Microwave-assisted extraction of oxygen heterocyclic compounds from Citrus-scented creams using a deep eutectic solvent and their determination by HPLC-PDA.
Cosmetics; Deep Eutectic Solvents (DES); Furocoumarins; HPLC-PDA; Microwave-Assisted Extraction (MAE); Deep Eutectic Solvents; Coumarins; Heterocyclic Compounds; Oils, Volatile; Microwaves; Chromatography, High Pressure Liquid/methods; Reproducibility of Results; Limit of Detection; Linear Models; Oils, Volatile/chemistry; Citrus/chemistry; Deep Eutectic Solvents/chemistry; Coumarins/analysis; Coumarins/isolation & purification; Furocoumarins/analysis; Furocoumarins/isolation & purification; Heterocyclic Compounds/isolation & purification; Heterocyclic Compounds/analysis; Citrus essential oil; Cosmetic products; Deep eutectic solvent; Furocoumarin; Heterocyclic compound; HPLC- PDA; Microwave-assisted extraction; Work-flows; Analytical Chemistry; Biochemistry; Organic Chemistry
Abstract :
[en] This study aimed to investigate the content of oxygen heterocyclic compounds, especially coumarin and furocoumarins, in cosmetics products scented with Citrus essential oils. A minor component of the non-volatile fraction of Citrus essences is composed by oxygen heterocyclic compounds, commonly known as coumarins, furocoumarins, and polymethoxyflavones. These molecules show several biological effects on human health. On the other hand, coumarin has the potential to induce skin sensitization and furocoumarins show phototoxic activity. For this reason, several regulation and opinions have been issued concerning the maximum amount of these compounds in cosmetics. Given the regulatory framework, an analytical workflow for extraction and quantification of OHCs from cosmetics is necessary. This research aims to address this challenge by exploring, for the first time, a deep eutectic solvent as eco-friendly alternative for microwave-assisted extraction of these molecules from Citrus-scented creams. A deep eutectic solvent made by chloride and urea, at a molar ratio 1:2, and 20 % of water in weight was selected. Due to the complexity of the sample, a SPE clean-up was mandatory to obtain an extract devoid of interferents. Finally, an HPLC-PDA analytical method was employed allowing the simultaneous separation and quantification of 35 oxygen heterocyclic compounds in less than ten minutes. The analytical workflow here proposed was developed, optimized and validated demonstrating the potentials of deep eutectic solvents and microwaves in this field.
Cafeo, Giovanna ; Messina Institute of Technology c/o Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, former Veterinary School, University of Messina, Viale G. Palatucci snc 98168 Messina, Italy
Beccaria, Marco ; Université de Liège - ULiège > Molecular Systems (MolSys) ; Department of Chemical, Pharmaceutical, and Agricultural Sciences, University of Ferrara, Via Luigi Borsari 46, 44121 Ferrara, Italy
Russo, Marina; Messina Institute of Technology c/o Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, former Veterinary School, University of Messina, Viale G. Palatucci snc 98168 Messina, Italy. Electronic address: marina.russo@unime.it
Mondello, Luigi ; Messina Institute of Technology c/o Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, former Veterinary School, University of Messina, Viale G. Palatucci snc 98168 Messina, Italy, Chromaleont s.r.l, c/o Messina Institute of Technology c/o Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, former Veterinary School, University of Messina, Viale G. Palatucci snc 98168 Messina, Italy
Dugo, Paola; Messina Institute of Technology c/o Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, former Veterinary School, University of Messina, Viale G. Palatucci snc 98168 Messina, Italy, Chromaleont s.r.l, c/o Messina Institute of Technology c/o Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, former Veterinary School, University of Messina, Viale G. Palatucci snc 98168 Messina, Italy
Purcaro, Giorgia ; Université de Liège - ULiège > Département GxABT > Chemistry for Sustainable Food and Environmental Systems (CSFES)
Language :
English
Title :
Microwave-assisted extraction of oxygen heterocyclic compounds from Citrus-scented creams using a deep eutectic solvent and their determination by HPLC-PDA.
Regulation (EC). No 1223/2009 of the European Parliament and of the Council, of 30 November 2009, on Cosmetic Products. Off. J. Eur. Union 342 (2009), 59–209 Available online: https://eur-lex.europa.eu/legal-content/EN/ALL/?uri=celex%3A32009R1223 accessed 06 September 2024.
Precedence Research. Cosmetics Market (By Category: skin & sun care products, hair care products, deodorants & fragrances, makeup & color cosmetics and forecast 2024–2034 by gender: men, women. by distribution channel: hypermarkets/supermarkets, specialty stores, pharmacies, online sales channels, Other)—global industry analysis, size, share, growth, trends, regional outlook. Available online: https://www.precedenceresearch.com/cosmetics-market (accessed 06 September 2024).
Cosmetics Europe the personal care association. European consumer perception study 2022. https://cosmeticseurope.eu/cosmetic-products/european-consumer-perception-study-2022/ (accessed 06 September 2024).
Modi, J., Rathore, S., Dwivedi, S., Saraogi, G., Formulation and evaluation of multipurpose herbal cream. Int. J. Newgen Res. Pharmacy Healthcare, 2, 2024, 1, 10.61554/ijnrph.v2i1.2024.82.
Sarkic, A., Stappen, I., Essential oils and their single compounds in cosmetics—a critical review. Cosmetics, 5, 2018, 11, 10.3390/cosmetics5010011.
Sharmeen, J.B., Mahomoodally, F.M., Zengin, G., Maggi, F., Essential oils as natural sources of fragrance compounds for cosmetics and Cosmeceuticals. Molecules, 26, 2021, 666, 10.3390/molecules26030666.
Guzmán, E., Lucia, A., Essential oils and their individual components in cosmetic products. Cosmetics, 8, 2021, 114, 10.3390/cosmetics8040114.
Maffei, M.E., Gertsch, J., Appendino, G., Plant volatiles: production, function and pharmacology. Nat. Prod. Rep. 28:8 (2011), 1359–1380, 10.1039/c1np00021g.
Dugo, P., Piperno, A., Romeo, R., Cambria, M., Russo, M., Carnovale, C., Mondello, L., Determination of oxygen heterocyclic components in citrus products by HPLC with UV detection. J. Agric. Food Chem. 57 (2009), 6543–6551, 10.1021/jf901209.
Pratiwi, R., Auliya As, N.N., Yusar, R.F., Shofwan, A.A.A., Analysis of prohibited and restricted ingredients in cosmetics. Cosmetics, 9, 2022, 87, 10.3390/cosmetics9040087.
Sayre, R.M., Dowdy, J.C., The increase in melanoma: are dietary furocoumarins responsible?. Med Hypotheses 4 (2008), 855–859, 10.1016/j.mehy.2007.07.029.
Burnett, C.L., Fiume, M.M., Bergfeld, W.F., Belsito, D.V., Hill, R.A., Klaassen, C.D., Liebler, D.C., Marks Jr, J.G., Shank, R.C., Slaga, T.J., Snyder, P.W., Gill, L.J., Heldreth, B., Safety assessment of citrus-derived peel oils as used in cosmetics. Int. J. Toxicol. 38 (2019), 33s–59s, 10.1177/1091581819862504.
International Fragrance Association, Brussels, information letter 799 Furocoumarins in finished cosmetic products, 2008.
International Fragrance Association. IFRA Standard documentation. IFRA Standard-49th Amendment, 2020, IFRA https://ifrafragrance.org/safe-use/standards-documentation accessed 09 September 2024.
International Fragrance Association. IFRA Standard documentation. IFRA Standard-50th Amendment, 2022, IFRA https://ifrafragrance.org/safe-use/standards-documentation accessed 09 September 2024.
Cafeo, G., Irrera, E., Russo, M., Dugo, P., Extraction and chromatographic approaches for Coumarin, Furocoumarin, and Polymethoxyflavone characterization in foods. Foods, 13, 2024, 2517, 10.3390/foods13162517.
Prosen, H., Kocar, D., Different sample preparation methods combined with LC–MS/MS and LC–UV for determination of some furocoumarin compounds in products containing citruses. Flavour Fragr. J. 23 (2008), 263–271, 10.1002/ffj.1881.
Macmaster, A.P., Owen, N., Brussaux, S., Brevardc, H., Hiserodt, R., Leijs, H., Bast, N., Weber, B., Loesinge, G., Sherlockf, A., Schippa, C., Vey, M., Frérot, E., Tissot, E., Chaintreau, A., Quantification of selected furocoumarins by high-performance liquid chromatography and UV-detection capabilities and limits. J. Chromatogr. A. 1257 (2012), 34–40, 10.1016/j.chroma.2012.07.048.
Solaiman, R., Al-Zehouri, J., Determination of coumarin in methanol extract of cinnamon (Cinnamomum cassia Blume) using reversed-phase high performance liquid chromatography. J. Pharmacogn. Phytochem. 6 (2017), 726–729.
Machynáková, A., Hrobonová, K., Simultaneous determination of coumarin derivatives in natural samples by ultra high performance liquid chromatography. J. Food Nutr. Res. 56 (2017), 179–188.
Hrobonová, K., Sádecká, J., Cižmárik, J., HPLC separation and determination of dicoumarol and other simple coumarins in sweet clover. Nova Biotechnol. Chim. 17 (2018), 95–102, 10.2478/nbec-2018-0010.
Arigò, A., Rigano, F., Micalizzi, G., Dugo, P., Mondello, L., Oxygen heterocyclic compound screening in Citrus essential oils by linear retention index approach applied to liquid chromatography coupled to photodiode array detector. Flavour. Fragr. J. 34 (2019), 349–364, 10.1002/ffj.3515.
International Fragrance Association (IFRA). IFRA Analytical method – quantitative determination of furocoumarins by HPLC-DAD. 2013. http://www.ifraorg.org (accessed 09 September 2024).
Ma, Q., Xi, H., Ma, H., Meng, X., Wang, Z., Bai, H., Li, W., Wang, C., Simultaneous separation and determination of 22 Coumarin derivatives in cosmetics by UPLC‑MS/MS. Chromatographia 78 (2015), 241–249, 10.1007/s10337-014-2841-3.
Kreidl, M., Rainer, M., Jakschitz, T., Bonn, G.K., Determination of phototoxic furanocoumarins in natural cosmetics using SPE with LC-MS. Anal. Chim. Acta. 1101 (2020), 211–221, 10.1016/j.aca.2019.12.015.
Arigò, A., Dugo, P., Rigano, F., Mondello, L., Linear retention index approach applied to liquid chromatography coupled to triple quadrupole mass spectrometry to determine oxygen heterocyclic compounds at trace level in finished cosmetics. J. Chromatogr. A., 1649, 2021, 462183, 10.1016/j.chroma.2021.462183.
Salerno, T.M.G., Trovato, E., Cafeo, G., Vento, F., Zoccali, M., Donato, P., Dugo, P., Mondello, L., Hidden threat lurking in extensive hand hygiene during the Covid‑19 pandemic: investigation of sensitizing molecules in gel products by hyphenated chromatography techniques. Anal. Bioanal. Chem. 415 (2023), 3327–3340, 10.1007/s00216-023-04714-7.
Cafeo, G., Russo, M., Mondello, L., Dugo, P., Quantitative analysis of oxygen heterocyclic compounds using liquid chromatography coupled to tandem mass spectrometry, method development and environmental assessment. J. Food Compos. Anal., 132, 2024, 106291, 10.1016/j.jfca.2024.106291.
Corbi, E., Pérès, C., David, N., Quantification of furocoumarins in hydroalcoholic fragrances by a liquid chromatography-high resolution/accurate mass method. Flavour Fragr. J. 29:3 (2014), 173–183, 10.1002/ffj.3193.
Cafeo, G., Russo, M., Mondello, L., Mondello, A., Routine oxygen heterocyclic compounds analysis of fragrances using an eco-friendly liquid chromatography coupled to tandem mass spectrometry method. J. Essent. Oil Res., 2024, 1–12, 10.1080/10412905.2024.2374770.
Cardoso, C.A.L., Vilegas, W., Honda, N.K., Rapid determination of furanocoumarins in creams and pomades using SPE and GC. J. Pharm. Biomed. Anal. 22 (2000), 203–214, 10.1016/s0731-7085(99)00255-1.
Li, Z.Y., Li, X.K., Yang, Z.L., Qiu, D., Feng, N., Zhang, X.Z., Li, B.Q., An accurate and reliable analytical strategy for simultaneous determination of target furanocoumarins and flavonoids in cosmetic and pharmaceutical samples by ultra-high performance supercritical fluid chromatography. J. Pharm. Biomed. Anal., 225, 2023, 115221, 10.1016/j.jpba.2022.115221.
Herrero, M., Towards green extraction of bioactive natural compounds. Anal. Bioanal. Chem. 416 (2024), 2039–2047, 10.1007/s00216-023-04969-0.
Oliveira Silva, D.I., Silva Siqueira, A., Araújo da Costa, W., Pontes, L.F.B.L., Duarte Fragoso, W., Coelho Pontes, M.J., Liquid-liquid microextraction method using a deep eutectic solvent for the determination of total paraben content by fluorescence spectroscopy and second-order calibration. Microchem. J., 193, 2023, 109128, 10.1016/j.microc.2023.109128.
Zhong, Z., Chen, W., Deng, J., An integrated method for rapid extraction of fluorescent whitening agents from selected cosmetics by in situ formation of deep eutectic solvent. Microchem. J., 200, 2024, 110409, 10.1016/j.microc.2024.110409.
Hansen, B.B., Spittle, S., Chen, B., Poe, D., Zhang, Y., Klein, J.M., Horton, A., Adhikari, L., Zelovich, T., Doherty, B.W., Gurkan, B., Maginn, E.J., Ragauskas, A., Dadmun, M., Zawodzinski, T.A., Baker, G.A., Tuckerman, M.E., Savinell, R.F., Sangoro, J.R., Deep eutectic solvents: a review of fundamentals and applications. Chem. Rev. 121:3 (2021), 1232–1285, 10.1021/acs.chemrev.0c00385.
Russo, M., Rigano, F., Arigò, A., Dugo, P., Mondello, L., Coumarins, Psoralens and Polymethoxyflavones in cold-pressed citrus essential oils: a review. J. Essent. Oil Res. 33:3 (2021), 221–239, 10.1080/10412905.2020.1857855.
Reichardt, C., Pyridinium-N-phenolate betaine dyes as empirical indicators of solvent polarity: some new findings. Pure Appl. Chem. 80 (2008), 1415–1432, 10.1351/pac200880071415.
Machado, C., Machado, V.G., An easy and versatile experiment to demonstrate solvent polarity using solvatochromic dyes. J. Chem. Educ. 78:5 (2001), 649–651, 10.1021/ed078p649.
Schincaglia, A., Pasti, L., Cavazzini, A., Purcaro, G., Beccaria, M., Optimization and validation of a cheaper, safer, and more sustainable methodology for Aflatoxins determination in Rich-Lipidic Matrices (Pistachio Nuts) using deep eutectic solvent extraction and UHPLC-FLD Analysis. J. Agric. Food Chem., 2024, 10.1021/acs.jafc.4c05094.
