Potential anticancer activity of lichen secondary metabolite physodic acid

Chemico-Biological Interactions

Volumn 263, Issue , 2017, Pages 36-45

  Cardile, V ^a   Graziano, A C E ^a   Avola, R ^a   Piovano, M ^b   Russo, A ^a  

^a UNIVERSITY OF CATANIA   (Italy)

^b DEPARTAMENTO DE FÍSICA   (Chile)

Author keywords

Apoptosis; Depsidones; Hsp70; Lichen compounds; Melanoma cells; Polyphenols; Reactive oxygen species

Indexed keywords

ATRANORIN; DEPSIDE; GYROPHORIC ACID; HEAT SHOCK PROTEIN 70; PHYSODIC ACID; PROTEIN BAX; PROTEIN BCL 2; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; BENZOIC ACID DERIVATIVE; CASPASE 3; DIBENZOXEPIN DERIVATIVE; HYDROXYBENZOIC ACID DERIVATIVE; REACTIVE OXYGEN METABOLITE;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BACIDIA STIPATA; CANCER INHIBITION; CHILE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG MECHANISM; DRUG STRUCTURE; FIBROBLAST; HUMAN; HUMAN CELL; HYPOGYMNIA LUGUBRIS; IN VITRO STUDY; LICHEN (ORGANISM); MELANOMA CELL LINE; OCHROLECHIA DECEPTIONIS; PLACOPSIS CONTORTUPLICATA; PROTEIN EXPRESSION; CELL PROLIFERATION; CHEMISTRY; DOWN REGULATION; DRUG EFFECTS; INFRARED SPECTROPHOTOMETRY; MATRIX-ASSISTED LASER DESORPTION-IONIZATION MASS SPECTROMETRY; METABOLISM; TUMOR CELL LINE; WESTERN BLOTTING;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; BCL-2-ASSOCIATED X PROTEIN; BENZOATES; BLOTTING, WESTERN; CASPASE 3; CELL LINE, TUMOR; CELL PROLIFERATION; DIBENZOXEPINS; DOWN-REGULATION; HSP70 HEAT-SHOCK PROTEINS; HUMANS; HYDROXYBENZOATES; LICHENS; PROTO-ONCOGENE PROTEINS C-BCL-2; REACTIVE OXYGEN SPECIES; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SPECTROPHOTOMETRY, INFRARED;

EID: 85007189040     PISSN: 00092797     EISSN: 18727786     Source Type: Journal    
DOI: 10.1016/j.cbi.2016.12.007     Document Type: Article

References (47)

1. [1] Muller, K., Pharmaceutically relevant metabolites from lichens. App. Microbiol. Biotechnol. 56 (2001), 9–16.
2. [2] Huneck, S., New results on the chemistry of lichen substances. Fortschr. Chem. Org. Naturst. 81 (2001), 1–276.
3. [3] Boustie, J.B., Tomasi, S., Grube, M., Bioactive lichen metabolites: alpine habitats as an untapped source. Phytochem. Rev. 10 (2011), 287–307.
4. [4] Cocchietto, M., Skert, N., Nimis, P.L., Sava, G., A review on usnic acid, an interesting natural compound. Naturwissenschaften 89 (2002), 137–146.
5. [5] Bezivin, C., Tomasi, S., Rouaud, I., Delcros, J.G., Boustie, J., Cytotoxic activity of compounds from the lichen: Cladoniaconvolute. Planta Med. 70 (2004), 874–877.
6. [6] Sahu, S.C., Amankwa-Sakyi, M., O'Donnell, M.W. Jr., Sprando, R.L., Effects of usnic acid exposure on human hepatoblastoma HepG2 cells in culture. J. Appl. Toxicol. 32 (2012), 722–730.
7. [7] Einarsdóttir, E., Groeneweg, J., Björnsdóttir, GG, Harethardottir, G., Omarsdottir, S., Ingolfsdottir, K., Ogmundsdottir, H.M., Cellular mechanisms of the anticancer effects of the lichen compound usnic acid. Planta Med. 76 (2010), 969–974.
8. [8] Bazin, M.A., Le Lamer, A.C., Delcros, J.G., Rouad, I., Uriac, P., Boustie, J., Corbel, J.C., Tomasi, S., Synthesis and cytotoxic activities of usnic acid derivatives. Bioorg. Med. Chem. 16 (2008), 6860–6866.
9. [9] Russo, A., Piovano, M., Lombardo, L., Vanella, L., Cardile, V., Garbarino, J., Pannarin inhibits cell growth and induces cell death in human prostate carcinoma DU-145 cells. Anti-Cancer Drugs 7 (2006), 1163–1169.
10. [10] 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. 83 (2008), 468–474.
11. [11] Haraldsdóttir, S., Guolaugsdóttir, E., Ingólfsdóttir, K., Ogmundsdóttir, H.M., Anti-proliferative effects of lichen-derived lipoxygenase inhibitors on twelve human cancer cell lines of different tissue origin in vitro. PlantaMed 70 (2004), 1098–1100.
12. [12] Russo, A., Caggia, S., Piovano, M., Garbarino, J., Cardile, V., Effect of vicanicin and protolichesterinic acid on human prostate cancer cells: role of Hsp70 protein. Chem. Biol. Interact. 195 (2012), 1–10.
13. [13] 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 invitro study. Phytother. Res. 27 (2013), 431–437.
14. [14] Bessadóttira, M., Skúladóttira, E.Á., Gowan, S., Eccles, S., Ómarsdóttir, S., Ögmundsdóttira, H.M., Effects of anti-proliferative lichen metabolite, protolichesterinic acid on fatty acid synthase, cell signalling and drug response in breastcancercells. Phytomedicine 21 (2014), 1717–1724.
15. [15] Piovano, M., Guzman, G., Garbarino, J.A., Chamy, M.C., Chemical study of Bacidia stipata (lichen). Biochem. Syst. Ecol. 27 (1999), 663–664.
16. [16] Chorrechè, E., Carrasco, M., Escudero, M., Velazquez, L., Guzman, A.M.S., De Giannini, F., Enriz, R., Jauregui, E., Cenal, J., Giordano, O., Study of the cytotoxic and antimicrobial activities of usnic acid and derivatives. Fitoterapia 69 (1998), 493–501.
17. [17] Piovano, M., Garbarino, J., Giannini, F.A., Correchè, E.R., Feresin, G., Tapia, A., Zacchino, S., Enriz, R.D., Evaluation of antifungal and antibacterial activities of aromatic metabolites from lichens. Bol. la Soc. Chil. Quimica 47 (2002), 235–240.
18. [18] Bradford, M.M., A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72 (1976), 248–254.
19. [19] Wojciechowski, Z.A., Goad, L.J., Goodwin, T.W., Sterols of lichen Pseudevernia furfuracea. Phytochemistry 12 (1973), 1433–1436.
20. [20] Edwards, H.G.M., Newton, E.M., Wynn-Williams, D.D., Molecular structural studies of lichen substances II: atranorin, gyrophoric acid, fumarprotocetraric acid, rhizocarpic acid, calycin, pulvinic dilactone and usnic acid. J. Mol. Struct. 651–653 (2003), 27–37.
21. [21] Bryan, A.J., Elix, J.A., Norfolk, S., Synthesis of orcinol tridepsides and aphthosin, an orcinol tetradepside. Aust. J. Chern. 29 (1976), 1079–1086.
22. [22] Hirayama, T., Fujikawa, F., Yosioka, I., Kitagawa, I., Vittatolic acid, a new depsidone isolated from the lichen Hypogymnia vittata (Ach.). Chem. Pharm. Bull. 23 (1975), 693–695.
23. [23] Galvano, F., Russo, A., Cardile, V., Galvano, G., Vanella, A., Renis, M., DNA damage in human fibroblasts exposed to fumonisin B(1). Food Chem. Toxicol. 40 (2002), 25–31.
24. [24] Sekine, T., Takahashi, J., Nishishiro, M., Arai, A., Wakabayashi, H., Kurihara, T., Kobayashi, M., Hashimoto, K., Kikuchi, H., Katayama, T., Kanda, Y., Kunii, S., Motohashi, N., Sakagami, H., Tumor-specific and type of cell death induced by trihaloacetylazulenes in human tumor cell lines. Anticancer Res. 27 (2007), 133–143.
25. [25] Shi, Y., Mechanisms of caspase activation and inhibition during apoptosis. Mol. Cell 9 (2002), 459–470.
26. [26] Bednarek, I., Sypniewski, D., Klama-Baryła, A., Gałka, S., Machnik, G., Single-cell gel electrophoresis (comet assay) as a tool for apoptosis determination in tumor cell lines HL-60 and Jurkat cultures treated with anisomycin. Ann. Acad. Med. 60 (2006), 278–284.
27. [27] Godard, T., Deslandes, E., Lebailly, P., Vigreux, C., Sichel, F., Poul, J.M., Gauduchon, P., Early detection of staurosporine-induced apoptosis by comet and annexin V assays,Histochem. Cell Biol. 112 (1999), 55–161.
28. [28] Callagy, G.M., Webber, M.J., Pharoah, P.D., Caldas, C., Meta-analysis confirms Bcl2 is an independent prognostic marker in breast cancer. BMC Cancer 8 (2008), 153–163.
29. [29] Smalley, K.S., Understanding melanoma signaling networks as the basis for molecular targeted therapy. J. Invest. Dermatol. 130 (2010), 28–37.
30. [30] Langhasova, L., Hanusova, V., Rezek, J., Stohanslova, B., Ambroz, M., Kralova, V., Vanek, T., Lou, J.D., Yun, Z.L., Yang, J., J., Essential oil from Myricarubra leaves inhibits cancer cell proliferation and induces apoptosis in several human intestinal lines. Ind. Crop Prod. 59 (2014), 20–26.
31. [31] Russo, A., Espinoza C., L., Caggia, S., Garbarino, J.A., Pena-Cortes, H., Carvajal, M., Cardile, V., A new jasmonic acid stereoisomeric derivative induces apoptosis via reactive oxygen species in human prostate cancer cells. Cancer Lett. 326 (2012), 199–205.
32. [32] Clark, R., Lee, S.H., Anticancer properties of Capsaicin against human cancer. Anticancer Res. 36 (2016), 837–843.
33. [33] Kumar, G., Mittal, S., Sak, K., Tuli, H.S., Molecular mechanisms underlying chemopreventive potential of curcumin: Current challenges and future perspectives. Life Sci. 148 (2016), 313–328.
34. [34] Singab, A.N., El-Hefnawy, H.M., Esmat, A., Gad, H.A., Nazeam, J.A., A systemic review on aloe arborescens pharmacological profile: biological activities and pilot clinical trials. Phytother. Res. 29 (2015), 1858–1867.
35. [35] Piovano, M., Garbarino, J.A., Giannini, F.A., Correché, E.R., Feresin, G., Tapia, A., Zacchino, S., Enriz, R.D., Evaluation of antifungal and antibacterial activities of aromatic metabolites from lichens. Bol. Soc. Chil. Quim. 47 (2002), 235–240.
36. [36] Talapatra, S.K., Rath, O., Clayton, E., Tomasi, S., Kozielski, F., Depsidones from lichens as natural product inhibitors of m-phase phosphoprotein 1, a human Kinesin required for Cytokinesis. J. Nat. Prod. 79 (2016), 1576–1585.
37. [37] Johnstone, R.W., Ruefli, A.A., Lowe, S.W., Apoptosis: a link between cancer genetics and chemotherapy. Cell 108 (2002), 153–164.
38. [38] Aggarwal, B.B., Shishodia, S., Molecular targets of dietary agents for prevention and therapy of cancer. Biochem. Pharmacol. 71 (2006), 1397–1421.
39. [39] Callagy, G.M., Webber, M.J., Pharoah, P.D., Caldas, C., Meta-analysis confirms Bcl2 is an independent prognostic marker in breast cancer. BMC Cancer, 8, 2008, 153.
40. [40] Zhang, Y.B., Ye, Y.P., Wu, X.D., Sun, X.S., A stilbotriterpenic acid induces growth arrest and apoptosis in HeLa cells through mitochondria-related pathways and reactive oxygen species (ROS) production. Chem. Biodivers. 6 (2009), 218–230.
41. [41] Nguyen, D.M., Hussain, M., The role of the mitochondria in mediating cytotoxicity of anti-cancer therapies. J. Bioenerg. Biomembr. 39 (2007), 13–21.
42. [42] Su, Y.T., Chang, H.L., Shyue, S.K., Hsu, S.L., Emodin induces apoptosis in human lung adenocarcinoma cells through a reactive oxygen species-dependent mitochondrial signaling pathway. Biochem. Pharmacol. 70 (2005), 229–241.
43. [43] Fujisawa, S., Atsumi, T., Kadoma, Y., Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity. Toxicol 177 (2002), 39–54.
44. [44] Loo, G., Redox-sensitive mechanisms of phytochemical-mediated inhibition of cancer cell proliferation. J. Nutr. Biochem. 14 (2003), 64–73.
45. [45] Atsumi, T., Fujisawa, S., Tonosaki, K., Relationship between intracellular ROS production and membrane mobility in curcumin- and tetrahydrocurcumin-treated human gingival fibroblasts and human submandibular gland carcinoma cells. Oral Dis. 11 (2005), 236–242.
46. [46] Garrido, C., Brunet, M., Didelot, C., Zemati, Y., Schimitt, E., Kroemer, G., Heat shock proteins 27 and 70 anti-apoptotic proteins with tumorigenic properties. Cell Cycle 5 (2006), 2592–2601.
47. [47] Nagai, N., Nakai, A., Nagata, K., Quercetin suppresses heat shock response by down regulation of HSF1. Biochem. Biophys. Res. Commun. 208 (1995), 1099–1105.