Atranorin

Atranorin is a depside lichen metabolite that has been found in S. alpinum and has diverse biological activities. It is active against the bacteria B. cereus, B. subtilis, S. aureus, S. faecalis, P. vulgaris, L. monocytogenes, and A. hydrophila (MICs = 1.67, 0.38, 26.7, 13.4, 3.34, 9.83, and 1.67 mM, respectively), the fungi C. albicans and C. glabrata (MIC = 26.7 mM for both), as well as the mycobacterium M. aurum (MIC = 250 µg/ml). Atranorin is cytotoxic to A270, HL-60, and Jurkat cancer cells (IC50s = 197.9, 93.5, and 181.6 µM, respectively) but not HeLa, MCF-7, SK-BR-3, or HT-29 cancer cells (IC50s = >200 µM). It inhibits acetic acid-induced writhing in mice when administered orally at doses of 200 and 400 mg/kg. Atranorin (200 and 400 mg/kg, p.o.) also reduces paw licking and biting in the second, but not first, phase of the formalin test when administered 30 minutes prior to formalin in mice.Formal Name: 3-formyl-2,4-dihydroxy-6-methyl-benzoic acid, 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester. CAS Number: 479-20-9. Synonyms: NSC 87512, NSC 249980, NSC 685591. Molecular Formula: C19H18O8. Formula Weight: 374.3. Purity: >95%. Formulation: (Request formulation change), A crystalline solid. Solubility: Chloroform: soluble, DMSO: soluble. lambdamax: 251 nm. SMILES: CC1=CC(OC(C2=C(O)C(C=O)=C(O)C=C2C)=O)=C(C)C(O)=C1C(OC)=O. InChi Code: 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. InChi Key: YLOYKYXNDHOHHT-UHFFFAOYSA-N. Origin: Plant/Litchi chinensis.