Leaf micromorphology, antioxidative activity and a new record of 3-deoxyamphoricarpolide of relict and limestone endemic Amphoricarpos elegans Albov (Compositae) from Georgia

Authors

  • Milan Gavrilović University of Belgrade, Faculty of Biology, Institute of Botany and Botanical Garden “Jevremovac”, Studentski trg 16, 11 000 Belgrade http://orcid.org/0000-0002-1325-9658
  • Vele Tešević University of Belgrade, Faculty of Chemistry, Studentski trg 12-16, 11000 Belgrade http://orcid.org/0000-0001-7060-9055
  • Iris Đorđević University of Belgrade, Faculty of Veterinary Medicine, Bulevar oslobođenja 18, 11000 Belgrade
  • Nemanja Rajčević University of Belgrade, Faculty of Biology, Institute of Botany and Botanical Garden “Jevremovac”, Studentski trg 16, 11 000 Belgrade http://orcid.org/0000-0003-2260-1205
  • Arsena Bakhia Ilia State University, School of Natural Sciences and Engineering, Cholokashvili Avenue 3/5, 0160 Tbilisi
  • Núria Garcia Jacas Botanic Institute of Barcelona (IBB,CSIC-ICUB), Pg. del Migdia s. n., 08038 Barcelona http://orcid.org/0000-0003-1893-5122
  • Alfonso Susanna Botanic Institute of Barcelona (IBB,CSIC-ICUB), Pg. del Migdia s. n., 08038 Barcelona http://orcid.org/0000-0003-4717-9063
  • Petar D. Marin University of Belgrade, Faculty of Biology, Institute of Botany and Botanical Garden “Jevremovac”, Studentski trg 16, 11 000 Belgrade http://orcid.org/0000-0002-9460-1012
  • Peđa Janaćković University of Belgrade, Faculty of Biology, Institute of Botany and Botanical Garden “Jevremovac”, Studentski trg 16, 11 000 Belgrade

Keywords:

Amphoricarpos elegans, glandular trichomes, 3-deoxyamphoricarpolide, antioxidative activity

Abstract

Paper description:

  • This is a first report on the micromorphology and phytochemical and biological activity investigations of the rare and stenoendemic Amphoricarpos elegans Albov (Compositae) from Georgia.
  • We detected the presence of glandular trichomes on leaves, we identified and characterized 3-deoxyamphoricarpolide, a known sesquiterpene lactone for this genus, and we examined the antioxidative activity of leaf extracts obtained using a Soxhlet apparatus.
  • With regard to the chemotaxonomic significance of amphoricarpolides, this compound represents a link between Balkan and Caucasian species of the same genus. The considerable antioxidative potential points to its possible pharmacological and medical applications.

Abstract: We examined for the first time the leaf micromorphology, phytochemistry and biological activity of the rare and stenoendemic Amphoricarpos elegans Albov (Compositae) from Georgia. Scanning electron microscopy (SEM) revealed the presence of glandular trichomes on the leaves, which appeared as glandular dots that are considered the main sites of biosynthesis and accumulation of sesquiterpene lactones. Using high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy analyses, we identify and characterized 3-deoxyamphoricarpolide, a known sesquiterpene lactone for the genus Amphoricarpos Vis. Regarding chemotaxonomic significance, 3-deoxyamphoricarpolide represents a link between Balkan and Caucasian species of the genus. The antioxidative capacity of different leaf extracts, obtained using a Soxhlet extractor, was evaluated by two radical scavenging assays: DPPH (1,1-diphenyl-2-picrylhydrazyl) radical and the 2,2′-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid (ABTS), and ferric ion reducing antioxidant power (FRAP). The total phenolic and flavonoid contents were also determined. The highest antioxidative activity and the highest phenolic and flavonoid contents were detected in the methanol fraction, as a result of the contribution of not only phenols, but probably also lactones. The considerable antioxidative potential indicates possible applications in pharmacy and medicine.

https://doi.org/10.2298/ABS180309022G

Received: March 9, 2018; Revised: May 5, 2018; Accepted: May 14, 2018; Published online: June 4, 2018

How to cite this article: Gavrilović M, Tešević V, Đorđević I, Rajčević N, Bakhia A, Garcia Jacas N, Susanna A, Marin PD, Janaćković P. Leaf micromorphology, antioxidative activity and a new record of 3-deoxyamphoricarpolide of relict and limestone endemic Amphoricarpos elegans Albov (compositae) from Georgia. Arch Biol Sci. 2018;70(4):613-20.

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References

Anderberg AA, Baldwin BG, Bayer RG, Breitwieser J, Jeffrey C, Dillon MO, Eldenäs P, Funk V, Garcia-Jacas N, Hind DJN, Karis PO, Lack HW, Nesom G, Nordenstam B, Oberprieler Ch, Panero JL, Puttock C, Robinson H, Stuessy TF, Susanna A, Urtubey E, Vogt R, Ward J., Watson LE. Compositae. In: Kubitzki K, editor. The families and genera of vascular plants. Vol. 8. Springer-Verlag Berlin Heidelberg; 2007. p. 61-588.

Robinson H. An introduction to micro-characters of Compositae. In: Funk VA, Susanna A, Stuessy TF, Bayer RJ, editors. Systematics, Evolution and Biogeography of Compositae. Vienna (Austria): IAPT; 2009. p. 89-100.

Taleb-Contini HS, Schorr K, Da Costa BF, Camilo D, de Oliveira R. Detection of flavonoids in glandular trichomes of Chromolaena species (Eupatorieae, Asteraceae) by reversed-phase high-performance liquid chromatography. Braz J Pharm Sci. 2007;43:2.

Fritz E. and Saukel J. Anatomy of subterranean organs of medicinally used Cardueae and related species and its value for discrimination. Sci Pharm. 2011;79:157-74.

Farrag NM, Abd El Aziz EM, El-Domiaty MM, El Shafea AM. Phytochemical investigation of Centaurea araneosa growing in Egypt. J Pharm Sci. 1993;2:29-45.

Font Quer P. Plantas Medicinales: El Dioscórides Renovado. 15th ed. Madrid: Labor; 1995. 1033 p.

Barrero AF, Herrador MM, Arteaga P, Cabrera E, Rodríguez-García I, García-Moreno M, Grávalos DG. Cytotoxic activity of flavonoids from Carthamus arborescens, Ononis natrix ssp. ramosissima and Centaurea malacitana. Fitoterapia. 1997;68:281-3.

Baba Aissa F. Flore d’Algérie et du Maghreb. Substances végétales d’Afrique, d’orient et d’occident. Encyclopédie des plantes utiles. Rouiba (Algeria): EDAS, Librairie moderne; 1999.

Vallejo JR, Pardo de Santayana M, Peral D, Carrasco MC, López D. Uso medicinal de Atractylis gummifera L. en Guadiana del Caudillo (Badajoz, Espana). Toxicidad y especies afines. Rev Fitoterapia. 2008;8:161-9.

Vallejo JR, Peral D, Gemio P, Carrasco MC, Heinrich M, Pardo de Santayana M. Atractylis gummifera and Centaurea ornata in the Province of Badajoz (Extremadura, Spain). Ethnopharmacological importance and toxicological risk. J Ethnopharmacol. 2009;126:366-70.

Gavrilović M, Soković MD, Stanković M, Marin PD, Stevanović ZD, Janaćković P. Antimicrobial and antioxidative activity of various leaf extracts of Amphoricarpos Vis. (Asteraceae) taxa. Arch Biol Sci. 2016;68:803-10.

Sokovic M, Ciric A, Glamoclija J, Skaltsa H. Biological activities of sesquiterpene lactones isolated from the genus Centaurea L. (Asteraceae). Curr Pharm Design. 2017;23:2767-86.

Milosavljević S, Bulatović V, Stefanović M. Sesquiterpene lactones from the Yugoslavian wild growing plant families Asteraceae and Apiaceae. J Serb Chem Soc. 1999;64:397-442.

Atrrog BAA, Natic M, Tosti T, Opsenica Milojković D, Djordjević I, Tešević V, Jadranin M, Milosavljević S, Lazić M, Radulović S, Tešić Z. Lipophilicity of some guaianolides isolated from two endemic subspecies of Amphoricarpos neumayeri (Asteraceae) from Montenegro. Biomed Chromatogr. 2008;23:250-6.

Repetto MG, Llesuy S. Antioxidant properties of natural compounds used in popular medicine for gastric ulcers. Braz J Med Biol Res. 2002;35:523-34.

Da Costa F, Terfloth L, Gasteiger J. Sesquiterpene lactone-based classification of three Asteraceae tribes: a study based on self-organizing neural networks applied to chemosystematics. Phytochemistry. 2005;66:345-53.

Repetto MG, Boveris A. Bioactivity of sesquiterpenes: compounds that protect from alcohol-induced gastric mucosal lesions and oxidative damage. Mini Rev Med Chem. 2010;10:615-23.

Susanna A, Garcia-Jacas N. Cardueae (Carduoideae). In: Funk VA, Susanna A, Stuessy TF, Bayer RJ, editors. Systematics, Evolution and Biogeography of Compositae. Vienna (Austria): IAPT; 2009. p. 293-313.

Susanna A, Garcia-Jacas N. Tribe Cardueae Cass. (1819). In: Kubitzki K, editor. The Families and Genera of Vascular Plants. VIII Flowering Plants-Eudicots. Springer-Verlag Berlin Heidelberg; 2007. p. 123-46.

Barres L, Sanmartín I, Anderson CL, Susanna A, Buerki S, Galbany‐Casals M, Vilatersana R. Reconstructing the evolution and biogeographic history of tribe Cardueae (Compositae). Am J Bot. 2013;100:867-82.

Shetekauri S, Kutateladze L. Diversity, ecotopology and hypsometric distribution of the endemic flora in high-mountain phytolandscapes of the Caucasus. Earth. 2017;6:38-48.

Akhalkatsi M, Ekhvaia J, Asanidze Z. Diversity and genetic erosion of ancient crops and wild relatives of agricultural cultivars for food: implications for nature conservation in Georgia (Caucasus). In: Tiefenbacher J, editor. Perspectives on Nature Conservation-Patterns, Pressures and Prospects. Rijeka, Croatia: InTech; 2012. p. 51-92.

Nakhutsrishvili G. The vegetation of Georgia (Caucasus). Camerino: Dipartimento di Botanica ed Ecologia dell' Univ; 1999. p. 74. (Braun-Blanquetia; Vol. 15).

Schatz G, Shulkina T, Nakhutsrishvili G, Batsatsashvili K, Tamanyan K, Ali-zade V, Kikodze D, Geltman D, Ekim T. Development of Plant Red List Assessments for the Caucasus Biodiversity Hotspot. In: Zazanashvili N, Mallon D, editors. Status and Protection of Globally Threatened Species in the Caucasus. Tbilisi: CEPF, WWF. Contour Ltd; 2009. p. 188-92.

Linczevsky IA. Compositae Tribes Echinopsideae and Cynareae. In: Schischkin BK, Bobrov FG, editors. Flora of the USSR. Vol. 27. Moscow, Leningrad: Akademiya Nauk SSSR; 1962. p. 74-9.

Djordjević I, Vajs V, Bulatović V, Menković N, Tešević V, Macura S, Janaćković P, Milosavljević S. Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro. Phytochemistry. 2004;65:2337-45.

Djordjević I, Jadranin M, Vajs V, Menković N, Tešević V, Macura S, Milosavljević S. Further Guaianolides from Amphoricarpos neumayeris ssp. murbeckii from Montenegro. Z Naturforsch. 2006;61b:1437-42.

Cvetković M, Ðorđević I, Jadranin M, Vajs V, Vučković I, Menković N, Milosavljevic S, Tešević V. Further Amphoricarpolides from the surface extracts of Amphoricarpos Complex from Montenegro. Chem Biodivers. 2014;11:1428-37.

Jadranin M, Djordjević I, Tešević V, Vajs V, Menković N, Soković M, Glamočlija J, Milosavljević S. Sesquiterpene Lactones of Amphoricarpos autariatus ssp. autariatus from Montenegro - Antifungal Leaf - Surface Constituents. Rec Nat Prod. 2013;7:234-8.

Petit DP. Generic interrelationships of the Cardueae (Compositae): A cladistic analysis of morphological data. Plant Syst Evol. 1997;207:173-203.

Caković D, Stešević D, Schönswetter P, Frajman B. How many taxa? Spatiotemporal evolution and taxonomy of Amphoricarpos (Asteraceae, Carduoideae) on the Balkan Peninsula. Org Divers Evol. 2015;15:429-45.

Singleton VL, Orthofer R, Lamuela-Raventós RM. Analysis of total phenols and other oxidation substrates and antioxidants by means of Folin-Ciocalteu reagent oxidants and antioxidants. Method Enzymol. 1999;299:152-78.

Matejić J, Džamić A, Mihajilov-Krstev T, Ranđelović V, Krivošej Z, Marin P. Total phenolic content, flavonoid concentration, antioxidant and antimicrobial activity of methanol extracts from three Seseli L. taxa. Cent Eur J Biol. 2012;7:1116-22.

Tekao T, Watanabe N, Yagi I, Sakata K. A simple screening method for antioxidant and isolation of several antioxidants produced by marine Bacteria from fish and shellfish. Biosci Biotechnol Biochem. 1994;58:1780-3.

Kumarasamy Y, Byres M, Cox PJ, Jasapars M, Nahar L, Sarker SD. Screening seeds of some scottish plants for free radical scavenging activity. Phytother Res. 2007;21:615-21.

Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Bio Med. 1999;26:1231-7.

Li HB, Wong CC, Cheng KW, Chen F. Antioxidant properties in vitro and total phenolic contents in methanol extracts from medicinal plants. Lebensm-Wiss Technol. 2008;41:385-90.

Hammer Ø, Harper DAT, Ryan PD. PAST: paleontological statistics software package for education and data analysis. Palaeontol Electronica. 2001;4:1-9.

Milan P, Hayashi AH, Appezzato-da-Glória B. Comparative leaf morphology and anatomy of three Asteraceae species. Braz Arch Biol Techn. 2006;49:135-44.

Duarte MR, Budel JM, Matzenbacher NI. Menarim DO. Microscopic diagnosis of the leaf and stem of Lucilia nitens Less., Asteraceae. Lat Am J Pharm. 2011;30:2070-5.

Camilotti JG, Biu CC, Farago PV, Santos VLPD, Franco CRC, Budel JM. Anatomical characters of leave and stem of Calea serrata Less., Asteraceae. Braz Arch Biol Techn. 2014;57:867-73.

Bartoli A, Galati BG, Tortosa RD. Anatomical studies of the secretory structures: glandular trichomes and ducts, in Grindelia pulchella Dunal (Astereae, Asteraceae). Flora. 2011;206:1063-8.

Spring O, Benz T, Ilg M. Sesquiterpene lactones of the capitate glandular trichomes of Helianthus annuus. Phytochemistry. 1989;28:745-9.

Spring O. Trichome microsampling of sesquiterpene lactones for the use of systematic studies. Recent Adv Phytochem. 1991;25:319-45.

Spring O, Zipper R, Reeb S, Vogler B, Da Costa FB. Sesquiterpene lactones and a myoinositol from glandular trichomes of Viguiera quinqueremis (Heliantheae; Asteraceae). Phytochemistry. 2001;57:267-72.

Sakamoto HT, Gobbo-Neto L, Cavalheiro AJ, Lopes NP, Lopes JLC. Quantitative HPLC analysis of sesquiterpene lactones and determination of chemotypes in Eremanthus seidelii MacLeish & Schumacher (Asteraceae). J Brazil Chem Soc. 2005;16:1396-401

Appezzato-da-Glória B, Da Costa FB, Silva VC, Gobbo-Neto L, Rehder VLG, Hayashi AH. Glandular trichomes on aerial and underground organs in Chrysolaena species (Vernonieae - Asteraceae): structure, ultrastructure and chemical composition. Flora. 2012;207:878-87

Lusa MG, Da Costa FB, Appezzato-da-Glória B. Histolocalization of chemotaxonomic markers in Brazilian Vernonieae (Asteraceae). Bot J Linn Soc. 2016;182:581-93.

Raola VK and Chakraborty K. Biogenic guaianolide-type sesquiterpene lactones with antioxidative and anti-inflammatory properties from natural mangrove hybrid Rhizophora annamalayana. Nat Prod Res. 2017;31:2719-29.

Chaturvedi, D. Sesquiterpene lactones: structural diversity and their biological activities. In: Tiwari VK, Mishra BB, editors. Opportunity, Challanges and Scope of Natural Products in Medicinal Chemistry. Trivandrum: Research Signpost; 2011. p. 313-34.

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Published

2018-12-04

How to Cite

1.
Gavrilović M, Tešević V, Đorđević I, Rajčević N, Bakhia A, Garcia Jacas N, Susanna A, Marin PD, Janaćković P. Leaf micromorphology, antioxidative activity and a new record of 3-deoxyamphoricarpolide of relict and limestone endemic Amphoricarpos elegans Albov (Compositae) from Georgia. Arch Biol Sci [Internet]. 2018Dec.4 [cited 2024Nov.24];70(4):613-20. Available from: https://serbiosoc.org.rs/arch/index.php/abs/article/view/2749

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Vol. 70 No. 4 (2018)

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