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Published November 30, 2021 | Version v1
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A robust method for simultaneous quantification of eugenol, eugenyl acetate, and β-caryophyllene in clove essential oil by vibrational spectroscopy

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Ismail, Tarhan (2021): A robust method for simultaneous quantification of eugenol, eugenyl acetate, and β-caryophyllene in clove essential oil by vibrational spectroscopy. Phytochemistry (112928) 191: 1-10, DOI: 10.1016/j.phytochem.2021.112928, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112928

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urn:lsid:plazi.org:pub:FF90C926FFC5FF833B241221FFA1FFE9

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Publication: 10.1063/1.4991186 (DOI)
Publication: 10.1016/j.fct.2007.09.106 (DOI)
Publication: 10.1002/jsfa.6427 (DOI)
Publication: 10.1002/ptr.2124 (DOI)
Publication: 10.1016/j.ejmech.2017.08.030 (DOI)
Publication: 10.3390/ma12182995 (DOI)
Publication: 10.1006/fstl.1998.0381 (DOI)
Publication: 10.1016/j.trac.2014.10.007 (DOI)
Publication: 10.1002/ptr.2072 (DOI)
Publication: 10.1016/j.ecoenv.2016.03.007 (DOI)
Publication: 10.3390/molecules24071402 (DOI)
Publication: 10.1016/j.foodchem.2006.04.009 (DOI)
Publication: 10.1021/jf060608c (DOI)
Publication: 10.1002/pca.895 (DOI)
Publication: 10.1016/j.procbio.2017.04.031 (DOI)
Publication: 10.1016/j.indcrop.2018.09.010 (DOI)
Publication: 10.1016/S0021-9673(01)01314-0 (DOI)
Publication: 10.1016/j.foodcont.2006.12.003 (DOI)
Publication: 10.5194/amt-12-4519-2019 (DOI)
Publication: 10.1080/01621459.1984.10478083 (DOI)
Publication: 10.1186/s40543-015-0073-2 (DOI)
Publication: 10.1007/s00210-010-0582-x (DOI)
Publication: 10.1021/ac60214a047 (DOI)
Publication: 10.1007/s12010-015-1611-5 (DOI)
Publication: 10.1002/ffj.1364 (DOI)
Publication: 10.1016/j.indcrop.2014.05.005 (DOI)
Publication: 10.1002/ptr.1637 (DOI)
Publication: 10.13040/IJPSR.0975-8232.8(2).895-99 (DOI)
Publication: 10.1007/s12010-014-1113-x (DOI)
Publication: 10.1002/ffj.3438 (DOI)
Publication: 10.3233/SPE-2011-0526 (DOI)
Publication: 10.1016/j.cej.2012.03.064 (DOI)
Publication: 10.1080/10610278.2019.1702663 (DOI)
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References

  • Adams, R., 2005. Identification of Essential Oil Components by Gas Chromatography/ Quadrupole Mass Spectroscopy. Allured Publishing Corporation, Illinois.
  • Amelia, B., Saepudin, E., Cahyana, A.H., Rahayu, D.U., Sulistyoningrum, A.S., Haib, J., 2017. GC-MS analysis of clove (Syzygium aromaticum) bud essential oil from Java and Manado. AIP Conf. Proc. 1862, 030082 https://doi.org/10.1063/1.4991186.
  • Bakkali, F., Averbeck, S., Averbeck, D., Idaomar, M., 2008. Biological effects of essential oils - a review. Food Chem. Toxicol. 46, 446-475. https://doi.org/10.1016/j. fct.2007.09.106.
  • Camps, C., G´erard, M., Quennoz, M., Brabant, C., Oberson, C., Simonnet, X., 2014. Prediction of essential oil content of oregano by handheld- and fourier transform- nir spectroscopy. J. Sci. Food Agric. 94, 1397-1402. https://doi.org/10.1002/jsfa.6427.
  • Chaieb, K., Hajlaoui, H., Zmantar, T., Nakbi, A., Rouabhia, M., Kacem, M., Bakhrouf, A., 2007. The Chemical composition and biological activity of clove essential oil, Eugenia caryophyllata (Syzigium aromaticum L. Myrtaceae): a short review. Phytother Res. 21, 501-506. https://doi.org/10.1002/ptr.2124.
  • Charan Raja, M.R., Velappan, A.B., Chellappan, D., Debnath, J., Kar Mahapatra, S., 2017. Eugenol derived immunomodulatory molecules against visceral leishmaniasis. Eur. J. Med. Chem. 139, 503-518. https://doi.org/10.1016/j.ejmech.2017.08.030.
  • Ciurczak, E.W., Drennen, J.K., 2002. III . Pharmaceutical and Medical Applications of Near-Infrared Spectroscopy. CRC Press, Florida.
  • de Oliveira, A.d.N., Leite Lima, E.T., de Oliveira, D.T., Ang´elica, R.S., de Aguiar Andrade, E.H., da Rocha Filho, G.N., Ferreira da Costa, C.E., Fernandes Costa, F., Luque, R., Santos do Nascimento, L.A., 2019. Acetylation of eugenol over 12- molybdophosphoric acid anchored in mesoporous silicate support synthesized from Flint Kaolin. Materials 12, 2995. https://doi.org/10.3390/ma12182995.
  • Della Porta, G., Taddeo, R., D' Urso, E., Reverchon, E., 1998. Isolation of clove bud and star anise essential oil by supercritical CO2Extraction. LWT - Food Sci. Technol. (Lebensmittel-Wissenschaft -Technol.) 31, 454-460. https://doi.org/10.1006/ fstl.1998.0381.
  • Do, T.K.T., Hadji-Minaglou, F., Antoniotti, S., Fernandez, X., 2015. Authenticity of essential oils. Trac. Trends Anal. Chem. 66, 146-157. https://doi.org/10.1016/j. trac.2014.10.007.
  • Edris, A.E., 2007. Pharmaceutical and therapeutic Potentials of essential oils and their individual volatile constituents: a review. Phytother Res. 21, 308-323. https://doi. org/10.1002/ptr.2072.
  • Govindarajan, M., Rajeswary, M., Benelli, G., 2016. Chemical composition, toxicity and non-target effects of Pinus kesiya essential oil: an eco-friendly and novel larvicide against malaria, dengue and lymphatic filariasis mosquito vectors. Ecotoxicol. Environ. Saf. 129, 85-90. https://doi.org/10.1016/j.ecoenv.2016.03.007.
  • Grabska, J., Bec ´, K.B., Kirchler, C.G., Ozaki, Y., Huck, C.W., 2019. Distinct difference in sensitivity of NIR vs. IR bands of melamine to inter-molecular interactions with impact on analytical spectroscopy explained by anharmonic quantum mechanical study. Molecules 24, 1402. https://doi.org/10.3390/molecules24071402.
  • Guan, W., Li, S., Yan, R., Tang, S., Quan, C., 2007. Comparison of essential oils of clove buds extracted with supercritical carbon dioxide and other three traditional extraction methods. Food Chem. 101, 1558-1564. https://doi.org/10.1016/j. foodchem.2006.04.009.
  • Huck, C.W., 2016. Infrared Spectroscopy in Near-Infrared/Infrared Bioanalysis Including Imaging. John Wiley & Sons, NJ, USA.
  • Jirovetz, L., Buchbauer, G., Stoilova, I., Stoyanova, A., Krastanov, A., Schmidt, E., 2006. Chemical composition and antioxidant properties of clove leaf essential oil. J. Agric. Food Chem. 54, 6303-6307. https://doi.org/10.1021/jf060608c.
  • Juliani, H., Kapteyn, J., Jones, D., Koroch, A., Wang, m., Charles, D., Simon, J., 2006. Application of near-infrared spectroscopy in quality control and determination of adulteration of African essential oils. Phytochem. Anal. 17, 121-128. https://doi. org/10.1002/pca.895.
  • Lis-Balchin, M., 2006. Aromatherapy Science: A Guide for Healthcare Professionals. Pharmaceutical Press, UK.
  • Machado, J.R., Pereira, G.N., dos Santos de Oliveira, P., Zenevicz, M.C., Lerin, L., dos Reis Barreto de Oliveira, R., Cabral de Holanda Cavalcanti, S., Ninow, J.L., de Oliveira, D., 2017. Synthesis of eugenyl acetate by immobilized lipase in a packed bed reactor and evaluation of its larvicidal activity. Process Biochem. 58, 114-119. https://doi.org/10.1016/j.procbio.2017.04.031.
  • Marincas, O., Feher, I., 2018. A new cost-effective approach for lavender essential oils quality assessment. Ind. Crop. Prod. 125, 241-247. https://doi.org/10.1016/j. indcrop.2018.09.010.
  • Marriott, P.J., Shellie, R., Cornwell, C., 2001. Gas chromatographic technologies for the analysis of essential oils. J. Chromatogr. A 936, 1-22. https://doi.org/10.1016/ S0021-9673(01)01314-0.
  • Omidbeygi, M., Barzegar, M., Hamidi Esfahani, Z., Naghdibadi, H., 2007. Antifungal activity of thyme, summer savory and clove essential oils against Aspergillus Xavus in liquid medium and tomato paste. Food Contr. 18, 1518-1523. https://doi.org/ 10.1016/j.foodcont.2006.12.003.
  • Ozaki, Y., Huck, C.W., Be´c, K.B., 2017. Near infrared spectroscopy and its applications. In: Gupta, V.P. (Ed.), Molecular and Laser Spectroscopy. Elsevier, Amsterdam.
  • Pereira, K.L., Rovelli, G., Song, Y.C., Mayhew, A.W., Reid, J.P., Hamilton, J.F., 2019.
  • A new aerosol flow reactor to study secondary organic aerosol. Atmos. Meas. Tech. 12, 4519-4541. https://doi.org/10.5194/amt-12-4519-2019.
  • Picard, R.R., Cook, R.D., 1984. Cross-validation of regression models. J. Am. Stat. Assoc. 79, 575-583. https://doi.org/10.1080/01621459.1984.10478083.
  • Pramod, K., Suneesh, C.V., Shanavas, S., Ansari, S.H., Ali, J., 2015. Unveiling the compatibility of eugenol with formulation excipients by systematic drug-excipient compatibility studies. J. Anal. Sci. Technol. 6, 34. https://doi.org/10.1186/s40543- 015-0073-2.
  • Santin, J.R., Lemos, M., Klein-Junior, L.C., Machado, I.D., Costa, P., de Oliveira, A.P., Tilia, C., de Souza, J.P., de Sousa, J.P.B., Bastos, J.K., de Andrade, S.F., 2011. Gastroprotective activity of essential oil of the Syzygium aromaticum and its major component eugenol in different animal models. N-S Arch. Pharmacol. 383, 149-158. https://doi.org/10.1007/s00210-010-0582-x.
  • Savitzky, A., Golay, M.J.E., 1964. Smoothing and differentiation of data by simplified least squares procedures. Anal. Chem. 36, 1627-1639. https://doi.org/10.1021/ ac60214a047.
  • Silva, M.J.A., Loss, R.A., Laroque, D.A., Lerin, L.A., Pereira, G.N., Thon, ´E., Oliveira, J.V., Ninow, J.L., Hense, H., Oliveira, D., 2015. Lipozyme TL IM as catalyst for the synthesis of eugenyl acetate in solvent-free acetylation. Appl. Biochem. Biotechnol. 176, 782-795. https://doi.org/10.1007/s12010-015-1611-5.
  • Srivastava, A., Srivastava, S., Kv, S., 2005. Bud and leaf essential oil composition of Syzygium aromaticum from India and Madagascar. Flavour Fragrance J. 20, 51-53. https://doi.org/10.1002/ffj.1364.
  • Tankeu, S.Y., Vermaak, I., Kamatou, G.P.P., Viljoen, A.M., 2014. Vibrational spectroscopy and chemometric modeling: an economical and robust quality control method for lavender oil. Ind. Crop. Prod. 59, 234-240. https://doi.org/10.1016/j. indcrop.2014.05.005.
  • Taraj, K., Andoni˙, A., Ylli, F., Ylli, A., Hoxha, R., Llupa, J., Malollari˙, ˙I., 2019. Spectroscopic investigation of syzygium aromaticum L. Oil by water distillation extraction. J. Int. Environ. Appl. Sci. 15, 122-126. http://www.dergipark.org.tr/en /pub/jieas/issue/54918/705980.
  • Trongtokit, Y., Rongsriyam, Y., Komalamisra, N., Apiwathnasorn, C., 2005. Comparative repellency of 38 essential oils against mosquito bites. Phytother Res. 19, 303-309. https://doi.org/10.1002/ptr.1637.
  • Uddin, M., Shahinuzzaman, M., Rana, S., Yaakob, Z., 2017. Study of chemical composition and medicinal properties of volatile oil from clove buds (Eugenia caryophyllus). Int. J. Pharma Sci. Res. 8, 895-899. https://doi.org/10.13040/ IJPSR.0975-8232.8(2).895-99.
  • Vanin, A.B., Orlando, T., Piazza, S.P., Puton, B.M.S., Cansian, R.L., Oliveira, D., Paroul, N., 2014. Antimicrobial and antioxidant activities of clove essential oil and eugenyl acetate produced by enzymatic esterification. Appl. Biochem. Biotechnol. 174, 1286-1298. https://doi.org/10.1007/s12010-014-1113-x.
  • Vargas, J.P., Gualpa, F., Ramos, L.A., Ciobot˘a, V., 2017. Adulteration of clove essential oil: detection using a handheld Raman spectrometer. Flavour Fragrance J. 33, 184-190. https://doi.org/10.1002/ffj.3438.
  • Wang, L.-H., Sung, W.-C., 2011. Rapid evaluation and quantitative analysis of eugenol derivatives in essential oils and cosmetic formulations on human skin using attenuated total reflectance-infrared spectroscopy. J. Spectrosc. 26, 176163. https://doi.org/10.3233/SPE-2011-0526.
  • Yadav, G.D., Yadav, A.R., 2012. Insight into esterification of eugenol to eugenol benzoate using a solid super acidic modified zirconia catalyst UDCaT-5. Chem. Eng. J. 192, 146-155. https://doi.org/10.1016/j.cej.2012.03.064.
  • Yang, Z., Chai, Y., Zhou, D., Yao, X., Ji, H., 2019. Mechanism for efficient separation of eugenol and eugenol acetate with β- cyclodextrin as a selective solvent. Supramol. Chem. 31, 767-775. https://doi.org/10.1080/10610278.2019.1702663.