Screening of volatiles of Allium tripedale Trautv. and evaluation of the biological activities of its methanol extract
محورهای موضوعی : Essential Oils: Classical and Advanced Techniques for Isolation and Biological Activities
Majid Mohammadhosseini
1
(Department of Chemistry, College of Basic Sciences, Shahrood Branch, Islamic Azad University, Shahrood, Iran)
Behnam Mahdavi
2
(Department of Chemistry, College of Basic Sciences, Shahrood Branch, Islamic Azad University, Shahrood, Iran)
Mousa Gholami
3
(Department of Chemistry, College of Basic Sciences, Shahrood Branch, Islamic Azad University, Shahrood, Iran)
کلید واژه: Allium tripedale Trautv., Antibacterial, Antioxidant, Experimental Design, Headspace-Solid Phase Microextraction (HS-SPME), Soxhelt,
چکیده مقاله :
In this report, the volatile profiles from the flowers, leaves, stems and roots of Allium tripedale Trautv. have been characterized using headspace solid phase microextraction (HS-SPME) coupled to gas chromatography-mass spectrometry (GC/MS). Accordingly, high quantities of non-terpene hydrocarbons have been identified as the major constituting groups of all the relevant chemical profiles. The impact of the experimental variables has also been optimized using Design-Expert software. In addition, antioxidant and antibacterial properties of the methanol extract of the plant material have been determined. The results of this study revealed that this plant can be considered a potent antioxidant and antibacterial agent, serving as an alternative to chemical drugs.
In this report, the volatile profiles from the flowers, leaves, stems and roots of Allium tripedale Trautv. have been characterized using headspace solid phase microextraction (HS-SPME) coupled to gas chromatography-mass spectrometry (GC/MS). Accordingly, high quantities of non-terpene hydrocarbons have been identified as the major constituting groups of all the relevant chemical profiles. The impact of the experimental variables has also been optimized using Design-Expert software. In addition, antioxidant and antibacterial properties of the methanol extract of the plant material have been determined. The results of this study revealed that this plant can be considered a potent antioxidant and antibacterial agent, serving as an alternative to chemical drugs.
Adhikari, D., Rangra, N., 2023. Antimicrobial activities of Acacia genus: A review. Asian Pac. J. Trop. Biomed. 13(2), 45-59.
Aggarwal, G., Sharma, M., Singh, R., Sharma, U., 2024. Ethnopharmacologically important highly subsidized Indian medicinal plants: Systematic review on their traditional uses, phytochemistry, pharmacology, quality control, conservation status and future prospective. J. Ethnopharmacol. 320, doi: 10.1016/j.jep.2023.117385.
Al-Kubeisi, A.K., 2022. Evaluation of antibacterial activity of aqueous and alcohol extracts of Zingiber officinale and Allium sativum on bacterial isolates from urinary tract infection patients. Int. J. Drug Deliv. Technol. 12(4), 1751-1756.
AlAgha, I., Elshawa, A., Alhayek, G., Ghabayen, M., Alkhattib, R., 2023. PalAST: A cross-platform mobile application for automated disk diffusion antimicrobial susceptibility testing. Int. J. Interact. Mob. Technol. 17(22), 85-99.
Amalia, N., Okta, F.N., Zahra, A.A., Nuari, D.A., 2024. Update review: Extraction, purification, and pharmacological activities of Gotu Kola terpenoids. Lett. Appl. NanoBioSci. 13(1), doi: 10.33263/LIANBS131.006.
Anusha, K., Balakrishnan, S., Sindhu, S., Hariram, S.B., 2014. Screening the metal chelating efficacy of Trichodesma Indicum. Res. J. Pharm., Biol. Chem. Sci. 5(2), 1259-1262.
Arment, S., 1999. Automated soxhlet extraction. LC GC: Liquid Chromatography, Gas Chromatography 17(6 SUPPL.), S38-S42.
Atkinson, A.C., Riani, M., Corbellini, A., 2021. The Box–Cox transformation: Review and extensions. Stat. Sci. 36(2), 239-255.
Ayala, A., Munoz, M.F., Arguelles, S., 2014. Lipid peroxidation: Production, metabolism, and signaling mechanisms of malondialdehyde and 4-hydroxy-2-nonenal. Oxid. Med. Cell. Longev. 2014, 360438.
Bhaskaracharya, R.K., Kentish, S., Ashokkumar, M., 2009. Selected applications of ultrasonics in food processing. Food. Eng. Rev. 1(1), 31-49.
Biancolillo, A., Aloia, R., Rossi, L., D'Archivio, A.A., 2022. Organosulfur volatile profiles in Italian red garlic (Allium sativum L.) varieties investigated by HS-SPME/GC-MS and chemometrics. Food Control 131, doi: 10.1016/j.foodcont.2021.108477.
Bienvenu, A.L., Leboucher, G., Picot, S., 2019. Comparison of fks gene mutations and minimum inhibitory concentrations for the detection of Candida glabrata resistance to micafungin: A systematic review and meta-analysis. Mycoses 62(9), 835-846.
Biscay Lirio, R., Valdés Sosa, P.A., Pascual Marqui, R.D., Jiménez-Sobrino, J.C., Alvarez Amador, A., Galán Garcia, L., 1989. Multivariate Box-Cox transformations with applications to neurometric data. Comput. Biol. Med. 19(4), 263-267.
Boshra, Y.R., Fahim, J.R., Hamed, A.N.E., Desoukey, S.Y., 2022. Phytochemical and biological attributes of Narcissus pseudonarcissus L. (Amaryllidaceae): A review. S. Afr. J. Bot. 146, 437-458.
Chagas, A.G.D.R., Spinelli, E., Souza, T.M., Pinto Junior, J.A., Pereira Netto, A.D., 2019. Simultaneous determination of alpha-, beta- and gamma-hydroxybutyric acids in micro-pulverized human hair by GC-MS: Method development, validation and application. Talanta 194, 576-584.
Chaudry, A.E., Klausner, J.D., 2021. A narrative review of clinical treatment outcomes of Neisseria gonorrhoeae infection with ciprofloxacin by minimum inhibitory concentration and anatomic site. Sex. Transm. Dis. 48(6), 385-392.
D'Auria, M., Racioppi, R., 2017. HS-SPME-GC-MS analysis of onion (Allium cepa L.) and shallot (Allium ascalonicum L.). Food Res. 1(5), 161-165.
Dadashpour, M., Rasooli, I., Sefidkon, F., Taghizadeh, M., Darvish Alipour Astaneh, S.H., 2011. Comparison of ferrous ion chelating, free radical scavenging and anti tyrosinase properties of Thymus daenensis essential oil with commercial thyme oil and thymol. J. Zanjan Univ. Med. Sci. Health Serv. 19(77), 41-52.
Dalton, B.R., 2023. What is the best vancomycin therapeutic drug monitoring parameter to assess efficacy? A critical review of experimental data and assessment of the need for individual patient minimum inhibitory concentration value. Microorg. 11(3), doi: 10.3390/microorganisms11030567.
Dalton, B.R., Rajakumar, I., Langevin, A., Ondro, C., Sabuda, D., Griener, T.P., Dersch-Mills, D., Rennert-May, E., 2020. Vancomycin area under the curve to minimum inhibitory concentration ratio predicting clinical outcome: A systematic review and meta-analysis with pooled sensitivity and specificity. Clin. Microbiol. Infect. 26(4), 436-446.
Desgagné-Penix, I., 2021. Biosynthesis of alkaloids in Amaryllidaceae plants: A review. Phytochem. Rev. 20(2), 409-431.
Dias, P.G.I., Sajiwanie, J.W.A., Rathnayaka, R.M.U.S.K., Awolu, O.O., 2021. Optimization of composite fruit peel powder as a texture modifier for fat free set yoghurt: A mixture design approach. J. Agri. Sci. Sri. Lanka 16(2), 226-236.
Dreger, M., Adamczak, A., Foksowicz-Flaczyk, J., 2023. Antibacterial and antimycotic activity of Epilobium angustifolium L. extracts: A review. Pharmaceuticals 16(10), doi: 10.3390/ph16101419.
Ebadi, Z., Ghaisari, H., Tajeddin, B., Shekarforoush, S.S., 2022. Evaluation of the properties and antibacterial activity of microchitosan film impregnated with Shirazi thyme (Zataria multiflora) and garlic (Allium sativum) essential oils. Iran. J. Vet. Res. 23(1), 53-60.
El Jabboury, Z., Bentaib, R., Stevanovic, Z.D., Ousaaid, D., Benjelloun, M., El Ghadraoui, L., 2023. Ammi visnaga (L.) Lam.: An overview of phytochemistry and biological functionalities. Trends Phytochem. Res. 7(3), 141-155.
Feyisa, K., Yismaw, M.B., Yehualaw, A., Tafere, C., Demsie, D.G., Bahiru, B., Kefale, B., 2024. Medicinal plants traditionally used to treat human ailments in Ethiopia: A systematic review. Phytomed. Plus 4(1), doi: 10.1016/j.phyplu.2023.100516.
Gangaram, T., Mohan Naidu, G., Balasiddamuni, P., 2014. Some alternative tests for heteroscedasticity using studentized and predicted residuals. Int. J. Agric. Stat. Sci. 10(1), 111-114.
Ghaffari, H., Sadeghi Dinani, M., 2018. Isolation of phenyl propanoid glycosides from Allium tripedale Trautv. J. Rep. Pharm. Sci. 7(2), 116-122.
Ghobadi, S., Dastan, D., Soleimani, M., Nili-Ahmadabadi, A., 2019. Hepatoprotective potential and antioxidant activity of Allium tripedale in acetaminophen-induced oxidative damage. Res. Pharm. Sci. 14(6), 488-495.
Gupta, M., Kumar, A., 2019. Comparison of minimum inhibitory concentration (MIC) value of statin drugs: A systematic review. Anti-Infect. Agents 17(1), 4-19.
Jaillais, B., Cadoux, F., Auger, J., 1999. SPME-HPLC analysis of Allium lacrymatory factor and thiosulfinates. Talanta 50(2), 423-431.
Kalil, A.C., Van Schooneveld, T.C., Fey, P.D., Rupp, M.E., 2014. Association between vancomycin minimum inhibitory concentration and mortality among patients with Staphylococcus aureus bloodstream infections: A systematic review and meta-analysis. JAMA 312(15), 1552-1564.
Keusgen, M., 2011. Volatile Compounds of the Genus Allium L.(Onions), Volatile Sulfur Compounds in Food. ACS Publications, pp. 183-214.
Kim, M.G., 2017. A cautionary note on the use of Cook's distance. Commun. Stat. Appl. Methods 24(3), 317-324.
Kim, N.Y., Park, M.H., Jang, E.Y., Lee, J., 2011. Volatile distribution in garlic (Allium sativum L.) by solid phase microextraction (SPME) with different processing conditions. Food Sci. Biotechnol. 20(3), 775-782.
Kiokias, S., Proestos, C., Oreopoulou, V., 2018. Effect of natural food antioxidants against LDL and DNA oxidative changes. Antioxidants 7(10), 133.
Laksmiani, N.P.L., Vidya Paramita, N.L.P., Wirasuta, I.M.A.G., 2016. In vitro and in silico antioxidant activity of purified fractions from purple sweet potato ethanolic extract. Int. J. Pharmcy Pharm. Sci. 8(8), 177-181.
Lamaison, J., Carnet, A., 1990. Teneurs en principaux flavonoids des fleurs de Crataegeus monogyna Jacq et de Crataegeus laevigata (Poiret D. C) en fonction de la vegetation. Pharm. Acta Helv. 65, 315-320.
Leszczyńska, D., Hallmann, A., Treder, N., Bączek, T., Roszkowska, A., 2024. Recent advances in the use of SPME for drug analysis in clinical, toxicological, and forensic medicine studies. Talanta 270, doi: 10.1016/j.talanta.2023.125613.
Li, F., Yang, W., Yang, M., Wang, Y., Zhang, J., 2024. Differences between two plants fruits: Amomum tsaoko and Amomum maximum, using the SPME-GC–MS and FT-NIR to classification. Arab. J. Chem. 17(4), doi: 10.1016/j.arabjc.2024.105665.
Luque de Castro, M.D., García-Ayuso, L.E., 1998. Soxhlet extraction of solid materials: An outdated technique with a promising innovative future. Anal. Chim. Acta 369(1-2), 1-10.
Luque de Castro, M.D., Priego-Capote, F., 2010. Soxhlet extraction: Past and present panacea. J. Chromatogr. A 1217(16), 2383-2389.
Mahdavi, B., Mohammadhosseini, M., 2022. Antioxidant, antimicrobial and anti-prostate cancer activity of the extracts from different parts of Etlingera velutina (Ridl.) R. M. Sm (Zingiberaceae). Trends Phytochem. Res. 6(4), 353-362.
Martín, N., 2015. Diagnostics in a simple correspondence analysis model: An approach based on Cook's distance for log-linear models. J. Multivariate Anal. 136, 175-189.
Martín, N., Pardo, L., 2009. On the asymptotic distribution of Cook's distance in logistic regression models. J. Appl. Stat. 36(10), 1119-1146.
Mohammadhosseini, M., Jeszka-Skowron, M., 2023. A systematic review on the ethnobotany, essential oils, bioactive compounds, and biological activities of Tanacetum species. Trends Phytochem. Res. 7(1), 1-29.
Morgan, E., 1991. Chemometrics: Experimental Design. John Wiley, London.
Mozuraityte, R., Kristinova, V., Rustad, T., 2016. Encyclopedia of Food and Health. Academic Press Oxford, UK.
Murti, Y., Singh, S., Pathak, K., 2024. Classical Techniques for Extracting Essential Oils from Plants, Essential Oils: Extraction Methods and Applications. Wiley, pp. 795-858.
Najafi, F., Zangeneh, M.M., Tahvilian, R., Zangeneh, A., Amiri, H., Amiri, N., Moradi, R., 2016. In vitro antibacterial efficacy of essential oil of Allium sativum against Staphylococcus aureus. Int. J. Pharmacogn. Phytochem. Res. 8(12), 2039-2043.
Nnamchi, C.I., Okefum, V.E., Amaechi, C.D., Ugwu, K., Nsofor, C.A., 2021. Antibacterial and synergistic effects of extracts of allium cepa, Alium sativum, zingiber officinale and garcinia kola on selected bacterial strains. Trop. J. Nat. Prod. Res. 5(4), 763-771.
Obradović, D., Komsta, Ł., Agbaba, D., 2020. Novel computational approaches to retention modeling in dual hydrophilic interactions/reversed phase chromatography. J. Chromatogr. A 1619.
Ortega-Ramirez, L.A., Silva-Espinoza, B.A., Vargas-Arispuro, I., Gonzalez-Aguilar, G.A., Cruz-Valenzuela, M.R., Nazzaro, F., Ayala-Zavala, J.F., 2016. Combination of cymbopogon citrates and Allium cepa essential oils increased antibacterial activity in leafy vegetables. J. Sci. Food Agric. 97(7), 2166-2173.
Otunola, G.A., Afolayan, A.J., Ajayi, E.O., Odeyemi, S.W., 2017. Characterization, antibacterial and antioxidant properties of silver nanoparticles synthesized from aqueous extracts of Allium sativum, Zingiber officinale, and Capsicum frutescens. Pharmacogn. Mag. 13(50), S201-S208.
Ourouadi, S., Hasib, A., El Mahi, F., 2022. Evaluation of biochemical, antioxidant and antibacterial activities of garlic extracts (Allium sativum. L) grown in five Moroccan eco-regions. Moroc. J. Chem. 10(4), 761-771.
Pandey, A.K., Sara, U.S., 2023. Quality by design approach for optimization of 5-fluorouracil microbeads using box–behnken design and desirability function for colon targeting. J. Pharm. Innov. 18(4), 2054-2065.
Pinho, L.G.B., Nobre, J.S., Singer, J.M., 2015. Cook's distance for generalized linear mixed models. Comput. Stat. Data Anal. 82, 126-136.
Rahn, K., 1998. Alliaceae, Flowering Plants· Monocotyledons: Lilianae (Except Orchidaceae). Springer, pp. 70-78.
Rajasekar, A., Moorthi, M., Deivasigamani, P., Sekar, S., Amar, G., 2023. A Review on Screening, Isolation, and Characterization of Phytochemicals in Plant Materials: Methods and Techniques, Pharmacological Benefits of Natural Agents. IGI Global, pp. 1-12.
Rivera, A., Viñado, B., Benito, N., Docobo-Pérez, F., Fernández-Cuenca, F., Fernández-Domínguez, J., Guinea, J., López-Navas, A., Moreno, M.Á., Larrosa, M.N., Oliver, A., Navarro, F., 2023. Recommendations of the Spanish antibiogram committee (COESANT) for in vitro susceptibility testing of antimicrobial agents by disk diffusion. Enferm. Infecc. Microbiol. Clin. 41(9), 571-576.
Rofouei, M.K., Kojoori, S.M.H., Moazeni-Pourasil, R.S., 2021. Optimization of chlorogenic acid extraction from Elm tree, Ulmus minor Mill., fruits, using response surface methodology. Sep. Purif. Technol. 256, 117773.
Samura, M., Kitahiro, Y., Tashiro, S., Moriyama, H., Hamamura, Y., Takahata, I., Kawabe, R., Enoki, Y., Taguchi, K., Takesue, Y., Matsumoto, K., 2022. Efficacy and safety of daptomycin versus vancomycin for bacteremia caused by methicillin-resistant Staphylococcus aureus with vancomycin minimum inhibitory concentration > 1 microg/mL: A systematic review and meta-analysis. Pharmaceutics 14(4), doi: 10.3390/pharmaceutics14040714.
Sen, T., Samanta, S.K., 2014. Medicinal plants, human health and biodiversity: A broad review. Adv. Biochem. Eng. Biotechnol. 147, 59-110.
Shi, C., Ye, J., Xu, R., Jin, W., Xu, S., Teng, F., Lin, N., 2021. Effect of the vancomycin minimum inhibitory concentration on clinical outcomes in patients with methicillin-susceptible Staphylococcus aureus bacteraemia: A systematic review and meta-analysis. BMJ Open 11(1), e040675.
Singh, D., Mittal, N., Siddiqui, M.H., 2023. A review on pharmacological potentials of phenolic diterpenes carnosic acid and carnosol obtained from Rosmarinus officinalis L. and modern extraction methods implicated in their recovery. Trends Phytochem. Res. 7(3), 156-169.
Singleton, V.L., Orthofer, R., Lamuela-Raventós, R.M., 1999. Analysis of total phenols and other oxidation substrates and antioxidants by means of Folin-Ciocalteu reagent. Methods Enzymol. 299, 152-178.
Stan, M., Popa, A., Toloman, D., Silipas, T.D., Vodnar, D.C., 2016. Antibacterial and antioxidant activities of ZnO nanoparticles synthesized using extracts of Allium sativum, Rosmarinus officinalis and Ocimum basilicum. Acta Metal. Sin. 29(3), 228-236.
Taiyari, H., Faiz, N.M., Abu, J., Zakaria, Z., 2021. Antimicrobial minimum inhibitory concentration of Mycoplasma gallisepticum: A systematic review. J. Appl. Poult. Res. 30(2), doi: 10.1016/j.japr.2021.100160.
Takahashi, M., 2022. A new robust ratio estimator by modified Cook’s distance for missing data imputation. Jpn. J. Stat. Data. Sci. 5(2), 783-830.
Tang, J., Zhu, X., Jambrak, A.R., Sun, D.-W., Tiwari, B.K., 2023. Mechanistic and synergistic aspects of ultrasonics and hydrodynamic cavitation for food processing. Crit. Rev. Food Sci. Nutr., 1-22, doi: 10.1080/10408398.2023.2201834.
Torres, E., Delgado, M., Valiente, A., Pascual, Á., Rodríguez-Baño, J., 2015. Impact of borderline minimum inhibitory concentration on the outcome of invasive infections caused by Enterobacteriaceae treated with β-lactams: A systematic review and meta-analysis. Eur. J. Clin. Microbiol. Infect. Dis. 34(9), 1751-1758.
Van de Vel, E., Sampers, I., Raes, K., 2019. A review on influencing factors on the minimum inhibitory concentration of essential oils. Crit. Rev. Food Sci. Nutr. 59(3), 357-378.
Van Hal, S.J., Lodise, T.P., Paterson, D.L., 2012. The clinical significance of vancomycin minimum inhibitory concentration in Staphylococcus aureus infections: A systematic review and meta-analysis. Clin. Infect. Dis. 54(6), 755-771.
Van Otterlo, W.A.L., Green, I.R., 2018. A review on recent syntheses of amaryllidaceae alkaloids and isocarbostyrils (time period mid-2016 to 2017). Nat. Prod. Comm. 13(3), 255-277.
Wieczorek, M.N., Zhou, W., Jeleń, H.H., Pawliszyn, J., 2024. Automated sequential SPME addressing the displacement effect in food samples. Food Chem. 439, doi: 10.1016/j.foodchem.2023.138093.
Xiang, G., Guo, S., Qin, J., Gao, H., Zhang, Y., Wang, S., 2024. Comprehensive insight into the pharmacology, pharmacokinetics, toxicity, detoxification and extraction of hypaconitine from Aconitum plants. J. Ethnopharmacol. 321, 117505.
Xie, B., Wu, Q., Wei, S., Li, H., Wei, J., Hanif, M., Li, J., Liu, Z., Xiao, X., Yu, J., 2022. Optimization of headspace solid-phase micro-extraction conditions (HS-SPME) and Identification of major volatile aroma-active compounds in Chinese chive (Allium tuberosum Rottler). Molecules 27(8), doi: 10.3390/molecules27082425.
Yerbanga, I.W., Nakanabo Diallo, S., Rouamba, T., Resendiz-Sharpe, A., Lagrou, K., Denis, O., Rodriguez-Villalobos, H., Montesinos, I., Bamba, S., 2023. Performances of disk diffusion method for determining triazole susceptibility of Aspergillus species: Systematic review. J. Med. Mycol. 33(4), doi: 10.1016/j.mycmed.2023.101413.
Yeşilyurt, V., Halfon, B., Öztürk, M., Topçu, G., 2008. Antioxidant potential and phenolic constituents of Salvia cedronella. Food Chem. 108(1), 31-39.
Yin, J., Wu, T., Zhu, B., Cui, P., Zhang, Y., Chen, X., Ding, H., Han, L., Bie, S., Li, F., Song, X., Yu, H., Li, Z., 2024. Comprehensive multicomponent characterization and quality assessment of Xiaoyao Wan by UPLC-Q-Orbitrap-MS, HS-SPME-GC-MS and HS-GC-IMS. J. Pharm. Biomed. Anal. 239, doi: 10.1016/j.jpba.2023.115910.
Zabihi, A., Akhondzadeh Basti, A., Amoabediny, G., Khanjari, A., Tavakkoly Bazzaz, J., Mohammadkhan, F., Hajjar Bargh, A., Vanaki, E., 2017. Physicochemical characteristics of nanoliposome garlic (Allium sativum L.) Essential Oil and its antibacterial effect on Escherichia coli O157:H7. J. Food Qual. Hazards Control 4(1), 24-28.
Zeaiter, M., Roger, J.M., Bellon-Maurel, V., Rutledge, D.N., 2004. Robustness of models developed by multivariate calibration. Part I: The assessment of robustness. TrAC Trends Anal. Chem. 23(2), 157-170.
Zhang, C., Wang, Y., Ding, D., Su, J., Zhao, Z., 2022a. Volatile profiles of Allium tenuissimum L. flower fried by four different oils, using SPME–GC–MS, and sensory evaluation coupled with partial least squares regression. J. Food Compos. Anal. 109, doi: 10.1016/j.jfca.2022.104461.
Zhang, S., Hou, Q., Fu, Z., Jiang, H., 2022b. Multi-response optimization of thermal cycling process for Al6092/SiC/ZrW2O8 composites using RSM-MOGA. Arab. J. Sci. Eng. 47(6), 7669-7682.
