Skip to main content
Log in

Identification and quantification of flavonoids in leafy by-products of Chinese jujube: Comparison between young and old leaves

  • Original Article
  • Published:
Biomass Conversion and Biorefinery Aims and scope Submit manuscript

Abstract

Jujube leaves are by-products of jujube plants, which contain various flavonoid compounds. The identification and quantification of these flavonoids from 14 cultivars of jujube, cultivated in Cangzhou, Hebei, China was explored in this study. Altogether, nine flavonoids were obtained using ethanol as the extraction solvent and using preparative reversed phase liquid chromatography. The identified nine compounds were quercetin-3-O-robinobioside, rutin, 3′,5′-Di-C-β-D-glucosylphloretin, kaempferol-3-O-rutinoside, quercetin-3-O-rhamnoside, quercetin-3-O-α-L-arabinosyl- (1→2)-α-L-rhamnoside, quercetin-3-O-α-L-rhamnopyranosyl-2″-(6′′′-p-coumaroyl)-β-D-glucoside, 3′,5′-Di-C-β-D-glucosyl-4-O-p-coumaroyl- phloretin, and quercetin-3-O-β-D- glucoside. Among them, three compounds, namely quercetin-3-O-rhamnoside, quercetin-3-O-α-L-rhamnopyranosyl-2″-(6′′′-p-coumaroyl)-β-D-glucoside, and 5′-Di-C-β-D-glucosyl-4-O-p-coumaroyl-phloretin were detected as the novel compounds in jujube leaves from Cangzhou, Hebei, China. All the detected compounds were confirmed through HPLC, LC-MS, 1H-NMR, and 13C-NMR. The quantification analysis through HPLC chromatography revealed that young leaves contained much higher amounts of these compounds than the old counterpart. In terms of dominant major flavonoids, quercetin-3-O-robinobioside, rutin and 3′,5′-Di-C-β-D-glucosylphloretin in young leaves, while quercetin-3-O-robinobioside and rutin in old leaves took the accounts. It is concluded that jujube leaves can be utilized as the source of such flavonoids, which can be used by incorporating such leaves into mainstream food products for the valorization of these underutilized by-products.

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
Fig. 5
Fig. 6

Similar content being viewed by others

Data availabilty

The data presented in this study are available in the article.

References

  1. Jin X (2018) Jujuba Ziziphus jujuba. In: Rodrigues S, de Oliveira Silva E, de Brito ES (eds) Exotic Fruits. Academic Press, pp 263–269

    Chapter  Google Scholar 

  2. Mahajan R, Chopda M (2009) Phyto-pharmacology of Ziziphus jujuba Mill- A plant review. Pharmacogn Rev 3:320–329

    Google Scholar 

  3. Memon AA, Memon N, Bhanger MI, Luthria DL (2013) Assay of phenolic compounds from four species of ber (Ziziphus mauritiana L.) fruits: Comparison of three base hydrolysis procedure for quantification of total phenolic acids. Food Chem 139:496–502. https://doi.org/10.1016/j.foodchem.2013.01.065

    Article  Google Scholar 

  4. Gao QH, Wu CS, Yu JG, Wang M, Ma YJ, Li CL (2012) Textural characteristic, antioxidant activity, sugar, organic acid, and phenolic profiles of 10 promising jujube (Ziziphus jujuba Mill.) selections. J Food Sci 77:C1218–C1225. https://doi.org/10.1111/j.1750-3841.2012.02946.x

    Article  Google Scholar 

  5. San B, Yildirim AN (2010) Phenolic, alpha-tocopherol, beta-carotene and fatty acid composition of four promising jujube (Ziziphus jujuba Miller) selections. J Food Compos Anal 23:706–710. https://doi.org/10.1016/j.jfca.2010.02.008

    Article  Google Scholar 

  6. Liu J, Chen B, Yao S (2007) Simultaneous analysis and identification of main bioactive constituents in extract of Zizyphus jujuba var. sapinosa (Zizyphi spinosi semen) by high-performance liquid chromatography–photodiode array detection–electrospray mass spectrometry. Talanta 71:668–675. https://doi.org/10.1016/j.talanta.2006.05.014

    Article  Google Scholar 

  7. Damiano S, Forino M, De A, Vitali LA, Lupidi G, Taglialatela-Scafati O (2017) Antioxidant and antibiofilm activities of secondary metabolites from Ziziphus jujuba leaves used for infusion preparation. Food Chem 230:24–29. https://doi.org/10.1016/j.foodchem.2017.02.141

    Article  Google Scholar 

  8. Zhang L, Liu P, Li L, Huang Y, Pu Y, Hou X, Song L (2018) Identification and antioxidant activity of flavonoids extracted from Xinjiang Jujube (Ziziphus jujube Mill.) leaves with ultra-high pressure extraction technology. Molecules 24. https://doi.org/10.3390/molecules24010122

  9. Zhao XH, Yi LN (2009) Effect of Ziziphus jujube leaf extract on the central nervous system. Lishizhen Med 20:463–464

    Google Scholar 

  10. Kim YJ, Son D-Y (2011) Hot water leaves extracts of Zizyphus jujube exert antioxidative effects in vitro and cytotoxicity in human cancer cell lines. Hortic Environ Biotechnol 52:635–640. https://doi.org/10.1007/s13580-011-0040-9

    Article  Google Scholar 

  11. Liu HX, Xu MQ, Li SP, Tian S, Guo MX, Qi JY, He CJ, Zhao XS (2017) Jujube leaf green tea extracts inhibits hepatocellular carcinoma cells by activating AMPK. Oncotarget 8:110566–110575. https://doi.org/10.18632/oncotarget.22821

    Article  Google Scholar 

  12. Guo S, Duan JA, Tang Y, Qian Y, Zhao J, Qian D, Su S, Shang E (2011) Simultaneous qualitative and quantitative analysis of triterpenic acids, saponins and flavonoids in the leaves of two Ziziphus species by HPLC-PDA-MS/ELSD. J Pharm Biomed Anal 56:264–270. https://doi.org/10.1016/j.jpba.2011.05.025

    Article  Google Scholar 

  13. Zhang R, Chen J, Shi Q, Li Z, Peng Z, Zheng L, Wang X (2014) Phytochemical analysis of Chinese commercial Ziziphus jujube leaf tea using high performance liquid chromatography–electrospray ionization-time of flight mass spectrometry. Food Res Int 56:47–54

    Article  Google Scholar 

  14. Zhang R, Chen J, Shi Q, Li Z, Peng Z, Zheng L, Wang X (2014) Quality control method for commercially available wild Jujube leaf tea based on HPLC characteristic fingerprint analysis of flavonoid compounds. J Sep Sci 37:45–52. https://doi.org/10.1002/jssc.201300841

    Article  Google Scholar 

  15. Yao B (2011) Determination of rutin from leaves of Ziziphus jujuba gathered in different areas and different periods by HPLC-UV. Chin J Exp Tradit Med Formulae 17(21):94–96

    Google Scholar 

  16. Wang Y, Kong L, Guo M, Zhang H (2013) Determination of rutin in leaves of Ziziphus jujuba var. spinosa by HPLC. Food Res Dev 34:56–57

    Google Scholar 

  17. Song L, Zheng J, Zhang L, Yan S, Huang W, He J, Liu P (2019) Phytochemical Profiling and Fingerprint Analysis of Chinese Jujube (Ziziphus jujuba Mill.) Leaves of 66 Cultivars from Xinjiang Province. Molecules 24(24):4528

    Article  Google Scholar 

  18. Song L, Liu P, Yan Y, Huang Y, Bai B, Hou X, Zhang L (2019) Supercritical CO2 fluid extraction of flavonoid compounds from Xinjiang jujube (Ziziphus jujuba Mill.) leaves and associated biological activities and flavonoid compositions. Ind Crop Prod 139:111508

    Article  Google Scholar 

  19. Liu Z, Bruins ME, de Bruijn WJC, Vincken J (2020) A comparison of the phenolic composition of old and young tea leaves reveals a decrease in flavanols and phenolic acids and an increase in flavonols upon tea leaf maturation. J Food Compos Anal 86:103385

    Article  Google Scholar 

  20. Peter SR, Peru KM, Fahlman B, McMartin DW, Headley JV (2015) The application of HPLC ESI MS in the investigation of the flavonoids and flavonoid glycosides of a Caribbean Lamiaceae plant with potential for bioaccumulation. J Environ Sci Health B 50:819–826. https://doi.org/10.1080/03601234.2015.1058103

    Article  Google Scholar 

  21. Hasler A, Sticher O, Meier B (1992) Identification and determination of the flavonoids from Ginkgo biloba by high-performance liquid chromatography. J Chromatogr A 605:41–48

    Article  Google Scholar 

Download references

Funding

This research was supported by the Introduced Talent Research Project of Hebei Agricultural University (YJ2022007).

Author information

Authors and Affiliations

Authors

Contributions

Conceptualization, Zhe Gao and Bimal ChitrakarInvestigation, Zhe GaoMethodology, Zhe Gao and Bimal ChitrakarSoftware, Bimal ChitrakarValidation, Bimal ChitrakarWriting – original draft, Zhe GaoWriting – review & editing, Bimal Chitrakar.

Corresponding author

Correspondence to Bimal Chitrakar.

Ethics declarations

Ethics Approval

This article contains no studies with human participants or animals performed by any of the authors.

Competing Interest

The authors declare no conflict of financial or personal interest.

Additional information

Publisher’s note

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

Supplementary information

ESM 1

(DOCX 13627 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

Gao, Z., Chitrakar, B. Identification and quantification of flavonoids in leafy by-products of Chinese jujube: Comparison between young and old leaves. Biomass Conv. Bioref. (2023). https://doi.org/10.1007/s13399-023-04617-8

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s13399-023-04617-8

Keywords

Navigation