Chemical composition and biological activities of „Umbilicaria crustulosa“ and „Umbilicaria cylindrica“ extracts

Chemia Naissensis Volume 2, No.2 (2019) (стр. 30-45) 

АУТОР(И) / AUTHOR(S): Zlatanović Ivana, Stojanović Gordana

Е-АДРЕСА / E-MAIL: ivana.zlatanovic@pmf.edu.rs

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DOI: 10.46793/ChemN2.2.030Z

САЖЕТАК / ABSTRACT:

The main compounds of acetone, methanol, ether and ethyl acetate extracts of Umbilicaria crustulosa are tridepsides, gyrophoric acid and crustinic acid, and didepside, lecanoric acid. Chemical composition of Umbilicaria cylindrica extracts depends on the solvent used for the extraction and the major components are depsidones, salazinic acid and norstictic acid or depsides, gyrophoric acid and atranorin. Extracts of U. crustulosa and U. cylindrica have shown antibacterial, antioxidant, cytotoxic, antiproliferative and anticlastogenic activity. Acetone extracts of U. crustulosa and U. cylindrica are promising candidates for in vivo experiments considering antioxidant and anticlastogenic activity.

КЉУЧНЕ РЕЧИ / KEYWORDS:

Umbilicaria crustulosa, Umbilicaria cylindrica, antioxidant activity, antimicrobial activity, cytotoxic activity, micronucleus test, cholinesterase inhibition

ЛИТЕРАТУРА / REFERENCES:

  • Bezivin, C., Tomasi, S., Rouaud, I., Delcros, J. G., & Boustie, J. (2004). Cytotoxic activity of compounds from the lichen: Cladonia convoluta. Planta Medica, 70, 874-877.
  • Buçukoglu, Z.T., Albayrak, S., Halici, G., & Tay, Y. (2013). Antimicrobial and antioxidant activities of extracts and lichen acids obtained from some Umbilicaria species from central Anatolia Turkey. Journal of Food Processing and Preservation, 37, 1103-1110.
  • Culberson, W.L. (1969). The use of chemistry in the systematics of the lichens. Taxon, 18, 152 – 166.
  • Correché, E., Carrasco, M., Giannini, F., Piovano, M., Garbarino, J., & Enriz, D. (2002). Cytotoxic screening activity of secondary lichen metabolites. Acta Farmaceutica Bonaerense, 21, 273-278.
  • Candan, M., Yilmaz, M., Tay, T., Kivanç, M., & Turk, H. (2006). Antimicrobial activity of extracts of the lichen Xanthoparmelia pokornyi and its Gyrophoric and Stenosporic acid constituents. Zeitschrift für Naturforschung. Section C: Journal of Biosciences, 61, 319-323.
  • Fenech, M., & Morley, A. A. (1993). The cytokinesis-block micronucleus technique: a detailed description of the method and its application to genotoxicity studies in human populations. Mutatation Research, 285, 35–44.
  • Frey, E. (1997). Die geographische Verbreitung der Umbilicariaceen und einiger alpiner Flechten. Berichte der Deutschen Botanischen Gesellschaft, 46, 412–444.
  • Giacobini, E. (2004). Drugs that target cholinesterase, In J.J. Buccafusco (Ed.), Cognitive Enhancing Drugs (pp. 11). Basel: Springer.
  • Hidalgo, M. E., Fernandez, E., Quilhot, W., & Lissi, E. (1994). Antioxidant activity of depsides and depsidones. Phytochemistry, 37, 6, 1585-1587.
  • Huneck, S., & Yoshimura, I. (1996). Identification of Lichen Substances. Springer-Verlag.
  • Lawrey, J. (1989). Lichen Secondary Compounds: Evidence for a Correspondence Between Antiherbivore and Antimicrobial Function. Bryologist, 92, 326–328.
  • Kupchan, S. M., & Kopperman, H. L. (1975). L-usnic acid: tumor inhibitor isolated from lichens. Experientia, 31, 6, 625.
  • Kumar, S., & Müller, K. (1999a). Lichen Metabolites. 1. Inhibitory Action Against Leukotriene B4 Biosynthesis by a Non-Redox Mechanism. Journal of Natural Products, 62, 817-820.
  • Kumar, S., & Müller, K. (1999b). Lichen Metabolites. 2. Antiproliferative and cytotoxic activity of gyrophoric, usnic, and diffractaic acid on human keratinocyte growth. Journal of Natural Products, 62, 821-823.
  • Kosanić, M., Šeklić, S., Marković, M., & Ranković, B. (2014). Evaluation of antioxidant, antimicrobial and anticancer properties of selected lichens from Serbia. Digest Journal of Nanomaterial and biostructures, 9 (1), 273-287.
  • Molnar, K., & Farkas, E. (2010). Current Results on Biological Activities of Lichen Secondary Metabolites: a Review. Zeitschrift für Naturforschung. Section C: Journal of Biosciences, 65, 157-173.
  • Manojlović, N., Vasiljević, P., Masković, P. Z., Jusković, M., & Bogdanović-Dusanović, G. (2012). Chemical composition, antioxidant, and antimicrobial ctivities of lichen Umbilicaria cylindrica (L.) Delise (Umbilicariaceae). Evidence-based Complementary and Alternative Medicine, 2012, 1-8.
  • Posner, B., Feige, G. B., & Huneck, S. (1992). Studies on the Chemistry of the Lichen Genus Umbilicaria Hoffm. Zeitschrift für Naturforschung. Section C: Journal of Biosciences, 47, 1 – 9.
  • Rojas, I., Lotina-Hennsen, B., & Mata, R. (2000). Effect of Lichen Metabolites on Thylakoid Electron Transport and Photophosphorylation in Isolated Spinach Chloroplasts 1. Journal of Natural Products, 63 (10), 1396-1399.
  • Ranković, B. Misic, M., & Sukdolak, S. (2009). The antimicrobial activity of substances derived from the lichens Physcia aipolia, Umbilicaria polyphylla, Parmelia caperata and Hypogimnia physodes. Byologia, 64 (1), 53-58.
  • Serina, E., & Arroyo, R. (1996). Lichen Substances and Their Intraspecifie Variability within Eleven Umbilicaria Species in Spain. Bryologist, 99, 335–342.
  • Stojanović, G., Stojanović, I., & Šmelcerović, A. (2012). Lichen Depsidones as Potential Novel Pharmacologically Active Compounds. Mini-reviews in Organic Chemistry, 9 (2), 1-7.
  • Stojanović, G., Stanković, M., Stojanović, I., Palić, I., Milovanović V., & Rančić, S. (2014). Clastogenic Effect of Atranorin, Evernic acid, and Usnic Acid on Human Lymphocytes. Natural product communication, 9 (4), 503-504.
  • Turk, H., Yilmaz, M., Tay, T., Turk, A.O., & Kivanc, M. (2006). Antimicrobial Activity of Extracts of Chemical Races of the Lichen Pseudevernia furfuracea and their Physodic Acid, Chloroatranorin, Atranorin and Olivetoric Acid Constituents. Zeitschrift für Naturforschung. Section C: Journal of Biosciences, 65, 499-507.
  • Zlatanović, I., Petrović, G., Jovanović, O., Zrnzević. I., & Stojanović, G. (2016). Isolation and identification of secondary metabolites of Umbilicaria crustulosa (Ach.) Frey. Facta Universitatis, Series Physics, Chemistry and Technology, 14 (2), 125-133.
  • Zlatanović, I., Stanković, M., Stankov-Jovanović, V., Mitić, V., Zrnzević. I., Djordjević, A., & Stojanović, G. (2017a). Biological activities of Umbilicaria crustulosa (Ach.) Frey acetone extract. Journal of Serbian Chemical Society, 82, 141-150.
  • Zlatanović, I., Zrnzević. I., Jovanović, O., Stojanović, I., Petrović, G., & Stojanović, G. (2017b). Chemical composition of Umbilicaria crustulosa (Ach.) Frey and Umbilicaria cylindrica (L.) Duby extracts. Natural Product Communication, 2017, 12 (7), 1105-1105.
  • Zlatanović, I., (2019). Chemical composition, antibacterial, antioxidant and genotoxic activity of lichens Umbilicaria crustulosa (Аch.) Frey, Umbilicaria cylindrica (L.) Delise, Hypogymnia tubulosa (Schaer.) Hav. and Evernia prunastri (L.) Ach. Doctoral dissertation, Faculty of sciences and mathematics, Niš: University of Niš.