Skip to main content
SpringerLink
Log in

A comprehensive characterization of polyphenol extracts from wasted sour fruits by LC–MS/MS and evaluation of their antioxidant potentials

  • Original Paper
  • Published:
Journal of Food Measurement and Characterization Aims and scope Submit manuscript

Abstract

Unripe grapes are pruned waste fruits of wine farming, while black lemons are dried products of agriculture waste lemons from lime fields. These fruit wastes are a rich source of bioactive molecules, especially polyphenols that are beneficial metabolites for human health to reduce or inhibit the oxidative stress and can be utilized in foods or pharmaceuticals. Therefore, this project aimed to study the wasted sour fruits for their polyphenols, antioxidant activities, and to support their symbiotic utilization as therapeutic and pharmaceutical products. This research was completed with solvent extraction optimization of polyphonic extracts, their in-vitro antioxidant activities using four different assays, and characterization of polyphenols by LC-ESI-QTOF-MS/MS. Efficient extraction for phenolic compounds was obtained using 80% acidified methanol with 0.1% formic acid. Results found that black lemons had a higher total phenolic content (TPC 10.11 ± 0.47 mg GAE/g), assimilated to unripe grapes (8.75 ± 0.33 mg GAE/g). Moreover, black lemons were also found with higher antioxidant potential than unripe grapes, possibly due to the presence of higher flavonoids, especially anthocyanins. 124 phenolic metabolites, including 21 phenolic acids, 45 flavonoids, 8 isoflavonoids, 2 chalcones, 7 stilbenes, 15 lignans and 25 other compounds were identified using mass spectrometry. In conclusion, these results supported the utilization of these products in combination as therapeutical ingredients in the food, biomedicine, and pharmaceutical industries.

Graphical abstract

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

Similar content being viewed by others

References

  1. C. Beres, G.N.S. Costa, I. Cabezudo, N.K. da Silva-James, A.S.C. Teles, A.P.G. Cruz, C. Mellinger-Silva, R.V. Tonon, L.M.C. Cabral, S.P. Freitas, Towards integral utilization of grape pomace from winemaking process: a review. Waste Manage. 68, 581–594 (2017)

    Article  Google Scholar 

  2. F. Cosme, T. Pinto, A. Vilela, Phenolic compounds and antioxidant activity in grape juices: a chemical and sensory view. Beverages 4, 22 (2018)

    Article  Google Scholar 

  3. A. Teixeira, N. Baenas, R. Dominguez-Perles, A. Barros, E. Rosa, D.A. Moreno, C. Garcia-Viguera, Natural bioactive compounds from winery by-products as health promoters: a review. Int. J. Mol. Sci. 15, 15638–15678 (2014)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Â.C. Salvador, M.M.Q. Simões, A.M.S. Silva, S.A.O. Santos, S.M. Rocha, A.J.D. Silvestre, Vine waste valorisation: integrated approach for the prospection of bioactive lipophilic phytochemicals. Int. J. Mol. Sci. 20, 4239 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. C. Dani, D. Bonatto, M. Salvador, M.D. Pereira, J.A.P. Henriques, E. Eleutherio, Antioxidant protection of resveratrol and catechin in Saccharomyces cerevisiae. J. Agric. Food Chem. 56, 4268–4272 (2008)

    Article  CAS  PubMed  Google Scholar 

  6. D.O. Adams, Phenolics and ripening in grape berries, Am. J. Enol. Viticult. (2006)

  7. F. Tinello, A. Lante, Evaluation of antibrowning and antioxidant activities in unripe grapes recovered during bunch thinning. Aust. J. Grape Wine Res. 23, 33–41 (2017)

    Article  CAS  Google Scholar 

  8. Ş Kıvrak, İ Kıvrak, E. Karababa, Nutritional value, phenolic, vitamin and mineral contents of a fermented beverage from grapes of’Merlot’and’Cabernet Sauvignon’. MITTEILUNGEN KLOSTERNEUBURG 66, 255–265 (2016)

    Google Scholar 

  9. S. Chaisawadi, W. Methawiriyasilp, D. Thongbute, T. Chayawattana, clean production of commercial freeze-dried lime powder for medicinal herb and nutritional health benefits, in, International Society for Horticultural Science (ISHS), Leuven, Belgium, pp. 29–35 (2005)

  10. N. Singh, N.S. Yarla, N.J. Siddiqi, M. de Lourdes Pereira, B. Sharma, Features, pharmacological chemistry, molecular mechanism and health benefits of lemon, medicinal chemistry (Shariqah (United Arab Emirates)), 17, 187–202 (2021)

  11. A.-M. Chiorcea-Paquim, T.A. Enache, E. De Souza Gil, A.M. Oliveira-Brett, Natural phenolic antioxidants electrochemistry: towards a new food science methodology. Compr. Rev. Food Sci. Food Saf. 19, 1680–1726 (2020)

    Article  CAS  PubMed  Google Scholar 

  12. Ş Kıvrak, T. Göktürk, İ Kıvrak, Determination of phenolic composition of Tilia Tomentosa flowers using UPLC-ESI-MS/MS. Int. J. Second. Metab. 4, 249–256 (2017)

    Article  Google Scholar 

  13. D. Del Rio, A. Rodriguez-Mateos, J.P. Spencer, M. Tognolini, G. Borges, A. Crozier, Dietary (poly)phenolics in human health: structures, bioavailability, and evidence of protective effects against chronic diseases. Antioxid. Redox Signal. 18, 1818–1892 (2013)

    Article  PubMed  PubMed Central  Google Scholar 

  14. G. Fia, C. Gori, G. Bucalossi, F. Borghini, B. Zanoni, A naturally occurring antioxidant complex from unripe grapes: the case of Sangiovese (v. Vitis vinifera). Antioxidants, 7, 27 (2018)

  15. Ş Kıvrak, İ Kıvrak, E. Karababa, Analytical evaluation of phenolic compounds and minerals of Opuntia robusta J.C. Wendl and Opuntia ficus-barbarica A. Berger. Int. J. Food Prop. 21, 229–241 (2018)

    Article  Google Scholar 

  16. B. Singh, J.P. Singh, A. Kaur, N. Singh, Phenolic composition, antioxidant potential and health benefits of citrus peel. Food Res. Int. 132, 109114 (2020)

    Article  CAS  PubMed  Google Scholar 

  17. H.S. Kiani, W. Ahmad, S. Nawaz, M.A. Farah, A. Ali, Optimized extraction of polyphenols from unconventional edible plants: LC-MS/MS profiling of polyphenols, biological functions, molecular docking, and pharmacokinetics study. Molecules 28, 6703 (2023)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. A. Ali, J.J. Cottrell, F.R. Dunshea, Identification and characterization of anthocyanins and non-anthocyanin phenolics from Australian native fruits and their antioxidant, antidiabetic, and anti-Alzheimer potential. Food Res. Int. 162, 111951 (2022)

    Article  CAS  PubMed  Google Scholar 

  19. A. Ali, J.J. Cottrell, F.R. Dunshea, Antioxidant, alpha-glucosidase inhibition activities, in silico molecular docking and pharmacokinetics study of phenolic compounds from native Australian fruits and spices. Antioxidants 12, 254 (2023)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. J.S. Park, J.-W. Woo, G.-H. Choi, D.S. Choi, M.Y. Jung, Chlorogenic acid profiles and antioxidant potentials of 17 sweet potato varieties cultivated in Korea: impact of extraction condition and classification by hierarchical clustering analysis (2015)

  21. H.S. Kiani, B. Ali, M.K. Al-Sadoon, H.S. Al-Otaibi, A. Ali, LC-MS/MS and GC-MS identification of metabolites from the selected herbs and spices, their antioxidant, anti-diabetic potential, and chemometric analysis. Processes 11, 2721 (2023)

    Article  CAS  Google Scholar 

  22. J. Sharifi-Rad, S. Song, A. Ali, V. Subbiah, Y. Taheri, H.A.R. Suleria, LC-ESI-QTOF-MS/MS characterization of phenolic compounds from Pyracantha coccinea M.Roem. and their antioxidant capacity. Cell. Mol. Biol. 67, 201–211 (2021)

    Article  PubMed  Google Scholar 

  23. A. Ali, H. Wu, E.N. Ponnampalam, J.J. Cottrell, F.R. Dunshea, H.A.R. Suleria, Comprehensive profiling of most widely used spices for their phenolic compounds through LC-ESI-QTOF-MS(2) and their antioxidant potential. Antioxidants 10(5), 721 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  24. A. Ali, Y.M. Bashmil, J.J. Cottrell, H.A.R. Suleria, F.R. Dunshea, LC-MS/MS-QTOF screening and identification of phenolic compounds from australian grown herbs and their antioxidant potential. Antioxidants 10(11), 1770 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. J. Severo, A. Tiecher, F.C. Chaves, J.A. Silva, C.V. Rombaldi, Gene transcript accumulation associated with physiological and chemical changes during developmental stages of strawberry cv. Camarosa. Food Chem. 126, 995–1000 (2011)

    Article  CAS  Google Scholar 

  26. R.M. Patel, Ferrous ion chelating activity (FICA)-a comparative antioxidant activity evaluation of extracts of eleven naturally growing plants of Gujarat, India. Int. J. Sci. Res. 2, 426–428 (2012)

    Google Scholar 

  27. A. Ali, S.M. Kiloni, P.R. Cáceres-Vélez, P.R. Jusuf, J.J. Cottrell, F.R. Dunshea, Phytochemicals, antioxidant activities, and toxicological screening of native australian fruits using Zebrafish embryonic model. Foods 11, 4038 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  28. A. Ali, J.J. Cottrell, F.R. Dunshea, Characterization, antioxidant potential, and pharmacokinetics properties of phenolic compounds from native australian herbs and fruits. Plants 12(5), 993 (2023)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. A. Ali, H.F. Zahid, J.J. Cottrell, F.R. Dunshea, A comparative study for nutritional and phytochemical profiling of Coffea arabica (C. arabica) from different origins and their antioxidant potential and molecular docking. Molecules 27, 5126 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. S. Kim, J. Chen, T. Cheng, A. Gindulyte, J. He, S. He, Q. Li, B. Shoemaker, P. Thiessen, B. Yu, L. Zaslavsky, J. Zhang, E. Bolton, PubChem 2023 update. Nucleic Acids Res. 51(D1), D1373–D1380 (2023). https://doi.org/10.1093/nar/gkac956

    Article  PubMed  Google Scholar 

  31. A.C. de Camargo, A.C.T. Biasoto, A.R. Schwember, D. Granato, G.B. Rasera, M. Franchin, P.L. Rosalen, S.M. Alencar, F. Shahidi, Should we ban total phenolics and antioxidant screening methods? The link between antioxidant potential and activation of NF-κB using phenolic compounds from grape by-products. Food Chem. 290, 229–238 (2019)

    Article  PubMed  Google Scholar 

  32. X. Dong, Y. Hu, Y. Li, Z. Zhou, The maturity degree, phenolic compounds and antioxidant activity of Eureka lemon [Citrus limon (L.) Burm f.]: a negative correlation between total phenolic content, antioxidant capacity and soluble solid content. Sci. Hortic. 243, 281–289 (2019)

    Article  CAS  Google Scholar 

  33. Y. Zhao, K. Tran, M. Brennan, C. Brennan, Kinetics of ultrasonic extraction of polyphenols, anthocyanins and tannins from five different New Zealand grape pomaces. Int. J. Food Sci. Technol. 56, 2687–2695 (2021)

    Article  CAS  Google Scholar 

  34. E. Ivanišová, A. Kántor, M. Kačániová, Antioxidant activity and total polyphenol content of different varieties of grape from the small Carpathians wine region of Slovakia (2019)

  35. N. Salah Eddine, S. Tlais, A. Alkhatib, R. Hamdan, Effect of four grape varieties on the physicochemical and sensory properties of unripe grape verjuice. Int. J. Food Sci. 2020, 6457982 (2020)

    Article  PubMed  PubMed Central  Google Scholar 

  36. A. Rauf, G. Uddin, J. Ali, Phytochemical analysis and radical scavenging profile of juices of Citrus sinensis, Citrus anrantifolia, and Citrus limonum. Organ. Med. Chem. Lett. 4, 5 (2014)

    Article  Google Scholar 

  37. H. Salih Mahdi, A. Parveen, Biosynthesis, characterization and antibacterial activity of gold nanoparticles (Au-NPs) using black lemon extract, Materials Today: Proceedings, 18 (2019) 5164–5169

  38. A.N. Panche, A.D. Diwan, S.R. Chandra, Flavonoids: an overview. J. Nutr. Sci. 5, e47 (2016)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  39. S.A. Aherne, N.M. O’Brien, Dietary flavonols: chemistry, food content, and metabolism. Nutrition 18, 75–81 (2002)

    Article  CAS  PubMed  Google Scholar 

  40. G. Garrido-Bañuelos, A. Buica, W. du Toit, Relationship between anthocyanins, proanthocyanidins, and cell wall polysaccharides in grapes and red wines. A current state-of-art review. Crit. Rev. Food Sci. Nutr. 62, 7743–7759 (2022)

    Article  PubMed  Google Scholar 

  41. S. Kumar, A. Singh, B. Kumar, Identification and characterization of phenolics and terpenoids from ethanolic extracts of Phyllanthus species by HPLC-ESI-QTOF-MS/MS. J. Pharm. Anal. 7, 214–222 (2017)

    Article  PubMed  PubMed Central  Google Scholar 

  42. A. Ali, J.J. Cottrell, F.R. Dunshea, Antioxidant, alpha-glucosidase inhibition activities, comprehensive metabolite fingerprinting of Australian black and green olives and their antioxidant and pharmacokinetics properties. Separations 10, 354 (2023)

    Article  CAS  Google Scholar 

  43. H. Piotrowska, M. Kucinska, M. Murias, Biological activity of piceatannol: leaving the shadow of resveratrol. Mutat. Res. 750, 60–82 (2012)

    Article  CAS  PubMed  Google Scholar 

  44. Y.-L. Tang, S.-W. Chan, A review of the pharmacological effects of piceatannol on cardiovascular diseases. Phytother. Res. 28, 1581–1588 (2014)

    Article  CAS  PubMed  Google Scholar 

  45. Q. Cui, R. Du, M. Liu, L. Rong, Lignans and their derivatives from plants as antivirals. Molecules 25 (2020)

  46. T.J. Shree, S. Poompavai, S.M. Begum, V. Gowrisree, S. Hemalatha, E. Sieni, R. Sundararajan, Cancer-fighting phytochemicals: another look. J. Nanomed. Biother. Discov. 9, 162 (2019)

    Google Scholar 

Download references

Acknowledgements

The authors thank all the team and funding sources (The National Key Research and Development Program of China (2022YFC2105100) and Shanghai Collaborative Innovation Center for Biomanufacturing Technology) for their support in this research work.

Author information

Authors and Affiliations

  1. State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai, 200237, China

    Waheed Ahmad, Ali Mohsin, Xiaoguo Ji, Li Wang & Liming Zhao

  2. School of Agriculture, Food and Ecosystem Sciences, Faculty of Science, The University of Melbourne, Parkville, VIC, 3010, Australia

    Akhtar Ali

  3. Department of Food Science and Technology, GCW University, Faisalabad, Pakistan

    Mahwash Aziz

  4. Shanghai Collaborative Innovation Center for Biomanufacturing Technology (SCICBT), Shanghai, 200237, China

    Liming Zhao

Authors
  1. Waheed Ahmad
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Akhtar Ali
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ali Mohsin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xiaoguo Ji
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Mahwash Aziz
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Li Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Liming Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Liming Zhao.

Ethics declarations

Conflict of interest

The authors declare no any conflict of interest.

Additional information

Publisher's Note

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

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ahmad, W., Ali, A., Mohsin, A. et al. A comprehensive characterization of polyphenol extracts from wasted sour fruits by LC–MS/MS and evaluation of their antioxidant potentials. Food Measure 18, 1302–1317 (2024). https://doi.org/10.1007/s11694-023-02272-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11694-023-02272-1

Keywords

Search

Navigation