A depside lichen metabolite with diverse biological activities
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Atranorin

Item No. 28106

Technical Information
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
Purity
≥95%
A crystalline solid
Chloroform: solubleDMSO: soluble
λmax
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
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Atranorin is a depside lichen metabolite that has been found in S. alpinum and has diverse biological activities.1,2,3,4 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).1,2 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).3 It inhibits acetic acid-induced writhing in mice when administered orally at doses of 200 and 400 mg/kg.4 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.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ingólfsdóttir, K., Chung, G.A., Skúlason, V.G., et alAntimycobacterial activity of lichen metabolites in vitro. Eur. J. Pharm. Sci. 6(2), 141-144 (1998).

    2. Yilmaz, M., Türk, A.O., Tay, T., et alThe antimicrobial activity of extracts of the lichen Cladonia foliacea and its (–)-usnic acid, atranorin, and fumarprotocetraric acid constituents. Z. Naturforsch. C. J. Biosci. 59(3-4), 249-254 (2004).

    3. Bačkorová, M., Bačkor, M., Mikeš, J., et alVariable responses of different human cancer cells to the lichen compounds parietin, atranorin, usnic acid and gyrophoric acid. Toxicol. In Vitro 25(1), 37-44 (2011).

    4. Melo, M.G.D., Araújo, A.A.S., Rocha, C.P.L., et alPurification, physicochemical properties, thermal analysis and antinociceptive effect of atranorin extracted from Cladina kalbii. Biol. Pharm. Bull. 31(10), 1977-1980 (2008).