Markers of conjugated octadecatrienoic acids in Raman spectra of vegetable oils: diagnostics of punicic and α-eleostearic acids

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Resumo

It is shown for the first time that using the method of Raman spectroscopy allows one to determine the content of conjugated octadecatrienoic (K-C18:3) acids in oil at their content of 8 wt. % at least. It is found that it is possible to reliably distinguish the isomers of the K-C18:3 acids containing conjugated (in punicic and α-eleostearic acids) and non-conjugated (in α-linolenic acid) C=C bonds by their Raman spectra. The obtained results can be used to develop efficient and non-destructive techniques for analyzing the composition and quality of oils, which contain conjugated octadecatrienic polyunsaturated fatty acids, and dietary supplements based on them.

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Sobre autores

S. Kuznetsov

Prokhorov General Physics Institute of the Russian Academy of Sciences

Email: sagitova@kapella.gpi.ru
Rússia, Moscow

V. Novikov

Prokhorov General Physics Institute of the Russian Academy of Sciences

Email: sagitova@kapella.gpi.ru
Rússia, Moscow

G. Nikolaeva

Prokhorov General Physics Institute of the Russian Academy of Sciences

Email: sagitova@kapella.gpi.ru
Rússia, Moscow

M. Moskovskiy

Federal Scientific Agroengineering Center VIM

Email: sagitova@kapella.gpi.ru
Rússia, Moscow

P. Laptinskaya

Prokhorov General Physics Institute of the Russian Academy of Sciences

Email: sagitova@kapella.gpi.ru
Rússia, Moscow

E. Sagitova

Prokhorov General Physics Institute of the Russian Academy of Sciences

Autor responsável pela correspondência
Email: sagitova@kapella.gpi.ru
Rússia, Moscow

Bibliografia

  1. Новрузов Э.Н., Зейналова А.М. Биологическая активность и терапевтическое действие гранатового масла // Растительные ресурсы. 2019. Т. 55. № 2. С. 186–194. https://doi.org/10.1134/s0033994619020080
  2. Schönemann A., Edwards H. G.M. Raman and FTIR microspectroscopic study of the alteration of Chinese tung oil and related drying oils during ageing // Anal. Bioanal. Chem. 2011. V. 400. № 4. P. 1173–1180. https://doi.org/10.1007/s00216-011-4855-0
  3. Тунговое масло [Electronic resource] // Большая советская энциклопедия. URL: https://dic.academic.ru/dic.nsf/bse/141675.
  4. Górnaś P., Rudzińska M., Raczyk M., Mišina I., Soliven A., Segliņa D. Composition of bioactive compounds in kernel oils recovered from sour cherry (Prunus cerasus L.) by-products: Impact of the cultivar on potential applications // Ind. Crops Prod. 2016. V. 82. P. 44–50. https://doi.org/10.1016/j.indcrop.2015.12.010
  5. Дейнека Л.А., Дейнека В.И., Сорокопудов В.Н., Шевченко С.М. Масла с конъюгированными двойными связями: масла косточек вишен и родственных родов семейства Rosaceae // Научные ведомости Белгородского государственного университета. Серия Естественные науки. 2010. Т. 21. № 92. С. 135–142.
  6. Cheikhyoussef N., Kandawa-schulz M., Böck R., Cheikhyoussef A. Mongongo/Manketti (Schinziophyton rautanenii) oil // Fruit Oils Chem. Funct. 2019. P. 627–640. https://doi.org/10.1007/978-3-030-12473-1_32
  7. ГОСТ 30623-2018. Масла растительные и продукты со смешанным составом жировой фазы. Метод обнаружения фальсификации. М.: Стандартинформ, 2018. 32 p.
  8. Дейнкеа В.И., Нгуен В.А., Дейнека Л.А. Особенности пробоподготовки при анализе масла с радикалами жирных кислот, содержащих сопряженные двойные связи: масло мормордики кохинхинской // Заводская лаборатория. Диагностика материалов. 2018. Т. 84. № 2. С. 18–23.
  9. Munnier E., Al Assaad A., David S., Mahut F., Vayer M., Van Gheluwe L., Yvergnaux F., Sinturel C., Soucé M., Chourpa I., Bonnier F. Homogeneous distribution of fatty ester-based active cosmetic ingredients in hydrophilic thin films by means of nanodispersion // Int. J. Cosmet. Sci. 2020. V. 42. № 5. P. 512–519. https://doi.org/10.1111/ics.12652
  10. Cleary M.P. Punicic acid is an ω-5 fatty acid capable of inhibiting breast cancer proliferation // Int. J. Oncol. 2009. V. 36. № 2. P. 547–557. https://doi.org/10.3892/ijo_00000515
  11. Boroushaki M.T., Mollazadeh H., Afshari A.R. Pomegranate seed oil: a comprehensive review on its therapeutic effects // Int. J. Pharm. Sci. Res. 2016. V. 7. № 2. https://doi.org/10.13040/IJPSR.0975-8232.7(2).430-42
  12. Галеев Р.Р. Современный подход к организации контроля качества лекарственных средств, находящихся в обращении на территории Российской Федерации // Вестник Росздравнадзора. 2017. Т. 2. С. 41–43.
  13. El-Abassy R.M., Donfack P., Materny A. Assessment of conventional and microwave heating induced degradation of carotenoids in olive oil by VIS Raman spectroscopy and classical methods // Food Res. Int. 2010. V. 43. № 3. P. 694–700. https://doi.org/10.1016/j.foodres.2009.10.021
  14. Vargas Jentzsch P., Ciobotă V. Raman spectroscopy as an analytical tool for analysis of vegetable and essential oils // Flavour Fragr. J. 2014. V. 29. № 5. P. 287–295. https://doi.org/10.1002/ffj.3203
  15. De Géa Neves M., Poppi R.J. Monitoring of adulteration and purity in coconut oil using Raman spectroscopy and multivariate curve resolution // Food Anal. Methods. Food Analytical Methods, 2018. V. 11. № 7. P. 1897–1905. https://doi.org/10.1007/s12161-017-1093-x
  16. Васимов Д.Д., Ашихмин А.А., Большаков М.А., Московский М.Н., Гудков С.В., Яныкин Д.В., Новиков В.С. Новые маркеры для определения химического и изомерного состава каротиноидов методом спектроскопии комбинационного рассеяния // Доклады РАН. Физика, технические науки. 2023. Т. 514. № 1. С. 10–17. https://doi.org/10.31857/S2686740023060147
  17. Schaffer H.E., Chance R.R., Silbey R.J., Knoll K., Schrock R.R. Conjugation length dependence of Raman scattering in a series of linear polyenes: Implications for polyacetylene // J. Chem. Phys. 1991. V. 94. № 6. P. 4161–4170. https://doi.org/10.1063/1.460649
  18. Новиков В.С., Кузнецов С.М., Кузьмин В.В., Прохоров К.А., Сагитова Е.А., Дарвин М.Е., Ладеманн Ю., Устынюк Л.Ю., Николаева Г.Ю. Анализ природных и синтетических соединений, содержащих полиеновые цепи, методом спектроскопии комбинационного рассеяния // Доклады РАН. Физика, технические науки. 2021. Т. 500. № 1. С. 26–33. https://doi.org/10.31857/s2686740021050060
  19. Zhuang Y., Ren Z., Jiang L., Zhang J., Wang H., Zhang G. Raman and FTIR spectroscopic studies on two hydroxylated tung oils (HTO) bearing conjugated double bonds // Spectrochim. Acta – Pt A. Mol. Biomol. Spectrosc. Elsevier B. V., 2018. V. 199. P. 146–152. https://doi.org/10.1016/j.saa.2018.03.020
  20. Tang T., Sui Z., Fei B. The microstructure of Moso bamboo (Phyllostachys heterocycla) with tung oil thermal treatment // IAWA J. 2022. V. 43. № 3. P. 322–336. https://doi.org/10.1163/22941932-bja10083
  21. Ako H., Kong N., Brown A. Fatty acid profiles of kukui nut oils over time and from different sources // Ind. Crops Prod. 2005. V. 22. № 2. P. 169–174. https://doi.org/10.1016/j.indcrop.2004.07.003
  22. Kuznetsov S.M., Novikov V.S., Sagitova E.A., Ustynyuk L.Y., Glikin A.A., Prokhorov K.A., Nikolaeva G.Y., Pashinin P.P. Raman spectra of n-pentane, n-hexane, and n-octadecane: Experimental and density functional theory (DFT) study // Laser Phys. 2019. V. 29. № 8. P. 085701. https://doi.org/10.1088/1555-6611/ab2908
  23. Peng H., Hou H.-Y., Chena X.-B. DFT calculation and Raman spectroscopy studies of α-linolenic acid // Quim. Nova. 2021. V. 44. № 8. P. 929–935. https://doi.org/10.21577/0100-4042.20170749
  24. Кузнецов С.М., Лаптинская П.К., Персидская О.К., Новиков В.С. Анализ растительных масел методом спектроскопии КР: определение содержания ненасыщенных жирных кислот и каротиноидов // Шестая ежегодная Школа-конференция молодых ученых “Прохоровские недели”, 24–26 октября 2023 г. Сб. тезисов. М., 2023. С. 163–165. https://doi.org/10.24412/cl-35673-2023-1-163-165
  25. El-Abassy R.M., Donfack P., Materny A. Visible Raman spectroscopy for the discrimination of olive oils from different vegetable oils and the detection of adulteration // J. Raman Spectrosc. 2009. V. 40. № 9. P. 1284–1289. https://doi.org/10.1002/jrs.2279

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2. Fig. 1. Structural formulas (C18H30O2) of mutually isomeric punicic, α-eleostearic and α-linolenic acids. Molecular structures were calculated using density functional theory (DFT, see Materials and Methods). Carbon-carbon double bonds are shown in green.

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3. Fig. 2. Simulated Raman spectra of punicic, α-eleostearic and α-linolenic acids and the experimental Raman spectrum of the Omega-5 dietary supplement.

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4. Fig. 3. Raman spectra of vegetable oils in the range of 600–1800 cm–1: blue and red curves are the spectra of samples containing punicic and α-eleostearic (K-C18:3) PUFA, respectively; black curves are oils that do not contain K-C18:3 PUFA.

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5. Fig. 4. Raman spectra of the studied vegetable oils and Omega-5 dietary supplements in the regions of (a) 2650–3200 cm–1 and (b) 2985–3075 cm–1. Blue and red curves are the spectra of samples containing punicic and α-eleostearic acids, respectively; black curves are oils that lack K-C18:3 PUFA.

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