Description
Atranorin, which can be found in the herbs of Parmelia tinctorum Despr, has a relevant redox-active action, acting as a pro-oxidant or antioxidant agent depending on the radical. Also, it will exert cytoprotective effects on cells under oxidative stress induced by H(2)O(2). It was found to be more efficient at equitoxic doses and correlated more strongly with an increased number of floating cells or a higher apoptotic index. It also exhibited significant anti-inflammatory activity in the acute model of inflammation (leukocyte migration to the peritoneal cavity), carrageenan- and arachidonic acid-induced hind paw edema in rats. Besides, Atranorin exhibited a dose-dependent antioxidant activity in vitro, as assessed by total radical-trapping antioxidant parameter and total antioxidant reactivity assays.
Synonyms
Atranoric acid; Atranorine; Parmelin; Usnarin; Benzoic acid, 3-formyl-2,4-dihydroxy-6-methyl-, 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester
IUPAC Name
(3-hydroxy-4-methoxycarbonyl-2,5-dimethylphenyl) 3-formyl-2,4-dihydroxy-6-methylbenzoate
Molecular Formula
C19H18O8
Canonical SMILES
CC1=CC(=C(C(=C1C(=O)OC2=C(C(=C(C(=C2)C)C(=O)OC)O)C)O)C=O)O
InChI
1S/C19H18O8/c1-8-5-12(21)11(7-20)17(23)15(8)19(25)27-13-6-9(2)14(18(24)26-4)16(22)10(13)3/h5-7,21-23H,1-4H3
InChIKey
YLOYKYXNDHOHHT-UHFFFAOYSA-N
Solubility
Soluble in methanol, chloroform, acetone
Application
Antinociceptive/antiinflammatory/antibacterial
Toxicity
skn-gpg 5% CODEDG 11,168,1984
Uses
antinociceptive, antiinflammatory, antibacterial
Water Solubility
Slightly soluble in water