A lichen metabolite with diverse biological activities
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Lobaric Acid

Item No. 25205

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
8-hydroxy-3-methoxy-11-oxo-1-(1-oxopentyl)-6-pentyl-11H-dibenzo[b,e][1,4]dioxepin-7-carboxylic acid
CAS Number
522-53-2
Molecular Formula
C25H28O8
Formula Weight
456.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
OC(C(C(O)=O)=C1CCCCC)=CC2=C1OC(C=C(OC)C=C3C(CCCC)=O)=C3C(O2)=O
InChi Code
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)
InChi Key
JHEWMLHQNRHTQX-UHFFFAOYSA-N
Origin
Fungus/Parmelia sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $148

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    2.5 mg

    $565

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    Product Description

    Lobaric acid is a depsidone metabolite that has been isolated from Stereocaulon lichen species with antioxidant, antiproliferative, antiviral, and enzyme inhibitory activites.1,2,3,4,5,6 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).2,3 Lobaric acid inhibits protein tyrosine phosphatase 1B (PTP1B; IC50 = 0.87 μM for the human recombinant enzyme) and production of 12(S)-HETE (Item No. 34570) by 12(S)-lipoxygenase (IC50 = 28.5 μM).5,6 In vivo, lobaric acid (250 μM) decreases lesion number, but not lesion diameter, in tobacco leaves infected with tobacco mosaic virus (TMV).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. González, A.G., Pérez, E.M.R., and Barrera, J.B. Chemical constituents of the lichen Stereocaulon azoreum. Z. Naturforsch. C J. Biosci. 47(7-8), 503-507 (1992).

    2. Thadhani, V.M., Choudhary, M.I., Ali, S., et al. Antioxidant activity of some lichen metabolites. Nat. Prod. Res. 25(19), 1827-1837 (2011).

    3. Haraldsdóttir, S., Guolaugsdóttir, E., Ingólfsdóttir, K., et al. Anti-proliferative effects of lichen-derived lipoxygenase inhibitors on twelve human cancer cell lines of different tissue origin in vitro. Planta Med. 70(11), 1098-1100 (2004).

    4. Ramírez, I., Araya, S., Piovano, M., et al. Lichen depsides and depsidones reduce symptoms of diseases caused by tobacco mosaic virus (TMV) in tobacco leaves. Nat. Prod. Commun. 7(5), 603-606 (2012).

    5. Seo, C.S., Sohn, J.H., Ahn, J.S., et al. Protein tyrosine phosphatase 1B inhibitory effects of depsidone and pseudodepsidone metabolites from the Antarctic lichen Stereocaulon alpinum. Bioorg. Med. Chem. Lett. 19(10), 2801-2803 (2009).

    6. Bucar, F., Schneider, I., Ögmundsdóttir, H., et al. Anti-proliferative lichen compounds with inhibitory activity on 12(S)-HETE production in human platelets. Phytomedicine 11(7-8), 602-606 (2004).