Skip to main content

Advertisement

SpringerLink
Log in

Oxidative stabilities of grass carp oil: possible mechanisms of volatile species formation in hydroperoxylated metabolites at high temperature

  • Original Paper
  • Published:
European Food Research and Technology Aims and scope Submit manuscript

Abstract

The mechanisms of volatile species formation for hydroperoxylated metabolites of unsaturated fatty acids in grass carp oil were investigated. All oil samples were heated at 110 °C for 8 various durations. The hydroperoxylated metabolites were evaluated by ultra-performance liquid chromatography coupled with time-of-flight mass spectrometry, solid-phase microextraction gas chromatography mass spectrometry and conventional chemical indicators. Compared to fresh fish oil, the content of monounsaturated fatty acids and saturated fatty acids with higher oxidation stability in the heating samples was significantly increased (P < 0.05), while the content of polyunsaturated fatty acids was significantly reduced (P < 0.05). A total of 35 triglycerides were determined, of these, the relative content of carbon numbers (CNs) 54, 56 and 58 was dramatically decreased, while CN50 and CN52 were gradually increased. Partial least-squares discriminant analysis indicated that continuous heating had different effects on volatile substances and twelve volatile species variables associated with lipid oxidation from the eight various heating periods were identified. In addition, sixteen oxidized metabolites were identified and their content was significantly increased (P < 0.05), except the 13-HODE, 9-HOTrE, 5-HETE and 12-HETE. The metabolic pathways of grass carp oil under continuous heating were clarified based on critical volatile components and oxidized metabolites, intending to reveal the oxidation paradigm of oil exposed to high temperatures.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

Abbreviations

UPLC-TOF–MS/MS:

Ultra-performance liquid chromatography-time-of-flight mass spectrometry

SPME–GC–MS:

Solid-phase microextraction gas chromatography mass spectrometry

MUFAs:

Monounsaturated fatty acids

SFAs:

Saturated fatty acids

PUFAs:

Polyunsaturated fatty acids

TAGs:

Triglycerides

CNs:

Carbon numbers

PLS-DA:

Partial least-squares discriminant analysis

OA:

Oleic acid

LA:

Linoleic acid

ALA:

Linolenic acid

ARA:

Arachidonic acid

EPA:

Eicosapentaenoic acid

DPA:

Docosapentaenoic acid

DHA:

Docosahexaenoic acid

8-HOME:

8-Hydroxy-octadecanoic acid

10-HOME:

10-Hydroxy-octadecanoic acid

11-HOME:

11-Hydroxy-octadecanoic acid

13-HODE:

13-Hydroxy-octadecadienoic acid

9-HOTrE:

9-Hydroxy-octadecatrienoic acid

5-HETE:

5-Hydroxy-eicosapentaenoic acid

12-HETE:

12-Hydroxy-eicosapentaenoic acid

15-HETE:

15-Hydroxy-eicosapentaenoic acid

10-HDPE:

10-Hydroxy-docosapentenoic acid

10-HDoHE:

10-Hydroxy-docosahexaenoic acid

9-HpOME:

9-Hydroperoxy-octadecanoic acid

10-HpOME:

10-Hydroperoxy-octadecanoic acid

9-HpODE:

9-Hydroperoxy-octadecadienoic acid

13-HpODE:

13-Hydroperoxy-octadecadienoic acid

9-HpOTrE:

9-Hydroperoxy-octadecatrienoic acid

9-KOME:

9-Oxo-octadecanoic acid

References

  1. FAO (2020) The state of world fisheries and aquaculture. Food and Agriculture Organization of the United Nations, Rome

    Google Scholar 

  2. Chiba T, Brash AR, Furue M (2016) The precise structures and stereochemistry of trihydroxy-linoleates esterified in human and porcine epidermis. J Biol Chem 291:14540–14554. https://doi.org/10.1074/jbc.M115.711267

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Xie D, Jin J, Sun J et al (2017) Comparison of solvents for extraction of krill oil from krill meal: Lipid yield, phospholipids content, fatty acids composition and minor components. Food Chem 233:434–441. https://doi.org/10.1016/j.foodchem.2017.04.138

    Article  CAS  PubMed  Google Scholar 

  4. Maríad G, Encarnación G (2009) Oxidation of corn oil at room temperature: primary and secondary oxidation products and determination of their concentration in the oil liquid matrix from 1H nuclear magnetic resonance data. Food Chem 116:183–192. https://doi.org/10.1016/j.foodchem.2009.02.029

    Article  CAS  Google Scholar 

  5. Morales A, Marmesat S, Dobarganes MC et al (2012) Quantitative analysis of hydroperoxy-, keto- and hydroxy-dienes in refined vegetable oils. J Chromatogr A 1229:190–197. https://doi.org/10.1016/j.chroma.2012.01.039

    Article  CAS  PubMed  Google Scholar 

  6. Giua L, Blasi F, Simonetti MS et al (2013) Oxidative modifications of conjugated and unconjugated linoleic acid during heating. Food Chem 140:680–685. https://doi.org/10.1016/j.foodchem.2012.09.067

    Article  CAS  PubMed  Google Scholar 

  7. Nogueira MS, Scolaro B, Milne GL et al (2018) Oxidation products from omega-3 and omega-6 fatty acids during a simulated shelf life of edible oils. LWT-Food Sci Technol 101:113–122. https://doi.org/10.1016/j.lwt.2018.11.044

    Article  CAS  Google Scholar 

  8. Cao J, Jiang X, Chen Q et al (2020) Oxidative stabilities of olive and camellia oils: possible mechanism of aldehydes formation in oleic acid triglyceride at high temperature. LWT-Food Sci Technol 118:108858. https://doi.org/10.1016/j.lwt.2019.108858

    Article  CAS  Google Scholar 

  9. Hu XF, Li JL, Zhang L et al (2022) Effect of frying on the lipid oxidation and volatile substances in grass carp (Ctenopharyngodon idellus) fillet. J Food Process Preserv 00:e16342. https://doi.org/10.1111/jfpp.16342

    Article  CAS  Google Scholar 

  10. Liu X, Wang S, Masui E et al (2020) Model for prediction of the carbonyl value of frying oil from the initial composition. LWT-Food Sci Technol 117:108660. https://doi.org/10.1016/j.lwt.2019.108660

    Article  CAS  Google Scholar 

  11. Mehta BM, Darji VB, Aparnathi KD (2015) Comparison of five analytical methods for the determination of peroxide value in oxidized ghee. Food Chem 185:449–453

    Article  CAS  Google Scholar 

  12. Li JL, Tu ZC, Sha XM et al (2016) Effect of frying on fatty acid profile, free amino acids and volatile compounds of grass carp (ctenopharyngodon idellus) fillets. J Food Process Preserv 41:e13088. https://doi.org/10.1111/jfpp.13088

    Article  CAS  Google Scholar 

  13. Choe E, Min DB (2020) Mechanisms and factors for edible oil oxidation. Compr Rev Food Sci Food Safety 5:169–186. https://doi.org/10.1111/j.1541-4337.2006.00009.x

    Article  Google Scholar 

  14. Parmar P, Kaushik K, Devaraja HC et al (2013) Journal of medicinal plants research the effects of alcoholic extract of Arjuna (Terminalia arjuna Wight & Arn.) bark on stability of clarified butterfat. J Med Plant Res 7:2545–2550. https://doi.org/10.5897/JMPR2013.5114

    Article  Google Scholar 

  15. Farhoosh R, Khodaparast M, Sharif A et al (2012) Olive oil oxidation: rejection points in terms of polar, conjugated diene, and carbonyl values. Food Chem 131:1385–1390. https://doi.org/10.1016/j.foodchem.2011.10.004

    Article  CAS  Google Scholar 

  16. Serhan CN, Levy BD (2018) Omega-3 fatty acid-derived mediators that control inflammation and tissue homeostasis emergence of the pro-resolving superfamily of mediators. J Clin Investig 128:2657–2669. https://doi.org/10.1172/JCI97943

    Article  PubMed  PubMed Central  Google Scholar 

  17. Chen J, Jayachandran M, Bai W et al (2022) A critical review on the health benefits of fish consumption and its bioactive constituents. Food Chem 369:130874. https://doi.org/10.1016/j.foodchem.2021.130874

    Article  CAS  PubMed  Google Scholar 

  18. Wang C, Xia W, Xu Y et al (2014) Comparative study on nutritional value and fatty acid profiles of brains and eyes from four freshwater fishes. J Am Oil Chem Soc 91:1471–1476. https://doi.org/10.1007/s11746-014-2449-7

    Article  CAS  Google Scholar 

  19. Xu J, Yan B, Teng Y et al (2010) Analysis of nutrient composition and fatty acid profiles of Japanese sea bass lateolabrax japonicus (cuvier) reared in seawater and freshwater. J Food Compos Anal 23:401–405. https://doi.org/10.1016/j.jfca.2010.01.010

    Article  CAS  Google Scholar 

  20. Foret MK, Lincoln R, Carmo SD et al (2020) Connecting the “dots”: from free radical lipid autoxidation to cell pathology and disease. Chem Rev 120:12757–12787. https://doi.org/10.1021/acs.chemrev.0c00761

    Article  CAS  PubMed  Google Scholar 

  21. Lehotay SJ, Sapozhnikova Y, Mol HGJ (2015) Current issues involving screening and identification of chemical contaminants in foods by mass spectrometry. TrAC, Trends Anal Chem 69:62–75. https://doi.org/10.1016/j.trac.2015.02.012

    Article  CAS  Google Scholar 

  22. Song G, Zhang M, Zhang Y et al (2019) In situ method for real-time discriminating salmon and rainbow trout without sample preparation using iknife and rapid evaporative ionization mass spectrometry-based lipidomics. J Agric Food Chem 67:4679–4688. https://doi.org/10.1021/acs.jafc.9b00751

    Article  CAS  PubMed  Google Scholar 

  23. Rincón-Cervera MÁ, González-Barriga V, Valenzuela R et al (2019) Profile and distribution of fatty acids in edible parts of commonly consumed marine fishes in Chile. Food Chem 274:123–129. https://doi.org/10.1016/j.foodchem.2018.08.113

    Article  CAS  PubMed  Google Scholar 

  24. Wang X, Zhang H, Song Y et al (2019) Comparative lipid profile analysis of four fish species by ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry. J Agric Food Chem 67:9423–9431

    Article  CAS  Google Scholar 

  25. Zhang D, Li X, Duan X et al (2021) Lipidomics reveals the changes in lipid profile of flaxseed oil affected by roasting. Food Chem 364:130431

    Article  CAS  Google Scholar 

  26. Ito J, Shimizu N, Kobayashi E et al (2017) A novel chiral stationary phase LC-MS/MS method to evaluate oxidation mechanisms of edible oils. Sci Rep 7:10026. https://doi.org/10.1038/s41598-017-10536-2

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  27. Oliw EH, Wennman A, Hoffmann I et al (2011) Stereoselective oxidation of regioisomeric octadecenoic acids by fatty acid dioxygenases. J Lipid Res 52:1995–2004. https://doi.org/10.1194/jlr.M018259

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  28. Du ZY, Jian Z, Wang C et al (2012) Risk–benefit evaluation of fish from Chinese markets: nutrients and contaminants in 24 fish species from five big cities and related assessment for human health. Sci Total Environ 416:187–199. https://doi.org/10.1016/j.scitotenv.2011.12.020

    Article  CAS  PubMed  Google Scholar 

  29. Yin H, Xu L, Porter NA (2011) Free radical lipid peroxidation: mechanisms and analysis. Chem Rev 111:5944–5972

    Article  CAS  Google Scholar 

  30. Zahradka P, Neumann S, Aukema HM et al (2017) Adipocyte lipid storage and adipokine production are modulated by lipoxygenase-derived oxylipins generated from 18-carbon fatty acids. Int J Biochem Cell Biol 88:23–30. https://doi.org/10.1016/j.biocel.2017.04.009

    Article  CAS  PubMed  Google Scholar 

  31. Pauls SD, Rodway LA, Winter T et al (2018) Anti-inflammatory effects of α-linolenic acid in M1-like macrophages are associated with enhanced production of oxylipins from α-linolenic and linoleic acid. J Nutr Biochem 57:121–129. https://doi.org/10.1016/j.jnutbio.2018.03.020

    Article  CAS  PubMed  Google Scholar 

  32. Isobe Y, Arita M (2014) Identification of novel omega-3 fatty acid-derived bioactive metabolites based on a targeted lipidomics approach. J Clin Biochem Nutr 55:79–84. https://doi.org/10.3164/jcbn.14-18

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  33. Zhang Q, Qin W, Lin D et al (2015) The changes in the volatile aldehydes formed during the deep-fat frying process. J Food Sci Technol 52:7683–7696. https://doi.org/10.1007/s13197-015-1923-z

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  34. Jiang Y, Zhao L, Yuan M et al (2017) Identification and changes of different volatile compounds in meat of crucian carp under short-term starvation by GC-MS coupled with HS-SPME. J Food Biochem 41:e12375. https://doi.org/10.1111/jfbc.12375

    Article  CAS  Google Scholar 

  35. Chang C, Wu G, Zhang H et al (2020) Deep-fried flavor: characteristics, formation mechanisms, and influencing factors. Crit Rev Food Sci Nutr 60:1496–1514. https://doi.org/10.1080/10408398.2019.1575792

    Article  CAS  PubMed  Google Scholar 

  36. Peroni E, Scali V, Balestri F et al (2020) Pathways of 4-hydroxy-2-nonenal detoxification in a human astrocytoma cell line. Antioxidants 9:385. https://doi.org/10.3390/antiox9050385

    Article  CAS  PubMed Central  Google Scholar 

  37. Fratini G, Lois S, Pazos M et al (2012) Volatile profile of Atlantic shellfish species by HS-SPME-GC/MS. Food Res Int 48:856–865. https://doi.org/10.1016/j.foodres.2012.06.033

    Article  CAS  Google Scholar 

  38. Lloyd MA, Drake MA, Gerard PD (2009) Flavor variability and flavor stability of U.S.-produced whole milk powder. J Food Sci 74:S334–S343. https://doi.org/10.1111/j.1750-3841.2009.01299.x

    Article  CAS  PubMed  Google Scholar 

  39. Ba HV, Ryu KS, Lan NTK et al (2013) Influence of particular breed on meat quality parameters, sensory characteristics, and volatile components. Food Sci Biotechnol 22:651–658. https://doi.org/10.1007/s10068-013-0127-4

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the Chinese National Natural Science Foundations (NO. 32060557), the open fund of State Key Laboratory of Food Science and Technology, Nanchang University (NO. SKLF-KF-202017). Key Research and Development projects in Jiangxi Province (NO. 20203BBFL63062). Key Research and Development projects in Jiujiang City, Jiangxi Province (NO. S2021DYFN076).

Author information

Authors and Affiliations

  1. State Key Laboratory of Food Science and Technology, Nanchang University, 235 East Nanjing Road, Nanchang, 330047, Jiangxi, China

    Xiangfei Hu, Zongcai Tu, Hui Wang & Yueming Hu

  2. National Research and Development Center of Freshwater Fish Processing, College of Life Sciences, Jiangxi Normal University, Jiangxi Normal University, 99 Ziyang Road, Nanchang, 330022, China

    Bin Peng, Zongcai Tu, Jinlin Li & Bizhen Zhong

  3. Key Laboratory for Mass Spectrometry and Instrumentation of Jiangxi Province, East China University of Technology, Nanchang, 330013, Jiangxi, China

    Shuanglong Wang

Authors
  1. Xiangfei Hu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Bin Peng
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shuanglong Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zongcai Tu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jinlin Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Hui Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yueming Hu
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Bizhen Zhong
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

Xiangfei Hu: Conceptualization, Methodology, Formal analysis, Visualization. Bin Peng: Data curation, Writing review and editing. Shuanglong Wang: Supervision, Data curation. Zongcai Tu: Supervision, Funding acquisition, Data curation. Jinlin Li: Supervision, Funding acquisition, Data curation. Hui Wang: Investigation. Yueming Hu: Investigation. Bizhen Zhong: Investigation.

Corresponding authors

Correspondence to Zongcai Tu or Jinlin Li.

Ethics declarations

Conflict of interest

We declare that we have no financial and personal relationships with other people or organizations that can inappropriately influence our work, there is no professional or other personal interest of any nature or kind in any product, service and/or company that could be construed as influencing the position presented in, or the review of, the manuscript entitled “Oxidative stabilities of grass carp oil: possible mechanisms of volatile species formation in hydroperoxylated metabolites at high temperature.”

Compliance with ethics requirements

This article does not contain any studies with human or animal subjects.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Xiangfei Hu and Bin Peng are co-first authors.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 1213 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hu, X., Peng, B., Wang, S. et al. Oxidative stabilities of grass carp oil: possible mechanisms of volatile species formation in hydroperoxylated metabolites at high temperature. Eur Food Res Technol 248, 2079–2095 (2022). https://doi.org/10.1007/s00217-022-04032-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00217-022-04032-9

Keywords

Search

Navigation