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Czasopismo
2015 | 60 | 3 | 461-468
Tytuł artykułu

Spin trapping studies of essential oils in lipid systems

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
In the present work, we report the results of a spin trapping ESR study of four essential oils widely used for skin care products such as creams and bath salts. The studied essential oils are Rosmarini aetheroleum (rosemary), Menthae piperitae aetheroleum (mint), Lavandulae aetheroleum (lavender), and Thymi aetheroleum (thyme). Fenton reaction in the presence of ethanol was used to generate free radicals. The N-tert-butyl-α-phenylnitrone (PBN) was used as a spin trap. In the Fenton reaction, the rosemary oil had the lowest effect on radical adduct formation as compared to the reference Fenton system. Since essential oils are known to be lipid soluble, we also conducted studies of essential oils in Fenton reaction in the presence of lipids. Two model lipids were used, namely 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) and 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC). The obtained results suggested that in the presence of DOPC lipids, the •OH and PBN/•CHCH3(OH) radicals are formed in both phases, that is, water and lipids, and all the studied essential oils affected the Fenton reaction in a similar way. Whereas, in the DPPC system, the additional type of PBN/X (aN = 16.1 G, aH = 2.9 G) radical adduct was generated. DFT calculations of hyperfine splittings were performed at B3LYP/6-311+G(d,p)/EPR-II level of theory for the set of c-centered PBN adducts in order to identify PBN/X radical.
Słowa kluczowe
Wydawca

Czasopismo
Rocznik
Tom
60
Numer
3
Strony
461-468
Opis fizyczny
Daty
wydano
2015-07-01
otrzymano
2014-09-24
zaakceptowano
2015-01-30
online
2015-08-06
Twórcy
  • Department of Physical Chemistry, Faculty of Pharmacy, Medical University of Warsaw, 1 Banacha Str., 02-097 Warsaw, Poland, Tel./Fax: +48 22 572 09 51, kmakarova@wum.edu.pl
  • Department of Physical Chemistry, Faculty of Pharmacy, Medical University of Warsaw, 1 Banacha Str., 02-097 Warsaw, Poland, Tel./Fax: +48 22 572 09 51
autor
  • Department of Physical Chemistry, Faculty of Pharmacy, Medical University of Warsaw, 1 Banacha Str., 02-097 Warsaw, Poland, Tel./Fax: +48 22 572 09 51
  • Department of Physical Chemistry, Faculty of Pharmacy, Medical University of Warsaw, 1 Banacha Str., 02-097 Warsaw, Poland, Tel./Fax: +48 22 572 09 51
autor
  • Department of Physical Chemistry, Faculty of Pharmacy, Medical University of Warsaw, 1 Banacha Str., 02-097 Warsaw, Poland, Tel./Fax: +48 22 572 09 51
Bibliografia
  • 1. Bakkali, F., Averbeck, S., Averbeck, D., & Idaomar, M. (2008). Biological effects of essential oils – a review. Food Chem. Toxicol., 46, 446–475.[WoS]
  • 2. Reische, D., Lillard, D., Eitenmiller, R., Akoh, C., & Min, D. (1998). Antioxidants. In C. C. Akoh & D. B. Min (Eds.), Food lipids: chemistry, nutrition and biotechnology, 3rd ed. (pp. 409–433). Boca Raton: CRC Press.
  • 3. Ormancey, X., Sisalli, S., & Coutiere, P. (2001). Formulation of essential oils in functional perfumery. Parfums, Cosmetiques, Actualites, 157, 30–40.
  • 4. Edris, A. E. (2007). Pharmaceutical and therapeutic potentials of essential oils and their individual volatile constituents: a review. Phytother. Res., 21, 308–323.[WoS]
  • 5. Smith, R., Cohen, S., Doull, J., Feron, V., Goodman, J., Marnett, L., Portoghese, P., Waddell, W., Wagner, B., & Hall, R. (2005). A procedure for the safety evaluation of natural flavor complexes used as ingredients in food: essential oils. Food Chem. Toxicol., 43, 345–363.
  • 6. Burt, S. (2004). Essential oils: their antibacterial properties and potential applications in foods – a review. Int. J. Food Microbiol., 94, 223–253.
  • 7. Sacchetti, G., Maietti, S., Muzzoli, M., Scaglianti, M., Manfredini, S., Radice, M., & Bruni, R. (2005). Comparative evaluation of 11 essential oils of different origin as functional antioxidants, antiradicals and antimicrobials in foods. Food Chem., 91, 621–632.
  • 8. Stoll, S., & Schweiger, A. (2006). EasySpin, a comprehensive software package for spectral simulation and analysis in EPR. J. Magn. Reson., 178, 42–55.
  • 9. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. A. Jr, Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Daniels, A. D., Farkas, O., Rabuck, A. D., Raghavachari, K., & Ortiz, J. V. (2009). Gaussian 03, Revision C.02. Wallingford CT: Gaussian, Inc.
  • 10. Buettner, G. R. (1987). Spin trapping: ESR parameters of spin adducts 1474 1528V. Free Radic. Biol. Med., 3, 259–303.
  • 11. Dilbeck, C. W., & Finlayson-Pitts, B. J. (2013). Hydroxyl radical oxidation of phospholipid-coated NaCl particles. Phys. Chem. Chem. Phys., 15, 9833–9844.[WoS]
  • 12. Chamulitrat, W., Parker, C. E., Tomer, K. B., & Mason, R. P. (1995). Phenyl N-tert-butyl nitrone forms nitric oxide as a result of its Fe(III)-catalyzed hydrolysis or hydroxyl radical adduct formation. Free Radic. Res., 23, 1–14.
  • 13. Jerzykiewicz, M., Ćwieląg-Piasecka, I., Witwicki, M., & Jezierski, A. (2010). EPR spin trapping and DFT studies on structure of active antioxidants in biogycerol. Chem. Phys. Lett., 497, 135–141.[WoS]
  • 14. Ucun, F., & Aydın, S. G. (2014). Calculated optimized structures and hyperfine coupling constants of some radical adducts of α-phenyl-N-tert-butyl nitrone in water and benzene solutions. J. Organomet. Chem., 759, 27–32.[WoS]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_1515_nuka-2015-0082
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