Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Chemosystematic evaluation of leaf and flower essential oils of eight Heracleum taxa from Southeastern Europe

  • 39 Accesses

Abstract

The composition of leaf and flower essential oils of eight Heracleum taxa (populations collected in Serbia, Montenegro, North Macedonia and Slovenia) was statistically analyzed to evaluate its chemosystematic significance. Investigated taxa included H. orphanidis and the representatives of H. sphondylium group: H. sphondylium, H. sibiricum, H. montanum, H. ternatum, H. pyrenaicum subsp. pollinianum, H. pyrenaicum subsp. orsinii and H. verticillatum. Hydrodistilled essential oils were analyzed by GC–FID and GC–MS. Chemosystematic significance was evaluated using multivariate statistics: principal component analysis (PCA), non-metric multidimensional scaling (NMDS) and unweighted pair-group arithmetic averages clustering (UPGMA). Statistical analyses included our previously published data on the composition of essential oils of eight leaf and three flower samples, as well as the data on the composition of the oils of additional eight leaf and five flower samples obtained in the current work. Leaf and flower essential oils of H. sphondylium group members were dominated by various sesquiterpenes, phenylpropanoids and/or monoterpenes. Heracleum orphanidis leaf and flower essential oils were rich in aliphatic esters, mostly octyl acetate. Statistical analysis of the composition of leaf essential oils, as well as of flower oils, demonstrated the grouping of investigated populations of these Heracleum taxa according to their systematics, i.e., separation of H. orphanidis from the representatives of H. sphondylium group, and grouping of H. pyrenaicum subspecies within this group. Morphologically related H. sibiricum and H. ternatum were closely located in PCA and NMDS and in UPGMA even shared the same cluster.

This is a preview of subscription content, log in to check access.

Fig. 1
Fig. 2

References

  1. Adams RP (2017) Identification of essential oil components by gas chromatography/mass spectrometry 4, 1st edn. Allured Publishing Corporation, Carol Stream

  2. Assyov B, Petrova A, Dimitrov D, Vassilev R (2012) Conspectus of the Bulgarian vascular flora, 4th edn. Bulgarian Biodiversity Foundation, Sofia

  3. Asuming WA, Beauchamp PS, Descalzo JT, Dev BC, Dev V, Frost S, Ma CW (2005) Essential oil composition of four Lomatium Raf. species and their chemotaxonomy. Biochem Syst Ecol 33:17–26. https://doi.org/10.1016/j.bse.2004.06.005

  4. Bartolucci F, Peruzzi L, Galasso G, Albano A, Alessandrini A, Ardenghi NMG, Astuti G, Bacchetta G, Ballelli S, Banfi E, Barberis G, Bernardo L, Bouvet D, Bovio M, Cecchi L, Di Pietro R, Dominao G, Fascetti S, Fenug G, Festi F, Foggi B, Gallo L, Gottschlich G, Gubellini L, Iamonico D, Iberite M, Jiménez-Mejías P, Lattanzi E, Marchetti D, Martinetto E, Masin RR, Medagli P, Passalacqua NG, Peccenini S, Pennesi R, Pierini B, Poldini L, Prosser F, Raimondo FM, Roma-Marzio F, Rosati L, Santangelo A, Scoppola A, Scortegagna S, Selvaggi A, Selvi F, Soldano A, Stinca A, Wagensommer RP, Wilhalm T, Conti F (2018) An updated checklist of the vascular flora native to Italy. Pl Biosyst 152:179–303. https://doi.org/10.1080/11263504.2017.1419996

  5. Brummitt RK (1968) Heracleum L. In: Tutin TG, Heywood VH, Burges NA, Moore DM, Valentine DH, Walters SM, Webb DA (eds) Flora Europaea, vol. 2. Cambridge University Press, London, pp 364–366

  6. Davis PH (1972) Heracleum L. In: Davis PH (ed) Flora of Turkey and the East Aegean Islands, vol. 4. Edinburgh University Press, Edinburgh, pp 488–500

  7. EDQM (2015a) Rosemary oil, Rosmarini aetheroleum. In: European Pharmacopoeia 9th edn, vol. 1. European Directorate for the Quality of Medicines & HealthCare (EDQM), Strasbourg, pp 1500–1501

  8. EDQM (2015b) Matricaria oil, Matricariae aetheroleum. In: European Pharmacopoeia 9th edn, vol. 1. European Directorate for the Quality of Medicines & HealthCare (EDQM), Strasbourg, pp 1434–435

  9. Evergetis E, Michaelakis A, Kioulos E, Koliopoulos G, Haroutounian SA (2009) Chemical composition and larvicidal activity of essential oils from six Apiaceae family taxa against the West Nile virus vector Culex pipiens. Parasitol Res 105:117–124. https://doi.org/10.1007/s00436-009-1370-8

  10. Figueiredo AC, Barroso JG, Pedro LG, Scheffer JJC (2008) Factors affecting secondary metabolite production in plants: volatile components and essential oils. Flav Fragr J 23:213–226. https://doi.org/10.1002/ffj.1875

  11. Hand R (2011) In: Euro+Med PlantBase—the information resource for Euro-Mediterranean plant diversity. Available at: http://ww2.bgbm.org/EuroPlusMed/. Accessed 1 Jul 2019

  12. Hartvig P (1986) Heracleum L. In: Strid A (ed) Mountain Flora of Greece, vol. 1. Cambridge University Press, Cambridge, pp 723–725

  13. Jogan N, Bačić T, Frajman B, Leskovar I, Naglič D, Podobnik A, Rozman B, Strgulc-Krajšek S, Trčak B (2001) Materials for the atlas of Flora of Slovenia. Center za kartografiijo favne i flore, Miklavž na Dravskem polju

  14. Kanani MR, Rahiminejad MR, Sonboli A, Mozaffarian V, Osaloo SK, Ebrahimi SN (2011) Chemotaxonomic significance of the essential oils of 18 Ferula species (Apiaceae) from Iran. Chem Biodivers 8:503–517. https://doi.org/10.1002/cbdv.201000148

  15. Logacheva MD, Valiejo-Roman CM, Pimenov MG (2008) ITS phylogeny of West Asian Heracleum species and related taxa of Umbelliferae-Tordylieae W.D.J. Koch, with notes on evolution of their psbA-trnH sequences. Pl Syst Evol 270:139–157. https://doi.org/10.1007/s00606-007-0619-x

  16. Mandenova IP (1950) Kavkazskie vidy roda Heracleum. Izdatel’stvo Akademii Nauk Gruzinskoj SSR, Tbilisi (In Russian)

  17. Mandenova IP (1951) Heracleum L. In: Schischkin BK (ed) Flora of the U.S.S.R., vol. 17. Botanical Institute of the Academy of Sciences of the USSR, Moscow, Leningrad, pp 222–260

  18. Mandenova IP (1962) Taxonomic review of Turkish species of Heracleum. Notes Roy Bot Gard Edinburgh 24:173–181

  19. Mandenova IP (1981) Conspectus systematis generis Heracleum L. (Umbelliferae). Zametki Sist Geogr Rast 37:19–20

  20. Mandenova IP (1987) Heracleum, Tetrataenium. In: Rechinger KH (ed) Flora Iranica, vol. 162. Akademische Druck-u. Verlagsanstalt, Graz, pp 492–506

  21. Martinčić A (1999) Heracleum L. In: Martinčić A (ed) Mala flora Slovenije. Tehniška založba Slovenije, Ljubljana, p 353

  22. Matevski V (2005) Heracleum L. In: Micevski K (ed) Flora na republika Makedonija 1 (6). Makedonska akademija na naukite i umetnostite, Skopje, pp 1637–1640

  23. Mileski KS, Ćirić AD, Trifunović SS, Ristić MS, Soković MD, Matevski VS, Tešević VV, Jadranin MB, Marin PD, Džamić AM (2016) Heracleum orphanidis: Chemical characterisation, and comparative evaluation of antioxidant and antimicrobial activities with specific interest in the influence on Pseudomonas aeruginosa PAO1. Food Funct 7:4061–4074. https://doi.org/10.1039/c6fo01018k

  24. Milutinović V, Niketić M, Ušjak L, Nikolić D, Krunić A, Zidorn C, Petrović S (2018a) Methanol extracts of 28 Hieracium species from the Balkan peninsula—comparative LC–MS analysis, chemosystematic evaluation of their flavonoid and phenolic acid profiles and antioxidant potentials. Phytochem Analysis 29:30–47. https://doi.org/10.1002/pca.2712

  25. Milutinović V, Niketić M, Krunić A, Nikolić D, Petković M, Ušjak L, Petrović S (2018b) Sesquiterpene lactones from the methanol extracts of twenty-eight Hieracium species from the Balkan peninsula and their chemosystematic significance. Phytochemistry 154:19–30. https://doi.org/10.1016/j.phytochem.2018.06.008

  26. Niketić M (2014) Nomenclature review of the plants published by Josif Pančić (Nomenclator Pancicianus novus). Bot Serbica 38:209–236

  27. Nikolić V (1973) Heracleum L. In: Josifović M (ed) Flora SR Srbije 5. Srpska akademija nauka i umetnosti (SANU), Belgrade, pp 298–304

  28. Nogueira T, Marcelo-Curto MJ, Figueiredo AC, Barroso JG, Pedro LG, Rubiolo P, Bicchi C (2008) Chemotaxonomy of Hypericum genus from Portugal: Geographical distribution and essential oils composition of Hypericum perfoliatum, Hypericum humifusum, Hypericum linarifolium and Hypericum pulchrum. Biochem Syst Ecol 36:40–50. https://doi.org/10.1016/j.bse.2007.07.004

  29. Peev D (1982) Heracleum L. In: Velčev V, Kožuharov S (eds) Flora na Narodna Republika Bălgaria, vol. VIII. Academia scientiarum Bulgaricae, Sofia, p 246 (In Bulgarian)

  30. Pignatti S (1982) Flora d’Italia, vol. 2. Edagricole, Bologna, pp 237–239

  31. POWO (2019) Plants of the world online. Facilitated by the Royal Botanic Gardens, Kew. Available at: http://www.plantsoftheworldonline.org/. Accessed 8 Sep 2019

  32. Stevanović V (1986) Heracleum orphanidis Boiss. In: Sarić M, Diklić N (eds) Flora SR Srbije, vol. 10. Srpska akademija nauka i umetnosti (SANU), Belgrade, p 152

  33. The Plant List (2013) Version 1.1. Available at: http://www.theplantlist.org/. Accessed 1 Jul 2019

  34. Tonascia N (1992) Biosystematische Untersuchungen an Heracleum sphondylium s.l. in der Schweiz. Ber Geobot Inst ETH Stiftung Rübel 58:101–120

  35. Ušjak L, Petrović S, Drobac M, Soković M, Stanojković T, Ćirić A, Niketić M (2016a) Chemical composition and bioactivity of the essential oils of Heracleum pyrenaicum subsp. pollinianum and Heracleum orphanidis. Nat Prod Commun 11:529–534

  36. Ušjak LJ, Petrović SD, Drobac MM, Soković MD, Stanojković TP, Ćirić AD, Grozdanić N, Niketić MS (2016b) Chemical composition, antimicrobial and cytotoxic activity of Heracleum verticillatum Pančić and H. ternatum Velen. (Apiaceae) essential oils. Chem Biodivers 13:466–476. https://doi.org/10.1002/cbdv.201500151

  37. Ušjak L, Petrović S, Drobac M, Soković M, Stanojković T, Ćirić A, Niketić M (2017a) Essential oils of three cow parsnips-composition and activity against nosocomial and foodborne pathogens and food contaminants. Food Funct 8:278–290. https://doi.org/10.1039/c6fo01698g

  38. Ušjak L, Petrović S, Drobac M, Soković M, Stanojković T, Ćirić A, Niketić M (2017b) Edible wild plant Heracleum pyrenaicum subsp. orsinii as a potential new source of bioactive essential oils. J Food Sci Technol 54:2193–2202. https://doi.org/10.1007/s13197-017-2610-z

  39. Ušjak LJ, Drobac MM, Niketić MS, Petrović SD (2018) Chemosystematic significance of essential oil constituents and furanocoumarins of underground parts and fruits of nine Heracleum L. taxa from Southeastern Europe. Chem Biodivers 15:e1800412. https://doi.org/10.1002/cbdv.201800412

  40. Wink M, Botschen F, Gosmann C, Schäfer H, Waterman PG (2010) Chemotaxonomy seen from a phylogenetic perspective and evolution of secondary metabolism. In: Wink M (ed) Annual plant reviews. Biochemistry of plant secondary metabolism, vol. 40, 2nd edn. Wiley Blackwell, Hoboken, pp 364–433. https://doi.org/10.1002/9781444320503.ch7

  41. Yu Y, Downie SR, He X, Deng X, Yan L (2011) Phylogeny and biogeography of Chinese Heracleum (Apiaceae tribe Tordylieae) with comments on their fruit morphology. Pl Syst Evol 296:179–203. https://doi.org/10.1007/s00606-011-0486-3

Download references

Acknowledgements

This work was supported by the Ministry of Education, Science and Technological Development of the Republic of Serbia (Grant Number 173021). We are particularly grateful to Prof. Dr. Nejc Jogan (Department of Biology, Biotechnical Faculty, University of Ljubljana, Večna pot 111, SI-1000 Ljubljana, Slovenia) who helped us to find species habitats in Slovenia.

Author information

Correspondence to Ljuboš Ušjak.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Contribution to “Plants of the Balkan Peninsula in Space and Time”.

Handling Editor: Stanislav Španiel.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Ušjak, L., Niketić, M., Drobac, M. et al. Chemosystematic evaluation of leaf and flower essential oils of eight Heracleum taxa from Southeastern Europe. Plant Syst Evol 306, 4 (2020). https://doi.org/10.1007/s00606-020-01645-z

Download citation

Keywords

  • GC–FID and GC–MS
  • Heracleum
  • Leaf and flower essential oils
  • NMDS
  • PCA
  • UPGMA