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Analysis of Fatty Acid Esters of Hydroxyl Fatty Acid in Selected Plant Food

  • Ana-Marija Liberati-Čizmek
  • Mirna Biluš
  • Antun Lovro Brkić
  • Irena Colić Barić
  • Miro Bakula
  • Amela Hozić
  • Mario CindrićEmail author
Original Paper

Abstract

Metabolic syndrome, characterized by obesity, low-grade inflammation, insulin resistance, hyperglycemia, dyslipidemia and hypertension, is a major risk factor for cardiovascular mortality. Preclinical studies on recently discovered classes of lipids – fatty acid esters of hydroxy fatty acids (FAHFA) have revealed their anti-inflammatory and insulin-sensitizing potential. The FAHFA levels are significantly decreased in insulin-resistant individuals, their application exhibited anti-inflammatory effects and restoring the glucose-insulin homeostasis. The aim of our research was to analyze the overall FAHFA composition in a common diet, as only a partial FAHFA composition has been revealed so far (only the PAHSA subclass was analyzed in a few foods). A new approach to the FAHFAs analysis includes nano-LC and post-column modifier followed by negative ion mass spectrometry, in order to obtain maximum sensitivity. Analysis of different foods – oat (whole grain, coarse flakes and fine flakes), apple, clementine, lemon, strawberry, blueberry, mango, kiwi, avocado, pineapple, banana, onion, garlic, cherry tomato, carrot, parsley root, pepper and radish – exhibited wide inter-food variation in the FAHFA profiles. Sixteen analyzed FAHFAs (palmitic, oleic, palmitoleic and stearic hydroxy-esters) showed microgram to low nanogram levels (0.165 ng/g – 32 μg/g FW), with the highest abundancy in oat, clementine, garlic and pineapple. Stearic acid hydroxy stearic acid (SAHSA) was the most abundant FAHFA, especially in the food with antioxidative, anti-inflammatory and beneficial metabolic effects. In contrary, the PAHSA - previously proven to have the strongest antihyperglycemic and insulin-sensitizing effects, was not present in some foods (radish, avocado, mango, lemon, cherry tomato, kiwi). Our study proves the importance of overall FAHFA analysis in food (especially in a functional food), because of their potential metabolic benefits and possible future incorporation in special diets.

Keywords

Bioactive food compounds Fatty acid esters of hydroxyl fatty acids FAHFA composition Food analysis Negative ion mass spectrometry 

Abbreviations

FAHFA

Fatty acid esters of hydroxy fatty acids

OAHOA

Oleic acid hydroxy oleic acid

OAHPA

Oleic acid hydroxy palmitic acid

OAHPO

Oleic acid hxdroxy palmitoleic acid

OAHSA

Oleic acid hydroxy stearic acid

PAHPA

Palmitic acid hydroxy palmitic acid

PAHPO

Palmitic acid hydroxy palmitoleic acid

PAHOA

Palmitic acid hydroxy oleic acid

PAHSA

Palmitic acid hydroxy stearic acid

POHOA

Palmitoleic acid hydroxy oleic acid

POHPA

Palmitoleic acid hydroxy palmitic acid

POHPO

Palmitoleic acid hydroxy palmitoleic acid

POHSA

Palmitoleic acid hydroxy stearic acid

SAHOA

Stearic acid hydroxy oleic acid

SAHPA

Stearic acid hydroxy palmitic acid

SAHPO

Stearic acid hydroxy palmitoleic acid

SAHSA

Stearic acid hydroxy stearic acid

MRM

Multiple reaction monitoring

RSD

Relative standard deviation

ANOVA

Analysis of variance

HSD

Honestly significant difference

DHAHLA

DocosaHexaenoic acid hydroxy linoleic acid

GLUT4

Glucose transporter type 4

UPLC

Ultra performance liquid chromatography

MRM

Multiple reaction monitoring

Notes

Acknowledgements

Authors thank dr. sc. Jasmina Ranilovic, PhD from Podravka for providing oat samples and HrZZ childARTHRITISevolve 4771 project for financing SPE columns.

Compliance with Ethical Standards

Conflict of Interest

The authors declare no conflict of interest.

Supplementary material

11130_2019_728_MOESM1_ESM.docx (32 kb)
ESM 1 (DOCX 31 kb)

References

  1. 1.
    O'Neill S, O'Driscoll L (2015) Metabolic syndrome: a closer look at the growing epidemic and its associated pathologies. Obes Rev 16(1):1–12.  https://doi.org/10.1111/obr.12229 CrossRefGoogle Scholar
  2. 2.
    Leroith D (2012) Pathophysiology of the metabolic syndrome: implications for the cardiometabolic risks associated with type 2 diabetes. Am J Med Sci 343(1):13–16.  https://doi.org/10.1097/MAJ.0b013e31823ea214 CrossRefGoogle Scholar
  3. 3.
    Mottillo S, Filion KB, Genest J, Joseph L, Pilote L, Poirier P, Rinfret S, Schiffrin EL, Eisenberg MJ (2010) The metabolic syndrome and cardiovascular risk a systematic review and meta-analysis. J Am Coll Cardiol 56(14):1113–1132.  https://doi.org/10.1016/j.jaac.2010.05.034 CrossRefGoogle Scholar
  4. 4.
    Tangvarasittichai S (2015) Oxidative stress, insulin resistance, dyslipidemia and type 2 diabetes mellitus. World J Diabetes 6(3):456–480.  https://doi.org/10.4239/wjd.v6.i3.456 CrossRefGoogle Scholar
  5. 5.
    Esser N, Legrand-Poels S, Piette J, Scheen AJ, Paquot N (2014) Inflammation as a link between obesity, metabolic syndrome and type 2 diabetes. Diabetes Res Clin Pract 105(2):141–150.  https://doi.org/10.1016/j.diabres.2014.04.006 CrossRefGoogle Scholar
  6. 6.
    Li G, Zhang P, Wang J, An Y, Gong Q, Gregg EW, Yang W, Zhang B, Shuai Y, Hong J, Engelgau MM, Li H, Roglic G, Hu Y, Bennett PH (2014) Cardiovascular mortality, all-cause mortality, and diabetes incidence after lifestyle intervention for people with impaired glucose tolerance in the Da Qing diabetes prevention study: a 23-year follow-up study. Lancet Diabetes Endocrinol 2:474–480.  https://doi.org/10.1016/S2213-8587(14)70057-9 CrossRefGoogle Scholar
  7. 7.
    Erlanson-Albertsson C, Albertsson PA (2015) The use of green leaf membranes to promote appetite control, suppress hedonic hunger and loose body weight. Plant Foods Hum Nutr 70:281–290.  https://doi.org/10.1007/s11130-015-0491-8
  8. 8.
    Suhaila M (2014) Functional foods against metabolic syndrome (obesity, diabetes, hypertension and dyslipidemia) and cardiovasular disease. Trends Food Sci Technol 35:114–128.  https://doi.org/10.1016/j.tifs.2013.11.001 CrossRefGoogle Scholar
  9. 9.
    Vendrame S, Del Bo C, Ciappellano S, Riso P, Klimis-Zacas D (2016) Berry fruit consumption and metabolic syndrome. Antioxidants 5(4):34.  https://doi.org/10.3390/antiox5040034 CrossRefGoogle Scholar
  10. 10.
    Carlson JJ, Eisenmann JC, Norman GJ, Ortiz KA, Young PC (2011) Dietary fiber and nutrient density are inversely associated with the metabolic syndrome in US adolescents. J Am Diet Assoc 111:1688–1695.  https://doi.org/10.1016/j.jada.2011.08.008
  11. 11.
    Poudyal H, Panchal SK, Diwan V, Brown L (2011) Omega-3 fatty acids and metabolic syndrome: effects and emerging mechanisms of action. Prog Lipid Res 50:372–387.  https://doi.org/10.1016/j.plipres.2011.06.003 CrossRefGoogle Scholar
  12. 12.
    Perez-Jimenez J, Diaz-Rubio ED, Saura-Calixto F (2015) Contribution of macromolecular antioxidants to dietary antioxidant capacity: a study in the Spanish Mediterranean diet. Plant Foods Hum Nutr 70(4):365–370.  https://doi.org/10.1007/s11130-015-0513-6 CrossRefGoogle Scholar
  13. 13.
    Hirai S, Takahashi N, Goto N, Lin S, Uemura T, Yu R, Kawada T (2010) Functional food targeting the regulation of obesity-induced inflammatory responses and pathologies. Mediat Inflamm 2010:367838.  https://doi.org/10.1155/2010/367838 CrossRefGoogle Scholar
  14. 14.
    Szajdek A, Borowska EJ (2008) Bioactive compounds and health-promoting properties of berry fruits: a review. Plant Foods Hum Nutr 63:147–156.  https://doi.org/10.1007/s11130-008-0097-5 CrossRefGoogle Scholar
  15. 15.
    Lin D, Xiao M, Zhao J, Li Z, Xing B, Li X, Kong M, Li L, Zhang Q, Liu Y, Chen H, Qin W, Wu H, Chen S (2016) An overview of plant phenolic compounds and their importance in human nutrition and management of type 2 diabetes. Molecules 21(10):E1374.  https://doi.org/10.3390/molecules21101374
  16. 16.
    Yore MM, Syed I, Moraes-Vieira PM, Zhang T, Herman MA, Homan EA, Patel RT, Lee J, Chen S, Peroni OD, Dhaneshwar AS, Hammarstedt A, Smith U, McGraw TE, Saghatelian A, Kahn BB (2014) Discovery of a class of endogenous mammalian lipids with anti-diabetic and anti-inflammatory effects. Cell 159:318–332.  https://doi.org/10.1016/j.cell.2014.09.035 CrossRefGoogle Scholar
  17. 17.
    Kuda O, Brezinova M, Rombaldova M, Slavikova B, Posta M, Beier P, Janovska P, Veleba J, Kopecky J, Kudova E, Pelikanova T, Kopecky J (2016) Docosahexaenoic acid-derived fatty acid esters of hydroxy fatty acids (FAHFAs) with anti-inflammatory properties. Diabetes 65:2580–2590.  https://doi.org/10.2337/db16-0385 CrossRefGoogle Scholar
  18. 18.
    Ma Y, Kind T, Vaniya A, Geenity I, Fahrmann JF, Fiehn O (2015) An in silico MS/MS library for automatic annotation of novel FAHFA lipids. J Cheminform 7:53.  https://doi.org/10.1186/s13321-015-0104-4
  19. 19.
    Nišavić M, Hozić A, Hameršak Z, Radić M, Butorac A, Duvnjak M, Cindrić M (2017) High-efficiency microflow and nanoflow negative electrospray ionization of peptides induced by gas-phase proton transfer reactions. Anal Chem 89(9):4847–4854.  https://doi.org/10.1021/acs.analchem.6b04466

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department for Endocrinology and Diabetology in Clinical Hospital Sveti DuhZagrebCroatia
  2. 2.BIOCentreCentral Lab ServicesZagrebCroatia
  3. 3.Department of PhysicsFaculty of ScienceZagrebCroatia
  4. 4.Department for Food Quality ControlFaculty of Food Technology and BiotechnologyZagrebCroatia
  5. 5.Division of Molecular Medicine Ruđer Bošković InstituteZagrebCroatia

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