Antioxidant activity and mechanisms of action of natural compounds isolated from lichens: A systematic review

Molecules

Volumn 19, Issue 9, 2014, Pages 14496-14527

  White, Pollyanna A S ^a   Oliveira, Rita C M ^b   Oliveira, Aldeidia P ^b   Serafini, Mairim R ^a   Araújo, Adriano A S ^a   Gelain, Daniel P ^c   Moreira, Jose C F ^c   Almeida, Jackson R G S ^d   Quintans, Jullyana S S ^a   Quintans Junior, Lucindo J ^a   Santos, Marcio R V ^a  

^a FEDERAL UNIVERSITY OF SERGIPE   (Brazil)

^b FEDERAL UNIVERSITY OF PIAUÍ   (Brazil)

^c FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^d University of San Francisco   (Brazil)

Author keywords

Antioxidant response elements; Antioxidants; Cancer; Chronic disease; DPPH; Lichens

Indexed keywords

2,2-DIPHENYL-1-PICRYLHYDRAZYL; ANTIOXIDANT; BENZOFURAN DERIVATIVE; BIPHENYL DERIVATIVE; PICRIC ACID; SCAVENGER; USNIC ACID;

ANTIOXIDANT RESPONSIVE ELEMENT; CHEMISTRY; HUMAN; LICHEN (ORGANISM); METABOLISM; NEOPLASMS; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS;

ANTIOXIDANT RESPONSE ELEMENTS; ANTIOXIDANTS; BENZOFURANS; BIPHENYL COMPOUNDS; FREE RADICAL SCAVENGERS; HUMANS; LICHENS; NEOPLASMS; OXIDATION-REDUCTION; OXIDATIVE STRESS; PICRATES;

EID: 84907095604     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules190914496     Document Type: Review

References (49)

1. McCord, J.M. The evolution of free radicals and oxidative stress. Am. J. Med. 2000, 108, 652-659.
2. Alam, M.N.; Bristi, N.J.; Rafiquzzaman, M. Review on in vivo and in vitro methods evaluation of antioxidant activity. Saudi Pharm. J. 2013, 21, 143-152.
3. Lotito, S.B.; Frei, B. Consumption of flavonoid-rich foods and increased plasma antioxidant capacity in humans: Cause, consequence, or epiphenomenon? Free Radic. Biol. Med. 2006, 41, 1727-1746.
4. Lobo, V.; Patil, A.; Phatak, A.; Chandra, N. Free radicals, antioxidants and functional foods: Impact on human health. Pharmacogn. Rev. 2010, 4, 118-126.
5. Brewer, M.S. Natural Antioxidants: Sources, Compounds, Mechanisms of Action, and Potential Applications. Compr. Rev. Food Sci. Food Saf. 2011, 10, 221-247.
6. Hale, L.J. The pattern of growth of Clytia johnstoni. J. Embryol. Exp. Morphol. 1973, 29, 283-309.
7. Thadhani, V.M.; Choudhary, M.I.; Ali, S.; Omar, I.; Siddique, H.; Karunaratne, V. Antioxidant activity of some lichen metabolites. Nat. Prod. Res. 2011, 25, 1827-1837.
8. Melo, M.G.D.; Santos, J.P.A.; Serafini, M.R.; Caregnato, F.F.; Pasquali, M.A.B.; Rabelo, T.K.; Rocha, R.F.; Quintans-Junior, L.J.; Araújo, A.A.S.; Silva, F.A.; et al. Redox properties and cytoprotective actions of atranorin, a lichen secondary metabolite. Toxicol. In Vitro 2011, 25, 462-468.
9. Molnár, K.; Farkas, E. Current results on biological activities of lichen secondary metabolites: A review. Z. Naturforsch. C 2010, 65, 157-173.
10. Schmitt, I.; Lumbsch, H.T. Molecular phylogeny of the Pertusariaceae supports secondary chemistry as an important systematic character set in lichen-forming ascomycetes. Mol. Phylogenet. Evol. 2004, 33, 43-55.
11. Shukla, V.; Joshi, G.P.; Rawat, M.S.M. Lichens as a potential natural source of bioactive compounds: A review. Phytochem. Rev. 2010, 9, 303-314.
12. Nunes, P.S.; Albuquerque-Junior, R.L.; Cavalcante, D.R.; Dantas, M.D.; Cardoso, J.C.; Bezerra, M.S.; Souza, J.C.; Serafini, M.R.; Quitans-Junior, L.J.; Bonjardim, L.R.; et al. Collagen-based films containing liposome-loaded usnic acid as dressing for dermal burn healing. J. Biomed. Biotechnol. 2011, 2011, doi:10.1155/2011/761593.
13. Nunes, P.S.; Bezerra, M.S.; Costa, L.P.; Cardoso, J.C.; Albuquerque-Junior, R.L.; Rodrigues, M.O.; Barin, G.B.; Silva, F.A.; Araujo, A.A.S. Thermal characterization of usnic acid/collagen-based films. J. Therm. Anal. Calorim. 2010, 99, 1011-1014.
14. Barreto, R.S.S.; Albuquerque-Júnior, R.L.C.; Araújo, A.A.S.; Almeida, J.R.G.S.; Santos, M.R.V.; Barreto, A.S.; DeSantana, J.M.; Siqueira-Lima, P.S.; Quintans, J.S.S.; Quintans-Júnior, L.J. A Systematic Review of the Wound-Healing Effects of Monoterpenes and Iridoid Derivatives. Molecules 2014, 19, 846-862.
15. Odabasoglu, F.; Cakir, A.; Suleyman, H.; Aslan, A.; Bayir, Y.; Halici, M.; Kazaz, C.J. Gastroprotective and antioxidant effects of usnic acid on indomethacin-induced gastric ulcer in rats. J. Ethnopharmacol. 2006, 103, 59-65.
16. Dévéhat, F.; Tomasi, S.; Elix, J.A.; Bernard, A.; Rouaud, I.; Uriac, P.; Boustie, J. Stictic Acid Derivatives from the Lichen Usnea articulata and Their Antioxidant Activities. J. Nat. Prod. 2007, 70, 1218-1220.
17. Behera, B.C.; Mahadik, N.; Morey, M. Antioxidative and cardiovascular-protective activities of metabolite usnic acid and psoromic acid produced by lichen species Usnea complanata under submerged fermentation. Pharm. Biol. 2012, 50, 968-979.
18. Santos, L.C.; Honda, N.K.; Carlos, I.Z.; Vilegas, W. Intermediate reactive oxygen and nitrogen from macrophages induced by Brazilian lichens. Fitoterapia 2004, 75, 473-479.
19. Ranković, B.; Kosanić, M.; Stanojković, T.; Vasiljević, P.; Manojlović, N. Biological Activities of Toninia candida and Usnea barbata Together with Their Norstictic Acid and Usnic Acid Constituents. Int. J. Mol. Sci. 2012, 13, 14707-14722.
20. Bessadottir, M.; Egilsson, M.; Einarsdottir, E.; Magnusdottir, I.H.; Ogmundsdottir, M.H.; Omarsdottir, S.; Ogmundsdottir, H.M. Proton-Shuttling Lichen Compound Usnic Acid Affects Mitochondrial and Lysosomal Function in Cancer Cells. PLoS One 2012, 7, e51296.
21. De Paz, G.A.; Raggio, J.; Gómez-Serranillos, M.P.; Palomino, O.M.; González-Burgos, E.; Carretero, M.E.; Crespo, A. HPLC isolation of antioxidant constituents from Xanthoparmelia spp. J. Pharm. Biomed. Anal. 2010, 53, 165-171.
22. Jin, J.Q.; Li, C.Q.; He, L.C. Down-regulatory effect of usnic acid on nuclear factor-kappaB-dependent tumor necrosis factor-alpha and inducible nitric oxide synthase expression in lipopolysaccharide-stimulated macrophages RAW 264.7. Phytother. Res. 2008, 22, 1605-1609.
23. Brisdelli, F.; Perilli, M.; Sellitri, D.; Piovano, M.; Garbarino, J.A.; Nicoletti, M.; Bozzi, A.; Amicosante, G.; Celenza, G. Cytotoxic activity and antioxidant capacity of purified lichen metabolites: An in vitro study. Phytother. Res. 2013, 27, 431-437.
24. Marante, F.J.T.; Castellano, A.G.; Rosas, F.E.; Aguiar, J.Q.; Barrera, J.J.B. Identification and quantitation of allelochemicals from the lichen Lethariella canariensis: Phytotoxicity and antioxidative activity. Chem. Ecol. 2003, 29, 2049-2071.
25. Bačkorová, M.; Bačkor, M.; Mikeš, J.; Jendželovský, R.; Fedoročko, P. Variable responses of different human cancer cells to the lichen compounds parietin, atranorin, usnic acid and gyrophoric acid. Toxicol. In Vitro 2011, 25, 37-44.
26. Polat, Z.; Aydin, E.; Türkez, H.; Aslan, A. In vitro risk assessment of usnic acid compound. Toxicol. Ind. Health 2013, doi:10.1177/0748233713504811.
27. Rabelo, T.K.; Zeidán-Chuliá, F.; Vasques, L.M.; Dos Santos, J.P.; Da Rocha, R.F.; Pasquali, M.A.; Rybarczyk-Filho, J.L.; Araújo, A.A.; Moreira, J.C.; Gelain, D.P. Redox characterization of usnic acid and its cytotoxic effect on human neuron-like cells (SH-SY5Y). Toxicol. In Vitro 2012, 26, 304-314.
28. Kosanić, M.; Ranković, B.; Stanojković, T.; Rančić, A.; Manojlović, N. Cladonia lichens and their major metabolites as possible natural antioxidant, antimicrobial and anticancer agents. LWT Food Sci. Technol. 2014, 59, 518-525.
29. Papadopoulou, P.; Tzakou, O.; Vagias, C.; Kefalas, P.; Roussis, V. Beta-orcinol metabolites from the lichen Hypotrachyna revoluta. Molecules 2007, 12, 997-1005.
30. Barreto, R.S.S.; Albuquerque-Júnior, R.L.C.; Pereira-Filho, R.N.; Quintans, J.S.S.; Barreto, A.S.; DeSantana, J.M.; Santana-Filho, V.J.; Santos, M.R.V.; Bonjardim, L.R.; Araújo, A.A.S.; et al. Evaluation of wound healing activity of atranorin, a lichen secondary metabolite, on rodents. Braz. J. Pharmacogn. 2013, 23, 310-319.
31. Jayaprakasha, G.K.; Rao, L.J. Phenolic constituents from the lichen Parmotrema stuppeum (Nyl.) Hale and their antioxidant activity. Z. Naturforsch. C 2000, 55, 1018-1022.
32. Lopes, T.I.; Coelho, R.G.; Yoshida, N.C.; Honda, N.K. Radical-scavenging activity of orsellinates. Chem. Pharm. Bull. 2008, 56, 1551-1554.
33. Bayir, Y.; Odabasoglu, F.; Cakir, A.; Aslan, A.; Suleyman, H.; Halici, M.; Kazaz, C. The inhibition of gastric mucosal lesion, oxidative stress and neutrophil-infiltration in rats by the lichen constituent diffractaic acid. Phytomedicine 2006, 13, 584-590.
34. Liu, W.; Xu, Z.; Yang, T.; Deng, Y.; Xu, B.; Feng, S.; Li, Y. The protective role of tea polyphenols against methylmercury-induced neurotoxic effects in rat cerebral cortex via inhibition of oxidative stress. Free Radic. Res. 2014, 48, 849-863.
35. Bhullar, K.S.; Rupasinghe, H.P. Polyphenols: Multipotent Therapeutic Agents in Neurodegenerative Diseases. Oxidative Med. Cell. Longev. 2013, 2013, 891748.
36. Odabasoglu, F.; Yildirim, O.S.; Aygun, H.; Halici, Z.; Halici, M.; Erdogan, F.; Cadirci, E.; Cakir, A.; Okumus, Z.; Aksakal, B.; et al. Diffractaic acid, a novel proapoptotic agent, induces with olive oil both apoptosis and antioxidative systems in Ti-implanted rabbits. Eur. J. Pharmacol. 2012, 674, 171-178.
37. Bhattarai, H.D.; Kim, T.; Oh, H.; Yim, J.H.J. A new pseudodepsidone from the Antarctic lichen Stereocaulon alpinum and its antioxidant, antibacterial activity. J. Antibiot 2013, 66, 559-561.
38. Manojlović, N.; Ranković, B.; Kosanić, M.; Vasiljević, P.; Stanojković, T. Chemical composition of three Parmelia lichens and antioxidant, antimicrobial and cytotoxic activities of some their major metabolites. Phytomedicine 2012, 19, 1166-1172.
39. Pavlovic, V.; Stojanovic, I.; Jadranin, M.; Vajs, V.; Djordjević, I.; Smelcerovic, A.; Stojanovic, G. Effect of four lichen acids isolated from Hypogymnia physodes on viability of rat thymocytes. Food Chem. Toxicol. 2013, 51, 160-164.
40. Kosanić, M.; Manojlović, N.; Janković, S.; Stanojković, T.; Ranković, B. Evernia prunastri and Pseudoevernia furfuraceae lichens and their major metabolites as antioxidant, antimicrobial and anticancer agents. Food Chem. Toxicol. 2013, 53, 112-118.
41. Stojanović, I.Ž.; Najman, S.; Jovanović, O.; Petrović, G.; Najdanović, J.; Vasiljević, P.; Šmelcerović, A. Effects of Depsidones from Hypogymnia physodes on HeLa Cell Viability and Growth. Folia Biol. 2014, 60, 89-94.
42. Kinoshita, K.; Togawa, T.; Hiraishi, A.; Nakajima, Y.; Koyama, K.; Narui, T.; Wang, L.S.; Takahashi, K. Antioxidant activity of red pigments from the lichens Lethariella sernanderi, L. cashmeriana, and L. sinensis. J. Nat. Med. 2010, 64, 85-88.
43. Paudel, B.; Bhattarai, H.D.; Koh, H.Y.; Lee, S.G.; Han, S.J.; Lee, H.K.; Oh, H.; Shin, H.W.; Yim, H. Ramalin, a novel nontoxic antioxidant compound from the Antarctic lichen Ramalina terebrata. Phytomedicine 2011, 18, 1285-1290.
44. Takenaka, Y.; Tanahashi, T.; Nagakura, N.; Hamada, N. Production of xanthones with free radical scavenging properties, emodin and sclerotiorin by the cultured lichen mycobionts of Pyrenula japonica. Z. Naturforsch. C 2000, 55, 910-914.
45. Russo, A.; Piovano, M.; Lombardo, L.; Garbarino, J.; Cardile, V. Lichen metabolites prevent UV light and nitric oxide-mediated plasmid DNA damage and induce apoptosis in human melanoma cells. Life Sci. 2008, 83, 468-474.
46. Luo, H.; Li, C.; Kim, J.C.; Liu, Y.; Jung, J.S.; Koh, Y.J.; Hur, J.S. Biruloquinone, an Acetylcholinesterase Inhibitor Produced by Lichen-Forming Fungus Cladonia macilenta. J. Microbiol. Biotechnol. 2013, 23, 161-166.
47. Boustie, J.; Grube, M. Lichens-A promising source of bioactive secondary metabolites. Plant Genet. Resour. 2005, 3, 273-287.
48. Cowan, D.A.; Green, T.G.A.; Wilson, A.T. Lichen metabolism-Aspects of light and dark physiology. New Phytol. 1979, 83, 761-769.
49. Liberati, A.; Altman, D.G.; Tetzlaff, J.; Mulrow, C.; Gøtzsche, P.C.; Ioannidis, J.P.A.; Clarke, M.; Devereaux, P.J.; Kleijnen, J.; Moher, D. The PRISMA statement for reporting systematic reviews and meta-analyses of studies that evaluate health care interventions: Explanation and elaboration. BMJ 2009, 339, b2700.