Fol. Biol. 2014, 60, 89-94

https://doi.org/10.14712/fb2014060020089

Effects of Depsidones from Hypogymnia physodes on HeLa Cell Viability and Growth

I. Ž. Stojanović1, S. Najman2, O. Jovanović3, G. Petrović3, J. Najdanović2, P. Vasiljević4, Andrija Šmelcerović1

1Department of Pharmacy, Faculty of Science and Mathematics, University of Nis, Nis, Serbia
2Institute of Biology and Human Genetics, Faculty of Medicine, University of Nis, Nis, Serbia
3Department of Chemistry, Faculty of Science and Mathematics, University of Nis, Nis, Serbia
4Department of Biology and Ecology, Faculty of Science and Mathematics, University of Nis, Nis, Serbia

Received November 2013
Accepted February 2014

References

1. Abdou, R., Scherlach, K., Dahse, M. H., Sattler, I., Hertweck, C. (2010) Botryorhodines A–D, antifungal and cytotoxic depsidones from Botryosphaeria rhodina; an endophyte of the medicinal plant Bidens pilosa. Phytochemistry 71, 110-116. <https://doi.org/10.1016/j.phytochem.2009.09.024>
2. Bačkorová, M., Bačkor, M., Mikeš, J., Jendželovský, R., Fe- doročko, P. (2011) Variable responses of different human cancer cells to the lichen compounds parietin, atranorin, usnic acid and gyrophoric acid. Toxicol. In Vitro 25, 37-44. <https://doi.org/10.1016/j.tiv.2010.09.004>
3. Correche, R. E., Carrasco, M. (2002) Cytotoxic screening activity of secondary lichen metabolites. ActaFarm. Bonaerense 21, 273-278.
4. Guo, P., Zhao, P., Liu, J., Ma, H., Bai, J., Cao, Y., Liu, Y., He, H., Qi, C. (2013) Preparation of a novel organoselenium compound and its anticancer effects on cervical cancer cell line HeLa. Biol. Trace Elem. Res. 151, 301-306. <https://doi.org/10.1007/s12011-012-9563-x>
5. Haralsdottir, S., Guolaugsdottir, E., Ingolfsdottir, K., Ogmundsdóttir, M. H. (2004) Anti-proliferative effects of lichen-derived lipoxygenase inhibitors on twelve human cancer cell lines of different tissue origin in vitro. Planta Med. 70, 1098-1110. <https://doi.org/10.1055/s-2004-832657>
6. Ito, C., Itougawa, M., Mishina, Y., Tomiyasu, H., Litaudon, M., Cosson, P. J., Mukainaka, T., Tokuda, H., Nishino, H., Furukawa, H. (2001) Cancer chemoprotective agents. New depsidones from Garcinia plants. J. Nat. Prod. 64, 147-150. <https://doi.org/10.1021/np000333+>
7. Jones, J. A., Elix, A. J., Engkaninan, U. (1976) The structure of the lichen depsidone hydroxyphysodic acid. A carbon-13 magnetic resonance study. Aust. J. Chem. 29, 1947-1954. <https://doi.org/10.1071/CH9761947>
8. Khumkomkhet, P., Kanokmedhakul, S., Kanokmedhakul, K., Hahnvajanawong, C., Soytong K. (2009) Antimalarial and cytotoxic depsidones from the fungus Chaetomium brasiliense. J. Nat. Prod. 72, 1487-1491. <https://doi.org/10.1021/np9003189>
9. Legaz, E. M., de Armas, R., Vicente, C. (2011) Bioproduction of depsidones for pharmaceutical purposes. In: Drug Development – a Case Study Based Insight into Modern Strategies, Ed. Rundfeld, C., pp. 487-508, InTech, Rijeka, Croatia.
10. Liu, M. R., Li, B. Y., Zhong, J. J. (2012) Cytotoxic and pro- apoptotic effects of novel ganoderic acid derivatives on human cervical cancer cells in vitro. Eur. J. Pharmacol. 681, 23-33. <https://doi.org/10.1016/j.ejphar.2012.02.007>
11. Lukač, M., Onderka, M. (2006) Application of DDQ (2,3-dichloro-5,6-dicyano-benzoquinone) in detection of lichen acids. Acta Fac. Pharm. Univ. Comen. 53, 160-166.
12. Micheletti, C. A., Beatriz, A., Pires de Lima, D., Honda, K. N., Pessoa, C., Odorico de Moraes, M., Lotufo, V. L., Magalhães, I. F. H., Carvalho, C. P. N. (2009) Chemical constituents of Parmotrema lichexanthonicum Eliasaro & Adler – isolation, structure modification and evaluation of antibiotic and cytotoxic activities. Quim. Nova 32, 12-20. <https://doi.org/10.1590/S0100-40422009000100003>
13. Millot, M., Tomasi, S., Articus, K., Rouaud, I., Bernard, A., Boustie, J. (2007) Metabolites from the lichen Ochrolechia parella growing under two different heliotropic conditions. J. Nat. Prod. 70, 316-318. <https://doi.org/10.1021/np060561p>
14. Millot, M., Tomasi, S., Studzinska, E., Rouaud, I., Boustie, J. (2009) Cytotoxic constituents of the lichen Diploicia canescens. J. Nat. Prod. 72, 2177-2180. <https://doi.org/10.1021/np9003728>
15. Mitrović, T., Stamenković, S., Cvetković, V., Tošić, S., Stanković, M., Radojević, I., Stefanović, O., Comić, L., Dačić, D., Curčić, M., Marković, S. (2011) Antioxidant, antimicrobial and antiproliferative activities of five lichen species. Int. J. Mol. Sci. 12, 5428-5448. <https://doi.org/10.3390/ijms12085428>
16. Neamati, N., Hong, H., Mazumder, A., Wang, S., Sunder, S., Nicklaus, C. M., Milne, W. G., Proksa, B., Pommier, Y. (1997) Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching. J. Med. Chem. 40, 942-951. <https://doi.org/10.1021/jm960759e>
17. Ogmundsdottir, M. H., Zoega, M. G., Gissurarson, R. S., Ingolfsdottir, K. (1998) Anti-proliferative effects of lichen- derived inhibitors of 5-lipoxygenase on malignant cell lines and mitogen­stimulated lymphocytes. J. Pharm. Pharmacol. 50, 107-115. <https://doi.org/10.1111/j.2042-7158.1998.tb03312.x>
18. Pavlovic, V., Stojanovic, I., Jadranin, M., Vajs, V., Djordjević, I., Smelcerovic, A., Stojanovic, G. (2013) Effect of four lichen acids isolated from Hypogymnia physodes on viability of rat thymocytes. Food Chem. Toxicol. 51, 160-164. <https://doi.org/10.1016/j.fct.2012.04.043>
19. Permana, D., Lajis, H. N., Mackeen, M. M., Ali, M. A., Aimi, N., Kitajima, M., Takayama, H. (2001) Isolation and bioactivities of constituents of the roots of Garcinia atroviridis. J. Nat. Prod. 64, 976-979. <https://doi.org/10.1021/np000563o>
20. Permana, D., Abas, F., Maulidiani, S., Shaari, K., Stanslas, J., Ali, M. A., Lajis, H. N. (2005) Atrovirisidone B, a new prenylated depsidone with cytotoxic property from the roots of Garcinia atroviridis. Z. Naturforsch. C. 60, 523-526. <https://doi.org/10.1515/znc-2005-7-802>
21. Russo, A., Piovano, M., Lombardo, L., Vanella, L., Cardile, V., Garbarino, J. (2006) Pannarin inhibits cell growth and induces cell death in human prostate carcinoma DU-145 cells. Anticancer Drugs 17, 1163-1169. <https://doi.org/10.1097/01.cad.0000236310.66080.ed>
22. Russo, A., Piovano, M., Lombardo, L., Vanella, L., Cardile, V. (2008) Lichen metabolites prevent UV light and nitric-oxide mediated plasmid DNA damage and induce apoptosis in human melanoma cells. Life Sci. 83, 468-474. <https://doi.org/10.1016/j.lfs.2008.07.012>
23. Stojanović, G., Stojanović, I., Šmelcerović, A. (2012) Lichen depsidones as potential novel pharmacologically active compounds. Mini. Rev. Org. Chem. 9, 178-184. <https://doi.org/10.2174/157019312800604689>
24. Stojanović, Ž. I., Stanković, M., Jovanović, O., Petrović, G., Šmelcerović, A., Stojanović, S. G. (2013) Effect of Hypogymnia physodes extracts and their depsidones on micronucleus distribution in human lymphocytes. Nat. Prod. Commun. 8, 109-113.
25. Tay, T., Türk, O. A., Yılmaz, M., Türka, H., Kıvan, M. (2004) Evaluation of the antimicrobial activity of the acetone extract of the lichen Ramalina farinacea and its (+)usnic acid, norstictic acid, and fumaroprotocetraric acid constituents. Z. Naturforsch. C. 59, 384-388. <https://doi.org/10.1515/znc-2004-5-617>
26. Xu, J. Y., Chiang, Y. P., Lai, H. Y., Vittal, J. J., Wu, H. X., Tan, H. K. B., Imiyabir, Z., Goh, H. S. (2000) Cytotoxic prenylated depsidones from Garcinia parvifolia. J. Nat. Prod. 63, 1361-1363. <https://doi.org/10.1021/np000141e>
27. Yoshimura, I., Kinoshita, Y., Yamamoto, Y., Huneck, S., Yamada, Y. (1994) Analysis of secondary metabolites from lichen by high performance liquid chromatography with a photodiode array detector. Phytochem. Anal. 5, 197-205. <https://doi.org/10.1002/pca.2800050405>
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