Chemical composition and antimicrobial activity of a newly identified chemotype of Achillea wilhelmsii K.Koch from Kashan, Iran.

Publisher: Nature Publishing Group Country of Publication: England NLM ID: 101563288 Publication Model: Electronic Cited Medium: Internet ISSN: 2045-2322 (Electronic) Linking ISSN: 20452322 NLM ISO Abbreviation: Sci Rep Subsets: MEDLINE

Original Publication: London : Nature Publishing Group, copyright 2011-

Achillea*/chemistry ; Microbial Sensitivity Tests* ; Oils, Volatile*/pharmacology ; Oils, Volatile*/chemistry; Iran ; Anti-Infective Agents/pharmacology ; Anti-Infective Agents/chemistry ; Anti-Bacterial Agents/pharmacology ; Anti-Bacterial Agents/chemistry ; Plant Extracts/pharmacology ; Plant Extracts/chemistry ; Candida albicans/drug effects ; Gas Chromatography-Mass Spectrometry

Achillea wilhelmsii K.Koch (Asteraceae) is traditionally used in Kashan (Iran) to control diabetes, headaches, kidney stones and heartburn. Due to its beneficial properties, the aerial parts of the plant were collected from the area of Maragheh (Kashan, Isfahan, Iran), in June 2022, during its full flowering, and the essential oil was obtained by hydrodistillation (Clevenger). The yield, composition and antimicrobial activity of the extractive solution were measured. Qualitative evaluation was performed by means of gas chromatography-mass spectroscopy method, and antimicrobial activity was determined against 12 strains of microorganisms by measuring inhibition halo, minimum inhibitory concentration, and minimum bactericidal concentration (MBC). The yield of essential oil was ~ 0.1071% (w/w) and it mainly contained oxygenated monoterpenes (47.87%), being for the first time fragranol (33.22%), fragranyl acetate (16.18%) and oleic acid (6.33%) the most abundant. The highest inhibitory halo was found against Candida albicans and Gram-positive Staphylococcus aureus (~ 10 mm). The essential oil was also effective against gram-negative bacteria such as Acinetobacter baumannii and Shigella dysenteriae, as the inhibition halo was ~ 9 mm and similar to that of rifampin, used as a reference. Therefore, it seems that this essential oil from and endemic species has a unique chemotype with potential antimicrobial activity, which may be a possible option for fragranol isolation and the production of natural antibiotics effective against various microorganisms.
(© 2024. The Author(s).)

Petrakoua, K., Iatroub, G. & Lamari, F. N. Ethnopharmacological survey of medicinal plants traded in herbal markets in the Peloponnisos, Greece. J. Herb. Med.19, 100305 (2020). (PMID: 10.1016/j.hermed.2019.100305)
Farooq, A. et al. Ethnomedicinal knowledge of the rural communities of Dhirkot, Azad Jammu and Kashmir, Pakistan. J. Ethnobiol. Ethnomed.15, 45 (2019). (PMID: 671683110.1186/s13002-019-0323-231470868)
Malik, K. et al. An ethnobotanical study of medicinal plants used to treat skin diseases in northern Pakistan. BMC Complement. Altern. Med.19, 210 (2019). (PMID: 669321010.1186/s12906-019-2605-631409400)
Zizka, A. et al. Traditional plant use in Burkina Faso (West Africa): A national-scale analysis with focus on traditional medicine. J. Ethnobiol. Ethnomed.11, 9 (2015). (PMID: 442946110.1186/1746-4269-11-925971673)
Aziz, Z. A. A. et al. Essential oils: Extraction techniqes, pharmaceutical and therapeutic potential—A review. Curr. Drug Metab.19, 1100–1110 (2018). (PMID: 10.2174/138920021966618072314485030039757)
Božović, M., Mladenović, M. & Ragno, R. Editorial: Chemical composition-and antimicrobial activity of essential oils. Front. Pharmacol.14, 1120756 (2023). (PMID: 988045910.3389/fphar.2023.112075636713842)
Kürekci, C. & Sakin, F. Uçucu Yağlar: Antimikrobiyal açıdan uçucu yağlar: In-vitro ve in-vivo çalışmalar. Türk. Klini. Hayvan Besleme Beslenme Hastalık. Derg. Özel Konular3, 15–20 (2017).
Ghavam, M. Antibacterial potential of biosynthesized silver nanoparticles using Nepeta sessilifolia Bunge and Salvia hydrangea DC. ex Benth. extracts from the natural habitats of Iran’s Rangelands. BMC Complement. Med. Ther.23, 299 (2023). (PMID: 1046363410.1186/s12906-023-04101-w37620931)
Şahan, Z. Bazı Bitki Uçucu Yağlarının Enerji, Protein ve Lif Kaynağı Yemlerin In Vitro Gerçek Sindirilebilirliğine ve Yüksek Verimli süt Sığırlarında süt Verimi ve süt Kompozisyonlarına Etkileri 1–147 (Çukurova Üniversitesi Fen Bilimleri Enstitüsü, 2012).
Kurkiazizi, M., Chizzola, R., Ghani, A. & Oroojalian, F. Composition at different development stages of the essential oil of four Achillea species grown in Iran. Nat. Prod. Commun.5(2), 283–290 (2010).
Taheri Boukani, K. & Najafzadeh, R. Evaluation of diversity of yarrow (Achillea biebersteinii Afan. and Achillea wilhelmsii C. Koch) populations in West-Azerbaijan province based on morphological traits, essential oil percentage and composition. Iran. J. Hortic. Sci.51, 215–228 (2019).
Vaez Shahrestani, A. & Sefidkon, F. Essential oil composition in different plant parts of Achillea biebersteinii Afam. Med. Aromat. Plan34, 40–49 (2018).
Achakzai, J. K. et al. In vitro antileishmanial activity and GC–MS analysis of whole plant hexane fraction of Achillea wilhelmsii (WHFAW). J. Microorg.Linalool. Mol.27, 6928 (2022).
Mozaffarian, V. A Dictionary of Iranian plant names 596 (Farhang Moaser Publication, 1996).
Aytac, Z., Duman, H. & Ekici, M. Two new Achillea L. (Asteraceae) species from Turkey. Turk. J. Bot.40, 373–379 (2016). (PMID: 10.3906/bot-1504-19)
Saeidnia, S., Gohari, A., Mokhber-Dezfuli, N. & Kiuchi, F. A. A review on phytochemistry and medicinal properties of the genus Achillea. DARU J. Fac. Pharm. Tehran Univ. Med. Sci.19, 173 (2011).
Applequist, W. L. & Moerman, D. E. Yarrow (Achillea millefolium L.): A neglected panacea? A review of ethnobotany, bioactivity, and biomedical research. Econ. Bot.65, 209–225 (2011). (PMID: 10.1007/s12231-011-9154-3)
Zargari, A. Medicinal Plants Vol. 3, 107–117 (Tehran University Publications, 1996).
Salehi, M., Kalvandi, R. & Salehi, F. Evaluation of morphological traits and essential oil constituents diversity in different populations of Achillea santolinoides subsp. wilhelmsii (K. Koch) Greuter in Hamedan Province. J. Hortic. Sci. In Press (2023).
Mohammadhosseini, M., Sarker, S. D. & Akbarzadeh, A. Chemical composition of the essential oils and extracts of Achillea species and their biological activities: A review. J. Ethnopharmacol.199, 257–315 (2017). (PMID: 10.1016/j.jep.2017.02.01028179115)
Fekri Qomi, S., Sefidkon, F. & Salehi Shanjani, P. Study of morphological characteristics and essential oil of different populations of Achillea wilhelmsii C. Koch. Iran. J. Med. Aromat. Plants Res.34, 579–593 (2018).
Ali, N. et al. Acute toxicity and antispasmodic activities of Achillea wilhelmsii C. Koch. Pak. J. Pharm. Sci.27, 309–315 (2014). (PMID: 24577920)
Ghavam, M. & Kiani, S. Ethnobutanical analysis of medicinal plants in Kashan. Nat. Ecosyst. Iran9, 103–125 (2018).
Delfan, E. D. & Azizi, K. Ethnobotany of native medicinal plants in Zagheh and Biranshahr districts, Lorestan Province, Iran. Eco-phytochem. J. Med. Plants7, 64–82 (2020).
Bazgir, A. & Mehdi, P. Ethnobotany of wild plants in Bestam region of Selseleh county, Lorestan Province. Indig. Knowl.8, 85–158 (2021).
Koushki, M., Farrokhi Yekta, R., Amiri-Dashatan, N., Dadpay, M. & Goshadrou, F. Therapeutic effects of hydro-alcoholic extract of Achillea wilhelmsii C. Koch on indomethacin-induced gastric ulcer in rats: a proteomic and metabolomic approach. BMC Complement. Altern. Med.19, 2623 (2019). (PMID: 10.1186/s12906-019-2623-4)
Asgary, S. et al. Antihypertensive and antihyperlipidemiceffects of Achillea wilhelmsii. Drugs Exp. Clin. Res.26, 89–93 (2000). (PMID: 10941601)
Ashtiani, M. et al. Effect of Achillea wilhelmsii extract on expression of the human telomerase reverse transcriptase mRNA in the PC3 prostate cancer cell line. Biomed. Rep.7, 251–256 (2017). (PMID: 554776710.3892/br.2017.95628811896)
Majnooni, M. B., Mohammadi-Farani, A., Gholivand, M. B., Nikbakht, M. R. & Bahrami, G. R. Chemical composition and anxiolytic evaluation of Achillea wilhelmsii C. Koch essential oil in rat. Res. Pharm. Sci.8, 269–275 (2013). (PMID: 375759224082896)
Raudone, L. et al. Distribution of phenolic compounds and antioxidant activity in plant parts and populations of seven under utilized wild Achillea species. Plants11, 447 (2022). (PMID: 883989610.3390/plants1103044735161428)
Akbar, A., Gul, Z., Chein, S. H. & Sadiq, M. B. Investigation of anti-inflammatory properties, phytochemical constituents, antioxidant, and antimicrobial potentials of the whole plant ethanolic extract of Achillea santolinoides subsp. wilhelmsii (K. Koch) Greuter of Balochistan. Oxid. Med. Cell. Longev. (2023).
Chalabian, F., Norouzi Arasi, H. & Moosavi, S. A study of growth inhibitory effect of essential oils of seven species from different families on some kinds of microbes. J. Med. Plants 2, 37–42 (2003). Chemistry 2019, 5734257, 26, (2019).
Azaz, A. D., Arabaci, T., Sangun, M. K. & Yildiz, B. Composition and the in vitro antimicrobial activities of the essential oils of Achillea wilhelmsii C. Koch and Achillea lycaonica Boiss & Heldr. Asian J. Chem.20, 1238–1244 (2008).
Ghadri, S., Falahati Hossein Abad, A., Sarailo, M. & Ghanbari, V. Investigating the compounds and antibacterial effect of three essential oils of coriander, yarrow and dill in laboratory conditions. J. Shahrekord Univ. Med. Sci.14, 74–82 (2012).
Nejadhabibvash, F. & Rezaee, M. Variation in the essential oil of Achillea wilhelmsii C. Koch and A. millefolium L. apical shoots in different developmental stages in Martyrs Valley, West Azerbaijan province: A Case example. Iran. J. Plant Biol.10, 17–38 (2018).
Rabbi Angourani, H. Investigation of phytochemical compounds of Achillea wilhelmsii C. Koch essential oil in Zanjan province natural habitats. J. Med. Plants Biotechnol.5, 57–63 (2020).
Azarnivand, H., Ghavam Arabani, M., Sefidkon, F. & Tavili, A. The effect of ecological characteristics on quality and quantity of the essential oils of Achillea millefolium L. subsp. Millefolium. Iran. J. Med. Aromat. Plants Res.25, 556–571 (2010).
Adams, R. P. Identification of Essential Oil Components by Gas Chromatography/Quadruple Mass Spectroscopy. Carol Stream IL, 804 (Allured Publishing Cropration, 2007).
CLSI. Clinical and Laboratory Standard Institute. Performance Standards for Antimicrobial Disk Susceptibility Testing: Approved Standard, vol. 29, 1–76 (National Committee for Clinical Laboratory Standards, 2012).
Azadbakht, M., Morteza-Semnani, K. & Khansari, N. The essential oils composition of Achillea wilhelmsii C. Koch leaves and flowers. J. Med. Plants2, 55–58 (2003).
Angourani, H. R., Zarei, A., Moghadam, M. M., Ramazani, A. & Mastinu, A. Investigation on the essential oils of the Achillea species: From chemical analysis to the in silico uptake against SARS-CoV-2 main protease. Life13, 378 (2023). (PMID: 996705710.3390/life1302037836836736)
Nejadhabibvash, F. et al. Study of the plant growth stages effect on the color, content and composition of essential oil of Achillea wilhelmsii C. Koch Case Study: Qushchi Ghat in West Azerbaijan province. Eco-phytochem. J. Med. Plants5, 47–64 (2017).
Ghavam, M., Azarnivand, H., Sefidkon, F. & Tavili, A. Comparison of the quantity and quality of the essential oils of the flowers and leaves of the two subspecies of Achillea millefolium L. with the pharmacy source approach. AUMJ9, 345–356 (2020).
Ghavam, M., Azarnivand, H., Sefidkon, F. & Tavili, A. Comparison of the quantity and quality of the essential oils of the flowers and leaves of the two subspecies of Achillea millefolium L. with the pharmacy source approach. Alborz Univ. Med. J.9, 345–356 (2020).
Najafzadeh, R., Aliyi, A. & Taheri Boukani, K. Comparing the essential oils percentage and compositions in different organs of Achillea wilhelmsii C. Koch. Technol. Med. Aromat. Plants Iran5, 14–21 (2023).
Turkmenoglu, F. P., Agar, O. T., Akaydin, G., Hayran, M. & Demirci, B. Characterization of volatile compounds of eleven Achillea species from Turkey and biological activities of essential oil and methanol extract of A. hamzaoglui Arabaci et Budak. Molecules20, 11432–11458 (2015). (PMID: 627222510.3390/molecules20061143226111175)
Bader, A. et al. Essential oil biodiversity of Achillea ligustica All. Obtained from Mainland and Island populations. Plants11, 1054 (2022). (PMID: 902738910.3390/plants1108105435448782)
Bohlmann, F., Zdero, C. & Faass, U. Naturally occurring terpene derivatives. XXVI. Constituents of Artemisia fragrans. Chem. Ber.106, 2904–2909 (1973). (PMID: 10.1002/cber.19731060919)
Dilika, F., Bremner, P. D. & Meyer, J. J. Antibacterial activity of linoleic and oleic acids isolated from Helichrysum pedunculatum: A plant used during circumcision rites. Fitoterapia71, 450–452 (2000). (PMID: 10.1016/S0367-326X(00)00150-710925024)
Mirbagheri Firoozabad, M. S. & Mohammadi, N. M. Antimicrobial activities of microbial essential fatty acid against foodborne pathogenic bacteria. Iran. J. Microbiol.14, 214–218 (2022). (PMID: 916825135765549)
Borges, M. F. D. A., Lacerda, R. D. S., Correia, J. P. D. A., de Melo, T. R. & Ferreira, S. B. Potential antibacterial action of α-pinene. Med. Sci. Forum12, 1–11 (2022).
Silva, A. C. R. et al. Biological activities of a-pinene and β-pinene enantiomers. Molecules17, 6305–6316 (2012). (PMID: 10.3390/molecules17066305)
Maczka, W. et al. A new approach to functionalized cyclobutanes: Stereoselective synthesis of the enantiomers of grandisol and fraganol. Tetrahedron Asymmetry6, 1151–1164 (1995). (PMID: 10.1016/0957-4166(95)00141-B)
Sikka, S. C. & Bartolome, A. R. Perfumery, essential oils, and household chemicals affecting reproductive and sexual health. In Bioenvironmental Issues Affecting Men’s Reproductive and Sexual Health, 557–569 (Academic Press, 2018).
Cai, Z. M. et al. 1, 8-Cineole: A review of source, biological activities, and application. J. Asian Nat. Prod. Res.23, 938–954 (2021). (PMID: 10.1080/10286020.2020.183943233111547)
Ghavam, M. A GC–MC analysis of chemical compounds and identification of the antibacterial characteristics of the essential oil of two species exclusive to Iranian habitats: New chemotypes. PLoS ONE17, e0273987 (2022). (PMID: 953659410.1371/journal.pone.027398736201544)
Ghavam, M. & Markabi, F. S. Evaluation of yield, chemical profile, and antimicrobial activity of Teucrium polium L. essential oil used in Iranian folk medicine. Appl. Biochem. Biotechnol. https://doi.org/10.1007/s12010-023-04847-6 (2024). (PMID: 10.1007/s12010-023-04847-638194183)
Janbon, G., Quintin, J., Lanternier, F. & d’Enfert, C. Studying fungal pathogens of humans and fungal infections: Fungal diversity and diversity of approaches. Genes Immun.20, 403–414 (2019). (PMID: 10.1038/s41435-019-0071-231019254)
Xiao, Z., Wang, Q., Zhu, F. & An, Y. Epidemiology, species distribution, antifungal susceptibility and mortality risk factors of candidemia among critically ill patients: A retrospective study from 2011 to 2017 in a teaching hospital in China. Antimicrob. Resist. Infect. Control8, 89 (2019). (PMID: 654207510.1186/s13756-019-0534-231161036)
Ghavam, M. In vitro biological potential of the essential oil of some aromatic species used in Iranian traditional medicine. Inflammopharmacology30, 855–874 (2022). (PMID: 10.1007/s10787-022-00934-y35322321)
Oroojalian, F., Kasra-Kermanshahi, R., Azizi, M. & Bassami, M. Synergistic antibacterial activity of the essential oils from three medicinal plants against some important food-borne pathogens by microdilution method. Iran. J. Med. Aromat. Plants Res.26, 133–146 (2010).
Khaleghi, M., Bokaiean, M. & Saeedi, S. Assessment of antimicrobial activity of Myrtus communis extract against methicillin-resistant Staphylococcus aureus. Appl. Biol.26, 37–46 (2014).
Gilsic, S., Milojeij, S., Dimitrjvi, J., Orlovij, A. & Skala, D. Antimicrobial activity of the essential oil and different fractions of Juniperus communis L. and a comparison with some commercial antibiotics. J. Serb. Chem. Soc.72, 311–320 (2007). (PMID: 10.2298/JSC0704311G)
Babapour, E., Haddadi, A., Mirnejad, R., Angaji, S. & Amirmozafari, N. Study of drug resistance and ompA gene existence in clinical Acinetobacter baumannii isolates. Iran. J. Med. Microbiol.11, 30–38 (2017).
Arianzad, S. A., Zeinoddini, M., Haddadi, A., Nazarian, S. & Hasan Sajedi, R. The effect of recombinant IpaB protein on the development of immune responses against Shigella dysenteriae in Guinea Pig. J. Microb. World15, 170–182 (2022).
Ghaderi, S., Falahati Hosein Abad, A., Sarailoo, M. H. & Ghanbari, V. Investigation of the components and antibacterial effects of three plant’s essential oil Coriandrum sativum, Achilleh millefolium, Anethum graveolens in vitro. J. Shahrekord Univ. Med. Sci.14, 74–82 (2012).
Holly, R. A. & Patal, D. Improvement in shelf life and safetey of perishable foods by plant essential oils and smoke antimicrobials. Food Chem.22, 273–292 (2005).

Keywords: Achillea; Antibacterial/yeast activity; Essential oil quantity; Ethnobotany; Fragranol

0 (Oils, Volatile)
0 (Anti-Infective Agents)
0 (Anti-Bacterial Agents)
0 (Plant Extracts)

Date Created: 20240930 Date Completed: 20240930 Latest Revision: 20241003

20241004

PMC11443101

10.1038/s41598-024-73284-0

39349567