoxide anion scavenging, as well as in reducing power assays among tested lichen metabolites. 

Most morphologically defined species have a constant chemistry, usually one cortical substance (e. g. usnic acid, atranorin) and one or more medullary substances, and justify the use of this criterion in lichen taxonomy. The three common patterns of chemical variation are those of replacement type compounds, accessory type compounds and chemosyn-dromic variation. These are discussed in turn. 

Whiton and Lawrey found that ascospore germination of the lichens Cladonia cristatella 724), Graphis scripta and Caloplaca citrina 725) was much reduced in the presence of lichen substances. Spore germination of Cladonia cristatella and Caloplaca citrina was inhibited by vulpinic acid, evernic acid and atranorin respectively stictic acid showed no activity. 

Large amounts of two lichens are processed for production of essential ingredients in the perfume industry thus in 1997 1900 tons of Pseudevernia furfuracea and 700 tons of Evernia prunastri were processed, mainly at Grasse, the centre of the essential oil industry in France (447). Usnic acid is used as a preservative in cosmetic creams (643) and atranorin, divaric acid, gyrophoric acid, pannarin, and usnic acid are potential sunscreen materials (294). 

This view was confirmed more directly when 5-methylorcylaldehyde (XXIV) but not orcylaldehyde was converted to substituted toluquinols and gliorosein (XXV) by Gliocladium roseum, implying that the C-methyltrans-ferase concerned could not accept the aromatic orcylaldehyde (Steward and Packter, 1968). In addition, whereas acetate (Yamazaki et al., 1%5) and or-sellinic acid (Yamazaki and Shibata, 1966) were both incorporated into the depside lecanoric acid (XXVI) (derived by esterification of two molecules of orsellinic acid) in the lichen Parmelia tinctorum, orsellinic acid was not converted to the related atranorin (XXVIl) (Yamazaki and Shibata, 1966) this... 

Extract of oak moss. Extract made mainly from Evernia prunastri (oak moss) and Pseudevernia furfuracea (tree moss). Oak moss concrete is prepared by hydrocarbon solvent extraction of the lichen Evernia PrunastrU collected mainly from oak trees in Yugoslavia, France, Italy, Corsica, Morocco, Hungary, and various central European countries. Contains atranorin, evernic acid and usnic acid Synonyms oak moss-resinoid oil Mousse concrete oak moss oak moss extra resinoid colourless MD oak moss LA oakmoss oil oak moss resin oak moss resinoid diethyl phthalate codistillate Evernia furfuraceae spp. absolute tree moss absolute Mousse d arbre absolute Evernia spp. absolute Mousse de chene absolute Evernia furfuraceae spp. concrete Mousse d arbre concrete tree moss concrete Evernia prunasti spp. concrete Evernia prunasti spp. oil Evernia prunasti spp. resin Uses fragrance in many perfume mixtures, after-shave lotions etc. (hay new-mown hay animal fern green). PA... 

Allergenic Activity. Numerous lichen substances like atranorin, barbatic, diffractaic, evernic, fumarprotocetraric, lobaric, per-latolic, physodic, physodalic, protolichesterinic, salazinic, stictic and usnic acids are allergenes (Brasch and Jacobsen 1991). 

Sometimes it is possible to separate a mixture of lichen substances by their different solubility. Usnic acid and atranorin are very soluble in chloroform, but nearly insoluble in methanol. Suitable solvents for recrystallization are n-hexane, benzene, diethyl ether, acetone, ethyl acetate, methanol, ethanol, acetic acid, dioxane or water often mixtures of these solvents are used. Sugar and low molecular carbohydrates are well known for their poor tendency to crystallize. Very important is the use of diethyl ether and dioxane free from peroxides, which are highly explosive. A simple reaction to test these solvents for peroxides is to shake about 3 ml of... 

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