Lobaric acid

• CAT Number: R074532
• CAS Number: 522-53-2
• PubChem Substance ID: 73157
• Molecular Formula: C25H28O8
• Molecular Weight: 456.491
• Purity: ≥95%
• IUPAC Name: 3-hydroxy-9-methoxy-6-oxo-7-pentanoyl-1-pentylbenzo[b][1,4]benzodioxepine-2-carboxylic acid
• InChI: InChI=1S/C25H28O8/c1-4-6-8-9-15-21(24(28)29)18(27)13-20-23(15)32-19-12-14(31-3)11-16(17(26)10-7-5-2)22(19)25(30)33-20/h11-13,27H,4-10H2,1-3H3,(H,28,29)
• InChIKey: JHEWMLHQNRHTQX-UHFFFAOYSA-N
• SMILES: CCCCCC1=C2C(=CC(=C1C(=O)O)O)OC(=O)C3=C(O2)C=C(C=C3C(=O)CCCC)OC

Lobaric acid (CAS 522-53-2) is a depsidone metabolite that has been isolated from Stereocaulon lichen species with antioxidant, antiproliferative, antiviral, and enzyme inhibitory activites. It scavenges superoxide radicals in a cell-free assay (IC50 = 97.9 μmol) and inhibits proliferation in a panel of leukemia, colorectal, gastric, breast, ovarian, prostate, pancreatic, and lung cancer cell lines (EC50s = 15.2-63.9 μg/ml). Lobaric acid inhibits protein tyrosine phosphatase 1B (PTP1B; IC50 = 0.87 μM for the human recombinant enzyme) and production of 12(S)-HETE by 12(S)-lipoxygenase (IC50 = 28.5 μM). In vivo, lobaric acid (250 μM) decreases lesion number, but not lesion diameter, in tobacco leaves infected with tobacco mosaic virus (TMV).

Reference

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4.Ramírez, Ingrid, et al. "Lichen depsides and depsidones reduce symptoms of diseases caused by tobacco mosaic virus (TMV) in tobacco leaves." Natural product communications 7.5 (2012): 1934578X1200700514.
5.Seo, Changon, et al. "Protein tyrosine phosphatase 1B inhibitory effects of depsidone and pseudodepsidone metabolites from the Antarctic lichen Stereocaulon alpinum." Bioorganic & medicinal chemistry letters 19.10 (2009): 2801-2803.
6.Bucar, F., et al. "Anti-proliferative lichen compounds with inhibitory activity on 12 (S)-HETE production in human platelets." Phytomedicine 11.7-8 (2004): 602-606.