Skip to main content
SpringerLink
Log in

Influence of Ultra-High-Pressure Pretreatment Method on Chemical Constituents, Antioxidant and Cytoprotective Activities of Free, Esterified, and Bound Phenolics from Anneslea Fragrans Wall. Leaves

  • Research
  • Published:
Plant Foods for Human Nutrition Aims and scope Submit manuscript

Abstract

Anneslea fragrans Wall., an edible and medicinal plant, is traditionally used to treat liver and gastrointestinal diseases. This paper aimed to investigate the influence of ultra-high pressure (UHP) pretreatment on the phenolics profiling, antioxidant, and cytoprotective activities of free (FP), esterified (EP), and bound (BP) phenolics from A. fragrans leaves. A total of 32 compounds were characterized and quantified. The davidigenin (44.46 and 113.37 mg/g extract) was the highest in A. fragrans leaves. The vitexin (9), afzelin (10), coreopsin (15), and davidigenin (28) were analyzed with MS2 fragment pathways. Results showed that UHP treated A. fragrans leaves had higher total phenolic (TPC) and total flavonoid (TFC) contents of FP, EP, and BP fractions than those in the raw leaves. Moreover, UHP pretreated A. fragrans leaves had higher scavenging activities on DPPH+• and ABTS+•, and inhibitory effects on the intracellular ROS generation in H2O2-induced HepG2 cells. UFP showed the highest inhibition of ROS production among the samples. Therefore, UHP pretreatment method might be used as an effective strategy for elevating the availabilities of A. fragrans leaves to develop functional foods.

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
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

Data Availability

Not applicable.

References

  1. Ahmadinejad F, Geir Møller S, Hashemzadeh-Chaleshtori M et al (2017) Molecular mechanisms behind free radical scavengers function against oxidative stress. Antioxidants 6:51

    Article  PubMed  PubMed Central  Google Scholar 

  2. Gowd V, Bao T, Wang LL et al (2018) Antioxidant and antidiabetic activity of blackberry after gastrointestinal digestion and human gut microbiota fermentation. Food Chem 269:618–627

    Article  CAS  PubMed  Google Scholar 

  3. Wang B, Liu L, Huang Q et al (2020) Quantitative assessment of phenolic acids, flavonoids and antioxidant activities of sixteen jujube cultivars from China. Plant Foods Hum Nutr 75:154–160

    Article  CAS  PubMed  Google Scholar 

  4. Paredes-López O, Cervantes-Ceja ML, Vigna-Pérez M et al (2010) Berries: improving human health and healthy aging, and promoting quality life—A review. Plant Foods Hum Nutr 65:299–308

    Article  PubMed  Google Scholar 

  5. Erkekoglou I, Nenadis N, Samara E, Mantzouridou FTh (2017) Functional teas from the leaves of Arbutus unedo: phenolic content, antioxidant activity, and detection of efficient radical scavengers. Plant Foods Hum Nutr 72:176–183

    Article  CAS  PubMed  Google Scholar 

  6. Paludo MC, de Oliveira LF, Hermosín-Gutiérrez I et al (2019) Extracts of peels and seeds of five varieties of brazilian jabuticaba present high capacity todeactivate reactive species of oxygen and nitrogen. Plant Foods Hum Nutr 74:135–140

    Article  CAS  PubMed  Google Scholar 

  7. Wang YP, Njateng GSS, Zhao TR et al (2021) Evaluation of acute and subacute toxicity of two different extracts from Que Zui tea in rats. eFood 2:81–91

    Article  Google Scholar 

  8. Madhujith T, Shahidi F (2009) Antioxidant potential of barley as affected by alkaline hydrolysis and release of insoluble-bound phenolics. Food Chem 117:615–620

    Article  CAS  Google Scholar 

  9. Wang ZY, Li SY, Ge SH, Lin SL (2020) Review of distribution, extraction methods, and health benefits of bound phenolics in food plants. J Agric Food Chem 68:3330–3343

    Article  CAS  PubMed  Google Scholar 

  10. Wang YP, Wang ZX, Xue QW et al (2023) Effect of ultra-high pressure pretreatment on the phenolic profiles, antioxidative activity and cytoprotective capacity of different phenolic fractions from Que Zui tea. Food Chem 409:135271

    Article  CAS  PubMed  Google Scholar 

  11. Zhang J, Wang YD, Xue QW et al (2022) The effect of ultra-high pretreatment on free, esterified and insoluble-bound phenolics from mango leaves and their antioxidant and cytoprotective activities. Food Chem 368:130864

    Article  CAS  PubMed  Google Scholar 

  12. He SY, Cui XY, Khan A et al (2021) Activity guided isolation of phenolic compositions from Anneslea fragrans Wall. And their cytoprotective effect against hydrogen peroxide induced oxidative stress in HepG2 cells. Molecules 26:3690

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Cui QM, Wang YD, Zhou WB et al (2021) Phenolic composition, antioxidant and cytoprotective effects of aqueous-methanol extract from Anneslea fragrans leaves as affected by drying methods. Int J Food Sci Tech 56:4807–4819

    Article  CAS  Google Scholar 

  14. Deng XC, Wang YD, Tian L et al (2021) Anneslea fragrans Wall. Ameliorates ulcerative colitis via inhibiting NF-κB and MAPK activation and mediating intestinal barrier integrity. J Ethnopharmacol 278:114304

    Article  CAS  PubMed  Google Scholar 

  15. Omar AM, Dibwe DF, Tawila AM et al (2019) Chemical constituents of Anneslea fragrans and their antiausterity activity against the PANC-1 human pancreatic cancer cell line. J Nat Prod 82:3133–3139

    Article  CAS  PubMed  Google Scholar 

  16. Omar AM, Sun S, Kim MJ et al (2020) Fragranol A: a new class of spiro-triflavanoid hybrid with an unprecedented carbon skeleton from Anneslea fragrans Tetrahedron Lett 61:152099

    Article  CAS  Google Scholar 

  17. Wang Q, Song W, Qiao X et al (2016) Simultaneous quantification of 50 bioactive compounds of the traditional chinese medicine formula Gegen-Qinlian decoction using ultra-high performance liquid chromatography coupled with tandem mass spectrometry. J Chromatogr A 1454:15–25

    Article  CAS  PubMed  Google Scholar 

  18. Pei KH, Ou JY, Huang JQ, Ou SY (2016) p -Coumaric acid and its conjugates: dietary sources pharmacokinetic properties and biological activities: p -Coumaric acid and its conjugates. J Sci Food Agric 96:2952–2962

    Article  CAS  PubMed  Google Scholar 

  19. Ma RK, Luo J, Qiao MJ et al (2022) Chemical composition of extracts from Dalbergia odorifera heartwood and its correlation with color. Ind Crops Prod 180:114728

    Article  CAS  Google Scholar 

  20. Duan L, Guo L, Liu K et al (2014) Characterization and classification of seven Citrus herbs by liquid chromatography–quadrupole time-of-flight mass spectrometry and genetic algorithm optimized support vector machines. J Chromatogr A 1339:118–127

    Article  CAS  PubMed  Google Scholar 

  21. Kapoor MP, Moriwaki M, Minoura K et al (2022) Structural investigation of hesperetin-7-O glucoside inclusion complex with β-Cyclodextrin: a spectroscopic assessment. Molecules 27:5395

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. Gampe N, Darcsi A, Lohner S et al (2016) Characterization and identification of isoflavonoid glycosides in the root of Spiny restharrow (Ononis spinosa L.) by HPLC-QTOF-MS, HPLC–MS/MS and NMR. J Pharm Biomed Anal 123:74–81

    Article  CAS  PubMed  Google Scholar 

  23. Abu-Reidah IM, Ali-Shtayeh MS, Jamous RM et al (2015) HPLC–DAD–ESI-MS/MS screening of bioactive components from Rhus coriaria L. (Sumac) fruits. Food Chem 166:179–191

    Article  CAS  PubMed  Google Scholar 

  24. Simirgiotis MJ, Caligari PDS, Schmeda-Hirschmann G (2009) Identification of phenolic compounds from the fruits of the mountain papaya Vasconcellea pubescens A. DC. Grown in Chile by liquid chromatography–UV detection–mass spectrometry. Food Chem 115:775–784

    Article  CAS  Google Scholar 

  25. Ferreira SS, Martins-Gomes C, Nunes FM, Silva AM (2022) Elderberry (Sambucus nigra L.) extracts promote anti-inflammatory and cellular antioxidant activity. Food Chem X 15:100437

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. Georgiev VG, Weber J, Kneschke E-M et al (2010) Antioxidant activity and phenolic content of Betalain extracts from intact plants and hairy root cultures of the red beetroot Beta vulgaris cv. Detroit Dark Red. Plant Foods Hum Nutr 65:105–111

    Article  CAS  PubMed  Google Scholar 

  27. Yang CS, Zhang J (2019) Studies on the prevention of cancer and cardiometabolic diseases by tea: issues on mechanisms, effective doses, and toxicities. J Agric Food Chem 67:5446–5456

    Article  CAS  PubMed  Google Scholar 

  28. Márquez K, Pérez-Navarro J, Hermosín-Gutiérrez I et al (2019) Systematic study of hydroxyl radical production in white wines as a function of chemical composition. Food Chem 288:377–385

    Article  PubMed  Google Scholar 

  29. Hedin PA, Phillips VA (1992) Electron impact mass spectral analysis of flavonoids. J Agric Food Chem 40:607–611

    Article  CAS  Google Scholar 

  30. Liu RX, Ye M, Guo HZ et al (2005) Liquid chromatography/electrospray ionization mass spectrometry for the characterization of twenty-three flavonoids in the extract of Dalbergia odorifera Rapid Commun Mass Spectrom 19:1557–1565

    Article  CAS  PubMed  Google Scholar 

  31. Berton SBR, Cabral MRP, de Jesus GAM et al (2020) Ultra-high-performance liquid chromatography supports a new reaction mechanism between free radicals and ferulic acid with antimicrobial and antioxidant activities. Ind Crops Prod 154:112701

    Article  CAS  Google Scholar 

  32. Cavalaro RI, Cruz RG da, Dupont S et al (2019) In vitro and in vivo antioxidant properties of bioactive compounds from green propolis obtained by ultrasound-assisted extraction. Food Chem X 4:100054

  33. Siddiqa A, Tajammal A, Irfan A et al (2023) Synthesis, molecular docking, bio-evaluation and quantitative structure activity relationship of new chalcone derivatives as antioxidants. J Mol Struct 1277:134814

  34. Tao Y, Zhang H, Wang Y (2023) Revealing and predicting the relationship between the molecular structure and antioxidant activity of flavonoids. LWT 174:114433

Download references

Funding

This work was financially supported by the 67th batch of China Postdoctoral Science Foundation (2020M673586XB) and Science and Technology Projects of Yunnan Province (2019ZF010).

Author information

Author notes

  1. Li Zhen and Shuyue He contributed equally to this work.

Authors and Affiliations

  1. Faculty of Chemical Engineering, Kunming University of Science and Technology, Kunming, 650500, China

    Li Zhen, Jianxin Cao & Guiguang Cheng

  2. Faculty of Food Science and Engineering, Kunming University of Science and Technology, Kunming, 650500, China

    Li Zhen, Shuyue He, Yaping Liu, Jianxin Cao, Tianrui Zhao, Guiguang Cheng & Yudan Wang

  3. Department of Chemistry, Liaocheng University, Liaocheng, 252059, China

    Qingwang Xue

  4. National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, Yunnan Minzu University, Kunming, 650500, China

    Yudan Wang

Authors
  1. Li Zhen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shuyue He
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Qingwang Xue
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yaping Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jianxin Cao
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Tianrui Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Guiguang Cheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Yudan Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

Li Zhen and Shuyue He: Methodology, investigation, writing. Qingwang Xue and Jianxin Cao: Formal analysis. Yaping Liu: Data curation. Tianrui Zhao: Resources. Yudan Wang and Guiguang Cheng: Funding acquisition, review & editing.

Corresponding authors

Correspondence to Guiguang Cheng or Yudan Wang.

Ethics declarations

Ethics Approval

Not applicable.

Consent to Participate

Not applicable.

Consent for Publication

Not applicable.

Competing Interests

The authors declare no competing interests.

Conflict of Interest

The authors declare no conflict of interest.

Additional information

Publisher’s Note

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

Supplementary Information

Below is the link to the electronic supplementary material.

ESM 1

(DOCX 28.7 KB)

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

Zhen, L., He, S., Xue, Q. et al. Influence of Ultra-High-Pressure Pretreatment Method on Chemical Constituents, Antioxidant and Cytoprotective Activities of Free, Esterified, and Bound Phenolics from Anneslea Fragrans Wall. Leaves. Plant Foods Hum Nutr 78, 407–418 (2023). https://doi.org/10.1007/s11130-023-01071-9

Download citation

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11130-023-01071-9

Keywords

Search

Navigation