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Separation and Characterization of Phenolamines and Flavonoids from Rape Bee Pollen, and Comparison of Their Antioxidant Activities and Protective Effects Against Oxidative Stress

Phenolamines and flavonoids are two important components in bee pollen. There are many reports on the bioactivity of flavonoids in bee pollen, but few on phenolamines. This study aims to separate and characterize the flavonoids and phenolamines from rape bee pollen, and compare their antioxidant act...

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Published in:Molecules (Basel, Switzerland) Switzerland), 2020-03, Vol.25 (6), p.1264
Main Authors: Zhang, Huifang, Liu, Rui, Lu, Qun
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description Phenolamines and flavonoids are two important components in bee pollen. There are many reports on the bioactivity of flavonoids in bee pollen, but few on phenolamines. This study aims to separate and characterize the flavonoids and phenolamines from rape bee pollen, and compare their antioxidant activities and protective effects against oxidative stress. The rape bee pollen was separated to obtain 35% and 50% fractions, which were characterized by HPLC-ESI-QTOF-MS/MS. The results showed that the compounds in 35% fraction were quercetin and kaempferol glycosides, while the compounds in 50% fraction were phenolamines, including di-p-coumaroyl spermidine, p-coumaroyl caffeoyl hydroxyferuloyl spermine, di-p-coumaroyl hydroxyferuloyl spermine, and tri-p-coumaroyl spermidine. The antioxidant activities of phenolamines and flavonoids were evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis-3-ethylbenzothiazoline-6-sulphonic acid (ABTS), and ferric reducing antioxidant power (FRAP) assays. It was found that the antioxidant activity of phenolamines was significantly higher than that of flavonoids. Moreover, phenolamines showed better protective effects than flavonoids on HepG2 cells injured by AAPH. Furthermore, phenolamines could significantly reduce the reactive oxygen species (ROS), alanine aminotransferase (ALT) and aspartate aminotransferase (AST) levels, and increase the superoxide dismutase (SOD) and glutathione (GSH) levels. This study lays a foundation for the further understanding of phenolamines in rape bee pollen.
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There are many reports on the bioactivity of flavonoids in bee pollen, but few on phenolamines. This study aims to separate and characterize the flavonoids and phenolamines from rape bee pollen, and compare their antioxidant activities and protective effects against oxidative stress. The rape bee pollen was separated to obtain 35% and 50% fractions, which were characterized by HPLC-ESI-QTOF-MS/MS. The results showed that the compounds in 35% fraction were quercetin and kaempferol glycosides, while the compounds in 50% fraction were phenolamines, including di-p-coumaroyl spermidine, p-coumaroyl caffeoyl hydroxyferuloyl spermine, di-p-coumaroyl hydroxyferuloyl spermine, and tri-p-coumaroyl spermidine. The antioxidant activities of phenolamines and flavonoids were evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis-3-ethylbenzothiazoline-6-sulphonic acid (ABTS), and ferric reducing antioxidant power (FRAP) assays. It was found that the antioxidant activity of phenolamines was significantly higher than that of flavonoids. Moreover, phenolamines showed better protective effects than flavonoids on HepG2 cells injured by AAPH. Furthermore, phenolamines could significantly reduce the reactive oxygen species (ROS), alanine aminotransferase (ALT) and aspartate aminotransferase (AST) levels, and increase the superoxide dismutase (SOD) and glutathione (GSH) levels. 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purification</subject><subject>Glycosides - pharmacology</subject><subject>Hep G2 Cells</subject><subject>High-performance liquid chromatography</subject><subject>Humans</subject><subject>hydroxycinnamic acid amides</subject><subject>Injury prevention</subject><subject>Kaempferol</subject><subject>Kaempferols - chemistry</subject><subject>Kaempferols - isolation &amp; purification</subject><subject>Kaempferols - pharmacology</subject><subject>Lipids</subject><subject>Liquid chromatography</subject><subject>Oxidants - antagonists &amp; inhibitors</subject><subject>Oxidants - pharmacology</subject><subject>Oxidative stress</subject><subject>Oxidative Stress - drug effects</subject><subject>Picrates - antagonists &amp; inhibitors</subject><subject>Picrates - chemistry</subject><subject>Plant Extracts - chemistry</subject><subject>Pollen</subject><subject>Pollen - chemistry</subject><subject>Proteins</subject><subject>Quercetin</subject><subject>Quercetin - chemistry</subject><subject>Quercetin - isolation &amp; purification</subject><subject>Quercetin - pharmacology</subject><subject>Reactive oxygen species</subject><subject>Reactive Oxygen Species - antagonists &amp; inhibitors</subject><subject>Reactive Oxygen Species - chemistry</subject><subject>Spermidine</subject><subject>Spermidine - analogs &amp; derivatives</subject><subject>Spermidine - chemistry</subject><subject>Spermidine - isolation &amp; purification</subject><subject>Spermidine - pharmacology</subject><subject>Spermine</subject><subject>Spermine - analogs &amp; derivatives</subject><subject>Spermine - chemistry</subject><subject>Spermine - isolation &amp; purification</subject><subject>Spermine - pharmacology</subject><subject>Sulfonic Acids - antagonists &amp; inhibitors</subject><subject>Sulfonic Acids - chemistry</subject><subject>Superoxide dismutase</subject><subject>Superoxide Dismutase - genetics</subject><subject>Superoxide Dismutase - metabolism</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNplkt1uEzEQhVcIREvhAbhBlrgl4L_17t4gpVELlSo1ouXaml2PE1e7drCdCHgtXpBNNlStuPLMmTOfbekUxVtGPwrR0E9D6LHb9ph4SRXjSj4rTpnkdCaobJ4_qk-KVyndU8qZZOXL4kRwpuqasdPizy1uIEJ2wRPwhizWY9dljO73JAZLlmv0oYfBeUwH02UPu-CDM4nYGAbyDTZIzhHJMvQ9-g8TKQwj2aWJcbdGF8ncj8yfzoDPZN5lt3PZHZnLGDLuJSQX1o5VIvMVOJ8yudlvHCa3OWJKr4sXFvqEb47nWfH98uJu8XV2ffPlajG_nnWyEXnGuaVCllZ00gom0VgQApSwDYCiykjLFYNajZ3krBaGlYhUCCYMLWlNxVlxNXFNgHu9iW6A-EsHcPoghLjSELPretSthFJR2jaVREkB6rZsGttWBlpWmaYaWZ8n1mbbDmg69DlC_wT6dOLdWq_CTldMSsrLEfD-CIjhxxZT1vdhG_34f81FVZVKcClGF5tcXQwpRbQPNzCq95nR_2Vm3Hn3-GkPG_9CIv4C6KDDRg</recordid><startdate>20200311</startdate><enddate>20200311</enddate><creator>Zhang, Huifang</creator><creator>Liu, Rui</creator><creator>Lu, Qun</creator><general>MDPI AG</general><general>MDPI</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20200311</creationdate><title>Separation and Characterization of Phenolamines and Flavonoids from Rape Bee Pollen, and Comparison of Their Antioxidant Activities and Protective Effects Against Oxidative Stress</title><author>Zhang, Huifang ; Liu, Rui ; Lu, Qun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c493t-22f0345f3c4f314edfa33a63f9aa606d4f261a86aa642183d15ee03313d050803</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alanine</topic><topic>Alanine transaminase</topic><topic>Alanine Transaminase - genetics</topic><topic>Alanine Transaminase - metabolism</topic><topic>Amidines - antagonists &amp; inhibitors</topic><topic>Amidines - pharmacology</topic><topic>Animals</topic><topic>antioxidant</topic><topic>Antioxidants</topic><topic>Antioxidants - chemistry</topic><topic>Antioxidants - isolation &amp; purification</topic><topic>Antioxidants - pharmacology</topic><topic>Aspartate aminotransferase</topic><topic>Aspartate Aminotransferases - genetics</topic><topic>Aspartate Aminotransferases - metabolism</topic><topic>Bees</topic><topic>Benzothiazoles - antagonists &amp; inhibitors</topic><topic>Benzothiazoles - chemistry</topic><topic>Biological activity</topic><topic>Biphenyl Compounds - antagonists &amp; inhibitors</topic><topic>Biphenyl Compounds - chemistry</topic><topic>Cytotoxicity</topic><topic>Enzymes</topic><topic>Flavonoids</topic><topic>Gene Expression - drug effects</topic><topic>Glutathione - genetics</topic><topic>Glutathione - metabolism</topic><topic>Glycosides</topic><topic>Glycosides - chemistry</topic><topic>Glycosides - isolation &amp; purification</topic><topic>Glycosides - pharmacology</topic><topic>Hep G2 Cells</topic><topic>High-performance liquid chromatography</topic><topic>Humans</topic><topic>hydroxycinnamic acid amides</topic><topic>Injury prevention</topic><topic>Kaempferol</topic><topic>Kaempferols - chemistry</topic><topic>Kaempferols - isolation &amp; purification</topic><topic>Kaempferols - pharmacology</topic><topic>Lipids</topic><topic>Liquid chromatography</topic><topic>Oxidants - antagonists &amp; inhibitors</topic><topic>Oxidants - pharmacology</topic><topic>Oxidative stress</topic><topic>Oxidative Stress - drug effects</topic><topic>Picrates - antagonists &amp; inhibitors</topic><topic>Picrates - chemistry</topic><topic>Plant Extracts - chemistry</topic><topic>Pollen</topic><topic>Pollen - chemistry</topic><topic>Proteins</topic><topic>Quercetin</topic><topic>Quercetin - chemistry</topic><topic>Quercetin - isolation &amp; purification</topic><topic>Quercetin - pharmacology</topic><topic>Reactive oxygen species</topic><topic>Reactive Oxygen Species - antagonists &amp; inhibitors</topic><topic>Reactive Oxygen Species - chemistry</topic><topic>Spermidine</topic><topic>Spermidine - analogs &amp; derivatives</topic><topic>Spermidine - chemistry</topic><topic>Spermidine - isolation &amp; purification</topic><topic>Spermidine - pharmacology</topic><topic>Spermine</topic><topic>Spermine - analogs &amp; derivatives</topic><topic>Spermine - chemistry</topic><topic>Spermine - isolation &amp; purification</topic><topic>Spermine - pharmacology</topic><topic>Sulfonic Acids - antagonists &amp; inhibitors</topic><topic>Sulfonic Acids - chemistry</topic><topic>Superoxide dismutase</topic><topic>Superoxide Dismutase - genetics</topic><topic>Superoxide Dismutase - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Huifang</creatorcontrib><creatorcontrib>Liu, Rui</creatorcontrib><creatorcontrib>Lu, Qun</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>ProQuest Health &amp; 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There are many reports on the bioactivity of flavonoids in bee pollen, but few on phenolamines. This study aims to separate and characterize the flavonoids and phenolamines from rape bee pollen, and compare their antioxidant activities and protective effects against oxidative stress. The rape bee pollen was separated to obtain 35% and 50% fractions, which were characterized by HPLC-ESI-QTOF-MS/MS. The results showed that the compounds in 35% fraction were quercetin and kaempferol glycosides, while the compounds in 50% fraction were phenolamines, including di-p-coumaroyl spermidine, p-coumaroyl caffeoyl hydroxyferuloyl spermine, di-p-coumaroyl hydroxyferuloyl spermine, and tri-p-coumaroyl spermidine. The antioxidant activities of phenolamines and flavonoids were evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis-3-ethylbenzothiazoline-6-sulphonic acid (ABTS), and ferric reducing antioxidant power (FRAP) assays. It was found that the antioxidant activity of phenolamines was significantly higher than that of flavonoids. Moreover, phenolamines showed better protective effects than flavonoids on HepG2 cells injured by AAPH. Furthermore, phenolamines could significantly reduce the reactive oxygen species (ROS), alanine aminotransferase (ALT) and aspartate aminotransferase (AST) levels, and increase the superoxide dismutase (SOD) and glutathione (GSH) levels. This study lays a foundation for the further understanding of phenolamines in rape bee pollen.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>32168811</pmid><doi>10.3390/molecules25061264</doi><oa>free_for_read</oa></addata></record>
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subjects Alanine
Alanine transaminase
Alanine Transaminase - genetics
Alanine Transaminase - metabolism
Amidines - antagonists & inhibitors
Amidines - pharmacology
Animals
antioxidant
Antioxidants
Antioxidants - chemistry
Antioxidants - isolation & purification
Antioxidants - pharmacology
Aspartate aminotransferase
Aspartate Aminotransferases - genetics
Aspartate Aminotransferases - metabolism
Bees
Benzothiazoles - antagonists & inhibitors
Benzothiazoles - chemistry
Biological activity
Biphenyl Compounds - antagonists & inhibitors
Biphenyl Compounds - chemistry
Cytotoxicity
Enzymes
Flavonoids
Gene Expression - drug effects
Glutathione - genetics
Glutathione - metabolism
Glycosides
Glycosides - chemistry
Glycosides - isolation & purification
Glycosides - pharmacology
Hep G2 Cells
High-performance liquid chromatography
Humans
hydroxycinnamic acid amides
Injury prevention
Kaempferol
Kaempferols - chemistry
Kaempferols - isolation & purification
Kaempferols - pharmacology
Lipids
Liquid chromatography
Oxidants - antagonists & inhibitors
Oxidants - pharmacology
Oxidative stress
Oxidative Stress - drug effects
Picrates - antagonists & inhibitors
Picrates - chemistry
Plant Extracts - chemistry
Pollen
Pollen - chemistry
Proteins
Quercetin
Quercetin - chemistry
Quercetin - isolation & purification
Quercetin - pharmacology
Reactive oxygen species
Reactive Oxygen Species - antagonists & inhibitors
Reactive Oxygen Species - chemistry
Spermidine
Spermidine - analogs & derivatives
Spermidine - chemistry
Spermidine - isolation & purification
Spermidine - pharmacology
Spermine
Spermine - analogs & derivatives
Spermine - chemistry
Spermine - isolation & purification
Spermine - pharmacology
Sulfonic Acids - antagonists & inhibitors
Sulfonic Acids - chemistry
Superoxide dismutase
Superoxide Dismutase - genetics
Superoxide Dismutase - metabolism
title Separation and Characterization of Phenolamines and Flavonoids from Rape Bee Pollen, and Comparison of Their Antioxidant Activities and Protective Effects Against Oxidative Stress
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-05T01%3A59%3A55IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Separation%20and%20Characterization%20of%20Phenolamines%20and%20Flavonoids%20from%20Rape%20Bee%20Pollen,%20and%20Comparison%20of%20Their%20Antioxidant%20Activities%20and%20Protective%20Effects%20Against%20Oxidative%20Stress&rft.jtitle=Molecules%20(Basel,%20Switzerland)&rft.au=Zhang,%20Huifang&rft.date=2020-03-11&rft.volume=25&rft.issue=6&rft.spage=1264&rft.pages=1264-&rft.issn=1420-3049&rft.eissn=1420-3049&rft_id=info:doi/10.3390/molecules25061264&rft_dat=%3Cproquest_doaj_%3E2377563243%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c493t-22f0345f3c4f314edfa33a63f9aa606d4f261a86aa642183d15ee03313d050803%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2377563243&rft_id=info:pmid/32168811&rfr_iscdi=true