ASSESSMENT OF THE CHEMICAL COMPOSITION AND BIOLOGICAL ACTIVITY OF ESSENTIAL OIL FROM BULGARIAN YARROW (ACHILLEA MILLEFOLIUM L.)

Authors

  • Krastena Nikolova Medical university -Varna
  • Natalina Panova Medical University of Varna
  • Anelia Gerasimova Medical University of Varna
  • Yulian Tumbarski University of Food Technologies
  • Ivan Ivanov University of Food Technologies
  • Ivayla Dincheva AgroBioInstitute, Agricultural Academy
  • Christina Tzvetkova Institute of General and Inorganic Chemistry, Bulgarian Academy of Sciences
  • Alexander Pashev Medical University-Pleven
  • Galia Gentscheva Medical University-Pleven

DOI:

https://doi.org/10.59957/jctm.v61.i1.2026.4

Keywords:

antioxidant activity, chemical composition, Achillea millefolium, antimicrobial activity, essential oil

Abstract

The present study aimed to investigate the chemical composition and biological activity of yarrow essential oil (Achillea millefolium) from Bulgaria. Gas chromatography-mass spectrometry (GC-MS) analysis, total reflection X-ray fluorescence (TXRF) technique, antioxidant activity (ABTS and DPPH methods), antimicrobial activity tests were used. Through an optimized procedure with Ga as an internal standard, thirteen elements - S, Cl, K, Ca, Cr, Mn, Fe, Ni, Cu, Zn, Se, and Br - were quantified. The highest concentrations were observed for S, Ca, and Fe (12.35 - 7.26 mg kg⁻¹), followed by Cl, K, Ni, Cu, and Zn (2.23 - 0.53 mg kg-1). The dominant compounds identified by GC-MS analysis are monoterpene hydrocarbons, of which α-pinene (41.29 %) and β-pinene (27.15 %), limonene and p-cymene are predominant. The ABTS method a moderate degree radical neutralization with an IC50 value of 9.15 ±
0.01 µg mL-1, while the DPPH method had a significantly lower IC50 of 205.00 ± 0.03 µg mL-1, indicating selective antioxidant activity depending on the type of radicals. The maximum inhibition observed at 100 µg mL-1 reached 95.13 % with the ABTS method and 29.82 % with the DPPH method. Bulgarian yarrow essential oil shows moderate activity against some Gram-negative bacteria, such as K. pneumoniae. and weak inhibitory activity against other pathogens, such as Staphylococcus aureus and Escherichia coli. It does not show activity against the molds Aspergillus niger and Aspergillus flavus.

References

K. Bimbiraitė-Survilienė, O. Ragažinskienė, A. Maruška, O. Kornyšova, Comparison of the chemical composition of four yarrow (Achilea millefolium L.) morphotypes, Biologija, 54, 3, 2008.

I.C.A. Alvarenga, P.F. Boldrin, F.V. Pacheco, S.T. Silva, S.K.V. Bertolucci, J.E.B.P. Pinto, Effects on growth, essential oil content and composition of the volatile fraction of Achillea millefolium L. cultivated in hydroponic systems deficient in macro-and microelements, Scientia Horticulturae, 197, 2015, 329-338. DOI: https://doi.org/10.1016/j.scienta.2015.09.046.

M. Mazandarani, S.Z. Mirdeilami, M. Pessarakli, Essential oil composition and antibacterial activity of Achillea millefolium L. from different regions in North east of Iran, Journal of Medicinal Plants Research, 7, 16, 2013, 1063-1069.

B. Yildirim, K. Ekici, M.Z. Kocak, Essential oil composition of yarrow species (Achillea millefolium L. and Achillea wilhelmsii): antioxidant and antibacterial activities of essential oils, Stud. Univ. Babes-Bolyai, Chem, 68, 1, 2023, 145-157. DOI: https://doi.org/10.24193/subbchem.2023.1.11.

S.T. Chou, H.Y. Peng, J.C. Hsu, C.C. Lin, Y. Shih, Achillea millefolium L. essential oil inhibits LPS-induced oxidative stress and nitric oxide production in RAW 264.7 macrophages. International journal of molecular sciences, 14, 7, 2013, 12978-12993, DOI: https://doi.org/10.3390/ijms140712978.

C. El-Kalamouni, P.R. Venskutonis, B. Zebib, O. Merah, C. Raynaud, T. Talou, Antioxidant and Antimicrobial Activities of the Essential Oil of Achillea millefolium L. Grown in France, Medicines, 4(2), 2017, 30. DOI: https://doi.org/10.3390/medicines4020030

I. Ivanov, N. Petkova, J. Tumbarski, I. Dincheva, I. Badjakov, P. Denev, A. Pavlov, GC-MS Characterization of N-Hexane Soluble Fraction from Dandelion (Taraxacum officinale Weber ex F.H. Wigg.) Aerial Parts and Its Antioxidant and Antimicrobial Properties, Z. Naturforsch. C., 73, 1-2, 2017, 41–47. DOI: https://doi.org/10.1515/znc-2017-0107.

A. A. Shaltout, E. S. S. Abdel‐Hameed, F. Bilo, L. Borgese, L.E. Depero, Direct analysis of essential oils by means of TXRF spectrometry, X‐Ray Spectrometry, 49, 2, 2020, 322-331. DOI: https://doi.org/10.1002/xrs.3131.

I. Ivanov, R. Vrancheva, A. Marchev, N. Petkova, I. Aneva, P. Denev, V. Georgiev, A. Pavlov, Antioxidant Activities and Phenolic Compounds in Bulgarian Fumaria Species, Int. J. Curr. Microbiol. Appl. Sci, 3, 2, 2014, 296-306.

Y. Tumbarski, I. Ivanov, M. Todorova, A. Gerasimova, I. Dincheva, L. Makedonski, K. Nikolova, Chemical Composition and Biological Activities of St John’s Wort (Hypericum perforatum L.) Essential Oil from Bulgaria, Appl. Sci., 14, 2024, 11754 -11764. DOI: https://doi.org/10.3390/app142411754.

G. G. Toplan, T. Taskin, G. Iscan, F. Goger, M. Kurkcuoglu, A. Civas, G. Ecevit-Genc, A. Mat, K.H.C. Baser, Comparative studies on essential oil and phenolic content with in vitro antioxidant, anticholinesterase, antimicrobial activities of Achillea biebersteinii Afan. and A. millefolium subsp. millefolium Afan. L. growing in Eastern Turkey, Molecules, 27, 6, 2022, 1956-1960. DOI: https://doi.org/10.3390/molecules27061956.

M. Acimovic, M. Zoric, V.D. Zheljazkov, L. Pezo, I. Cabarkapa, J.S. Jeremic, M. Cvetkovic, Chemical characterization and antibacterial activity of essential oil of medicinal plants from Eastern Serbia, Molecules, 25, 22, 2020, 5482-5492. DOI: https://doi.org/10.3390/molecules25225482.

C. El-Kalamouni, P.R. Venskutonis, B. Zebib, O. Merah, C. Raynaud, T. Talou, Antioxidant and antimicrobial activities of the essential oil of Achillea millefolium L. grown in France, Medicines, 4, 2, 2017, 30-37.

A. S. Shawl, S. K. Srivastava, K.V. Syamasundar, S. Tripathi, V. K. Raina, Essential oil composition of Achillea millefolium L. growing wild in Kashmir, India, Flavour and Fragrance Journal, 17, 3, 2002, 165-168. DOI: https://doi.org/10.1002/ffj.1074.

N. Simic, S. Andjelkovic, R. Palic, V. Vajs, S. Milosavljevic, Volatile constituents of Achillea serbica Nym., Flavour and Fragrance Journal, 15, 3, 2000, 141-143. DOI: https://doi.org/10.1002/1099-1026(200005/06).

J. Tampe, L. Parra, K. Huaiquil, A. Mutis, A. Quiroz, Repellent effect and metabolite volatile profile of the essential oil of Achillea millefolium against Aegorhinus nodipennis (Hope) (Coleoptera: Curculionidae), Neotrop. Entomol., 44, 3, 2015, 279–285. DOI: https://doi.org/10.1007/s13744-015-0278-5.

National Toxicology Program, Toxicology and carcinogenesis studies of alpha, beta-thujone (CAS No. 76231-76-0) in F344/N rats and B6C3F1 mice (gavage studies), Natl Toxicol Program Tech Rep Ser., 2011 Nov;(570):1-260. PMID: 22127327

J. Rohloff, E.B. Skagen, A.H. Steen, T.H. Iversen, Production of yarrow (Achillea millefolium L.) in Norway: Essential oil content and quality, J. Agric. Food Chem., 48, 12, 2000, 6205–62059. DOI: https://doi.org/10.1021/jf000720p.

A. Orav, T. Kailas, K. Ivask, Composition of the essential oil from Achillea millefolium L. from Estonia, J. Essent. Oil Res., 13, 4, 2001, 290–294. DOI: https://doi.org/10.1080/10412905.2001.9699697.

N. Farhadi, K. Babaei, S. Farsaraei, M. Moghaddam, A.G. Pirbaloti, Changes in essential oil compositions, total phenol, flavonoids and antioxidant capacity of Achillea millefolium at different growth stages, Ind. Crops Prod., 152, 8, 2020, 112570–112576. DOI: https://doi.org/10.1016/j.indcrop.2020.112570

A. Judzentiene, D. Mockute, Essential oil composition of two yarrow taxonomic forms, Cent. Eur. J. Biol., 5, 3, 2010, 346–352. DOI: https://doi.org/10.2478/s11535-010-0011-7.

Bruker Nano GmbH (2017), S2 Picofox user manual.

A.M. Iordache, C. Nechita, C. Voica, C. Roba, O.R. Botoran, and R.E. Ionete, Assessing the Health Risk and the Metal Content of Thirty-Four Plant Essential Oils Using the ICP-MS Technique, Nutrients, 14, 2022, 2363-2373. DOI: https://doi.org/10.3390/nu14122363.

S. Bozhanov, I. Karadjova, S. Alexandrov, Determination of trace elements in the Lavender inflorescence (Lavandula angustifolia Mill.) — Lavender oil system, Microchemical Journal, 86, 2007, 119–123. DOI: https://doi.org/10.1016/j.microc.2007.01.001.

D. Bakircioglu, N. Topraksever, S. Yurtsever, Y. Bakircioglu, A. Spectroscopy, ICP-OES determination of some trace elements in herbal oils using a three-phase emulsion method and comparison with conventional methods, Atomic Spectrometry, 39, 1, 2018, 38-45. DOI: https://doi.org/10.46770/AS.2018.01.005.

World Health Organization (WHO). Trace Elements in Human Nutrition and Health; World Health Organization: Geneva, Switzerland, 1996.

V. Angelova, M. Ihtyarova, Heavy metal accumulation and chemical composition of the essential oils of yarrow (Achillea millefolium L.) cultivated on heavy metal-contaminated soils, Agricultural Sciences, 15, 36, 2023, DOI: https://doi.org/10.22620/agrisci.2023.36.006.

J. Stanojević, L. Stanojević, V. Bulatović, J.B. Zvezdanović, A.N. Milenković, N.M. Simonović, D.J. Cvetković, Chemical composition and antioxidant activity of immortelle (Helichrysum italicum) (Roth) G. Don) and yarrow (Achillea millefolium L.) essential oils, Adv. Technol, 11, 1, 2022, 93-103. DOI: https://doi.org/10.5937/savteh2201093S.

D. Čulum, A. Čopra-Janićijević, E. Muratović, S. Siljak-Yakovlev, M. Maksimović, D. Vidic, Essential oil composition and antioxidant activity of endemic Achillea lingulata Waldst. & Kit. compared to common A. millefolium L, Records of natural products, 16, 4, 2021, 335-345. DOI: https://doi.org/10.25135/rnp.285.2107.2143.

M. Ghanbari, M.K. Souri, R. Omidbaigi, Chemical composition of the essential oil of Achillea millefolium L. from north-west of Iran, Zeitschrift fur Arznei- und Gewurzpflanzen, 22, 2, 2017, 69-71.

B. Salehi, S. Upadhyay, I.E. Orhan, A.K. Jugran, S.L.D. Jayaweera, D.A. Dias, F. Sharopov, Y. Taheri, N. Martins, N. Baghalpour, W.C. Cho, J. Sharifi-Rad, Therapeutic Potential of α- and β-Pinene: A Miracle Gift of Nature, Biomolecules, 9, 11, 2019, 738-742. DOI: https://doi.org/10.3390/biom9110738.

M. Kazemi, Phytochemical and antioxidant properties of Achillea millefoliumfrom the eastern region of Iran, International Journal of Food Properties, 18, 10, 2015, 2187–2192. DOI: https://doi.org/10.1080/10942912.2014.966388.

Downloads

Published

2026-01-03

Issue

Section

Articles