The use of tris (tetraphenylimidodiphosphinate) of praseodymium chemical shift reagent in proton NMR for the evaluation of the argan oil fatty acids autoxidation and the analysis of the argan pulp fatty acids

Authors

  • Souad Hamdouch Biomolecular and Organic Synthesis Laboratory, Faculty of Sciences Ben M'sik (FSBM), University Hassan II of Casablanca, Morocco
  • Latifa Barkaoui Laboratory of Physical Chemistry and Bioorganic Chemistry, URAC 22, Faculty of Science and Technology, University Hassan II of Casablanca, Morocco
  • Merriem Tarbaoui LIMAT-Thermostructural Materials and Polymers Team, Faculty of science Ben M’sik (FSBM), University Hassan II of Casablanca, Morocco
  • Amine Ouaket Biomolecular and Organic Synthesis Laboratory, Faculty of Sciences Ben M'sik (FSBM), University Hassan II of Casablanca, Morocco

DOI:

https://doi.org/10.13171/mjc8219042706sh

Abstract

Proton NMR is a method of molecular investigation that has its limitations when applied to complex molecules or molecules with many nearly equivalent sites. Previous studies have resorted to the use of paramagnetic chemical shift reagents, having as formula tris (tetraphenylimidodiphosphinate) of lanthanides ln((tpip.)3. The use of reagent Pr(tpip)3 in proton RMN has allowed us to evaluate the autoxidation of fatty acids mixture (stored 6 and 12 months after oil extraction) by the dosage of saturated and unsaturated acids on the one hand, and that of oleic and linoleic acids on the other. We note between 6 and 12 months of storage at 4°C a decrease in the percentage of unsaturated acids (76% to 63%) and an increase in the percentage of saturated acids (24% to 36%). The results show that the oleic acid maintained the same percentage (35%) as it is not easily oxidized whereas, for the linoleic acid, we observe a decrease in percentage from 22.5% to 18.5% (slow autoxidation at 4°C). We also used this NMR method for the analysis of the argan pulp fatty part. The GC analysis shows that it contains very few unsaturated fatty acids and that the main fatty acids are myristic (C14:0) and palmitic (C16:0) acids. The proton NMR with Pr(tpip)3 allowed us to confirm these results. This method that does not require derivation has proven to be interesting, simple and efficient.

References

- Y. El Bahloul, N. Dauchot, I. Machtoum, F. Gaboun, P. Van Cutsem. Development and characterization of microsatellite loci for the Moroccan endemic endangered species Argania spinosa (Sapotaceae). Appl Plant Sci. Botanical Society of America, 2014, 2 (4), pp. 4.

- F. Ain-Lhout, S. Boutaleb, M.C. Diaz-Barradas, J. Jauregui and M. Zunzunegui. Monitoring the evolution of soil moisture in root zone systeme of Argania Spinosa using electrical resistivity imaging. Agricultural Water Management, 2016, 164, 158-166.

- M. P. Ruas, J. Ros, J.F Terral, S. Ivorra, H. Andrianarinosy, A.S. Ettahiri, A. Fili, J.P Van Staëvel. History and archaeology of the

emblematic argan tree in the medieval AntiAtlas Mountains (Morocco) Quaternary International, 2016, 404, 114-136.

- A. Chakhchar, M. Haworth, C. El Modafar, M; Lauteri, C. Mattioni, S. Wahbi, and M. Centritto. An assessment of genetic diversity and drought tolerance in Argan Tree (Argania spinosa) Populations: Potential for the development of improved drought tolerance. Front Plant Sci, 2017, 8, 276.

- M. Farines, J. Soulier, M. Charrouf, R. Soulier, Étude de l’huile de graine d’Argania spinosa (L.), Sapotaceae. I. La fraction glycéridique.

Rev. Franç. Corps Gras, 1984, 31, 283-286.

- H. Chimi, M. Rahmani, J. Collard, P. Collard, Rôle des Composés phénoliques. Rev. Fr. Corps Gras, 1990, 37, 363–367

- F. Khallouki, C. Younos, R. Soulimani, and Z. Charrouf. Consumption of argan oil (Morocco) with its unique profile of fatty acids, tocopherols, squalene, sterols and phenolic compounds should confer valuable cancer chemopreventive effects. Eur. J. Cancer Prev, 2003, 12, 67-75.

- M. Hilali, Z. Charrouf, A.El Aziz Soulhi, L. hachimi, and D. Guillaume. Influence of origin and extraction method on argan oil physico-chemical characteristics and composition. J. Agric. Food Chem, 2005, 53, 6, 2081-2087.

- Z. Charrouf, D. Guillaume, L’huile d’argane. Composition et propriétés chimiques de l’huile d’argane, L. Kenny & I. De Zborowski (Eds.),

Atlas de l’arganier et de l’arganeraie, IAV Hassan II, Rabat, 2007, 161–169.

- Z. Charrouf, D. Pioch; Research Contract n°AR05A061P704 between Social Development Agency (Morroco) and Agropolis International, 2009

- S. Gharby, H. Harhar, D. Guillaume, A. Haddad, B. Matthäus, and Z. Charrouf, “Oxidative stability of edible argan oil: a twoyear study,” LWT, 2011, 44(1), 1–8.

- H. Harhar, S. Gharby, D. Guillaume and Z. Charrouf. Effect of argan kernel storage conditions on argan oil quality. Eur. J. Lipid Sci. Technol, 2010, 112(8), 915-920.

- H. Harhar, S. Gharby, B. Kartah, H. El Monfalouti, D. Guillaume, and Z. Charrouf. Influence of argan kernel roasting-time on virgin argan oil composition and oxidative stability. Plant Foods Hum Nutr, 2011, 66, 163-168.

- N. Ait Aabd, A. El Asbahani, Y. El Alem, A. El Finti, F. Msanda, A. El Mousadik, Variation in oil content and fatty acid composition in preselected argan trees with morphological characters and geographical localization, Med J Nutrition Metab, 2013, 6(3), 217-225.

- M. Cherki, A. Drissi, A. Derouiche, M. El Messal, Y. Bamou, A. Idrissi Oudghiri, A. Khalil, A. Adlouni, 4 P-0949 Influence of argan oil administration on lipid peroxidation and paraoxonase activities in healthy Moroccan men, Atherosclerosis Supplements, 2003, 4(2), 282.

- Z. Charrouf, D. Guillaume, argan oil: occurrence, composition and impact on human health, Eur. J. Lipid. Sci. Technol., 2008, 110, 632-636.

- Z. Charrouf, D. Guillaume, Argan oil and other argan products; use in dermocosmetology, Eur. J. Lipid. Sci. Technol., 2011, 113, 403-408.

- A. Moukal, L’arganier, Argania spinosa L. (skeels), usage thérapeutique, cosmétique et alimentaire, Phytothérapie, 2004, 5, 135-141.

- A. Adlouni. L'huile d’argan, de la nutrition à la santé. Phytotherapie, 2010, 8(2), 89-97.

- K. Fellat-Zerrouk, S. Smoughen, R. Maurin, Etude de la pulpe du fruit de l'arganier (Argania spinosa) du Maroc, Matière grasse et latex. Actes Institut. Agron. Vét. Rabat, 1987, 7, 17-22.

- B. D. Flockhart and J. Jonas. Lanthanide Shift Reagents in Nuclear Magnetic Resonance Spectroscopy. Critical Reviews in Analytical Chemistry 2008, 2(1), 69-130.

- N. Platzer, C. Alvarez, L. Barkaoui, H. Rudler, Praseodinium NMR –Shift reagent for carboxylic acids and their carboxylates synthesis, X-ray structure and application. Soc. Chem. France, 1995, 132(1), 95 -113.

- L. Barkaoui, M. Charrouf, MN. Rager, B. Denise, N. Platzer, H. Rudler Tris(tetraphenylimidodi-phosphinato) gadolinium, Gd(tpip)3, a new relaxation reagent for strutural studies of acyclic and polycyclic carboxylic-acids and phenols, Bull. Soc chem. Fr, 1997, 134(2), 167-175.

- G. Otting. Prospects for lanthanides in structural biology by NMR. J. Biomol. NMR. 2008, 42(1), 1-9.

- J. W. Emsley. And J. Feeney. Forty years of Progress in Nuclear Magnetic Resonance Spectroscopy. Progress in Nuclear Magnetic Resonance Spectroscopy. 2007, 50(4), 179-198.

- R. Berardozzi and L. Di Bari. A simple and general method to determine reliable pseudocontact shifts in Lanthanide Complexes. Inorg. Chem. 2013, 52(19), 11514-11518.

- H. Chimi., J. Cillard.et P. Cillard. Autoxydation de l'huile d'argan. Argania spinosa. L du Maroc. Sciences des Aliments. 1994, 14, 117-124.

- H. El Monfalouti., Z. Charrouf., S. Belviso, D. Ghirardello., B. Scursatone., D. Guillaume., C. Denhez., G. Zeppa. Analysis and antioxidant capacity of the phenolic compounds from argan fruit (Argania spinosa (L.) Skeels). Eur. J. Lipid. Sci. Technol, 2012, 114(4), 446-452.

- Kamel-eldine A., Andersson R. A multivariate study of the correlation between tocopherol content and fatty acid composition in vegetable oils, J. Am. Oil Chem. Soc. 1997, 74(4), 375-380.

- M. M. Polvillo, M. G. Ruiz, and M. C. Dobarganes. Oxidative stability of sunflower oils differing in unsaturation degree during long-term storage at room temperature. J. Am. Oil Chem. Soc, 2004, 81(6), 577-583.

- D.A, Pratt, K.A. Tallman and NA. Porter. Free Radical Oxidation of Polyunsaturated Lipids: New mechanistic insights and the development of peroxyl radical clocks. Acc Chem Res. 2011, 44(6), 458-67.

- S. Kubow. Routes of formation and toxic consequences of lipid oxidation products in foods. Free Radical Biology and Medecine, 1992, 12(1), 63-81.

- H. Moussaoui, Y. Bahammou, A. Idlimam, A. Lamharrar, N. Abdenour. Investigation of hygroscopic equilibrium and modeling sorption isotherms of the argan products: A comparative study of leaves, pulps, and fruits, Food and Bioproducts, 2019, 114, 12-22.

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Published

2019-04-27

Issue

Vol. 8 No. 2 (2019)

Section

Organic Chemistry

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