Skip to main content
Log in

2-(4-Amino)-Phenyl-1-Hydrogen-Phenanthrene [9,10-d] Imidazole as a Novel Fluorescent Labeling Reagent for Determination of Fatty Acids in Raspberry

  • Published:
Food Analytical Methods Aims and scope Submit manuscript

Abstract

A novel method has been established for the rapid separation and determination of free fatty acids from 37 different varieties of raspberry. In this study, a new fluorescent labeling reagent for fatty acids, 2-(4-amino)-phenyl-1-hydrogen-phenanthrene [9, 10-d] imidazole (PIA), has been synthesized and successfully applied to the high-performance liquid chromatography (HPLC) determination of fatty acids in raspberry. The novel method has been optimized by HPLC with fluorescence detection and online mass spectrometry identification (HPLC–FLD–MS/MS). The 22 main fatty acids (FAs) present in raspberry were derivatized by PIA and separated on a reversed-phase Hypersil GOLD column with gradient elution. The main experimental parameters affecting extraction efficiency and derivatization yield were investigated and optimized by response surface methodology (RSM) combined with Box–Behnken design (BBD). Under the optimum conditions, the method was successfully applied for the analysis of 22 fatty acids in 37 different varieties of raspberry. Good linear correlations were observed for all fatty acids with correlation coefficients of > 0.9978. Limits of detection and quantification (LOD and LOQ) were in the range of 0.12 to 0.49 ng/mL and 1.07 to 2.81 ng/mL, respectively. Furthermore, the results indicated that the raspberries were rich in fatty acids, but the contents of the fatty acids varied among the different varieties.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  • Arvindakshan M, Ghate M, Ranjekar PK, Evans DR, Mahadik SP (2003) Supplementation with a combination of ω-3 fatty acids and antioxidants (vitamins E and C) improves the outcome of schizophrenia. Schizoph Res 62:195–204

    Article  Google Scholar 

  • Bobinaitė R, Viškelis P, Venskutonis PR (2012) Variation of total phenolics, anthocyanins, ellagic acid and radical scavenging capacity in various raspberry (Rubus spp.) cultivars. Food Chem 132:1495–1501

    Article  Google Scholar 

  • Bougnoux P, Hajjaji N, Maheo K, Couet C, Chevalier S (2010) Fatty acids and breast cancer: sensitization to treatments and prevention of metastatic re-growth. Prog Lipid Res 49:76–86

    Article  CAS  Google Scholar 

  • Calder PC (2006) Polyunsaturated fatty acids, inflammation, and inflammatory diseases. Am J Clin Nutr 83:1505S–1519S

    CAS  Google Scholar 

  • Dariush M, Wu JHY (2011) Omega-3 fatty acids and cardiovascular disease: effects on risk factors, molecular pathways, and clinical events. J Am Coll Cardiol 58:2047–2067

    Article  Google Scholar 

  • Gonzalez-Barrio R, Edwards CA, Crozier A (2011) Colonic catabolism of ellagitannins, ellagic acid, and raspberry anthocyanins: in vivo and in vitro studies. Drug Metab Dispos 39:1680–1688

    Article  CAS  Google Scholar 

  • Hoffman DR, Uauy R, Birch DG (1995) Metabolism of omega-3 fatty acids in patients with autosomal. Exp Eye Res 60:279–289

    Article  CAS  Google Scholar 

  • Hu N, Zhang S, Ji Z, You J, Suo Y (2014) Determination of fatty acids in three Nitraria species by precolumn fluorescence labeling for high-performance liquid chromatography and atmospheric pressure chemical ionization–mass spectrometry. Anal Lett 47:2475–2487

    Article  CAS  Google Scholar 

  • Jing N, Shi J, Li G, Sun Z, You J (2012) Determination of fatty acids from mushrooms using high performance. Food Res Int 48:155–163

    Article  CAS  Google Scholar 

  • Lacaze JP, Stobo LA, Turrell EA, Quilliam MA (2007) Solid-phase extraction and liquid chromatography-mass spectrometry for the determination of free fatty acids in shellfish. J Chromatogr A 1145:51–57

    Article  CAS  Google Scholar 

  • Larsson SC, Kumlin M, Ingelman-Sundberg M, Wolk A (2004) Dietary long-chain n-3 fatty acids for the prevention of cancer: a review of potential mechanisms1–3. Am J Clin Nutr 79:935–945

    CAS  Google Scholar 

  • Lee J, Dossett M, Finn CE (2012) Rubus fruit phenolic research: the good, the bad, and the confusing. Food Chem 130:785–796

    Article  CAS  Google Scholar 

  • Makahleh A, Saad B, Siang GH, Saleh MI, Osman H, Salleh B (2010) Determination of underivatized long chain fatty acids using RP-HPLC with capacitively coupled contactless conductivity detection. Talanta 81:20–24

    Article  CAS  Google Scholar 

  • Manzano P, Diego JC, Nozal MJ, Bernal JL, Bernal J (2012) Gas chromatography–mass spectrometry approach to study fatty acid profiles in fried potato crisps. J Food Compos Anal 28:31–39

    Article  CAS  Google Scholar 

  • Morales-Muñoz S, de Castro MDL (2005) Dynamic ultrasound-assisted extraction of colistin from feeds with on-line pre-column derivatization and liquid chromatography-fluorimetric detection. J Chromatogr A 1066:1–7

    Article  Google Scholar 

  • Mullen W, Mcginn J, Lean MEJ, Maclean MR, Gardner P, Duthie GG, Yokota T, Crozier A (2002a) Ellagitannins, flavonoids, and other phenolics in red raspberries and their contribution to antioxidant capacity and vasorelaxation properties. Exp Eye Res 50:5191–5196

    CAS  Google Scholar 

  • Mullen W, Stewart AJ, Lean MEJ, Gardner P, Duthie GG, Crozier A (2002b) Effect of freezing and storage on the phenolics, ellagitannins, flavonoids, and antioxidant capacity of red raspberries. J Agr Food Chem 50:5197–5201

    Article  CAS  Google Scholar 

  • Ong ES, Chor CF, Zou L, Ong CN (2009) A multi-analytical approach for metabolomic profiling of zebrafish (Danio rerio) livers. Mol BioSyst 5:288–298

    Article  CAS  Google Scholar 

  • Parry J, Su L, Luther M, Zhou K, Yurawecz MP, Whittaker P, Yu L (2005) Fatty acid composition and antioxidant properties of cold-pressed marionberry, boysenberry, red raspberry, and blueberry seed oils. J Agri food chem 53:566–573

    Article  CAS  Google Scholar 

  • Quehenberger O, Armando AM, Dennis EA (2011) High sensitivity quantitative lipidomics analysis of fatty acids in biological samples by gas chromatography-mass spectrometry. Biochim Biophys Acta 1811:648–656

    Article  CAS  Google Scholar 

  • Ruiz-Rodriguez A, Reglero G, Ibanez E (2010) Recent trends in the advanced analysis of bioactive fatty acids. J Pharm Biomed Anal 51:305–326

    Article  CAS  Google Scholar 

  • Soliman LC, Andrucson EM, Donkor KK, Church JS, Cinel B (2015) Determination of fatty acids in beef by liquid chromatography-electrospray ionization tandem mass spectrometry. Food Anal Methods 9:630–637

    Article  Google Scholar 

  • Sun Y, Zhang X, Ji Z, Song C, Sun Z, You J (2016) Determination of free fatty acids of Chinese Coriandrum sativum L. using benzimidazo[2,1-b]quinazolin-12(6H)-one-5-ethyl-p-toluenesulfonate as precolumn labeling reagent by LC with fluorescence detection. Chromatographia 79:547–559

    Article  CAS  Google Scholar 

  • Takahashi K, Goto-Yamamoto N (2011) Simple method for the simultaneous quantification of medium-chain fatty acids and ethyl hexanoate in alcoholic beverages by gas chromatography-flame ionization detector: Development of a direct injection method. J Chromatogr A 1218:7850–7856

  • Verbeyst L, Crombruggen KV, Van der Plancken I, Hendrickx M, Van Loey A (2011) Anthocyanin degradation kinetics during thermal and high pressure treatments of raspberries. J Food Eng 105:513–521

    Article  CAS  Google Scholar 

  • Vicente JP, Adelantadoa JVG, Carbó MTD, Castro RM, Reig FB (2004) Identification of drying oils used in pictorial works of art by liquid chromatography of the 2-nitrophenylhydrazides derivatives of fatty acids. Talanta 64:326–233

    Article  Google Scholar 

  • Wigmore SJ, Ross JA, Falconer JS, Plester CE, Tisdale MJ, Carter DC, Fearon KCH (1996) The effect of polyunsaturated fatty acids on the progress of cachexia in patients with pancreatic cancer. Supplement to Nutrition 12:s27–s30

    CAS  Google Scholar 

  • Xie Y, Li G, You J, Bai X, Wang C, Zhang L, Zhao F, Wu X, Ji Z, Sun Z (2012) A novel labeling reagent of 2-(12-Benzo[b]acridin-5-(12H)-yl)-acetohydrazide for determination of saturated and unsaturated fatty acids in traditional Chinese herbs by HPLC-APCI-MS. Chromatographia 75:571–583

    Article  CAS  Google Scholar 

  • Yamaguchi M, Hara S, Matsunaga R, Nakamura M (1985) 3-Bromomethyl-6,7-dimethoxy-1-methyl-2(1H)-quinoxalinone as a new fluorescence derivatization reagent for carboxylic acids in high-performance liquid chromatography. J Chromatogr A 346:227–236

    Article  CAS  Google Scholar 

  • Yang FQ, Feng K, Zhao J, Li SP (2009) Analysis of sterols and fatty acids in natural and cultured Cordyceps by one-step derivatization followed with gas chromatography-mass spectrometry. J Pharm Biomed Anal 49:1172–1178

    Article  CAS  Google Scholar 

  • Yang ZH, Miyahara H, Mori T, Doisaki N, Hatanaka A (2011) Beneficial effects of dietary fish-oil-derived monounsaturated fatty acids on metabolic syndrome risk factors and insulin resistance in mice. J Agric Food Chem 59:7482–7489

    Article  CAS  Google Scholar 

  • Zhang L, Keung W, Samokhvalov V, Wang W, Lopaschuk GD (2010) Role of fatty acid uptake and fatty acid beta-oxidation in mediating insulin resistance in heart and skeletal muscle. Biochim Biophys Acta 1801:1–22

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors acknowledge financial support from major science and technology projects of Qinghai province: utilization and development with high value and further process technology of medlar (2015-NK-A2), the unit of science and technology office of Qinghai province: manufacture integration technology and demonstration of high standards medlar with antioxidant and anti-cohesion (2015-SF-120), Qinghai Provincial Science Foundation (2016-ZJ-928Q) and CAS “Light of West China” Program (2016): Study on the effect of Lycium ruthenicum Murr. anthocyanin on the liver – protecting.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Na Hu or Yourui Suo.

Ethics declarations

Conflict of Interest

Yuwei Wang declares that she has no conflict of interest. Guangxiang Luan declares that he has no conflict of interest. Wu Zhou declares that he has no conflict of interest. Jinmao You declares that he has no conflict of interest. Na Hu declares that she has no conflict of interest. Yourui Suo declares that he has no conflict of interest.

Ethical Approval

This article does not contain any studies with human participants or animals performed by any of the authors.

Informed Consent

Not applicable.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wang, Y., Luan, G., Zhou, W. et al. 2-(4-Amino)-Phenyl-1-Hydrogen-Phenanthrene [9,10-d] Imidazole as a Novel Fluorescent Labeling Reagent for Determination of Fatty Acids in Raspberry. Food Anal. Methods 11, 451–465 (2018). https://doi.org/10.1007/s12161-017-1016-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12161-017-1016-x

Keywords

Navigation