In collaboration with Scientific Association of Iranian Medicinal Plants

Document Type : Research Paper

Authors

1 Ph.D. student, Department of Horticultural Science, Faculty of Agriculture, Tarbiat Modares University, Tehran, Iran

2 Department of Horticultural Science, Faculty of Agriculture, Tarbiat Modares University, Tehran, Iran

10.22092/ijmapr.2025.368555.3519

Abstract

Background and Objectives: Eryngium billardieri, known as “Zul” or “Boghnagh,” and Eryngium caucasicum, known as “Chuchagh,” are two important species among the 11 known species of the Eryngium genus in Iran. Plants of this genus are used to produce hydrosol, which is claimed to reduce blood glucose levels. Although the essential oil content of these species is relatively low, their diversity of volatile compounds is high. The aim of this study, consistent with previous research, is to investigate the water-soluble and water-insoluble volatile compounds of these two species. During hydrosol extraction from these plants, known as "Aragh-e Boghnagh," volatile compounds are transferred into the water; therefore, identifying water-soluble and water-insoluble volatile compounds is crucial for understanding the chemical composition of these species.
Material and Methods: In this study, E. billardieri (Zul or Boghnagh) was collected from three locations: Ganjname (GN, Hamedan province), Lardam (DL, Damavand, Tehran province), and Razghan (RZ), and E. caucasicum (Chuchagh) from Bojaq (BO) National Park (Gilan province) and Abr village (RA, Semnan province) at altitudes of 2800, 2450, 1750, -11, and 2056 m above sea level, respectively. Shade-dried plant materials were subjected to hydrodistillation using a Clevenger-type apparatus. Essential oil content was calculated on a weight/weight (%) basis. After essential oil extraction, 100 ml of hydrosol was collected for fractionation using 100 ml ethyl acetate, performed in three replicates. The percentage of the organic fraction was calculated as weight/volume (grams per 100 ml of hydrosol). Essential oil composition was analyzed using gas chromatography/mass spectrometry (GC/MS) and quantified by GC-FID.
Results: The essential oil yields for all samples were 0.15%, 0.11%, 0.37%, 0.10%, and 0.12% w/w for GN, DL, RZ, BO, and RA, respectively. The main components of E. billardieri essential oils were 2,3,6-trimethylbenzaldehyde (18.8%, 16.8%, 12.3%), sesquicineole (31.3%, 28.8%, 40.5%), and β-bisabolenal (9.2%, 13.8%, 7.3%) for GN, DL, and RZ, respectively. The main components of E. caucasicum essential oils were trans-caryophyllene (20.3% and 26.5%), β-bisabolene (7.4% and 9.8%), β-sesquiphellandrene (30.1% and 20.2%), and cis-falcarinol (16.6% and 23.2%) for RA and BO, respectively. The yields of ethyl acetate fractions were 0.031, 0.012, 0.023, 0.024, and 0.008 g per 100 ml of hydrosol for Of-GN, Of-DL, Of-RZ, Of-BO, and Of-RA, respectively. The main components of these fractions were 2,3,6-trimethylbenzaldehyde (45.5%, 30.2%, 22.9%), sesquicineole (12.0%, 8.1%, 14.6%), 3-methyl-2(5H)-furanone (9.1%, 12.4%, 17.8%), and p-vinyl-guaiacol (11.4%, 14.6%, 12.3%) for Of-GN, Of-DL, and Of-RZ, respectively. For Of-RA and Of-BO, the main components were 3-methyl-2(5H)-furanone (6.7% and 21.8%), trans-β-ocimene (7.8% and 16.8%), p-vinyl-guaiacol (15.2% and 11.6%), and caryophyllene oxide (23.7% and 14.8%), respectively.
Conclusion: By identifying water-soluble and water-insoluble volatile compounds, the relationships between these compounds were clarified. In the fractions of both species, p-vinyl-guaiacol and 3-methyl-2(5H)-furanone were the main compounds, which were not detected even in trace amounts in the essential oils. Additionally, 2,3,6-trimethylbenzaldehyde was observed in the essential oil and organic fractions of both species, with higher content in E. billardieri than in E. caucasicum. Moreover, 2,3,4-trimethylbenzaldehyde was in both the essential oil and organic fraction of E. caucasicum hydrosol but only in the essential oil of E. billardieri.

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Main Subjects

- British Pharmacopoeia, 1988. British Pharmacopoeia. H.M. Stationery Office, London. https://books.google.com/books/about/British_Pharmacopoeia_1988.html?id=tMpKAQAAIAAJ
- Brophy, J.J., Goldsack, R.J., Copeland, L.M. and Palá-Paúl, J., 2003. Essential oil of Eryngium L. species from New South Wales (Australia). Journal of Essential Oil Research, 15(6): 392-397. https://doi.org/10.1080/10412905.2003.9698619
- Darriet, F., Andreani, S., Cian, M.C., Costa, J. and Muselli, A., 2014. Chemical variability and antioxidant activity of Eryngium maritimum L. essential oils from Corsica and Sardinia. Flavour and Fragrance Journal, 29(1): 3-13. https://doi.org/10.1002/ffj.3160
- Hashemabadi, D. and Kaviani, B., 2011. Chemical constituents of essential oils extracted from the leaves and stems of Eryngium caucasicum Trautv. from Iran. Journal of Essential Oil Bearing Plants, 14(6): 693-698. https://doi.org/10.1080/0972060X.2011.10643991
- Hashemabadi, D., Kaviani, B., Erfatpour, M. and Larijani, K., 2010. Comparison of essential oils compositions of eryngo (Eryngium caucasicum Trautv.) at different growth phases by hydrodistillation method. Plant Omics Journal, 3(4): 135-139. https://www.pomics.com/hashemabadi_3_4_2010_135_139.pdf
- Judd, W.S., Campbell, C.S., Kellogg, E.A., Stevens, P.F. and Donoghue, M.J., 2007. Plant Systematics: A Phylogenetic Approach. Sinauer Associate Inc, 3rd edition Publishers, Sunderland Massachusetts U.S.A., 611p. https://doi.org/10.1111/j.1096-0031.2008.00212.x
- Küpeli, E., Kartal, M., Aslan, S. and Yesilada, E., 2006. Comparative evaluation of the anti-inflammatory and antinociceptive activity of Turkish Eryngium species. Journal of Ethnopharmacology, 107(1): 32-37. https://doi.org/10.1016/j.jep.2006.02.005
- Landoulsi, A., Roumy, V., Duhal, N., Skhiri, F.H., Rivière, C., Sahpaz, S. and Hennebelle, T., 2016. Chemical composition and antimicrobial activity of the essential oil from aerial parts and roots of Eryngium barrelieri Boiss. and Eryngium glomeratum Lam. from Tunisia. Chemistry & Biodiversity, 13(12): 1720-1729. https://doi.org/10.1002/cbdv.201600136
- Mahmoudi, A., Ebadi, M.T. and Ayyari, M., 2020. Aerial parts volatile components of three different accessions of Eryngium thyrsoideum Boiss. from Iran. Iranian Journal of Medicinal and Aromatic Plants, 36(2): 245-258. https://doi:10.30495/ejmp.2023.702346
- Mahmoudi, A., Ebadi, M.T. and Ayyari, M., 2024. Qualitative changes of Blue eryngo (Eryngium planum L.) phytochemicals as affected by different drying methods. Journal of Applied Research on Medicinal and Aromatic Plants, 40: 100543. https://doi.org/10.1016/j.jarmap.2024.100543
- Mahmoudi, A., Ebadi, M.T. and Ayyari, M., 2022. Comparison of the essential oils of medicinal plant populations of Eryngium noeanum Boiss. and Eryngium iranicum Mozaff. in Iran. Eco-phytochemical Journal of Medicinal Plants, 11(1): 49-64. https://doi: 10.30495/ejmp.2023.702346
- Marcetic, M., Petrovic, S., Milenkovic, M., Vujisic, L., Tesevic, V. and Niketic, M., 2014. Composition and antimicrobial activity of root essential oil of Balkan endemic species Eryngium palmatum. Chemistry of Natural Compounds, 49(6): 1140-1142. https://doi.org/10.1007/s10600-014-0843-x
- Merghache, D., Boucherit-Otmani, Z., Merghache, S., Chikhi, I., Selles, C. and Boucherit, K., 2014. Chemical composition, antibacterial, antifungal and antioxidant activities of Algerian Eryngium tricuspidatum L. essential oil. Natural Product Research, 28(11): 795-807. https://doi.org/10.1080/14786419.2014.883392
- Mozaffarian, V., 2012. Identification of Medicinal and Aromatic plants of Iran. Farhang Moaser Press, Iran, 1350p. (In persian) https://www.gisoom.com/book/11131259/
- Mozaffarian, V., 2008. Iranian Flora, Umbelliferae. Research Institute of Forests and Ranglands, Iran, 596p. (In persian). https://www.gisoom.com/book/1444803/
- Mozaffarian, V., 2013. Two new species and two new records of Apiaceae from Iran. Rostaniha, 14(1): 36-42. https://doi.org/10.22092/botany.2013.101307
- Nejadhabibvash, F., Rezaee, M.B., Mahmudi, A. and Jaimand, K., 2018. Effect of harvesting time on content and chemical composition of essential oil from Stachys lavandulifolia Vahl. (Lamiaceae). Journal of Medicinal Plants and By-products, 7(2): 181-187. https://doi.org/10.22092/jmpb.2018.118146
- Motalledi Riekandeh, S.M., Mazandarani, M., Ebrahimzadeh, M.A. and Zargari, M., 2016. Antioxidant activities of Eryngium caucasicum inflorescence. European Review for Medical and Pharmacological Sciences, 20(5): 946-949. https://www.europeanreview.org/wp/wp-content/uploads/946-949.pdf
- Roshanravan, N., Asgharian, P., Dariushnejad, H., Alamdari, N.M., Mansoori, B., Mohammadi, A., Alipour, S., Barati, M., Ghavami, A., Ghorbanzadeh, V., Aamazadeh, F. and Ostadrahimi, A., 2018. Eryngium billardieri induces apoptosis via bax gene expression in pancreatic cancer cells. Advanced Pharmaceutical Bulletin, 8(4): 667. https://doi.org/10.15171/apb.2018.075
- Santos-Gomes, P.C. and Fernandes-Ferreira, M., 2001. Organ-and season-dependent variation in the essential oil composition of Salvia officinalis L. cultivated at two different sites. Journal of Agricultural and Food Chemistry, 49(6): 2908-2916. https://doi.org/10.1021/jf001102b
- Sefidkon, F., Dabiri, M. and Alamshahi, A., 2004. Chemical composition of the essential oil of Eryngium billardieri F. Delaroche from Iran. Journal of Essential Oil Research, 16(1): 42-43. https://doi.org/10.1080/10412905.2004.9698648
- Sepanlou, M.G., Ardakani, M.M., Hajimahmoodi, M., Sadrai, S., Amin, G.R., Sadeghi, N. and Lamardi, S.N.S., 2019. Ethnobotanical and traditional uses, phytochemical constituents and biological activities of Eryngium species growing in Iran. Traditional Medicine Research, 4(3): 148-159. https://doi.org/10.12032/TMR20190412114
- Singh, V. and Jain, D.K., 2007. Taxonomy of Angiosperms. Rastogi publications, India, 298p. https://uou.ac.in/sites/default/files/slm/BOT(N)-201.pdf
- Thiem, B., Kikowska, M., Kurowska, A. and Kalemba, D., 2011. Essential oil composition of the different parts and in vitro shoot culture of Eryngium planum L. Molecules, 16(8): 7115-7124. https://doi:10.3390/molecules16087115
- Thomas, P., Essien, E., Ntuk, S. and Choudhary, M., 2017. Eryngium foetidum L. essential oils: chemical composition and antioxidant capacity. Medicines, 4(2): 24. https://doi:10.3390/medicines4020024
- Wang, P., Su, Z., Yuan, W., Deng, G. and Li, S., 2012. Phytochemical constituents and pharmacological activities of Eryngium L. (Apiaceae). Pharmaceutical Crops, 3: 99-120. http://dx.doi.org/10.2174/2210290601203010099
- Wörz, A. and Diekmann, H., 2010. Classification and evolution of the genus Eryngium L. (Apiaceae-Saniculoideae): results of fruit anatomical and petal morphological studies. Plant Diversity and Evolution, 128(3-4): 387-408. https://doi.org/10.1127/1869-6155/2010/0128-0018
- Wörz, A., 2005. A new subgeneric classification of the genus Eryngium L. (Apiaceae, Saniculoideae). Botanische Jahrbücher für Systematik, Pflanzengeschichte und Pflanzengeographie, 126(2): 253-259. https://doi.org/10.1127/0006-8152/2005/0126-0253
- Yesilada. E., Tanaka. S., Tabata, M. and Sezik, E., 1989. The anti-inflammatory activity of the fractions from Eryngium billardieri in mice. Phytotherapy Research, 3(1): 38-40. https://doi.org/10.1002/ptr.2650030111
- Zargari, A., 1996. Medicinal Plants. University of Tehran Press, Iran, 976p. https://heremap.dm3.ir/content/3388