Chemical compositions of essential oils, antimicrobial effect and antioxidant activity studies of Hyoscyamus niger L. from Türkiye

Abstract

This study investigated the essential oil components of Hyoscyamus niger L. and their antimicrobial and antioxidant properties. Essential oils were extracted separately from the aerial parts and seeds of the plant using the hydrodistillation method. Antimicrobial activity was evaluated using the disk diffusion method, while antioxidant activity was assessed by measuring the total antioxidant status (TAS), total oxidant status (TOS), and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging capacity. The primary essential oil components of the aerial parts were identified as phytol (52.09%) and hexahydrofarnesyl acetone (19.66%). Hydrodistillation of the seeds yielded 0.7% (v/w) yellow oils, comprising 41 components that accounted for 99.0% of the oil. The major components in the seed oils were hexahydrofarnesyl acetone (46.36%) and hexanal (9.05%). Methanol extracts of the aerial parts demonstrated inhibitory effects on pathogenic microorganisms, with inhibition zones ranging from 13±0.46 to 32±0.11 mm. The TAS and TOS values of the methanol extracts were calculated as 3.77±0.0 mmol and 6.94±0.0 μmol, respectively. The DPPH radical scavenging activity increased with rising extract concentrations. These findings highlight the potential antimicrobial and antioxidant applications of H. niger essential oils and methanol extracts.

Keywords

• Antimicrobial and Antioxidant activity
• Essential oil composition
• Hyoscyamus niger L.
• Türkiye

References

1. Akbaş, P., Uslu, H., Uslu, G.A., & Alkan, H. (2020). Investigation of the Antimicrobial and Apoptotic Efficacy of Hyoscyamus reticulatus L. Seed Extract. Süleyman Demirel University Journal of Natural and Applied Sciences, 24(2), 317 322. https://doi.org/10.19113/sdufenbed.631074
2. Ayari-Guentri, S., Djemouai, N., Gaceb-Terrak, R., & Rahmania, F. (2017). Chemical Composition and Antioxidant Activity of Hyoscyamus muticus L. subsp. falezlez (Coss.) Maire from Algeria. Journal of Essential Oil Bearing Plants, 20(5), 1370-1379. https://doi.org/10.1080/0972060x.2017.1396930
3. Balogun, O.S., Ajayi, O.S., & Adeleke, A.J. (2017). Hexahydrofarnesyl acetone-rich extractives from Hildegardia barteri. Journal of Herbs, Spices & Medicinal Plants, 23(4), 393-400. https://doi.org/10.1080/10496475.2017.1350614
4. Benhouda, A., Yahia, M., Benhouda, D., Bousnane, N.E., Benbia, S., Hannachi, N.E., & Ghecham, A. (2014). Antimicrobial and antioxidant activities of various extracts of Hyoscyamus albus L. and Umbilicus rupestris L. leaves. Algerian journal of natural products, 2(1), 4-17. https://doaj.org/article/93eed476c2f343fca25d2619cc26d186
5. Chalabian, F., Majd, A., Mehrabian, S., & Falahian, F. (2002). A study of growth inhibitory effect of alkaloids of two species of genus Hyoscyamus on some kinds of microbes of skin. Journal of Sciences, 12(43), 3371 3378. https://www.sid.ir/paper/70539/en
6. Collins, C.H., & Lyne, P.M. (2004). Collins and Lyne’s microbiological methods (8th ed.). Arnold.
7. Cuendet, M., Hostettmann, K., Potterat, O., & Dyatmiko, W. (1997). Iridoid Glucosides with Free Radical Scavenging Properties from Fagraea blumei. Helvetica Chimica Acta, 80(4), 1144-1152. https://doi.org/10.1002/hlca.19970800411
8. de Moraes, J., de Oliveira, R.N., Costa, J.P., Junior, A.L.G., de Sousa, D.P., Freitas, R.M., … Pinto, P.L.S. (2014). Phytol, a Diterpene Alcohol from Chlorophyll, as a Drug against Neglected Tropical Disease Schistosomiasis Mansoni. PLOS Neglected Tropical Diseases, 8(1), e2617. https://doi.org/10.1371/journal.pntd.0002617

9. Demirpolat, A. (2023). Essential oil composition analysis, antimicrobial activities, and biosystematic studies on six species of Salvia. Life, 13(3), 634. https://doi.org/10.3390/life13030634
10. Dehghan, E., Häkkinen, S.T., Oksman-Caldentey, K.M., & Ahmadi, F.S. (2012). Production of tropane alkaloids in diploid and tetraploid plants and in vitro hairy root cultures of Egyptian henbane (Hyoscyamus muticus L.). Plant Cell, Tissue and Organ Culture, 110(1), 35-44. https://doi.org/10.1007/s11240-012-0127-8
11. Dulger, B., Goncu, B.S., & Gucin, F. (2010a). Antibacterial activity of the seeds of Hyoscyamus niger L. (Henbane). Asian Journal of Chemistry, 22(9), 6879-6883.
12. Dulger, B., Hacioglu, N., Goncu, B.S., & Gucin, F. (2010b). Antifungal activity of seeds of Hyoscyamus niger L. (Henbane) against some clinically relevant fungal pathogens. Asian Journal of Chemistry, 22(8), 6321-6324.
13. Dulger, G., & Dulger, B. (2015). Antimicrobial activity of the seeds of Hyoscyamus niger L. (Henbane) on microorganisms isolated from urinary tract infections. Journal of Medicinal Plants Studies, 3(5), 92-95.
14. Elsharkawy, E.R., Ed-dra, A., Abdallah, E.M., & Ali, A.M.H. (2018). Antioxidant, antimicrobial and antifeedant activity of phenolic compounds accumulated in Hyoscyamus muticus L.. African Journal of Biotechnology, 17(10), 311 321. https://doi.org/10.5897/AJB2017.16316
15. Erel, O. (2004). A novel automated direct measurement method for total antioxidant capacity using a new generation, more stable ABTS radical cation. Clinical Biochemistry, 37(4), 277- 285. https://doi.org/10.1016/j.clinbiochem.2003.11.015
16. Erel, O. (2005). A new automated colorimetric method for measuring total oxidant status. Clinical Biochemistry, 38(12), 1103 1111. https://doi.org/10.1016/j.clinbiochem.2005.08.008
17. Filipowicz, N., Kaminski, M., & Kurlenda, J. (2003). Antibacterial and antifungal activity of Juniper berry oil and its selected components. Phytotherapy Research, 17, 227–231. https://doi.org/10.1002/ptr.1110
18. Guha, S., & Maheshwari, S.C. (1966). Cell division and differentiation of embryos in the pollen grains of Datura in vitro. Nature, 212, 97–98. https://doi.org/10.1038/212097a0
19. Haas, L.F. (1995). Hyoscyamus niger L. (henbane). Journal of Neurology, Neurosurgery and Psychiatry, 59, 114. https://doi.org/10.1136/jnnp.59.2.114
20. Hajipoor, K., Sani, A.M., & Mohammad, A. (2015). In vitro antioxidant activity and phenolic profile of Hyoscyamus niger. International Journal of Biology, Pharmacy and Allied Sciences, 4(7), 4882-4890.
21. Hossain, M.A., & Al-Touby, S.S.J. (2021). A phytopharmacological review on an important indigenous medicinal plant Hyoscyamus gallagheri. Arabian Journal of Medicinal & Aromatic Plants, 3, 367.
22. Jassbi, A.R., Miri, R., Masroorbabanari, M., Asadollahi, M., Attarroshan, M., & Baldwin, I.T. (2014). HPLC-DAD-ESIMS analyses of Hyoscyamus niger and H. reticulatus for their antioxidant constituents. Austin Chromatography, 1(5), 1022-1027.
23. John, H., Binder, T., Höchstetter, H., & Thiermann, H. (2010). LC-ESI MS/MS quantification of atropine and six other antimuscarinic tropane alkaloids in plasma. Analytical and Bioanalytical Chemistry, 396(2), 751 763. https://doi.org/10.1007/s00216-009-3209-7
24. Kareem, Z.J. (2020). Biomedical applications and secondary metabolite profiling of Hyoscyamus niger and Sesamum indicum seed, root and hairy root cultures [Doctoral dissertation, Georg August Universität Göttingen]. 630. http://dx.doi.org/10.53846/goediss-8301
25. Kirby, A.J., & Schmidt, R.J. (1997). The antioxidant activity of Chinese herbs for eczema and of placebo herbs I. Jounal of Ethnopharmacology, 56(2), 103 108. https://doi.org/10.1016/s0378-8741(97)01510-9
26. Koçpınar, E.F. (2020). Antioxidant behavior of Hyoscyamus niger having narcotic effect on heavy metal reduction and radical scavenging. Journal of Physical Chemistry and Functional Materials, 3(2), 68-71.
27. Kosari, M., Noureddini, M., Khamechi, S.P., Najafi, A., Ghaderi, A., Sehat, M., & Banafshe, H.R. (2021). The effect of propolis plus Hyoscyamus niger L. methanolic extract on clinical symptoms in patients with acute respiratory syndrome suspected to COVID 19: A clinical trial. Phytotherapy Research, 35, 4000 4006. https://doi.org/10.1002/ptr.7116
28. Küpeli Akkol, E., Ilhan, M., Kozan, E., Gürağaç Dereli, F.T., Sak, M., & Sobarzo-Sánchez, E. (2020). Insecticidal activity of Hyoscyamus niger L. on Lucilia sericata causing myiasis. MDPI Plants (Basel), 22, 9(5), 655. https://doi.org/10.3390/plants9050655
29. Li, J., Shi, J., Yu, X.W., & Sun Jk, Q.M. (2011). Chemical and pharmacological researches on Hyoscyamus niger. Chinese Herbal Medicine, 3, 117 126. https://doi.org/10.3969/j.issn.1674-6384.2011.02.006
30. Maiti, R.K., Cerda, V., Villarreal, R., & Treviño, V. (2002). Some aspects on pharmacognosy of ten species of the family Solanaceae utiliz. Caldasia, 24(2), 317-321.
31. Mateen, A., Tanveer, Z., Janardhan, K., & Gupta, V.C. (2015). Screening and purification of antibacterial proteins and peptides from some of the medicinal plants seeds. International Journal of Pharma and Bio Sciences, 6(4), 774-781.
32. Moradi, H., Ghavam, M., & Tavili, A. (2020). Study of antioxidant activity and some herbal compounds of Dracocephalum kotschyi Boiss. in different ages of growth. Biotechnology Reports, 25, e00408. https://doi.org/10.1016/j.btre.2019.e00408
33. Orbak, Z., Hüseyin, T.A.N., Karakelleoğlu, C., Handan, A.L.P., & Akdag, R. (1998). Hyoscyamus niger (Henbane) poisonings in the rural area of east Turkey. Headache, 14, 6-5.
34. Pudersell, K., Vardja, T., Vardja, R., Matto, V., Arak, E., & Raal, A. (2012). Inorganic ions in the medium modify tropane alkaloids and riboflavin output in Hyoscyamus niger root cultures. Pharmacognosy Magazine, 8(29), 73 79. https://doi.org/10.4103/0973-1296.93330
35. Radulovic, N., Stojanovic, G., & Palic, R. (2006). Composition and antimicrobial activity of Equisetum arvense L. essential oil. Phytotherapy Research, 20, 85 88. https://doi.org/10.1002/ptr.1815
36. Tanker, N., Koyuncu, M., & Coşkun, M. (1998). Farmasötik botanik [Pharmaceutical botany]. Ankara Üniversitesi Eczacılık Fakültesi Yayınları, Ders Kitapları.
37. Ting-guo, K. (2013). Analysis of volatile oil in processed samples of seeds of Hyoscyamus niger with GC MS. Chinese Archives of Traditional Chinese Medicine, https://www.semanticscholar.org/paper/Analysis-of-Volatile-Oil-in-Processed-Samples-of-of-Ting-guo/a4bb424ed36905a988d3bd83a285db534788eaec
38. Ugur, D. (2013). Investigation of sitotoxic effects of certain medically used plants on cancer cells [Unpublished Master Thesis, Muğla Sıtkı Koçman University]. 343631. https://tez.yok.gov.tr/UlusalTezMerkezi/tezSorguSonucYeni.jsp
39. Wang, Z., Zhou, J., & Li, W. (2006). Insecticidal activity of extracts from plant recourses in Xinjiang. Modern Agrochemicals, 5(5), 34-42.
40. Wei, G., Kong, L., Zhang, J., Ma, C., Wu, X., Li, X., & Jiang, H. (2016). Essential oil composition and antibacterial activity of Lindera nacusua (D. Don) Merr. Natural Product Research, 30(23), 2704 2706. https://doi.org/10.1080/14786419.2015.1135145
41. Yücel, U.M., & Yılmaz, O. (2014). Total alkaloid amounts of two Hyoscyamus species (Henbane) grown in Van region. Van Veterinary Journal, 25(3), 77-80.