Anticholinergic and Antioxidant Activities of Usnic Acid-an Activity-structure Insight

Overview

Journal Toxicol Rep

Date 2019 Dec 14

PMID 31832335

Citations 44

Authors

Kader Cetin Cakmak

Ilhami Gulcin

Affiliations

Soon will be listed here.

Abstract

Usnic acid, as active dibenzofuran derivative, isolated and characterized from some lichen species. The aim of manuscript was to evaluate antioxidant, anticholinergic and antidiabetic potentials of usnic acid as an important natural product. Antioxidant profile of usnic acid determined by eight distinguishes bioanalytical antioxidant methods including 1,1-diphenyl-2-picrylhydrazyl (DPPH·), 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS ), superoxide anion radical (O ) and N,N-dimethyl-p-phenylenediamine (DMPD ) scavenging activities, cupric ion (Cu), ferric ion (Fe) and Fe-TPTZ reducing abilities and ferrous ion (Fe) chelating activity. Usnic acid was found as potent DPPH· (IC: 49.50 μg/mL), DMPD (IC: 33.00 μg/mL), O (IC: 18.68 μg/mL), and ABTS (IC: 10.41 μg/mL) scavenging effects. Also, the inhibition effects of usnic acid were tested against some metabolic enzymes including acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) linked to neurodegenerative diseases. Both enzymes play important roles in cholinergic transmission by hydrolyzing the neurotransmitter acetylcholine in cholinergic synapses, central nervous system, neuromuscular junctions and autonomic ganglia. Their inhibitors were used for clinical treatment of some neurodegenerative conditions including myasthenia gravis, Alzheimer's disease, apathy, glaucoma, postural tachycardia syndrome and dementia. Furthermore, usnic acid showed the potent inhibition profiles against AChE (IC: 1.273 nM) and BChE (IC: 0.239 nM) enzymes. The results clearly showed that usnic acid is an important natural product with antioxidant and anticholinergic potentials.

Citing Articles

A multidimensional study for design of phytochemical profiling, antioxidant potential, and enzyme inhibition effects of ışgın () as an edible plant.

Tel A, Aslan K, Yilmaz M, Gulcin I Food Chem X. 2025; 25:102125.

PMID: 39974533 PMC: 11838142. DOI: 10.1016/j.fochx.2024.102125.

Flaxseed polyphenols: Effects of varieties on its composition and antioxidant capacity.

Huang X, Wang N, Ma Y, Liu X, Guo H, Song L Food Chem X. 2024; 23:101597.

PMID: 39071936 PMC: 11282950. DOI: 10.1016/j.fochx.2024.101597.

GC-MS Profiling and Pharmacological Potential of (Ach.) Poelt.

Zeghina I, El Ouar I, Tartouga M, Mokhtari M, Elieh-Ali-Komi D, Gali L Turk J Pharm Sci. 2024; 21(3):243-251.

PMID: 38994865 PMC: 11590548. DOI: 10.4274/tjps.galenos.2023.91126.

Design, synthesis, molecular docking study, and α-glucosidase inhibitory evaluation of novel hydrazide-hydrazone derivatives of 3,4-dihydroxyphenylacetic acid.

Khan H, Jan F, Shakoor A, Khan A, Alasmari A, Alasmari F Sci Rep. 2024; 14(1):11410.

PMID: 38762658 PMC: 11102520. DOI: 10.1038/s41598-024-62034-x.

Contemporary strategies and approaches for characterizing composition and enhancing biofilm penetration targeting bacterial extracellular polymeric substances.

Lu L, Zhao Y, Li M, Wang X, Zhu J, Liao L J Pharm Anal. 2024; 14(4):100906.

PMID: 38634060 PMC: 11022105. DOI: 10.1016/j.jpha.2023.11.013.

References

Beauchamp C, Fridovich I . Superoxide dismutase: improved assays and an assay applicable to acrylamide gels. Anal Biochem. 1971; 44(1):276-87. DOI: 10.1016/0003-2697(71)90370-8. View

Gulcin I . Antioxidant activity of food constituents: an overview. Arch Toxicol. 2011; 86(3):345-91. DOI: 10.1007/s00204-011-0774-2. View

Fernandez-Moriano C, Divakar P, Crespo A, Gomez-Serranillos M . Protective effects of lichen metabolites evernic and usnic acids against redox impairment-mediated cytotoxicity in central nervous system-like cells. Food Chem Toxicol. 2017; 105:262-277. DOI: 10.1016/j.fct.2017.04.030. View

Sehitoglu M, Han H, Kalin P, Gulcin I, Ozkan A, Aboul-Enein H . Pistachio (Pistacia vera L.) gum: a potent inhibitor of reactive oxygen species. J Enzyme Inhib Med Chem. 2014; 30(2):264-9. DOI: 10.3109/14756366.2014.915395. View

Gulcin I . Antioxidant activity of L-adrenaline: a structure-activity insight. Chem Biol Interact. 2008; 179(2-3):71-80. DOI: 10.1016/j.cbi.2008.09.023. View

Lu Y, Foo L . Polyphenolics of Salvia--a review. Phytochemistry. 2002; 59(2):117-40. DOI: 10.1016/s0031-9422(01)00415-0. View

Benzie I, Strain J . Ferric reducing/antioxidant power assay: direct measure of total antioxidant activity of biological fluids and modified version for simultaneous measurement of total antioxidant power and ascorbic acid concentration. Methods Enzymol. 1999; 299:15-27. DOI: 10.1016/s0076-6879(99)99005-5. View

Araujo A, de Melo M, Rabelo T, Nunes P, Santos S, Serafini M . Review of the biological properties and toxicity of usnic acid. Nat Prod Res. 2015; 29(23):2167-80. DOI: 10.1080/14786419.2015.1007455. View

Gulcin I . Antioxidant activity of eugenol: a structure-activity relationship study. J Med Food. 2011; 14(9):975-85. DOI: 10.1089/jmf.2010.0197. View

10.

Caglayan C, Demir Y, Kucukler S, Taslimi P, Kandemir F, Gulcin I . The effects of hesperidin on sodium arsenite-induced different organ toxicity in rats on metabolic enzymes as antidiabetic and anticholinergics potentials: A biochemical approach. J Food Biochem. 2019; 43(2):e12720. DOI: 10.1111/jfbc.12720. View

11.

Gulcin I, Oktay M, Kufrevioglu O, Aslan A . Determination of antioxidant activity of lichen Cetraria islandica (L) Ach. J Ethnopharmacol. 2002; 79(3):325-9. DOI: 10.1016/s0378-8741(01)00396-8. View

12.

Koksal E, Gulcin I, Beyza S, Sarikaya O, Bursal E . In vitro antioxidant activity of silymarin. J Enzyme Inhib Med Chem. 2008; 24(2):395-405. DOI: 10.1080/14756360802188081. View

13.

Gulcin I . Antioxidant and antiradical activities of L-carnitine. Life Sci. 2005; 78(8):803-11. DOI: 10.1016/j.lfs.2005.05.103. View

14.

Campanella L, Delfini M, Ercole P, Iacoangeli A, Risuleo G . Molecular characterization and action of usnic acid: a drug that inhibits proliferation of mouse polyomavirus in vitro and whose main target is RNA transcription. Biochimie. 2002; 84(4):329-34. DOI: 10.1016/s0300-9084(02)01386-x. View

15.

Galanty A, Koczurkiewicz P, Wnuk D, Paw M, Karnas E, Podolak I . Usnic acid and atranorin exert selective cytostatic and anti-invasive effects on human prostate and melanoma cancer cells. Toxicol In Vitro. 2017; 40:161-169. DOI: 10.1016/j.tiv.2017.01.008. View

16.

Gulcin I . Comparison of in vitro antioxidant and antiradical activities of L-tyrosine and L-Dopa. Amino Acids. 2006; 32(3):431-8. DOI: 10.1007/s00726-006-0379-x. View

17.

Ozbey F, Taslimi P, Gulcin I, Maras A, Goksu S, Supuran C . Synthesis of diaryl ethers with acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase inhibitory actions. J Enzyme Inhib Med Chem. 2016; 31(sup2):79-85. DOI: 10.1080/14756366.2016.1189422. View

18.

Ozturk Sarikaya S, Topal F, Senturk M, Gulcin I, Supuran C . In vitro inhibition of α-carbonic anhydrase isozymes by some phenolic compounds. Bioorg Med Chem Lett. 2011; 21(14):4259-62. DOI: 10.1016/j.bmcl.2011.05.071. View

19.

Gocer H, Akincioglu A, Oztaskin N, Goksu S, Gulcin I . Synthesis, antioxidant, and antiacetylcholinesterase activities of sulfonamide derivatives of dopamine-related compounds. Arch Pharm (Weinheim). 2014; 346(11):783-92. DOI: 10.1002/ardp.201300228. View

20.

Xiao Z, Storms R, Tsang A . A quantitative starch-iodine method for measuring alpha-amylase and glucoamylase activities. Anal Biochem. 2006; 351(1):146-8. DOI: 10.1016/j.ab.2006.01.036. View