Abstract
Recent epidemiologic studies have demonstrated a link between the consumption of daily functional fruits rich in phenols and the prevention of disease for neurodegenerative disorders. Hawthorn products are derived from the functional fruit hawthorn, which is rich in phenols and has been used around the world for centuries. In order to explore the phenolic components in hawthorn, the investigation of the ethanol extract led to the separation of five new phenol compounds (1a/1b, 2–4), including one pair of enantiomers (1a/1b), along with seven disclosed analogs (5–11). Their structures were elucidated based on extensive spectroscopic analyses and electronic circular dichroism (ECD). The compounds (1–11) were tested for antioxidant activities by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulphonicacid) (ABTS), and ferric reducing antioxidant power (FRAP) methods. Apart from that, monomeric compounds 2, 4, and 6 exhibited more potent protective capabilities against H2O2 (hydrogen peroxide)-induced SH-SY5Y cells. Meanwhile, electronic analyses were performed using the highest occupied molecular orbital (HOMO), and the lowest unoccupied molecular orbital (LUMO) to analyze compounds 2, 4, and 6. Furthermore, compounds (1–11) measured acetylcholinesterase (AChE) inhibitory activities, and 2, 4, and 6 possessed greater AChE inhibitory activity than donepezil. At the same time, molecular docking was used to investigate the possible mechanism of the interaction between active compounds (2, 4, and 6) and AChE.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Data Availability
Not applicable.
Code Availability
Not applicable.
References
Alkadi H (2020) A review on free radicals and antioxidants. Infect Disord Drug Targets 20(1):16–26. https://doi.org/10.2174/1871526518666180628124323
Xu Y, Li LZ, Cong Q, Wang W, Qi XL, Peng Y, Song SJ (2017) Bioactive lignans and flavones with in vitro antioxidant and neuroprotective properties from Rubus idaeus rhizome. J Funct Foods 32:160–169. https://doi.org/10.1016/j.jff.2017.02.022
BaevArtyom Y, Vinokurov AY, Novikova IN, Dremin VV, Potapova EV, Abramov AY (2022) Interaction of mitochondrial calcium and ROS in neurodegeneration. Cells 11(4):706. https://doi.org/10.3390/cells11040706
Pearson-Smith JN, Patel M (2019) Antioxidant drug therapy as a neuroprotective countermeasure of nerve agent toxicity. Neurobiol Dis. https://doi.org/10.1016/j.nbd.2019.04.013
Wen L, Guo X, Liu RH, You L, Abbasi AM, Fu X (2015) Phenolic contents and cellular antioxidant activity of chinese hawthorn “Crataegus pinnatifida”. Food Chem 186:54–62. https://doi.org/10.1016/j.foodchem.2015.03.017
Zhao P, Qiu S, Hou ZL, Xue XB, Yao GD, Huang XX, Song SJ (2020) Sesquineolignans derivatives with neuroprotective activity from the fruits of Crataegus pinnatifida. Fitoterapia. https://doi.org/10.1016/j.fitote.2020.104591
Lou XM, Xiong JJ, Tian HX, Yu HY, Chen C, Huang J, Yuan HB, Hanna M, Yuan L, Xu HD (2022) Effect of high-pressure processing on the bioaccessibility of phenolic compounds from cloudy hawthorn berry (Crataegus pinnatifida) juice. J Food Compos Anal. https://doi.org/10.1016/j.jfca.2022.104540
Yang B, Liu P (2012) Composition and health effects of phenolic compounds in hawthorn (Crataegus spp.) of different origins. J Sci Food Agric 92(8):1578–1590. https://doi.org/10.1002/jsfa.5671
Liu P, Yang B, Kallio H (2010) Characterization of phenolic compounds in chinese hawthorn (Crataegus pinnatifida bge. var. major) fruit by high performance liquid chromatography-electrospray ionization mass spectrometry. Food Chem 121(4):1188–1197
Niu ZZ, Yan MX, Zhao XL, Jin H, Gong YL (2020) Effect of hawthorn seed extract on the gastrointestinal function of rats with diabetic gastroparesis. S Afr J Bot 130:448–455. https://doi.org/10.1016/j.sajb.2020.01.032
Ruan WL, Shen SH, Xu Y, Ran N, Zhang H (2021) Mechanistic insights into procyanidins as therapies for alzheimer’s disease: a review. J Funct Foods. https://doi.org/10.1016/j.jff.2021.104683
Xi YF, Liu SF, Hong W, Song XY, Lou LL, Zhou L, Yao GD, Lin B, Wang XB, Huang XX, Song SJ (2019) Discovery of cycloneolignan enantiomers from Isatis indigotica fortune with neuroprotective effects against mpp+-induced SH-SY5Y cell injury. Bioorg Chem. https://doi.org/10.1016/j.bioorg.2019.102926
Sang Z, Qiang X, Li Y, Yuan W, Liu Q, Shi Y, Ang W, Luo Y, Tan Z, Deng Y (2015) Design, synthesis and evaluation of scutellarein-O-alkylamines as multifunctional agents for the treatment of Alzheimer’s disease. Eur J Med Chem 94:348–366. https://doi.org/10.1016/j.ejmech.2015.02.063
Chang Y, Bai M, Xue XB, Zou CX, Huang XX, Song SJ (2022) Isolation of chemical compositions as dietary antioxidant supplements and neuroprotectants from chaga mushroom (Inonotus obliquus). Food Biosci. https://doi.org/10.1016/j.fbio.2022.101623b
Yang J, Chen JX, Hao YX, Liu YP (2021) Identification of the DPPH radical scavenging reaction adducts of ferulic acid and sinapic acid and their structure-antioxidant activity relationship. LWT-Food Sci Technol. https://doi.org/10.1016/j.lwt.2021.111411
Lu T, Chen F (2012) Multiwfn: a multifunctional wavefunction analyzer. J Comput Chem 33(5):580–592. https://doi.org/10.1002/jcc.22885
Lan JS, Zeng RF, Jiang XY, Hou JW, Zhang T (2019) Design, synthesis and evaluation of novel ferulic acid derivatives as multi-target-directed ligands for the treatment of Alzheimer’s disease. Bio Chem. https://doi.org/10.1016/j.bioorg.2019.103413
Funding
This work was supported by Liaoning Revitalization Talents Program (XLYC2007180), Program for Major Scientific and Medical Technology Problems of China Medicine Education Association in 2020 (2020KTS003), Science and Technology Planning Project of Liaoning Province (2021JH1/10400049), Career Development Support Plan for Young and Middle-aged Teachers in Shenyang Pharmaceutical University (ZQN2018006).
Author information
Authors and Affiliations
Contributions
D. F. Liu, M. Bai, S. J. Song, and X. X. Huang designed the steps of the experiment. D. F. Liu, M. Bai, and R. Guo performed the chemical experiments and analyzed the data. D. F. Liu, N. N. Du, S. Shen, and G. D. Yao performed the pharmacology experiments. Z. Y. Li and X. Zhang performed the molecular modeling part. D. F. Liu drafted the manuscript. M. Bai and X. X. Huang altered some issues in the manuscript. The manuscript was a combination of all authors’ contributions and all authors agreed to its final version.
Corresponding author
Ethics declarations
Competing Interests
The authors declare no competing interests.
Ethics Approval
Not applicable.
Consent to Participate
Not applicable.
Consent for Publication
Not applicable.
Conflict of Interest
The authors declare no confict 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.
Rights and permissions
Springer Nature or its licensor 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.
About this article
Cite this article
Liu, DF., Bai, M., Du, NN. et al. Insight into Isolation and Characterization of Phenolic Compounds from Hawthorn (Crataegus pinnatifida Bge.) with Antioxidant, Anti-Acetylcholinesterase, and Neuroprotective Activities. Plant Foods Hum Nutr 77, 538–544 (2022). https://doi.org/10.1007/s11130-022-01004-y
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11130-022-01004-y