Release behavior and kinetic analysis of eugenol from clove particles using P&T–GC-MS method
Main Article Content
Keywords
clove, eugenol, kinetic equation, P&T–GC-MS, release behavior
Abstract
In this study, the release behavior and kinetic characteristics of eugenol from clove particles under different temperatures were investigated by using purge and trap and gas chromatography–mass spectrometry (P&T–GC-MS) method. The results showed that the established P&T–GC-MS method could efficiently determine eugenol content in clove particles. The high temperature could promote the release of eugenol in the early stages of heating, while low temperature delayed the time to reach the maximum ratio. Kinetic analysis showed that the release behavior of eugenol at different temperatures was consistent with the first-order release model. The release activation energy for eugenol was calculated as 58.29 kJ/mol by using the Arrhenius equation.
References
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Golmakani, M.T., Zare, M. and Razzaghi, S. 2017. Eugenol enrichment of clove bud essential oil using different microwave-assisted distillation methods. Food Sci Technol Res. 23(3): 385–394. 10.3136/fstr.23.38
Guan, W., Li, S., Yan, R., Tang, S. and Quan, C. 2006. Comparison of essential oils of clove buds extracted with supercritical carbon dioxide and other three traditional extraction methods. Food Chem. 101(4): 1558–1564. 10.1016/j.foodchem.2006.04.009
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Gürbüz, M. and İrem O.K.B. 2022. The anti-campylobacter activity of eugenol and its potential for poultry meat safety: a review. Food Chem. 394: 133519. 10.1016/j.foodchem.2022.133519
Huang, K., Xu, K.J., Chen, K., Liang, M., Yang, J.C. and Zhang, J.S. 2022. Analysis of the release behavior of limonene in tangerine pee based on P&T-GC/MS. J Chinese Institute Food Sci Technol. 22(05): 309–319. 10.16429/j.1009-7848.2022.05.033
Irovetz, L., Buchbauer, G., Stoilova, I., Stoyanova, A., Krastanov, A. and Schmidt, E. 2006. Chemical composition and antioxidant properties of clove leaf essential oil. J Agric Food Chem. 54(17): 6303–6307. 10.1021/jf060608c
Jing, B., Shirley, M.B., Renee, M.G.S., Naim, M. and Paul, J.S. 2019. Aroma profile characterization of mahi-mahi and tuna for determining spoilage using purge and trap gas chromatography-mass spectrometry. J Food Sci. 84(3): 481–489. 10.1111/1750-3841.14478
Ju, J., Xie, Y., Yu, H., Guo, Y., Cheng, Y., Qian, H. and Yao, W. 2020. A novel method to prolong bread shelf life: sachets containing essential oils components. LWT 131: 109744. 10.1016/j.lwt.2020.109744
Kanavouras, A., Kiritsakis, A. and Hernandez, R.J. 2005. Comparative study on volatile analysis of extra virgin olive oil by dynamic head-space and solid phase micro-extraction. Food Chem. 90(1–2): 69–79. 10.1016/j.foodchem.2004.03.025
Konteles, S.J., Strati, I.F., Giannakourou, M., Batrinou, A., Papadakis, S., Ourailoglou, D., Zoumpoulakis, P. and Sinanoglou, V.J. 2022. Instant herbal powder: functionality assessment through chemical, microbiological and shelf life kinetics. Anal Lett. 55(9): 1505–1516. 10.1080/00032719.2021.2011897
Lukasz, M., Marjorie, G.W., Santiago, R.R., Erik, H., William, T.W. and Thomas, E. 2016. Olfactory specialization for perfume collection in male orchid bees. J Exp Biol. 219(10): 1467–1475. 10.1242/jeb.136754
Moemenbellah-Fard, M.D., Abdollahi, A., Ghanbariasad, A. and Osanloo, M. 2020. Antibacterial and leishmanicidal activities of Syzygium aromaticum essential oil versus its major ingredient, eugenol. Flavour Fragr J. 35(5): 534–540. 10.1002/ffj.3595
Moneera, O.A. 2022. Physicochemical, nutritional, and sensory quality and storage stability of cookies: effect of clove powder. Int J Food Prop. 25(1): 1009–1020. 10.1080/10942912.2022.2071290
Nabor, H.J., Adolfo, C.G., Moisés, M. and Hugo, E. 2021. Clove essential oil (Syzygium aromaticum L. Myrtaceae): extraction, chemical composition, food applications, and essential bioactivity for human health. Molecules 26(21): 6387. 10.3390/molecules26216387
Orlo, E., Russo, C., Nugnes, R., Lavorgna, M. and Isidori, M. 2021. Natural methoxyphenol compounds: antimicrobial activity against food borne pathogens and food spoilage bacteria, and role in antioxidant processes. Foods 10(8): 1807. 10.3390/foods10081807
Riyandari, B.A., Suherman, S. and Siswanta, D. 2018. The physico-mechanical properties and release kinetics of eugenol in chitosan-alginate polyelectrolyte complex films as active food packaging. Indones J Chem. 18(1). 10.22146/ijc.26525
Shan, B., Cai, Y,Z., Brooks, J.D. and Corke, H. 2011. Potential application of spice and herb extracts as natural preservatives in cheese. J Med Food. 14(3): 284–290. 10.1089/jmf.2010.0009
Shen, J., Xu, T., Shi, C., Cheng, T., Wang, J., Pan, H. and Zhang, Q. 2017. Obtainment of an intergeneric hybrid between Forsythia and Abeliophyllum. Euphytica. 213(4). 10.1007/s10681-017-1880-x
Sevindik, O., Amanpour, A., Sarhir, S.T., Kelebek, H. and Selli, S. 2019. Characterization of key odorants in Moroccan argan oil by aroma extract dilution analysis. Eur J Lipid Sci Tech. 121(5): 1800437. 10.1002/ejlt.201800437
Sueishi, Y. and Nii, R. 2019. Comparative profiling of clove extract and its component antioxidant activities against five reactive oxygen species using multiple free radical scavenging. Food Sci Technol Res. 25: 885–890. 10.3136/fstr.25.885
Taleuzzaman, M., Jain, P., Verma, R., Iqbal, Z. and Mirza, M.A. 2021. Eugenol as a potential drug candidate: a review. Curr Top Med Chem. 21: 1804–1815. 10.2174/1568026621666210701141433
Tamaru, S., Ono, A., Igura, N. and Shimoda, M. 2019. High correlation between octanol-air partition coefficient and aroma release rate from O/W emulsions under non-equilibrium. Food Res Int. 116: 883–887. 10.1016/j.foodres.2018.09.024
Yang, J., Kuang, X., Li, B., Zhou, B., Li, J., Cui, B. and Ma, M. 2012. Study on release mechanism of inhibitory components from cinnamon and clove powders. J Food Safety. 32(2): 189–197. 10.1111/j.1745-4565.2012.00367.x
Yassin, M.T., Al-Askar, A.A. and Mostafa, A.A.F. 2020. Bioactivity of Syzygium aromaticum (L.) Merr. & L.M. Perry extracts as potential antimicrobial and anticancer agents. J King Saud Univ Sci. 32: 3273–3278. 10.1016/j.jksus.2020.09.009
Yasuhiko, H. and Fujii, Y. 2011. HPLC-UV analysis of eugenol in clove and cinnamon oils after pre-column derivatization with 4-fluoro-7-nitro-2,1,3-benzoxadiazole. J Liq Chromatogr R.T. 34(1): 18–25. 10.1080/10826076.2011.534689
Yun, S.M., Lee, M.H., Lee, K.J., Ku, H.O., Son, S.W. and Joo, Y.S. 2010. Quantitative analysis of eugenol in clove extract by a validated HPLC method. J AOAC Int. 93: 1806–1810. 10.1093/jaoac/93.6.1806
Zanin, R., Smrke, S., Kurozawa, L. E., Yamashita, F., and Yeretzian, C. 2020. Novel experimental approach to study aroma release upon reconstitution of instant coffee products. Food Chem. 317: 126455. 10.1016/j.foodchem.2020.126455
Zhu, M., Hu, Z., Liang, M., Song, L., Wu, W., Li, R., Li, Z. and Zhang, J. 2022. Evaluation of the flavor compounds of Pleurotus eryngii as affected by baking temperatures using HS-SPME-GC–MS and electronic nose. J Food Process Pres. 46(11): e17056. 10.1111/jfpp.17056
Ana, Ć., Đorđe, M., Bojan, Č., Vladimir, D., Milena, R., Tanja, B., Anđelija, M. and Ljiljana, D. 2021. Effect of ibuprofen entrapment procedure on physicochemical and controlled drug release performances of chitosan/xanthan gum polyelectrolyte complexes. Iny J Biol Macromol. 167: 547–558. 10.1016/j.ijbiomac.2020.11.201
Balestri, D., Mazzeo, P.P., Perrone, R., Fornari, F., Bianchi, F., Careri, M., Bacchi, A. and Pelagatti, P. 2021. Deciphering the supra-molecular organization of multiple guests inside a microporous MOF to understand their release profile (Edit). Angew Chem Int. 133(18): 10282–10290. 10.1002/ange.202017105
Chen, M., Wang, Z.W., Hu, C.Y. and Wang, J.L. 2012. Effects of temperature on release of eugenol and isoeugenol from soy protein isolate films into simulated fatty food. Package Technol Sci. 25(8): 485–492. 10.1002/pts.995
Dehkordi, N.H., Tajik, H., Moradi, M., Kousheh, S.A. and Molaei, R. 2019. Antibacterial interactions of colloid nanosilver with eugenol and food ingredients. J Food Prot. 82(10): 1873–1792. 10.4315/0362-028X.JFP-19-174
El Ghannam, M., Dar, Y., El Mehlawy, M.H., Mokhtar, F.A. and Bakr, L. 2023. Effective anthelmintic compound against foodborne parasite Trichinella spiralis muscle larvae and adult. Pathogens 12: 127. 10.3390/pathogens12010127
Esmaeili, F., Rajabnejhad, S., Partoazar, A.R., Mehr, S.E., Faridi-Majidi, R., Sahebgharani, M., Syedmoradi, L., Rajabnejhad, M.R. and Amani, A. 2016. Anti-inflammatory effects of eugenol nanoemulsion as a topical delivery system. Pharm Dev Technol. 21: 887–893. 10.3109/10837450.2015.1078353
Fredes, A., Sales, C., Barreda, M., Valcárcel, M., Roselló, S. and Beltrán, J. 2016. Quantification of prominent volatile compounds responsible for muskmelon and watermelon aroma by purge and trap extraction followed by gas chromatography–mass spectrometry determination. Food Chem. 190: 689–700. 10.1016/j.foodchem.2015.06.011
Golmakani, M.T., Zare, M. and Razzaghi, S. 2017. Eugenol enrichment of clove bud essential oil using different microwave-assisted distillation methods. Food Sci Technol Res. 23(3): 385–394. 10.3136/fstr.23.38
Guan, W., Li, S., Yan, R., Tang, S. and Quan, C. 2006. Comparison of essential oils of clove buds extracted with supercritical carbon dioxide and other three traditional extraction methods. Food Chem. 101(4): 1558–1564. 10.1016/j.foodchem.2006.04.009
Guan, W., Zhu, T., Wang, Y., Zhang, Z., Jin, Z., Wang, C. and Bai, F. 2016. Efficacy of head space solid-phase microextraction coupled to gas chromatography-mass spectrometry method for determination of the trace extracellular hydrocarbons of cyanobacteria. J Chromatogr B. 1029–1030: 113–120. 10.1016/j.jchromb.2016.06.050
Gürbüz, M. and İrem O.K.B. 2022. The anti-campylobacter activity of eugenol and its potential for poultry meat safety: a review. Food Chem. 394: 133519. 10.1016/j.foodchem.2022.133519
Huang, K., Xu, K.J., Chen, K., Liang, M., Yang, J.C. and Zhang, J.S. 2022. Analysis of the release behavior of limonene in tangerine pee based on P&T-GC/MS. J Chinese Institute Food Sci Technol. 22(05): 309–319. 10.16429/j.1009-7848.2022.05.033
Irovetz, L., Buchbauer, G., Stoilova, I., Stoyanova, A., Krastanov, A. and Schmidt, E. 2006. Chemical composition and antioxidant properties of clove leaf essential oil. J Agric Food Chem. 54(17): 6303–6307. 10.1021/jf060608c
Jing, B., Shirley, M.B., Renee, M.G.S., Naim, M. and Paul, J.S. 2019. Aroma profile characterization of mahi-mahi and tuna for determining spoilage using purge and trap gas chromatography-mass spectrometry. J Food Sci. 84(3): 481–489. 10.1111/1750-3841.14478
Ju, J., Xie, Y., Yu, H., Guo, Y., Cheng, Y., Qian, H. and Yao, W. 2020. A novel method to prolong bread shelf life: sachets containing essential oils components. LWT 131: 109744. 10.1016/j.lwt.2020.109744
Kanavouras, A., Kiritsakis, A. and Hernandez, R.J. 2005. Comparative study on volatile analysis of extra virgin olive oil by dynamic head-space and solid phase micro-extraction. Food Chem. 90(1–2): 69–79. 10.1016/j.foodchem.2004.03.025
Konteles, S.J., Strati, I.F., Giannakourou, M., Batrinou, A., Papadakis, S., Ourailoglou, D., Zoumpoulakis, P. and Sinanoglou, V.J. 2022. Instant herbal powder: functionality assessment through chemical, microbiological and shelf life kinetics. Anal Lett. 55(9): 1505–1516. 10.1080/00032719.2021.2011897
Lukasz, M., Marjorie, G.W., Santiago, R.R., Erik, H., William, T.W. and Thomas, E. 2016. Olfactory specialization for perfume collection in male orchid bees. J Exp Biol. 219(10): 1467–1475. 10.1242/jeb.136754
Moemenbellah-Fard, M.D., Abdollahi, A., Ghanbariasad, A. and Osanloo, M. 2020. Antibacterial and leishmanicidal activities of Syzygium aromaticum essential oil versus its major ingredient, eugenol. Flavour Fragr J. 35(5): 534–540. 10.1002/ffj.3595
Moneera, O.A. 2022. Physicochemical, nutritional, and sensory quality and storage stability of cookies: effect of clove powder. Int J Food Prop. 25(1): 1009–1020. 10.1080/10942912.2022.2071290
Nabor, H.J., Adolfo, C.G., Moisés, M. and Hugo, E. 2021. Clove essential oil (Syzygium aromaticum L. Myrtaceae): extraction, chemical composition, food applications, and essential bioactivity for human health. Molecules 26(21): 6387. 10.3390/molecules26216387
Orlo, E., Russo, C., Nugnes, R., Lavorgna, M. and Isidori, M. 2021. Natural methoxyphenol compounds: antimicrobial activity against food borne pathogens and food spoilage bacteria, and role in antioxidant processes. Foods 10(8): 1807. 10.3390/foods10081807
Riyandari, B.A., Suherman, S. and Siswanta, D. 2018. The physico-mechanical properties and release kinetics of eugenol in chitosan-alginate polyelectrolyte complex films as active food packaging. Indones J Chem. 18(1). 10.22146/ijc.26525
Shan, B., Cai, Y,Z., Brooks, J.D. and Corke, H. 2011. Potential application of spice and herb extracts as natural preservatives in cheese. J Med Food. 14(3): 284–290. 10.1089/jmf.2010.0009
Shen, J., Xu, T., Shi, C., Cheng, T., Wang, J., Pan, H. and Zhang, Q. 2017. Obtainment of an intergeneric hybrid between Forsythia and Abeliophyllum. Euphytica. 213(4). 10.1007/s10681-017-1880-x
Sevindik, O., Amanpour, A., Sarhir, S.T., Kelebek, H. and Selli, S. 2019. Characterization of key odorants in Moroccan argan oil by aroma extract dilution analysis. Eur J Lipid Sci Tech. 121(5): 1800437. 10.1002/ejlt.201800437
Sueishi, Y. and Nii, R. 2019. Comparative profiling of clove extract and its component antioxidant activities against five reactive oxygen species using multiple free radical scavenging. Food Sci Technol Res. 25: 885–890. 10.3136/fstr.25.885
Taleuzzaman, M., Jain, P., Verma, R., Iqbal, Z. and Mirza, M.A. 2021. Eugenol as a potential drug candidate: a review. Curr Top Med Chem. 21: 1804–1815. 10.2174/1568026621666210701141433
Tamaru, S., Ono, A., Igura, N. and Shimoda, M. 2019. High correlation between octanol-air partition coefficient and aroma release rate from O/W emulsions under non-equilibrium. Food Res Int. 116: 883–887. 10.1016/j.foodres.2018.09.024
Yang, J., Kuang, X., Li, B., Zhou, B., Li, J., Cui, B. and Ma, M. 2012. Study on release mechanism of inhibitory components from cinnamon and clove powders. J Food Safety. 32(2): 189–197. 10.1111/j.1745-4565.2012.00367.x
Yassin, M.T., Al-Askar, A.A. and Mostafa, A.A.F. 2020. Bioactivity of Syzygium aromaticum (L.) Merr. & L.M. Perry extracts as potential antimicrobial and anticancer agents. J King Saud Univ Sci. 32: 3273–3278. 10.1016/j.jksus.2020.09.009
Yasuhiko, H. and Fujii, Y. 2011. HPLC-UV analysis of eugenol in clove and cinnamon oils after pre-column derivatization with 4-fluoro-7-nitro-2,1,3-benzoxadiazole. J Liq Chromatogr R.T. 34(1): 18–25. 10.1080/10826076.2011.534689
Yun, S.M., Lee, M.H., Lee, K.J., Ku, H.O., Son, S.W. and Joo, Y.S. 2010. Quantitative analysis of eugenol in clove extract by a validated HPLC method. J AOAC Int. 93: 1806–1810. 10.1093/jaoac/93.6.1806
Zanin, R., Smrke, S., Kurozawa, L. E., Yamashita, F., and Yeretzian, C. 2020. Novel experimental approach to study aroma release upon reconstitution of instant coffee products. Food Chem. 317: 126455. 10.1016/j.foodchem.2020.126455
Zhu, M., Hu, Z., Liang, M., Song, L., Wu, W., Li, R., Li, Z. and Zhang, J. 2022. Evaluation of the flavor compounds of Pleurotus eryngii as affected by baking temperatures using HS-SPME-GC–MS and electronic nose. J Food Process Pres. 46(11): e17056. 10.1111/jfpp.17056
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