Identification and quantification of free and bound phenolic compounds contained in the high-molecular weight melanoidin fractions derived from two different types of cocoa beans by UHPLC-DAD-ESI-HR-MSn.
Food Res Int. 2019 01; 115:135-149.FR

Abstract

The aim of the present study was to establish the profiles of soluble free phenolics (SFPs) and bound phenolics (BPs) in high molecular weight (HMW) melanoidin fractions isolated from raw and roasted beans of two Theobroma cacao L. varieties. Samples were prepared using three methods (saline treatment and acidic and alkaline hydrolysis) to obtain different forms of phenolic compounds. A total of fifteen phenolics, including three flavan-3-ols, seven phenolic acids, one phenolic aldehyde, and four N-phenylpropenoyl-L-amino acids (NPAs), were identified using ultra-high-performance liquid chromatography coupled to diode array detection and electrospray ionization high-resolution mass spectrometry (UHPLC-DAD-ESI-HR-MSn). In HMW fractions from both studied cocoa types, the main SFPs were N-caffeoyl-L-Asp and procyanidin B2, whereas the main BPs were catechin, epicatechin, ellagic acid, protocatechualdehyde, and N-caffeoyl-L-Asp. The concentrations of individual BPs were much higher than the content of total SFPs. It was also found that, as compared to alkaline hydrolysis, acid hydrolysis released a significantly higher amount of BPs from HMW melanoidin fractions. A comprehensive quantitative analysis indicated significant variation in the investigated phenolic compounds depending on the cocoa type and roasting conditions. An increase in treatment temperature from 110 to 150 °C led to a decline in SFPs and an increment in BPs. The HMW fractions of unroasted Criollo beans exhibited the highest content of SFPs and the lowest content of BPs. The highest BP concentrations were obtained for both cocoa bean varieties roasted at 150 °C. The present study revealed that HMW melanoidin fractions from cocoa beans of different varieties roasted at higher temperatures are a good source of phenolic compounds that can be released under both acidic and alkaline conditions.

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Authors+Show Affiliations

Oracz J

Institute of Food Technology and Analysis, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, 4/10 Stefanowskiego Street, 90-924 Lodz, Poland. Electronic address: joanna.oracz@p.lodz.pl.

Nebesny E

Institute of Food Technology and Analysis, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, 4/10 Stefanowskiego Street, 90-924 Lodz, Poland.

Żyżelewicz D

Institute of Food Technology and Analysis, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, 4/10 Stefanowskiego Street, 90-924 Lodz, Poland.

MeSH

Amino AcidsBiflavonoidsCacaoCatechinChromatography, High Pressure LiquidFlavonoidsHot TemperatureHydroxybenzoatesMolecular WeightPhenolsPlant ExtractsPolymersProanthocyanidinsSeedsSpectrometry, Mass, Electrospray Ionization

Pub Type(s)

Journal Article

Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

30599925

Citation

Oracz, Joanna, et al. "Identification and Quantification of Free and Bound Phenolic Compounds Contained in the High-molecular Weight Melanoidin Fractions Derived From Two Different Types of Cocoa Beans By UHPLC-DAD-ESI-HR-MSn." Food Research International (Ottawa, Ont.), vol. 115, 2019, pp. 135-149.

Oracz J, Nebesny E, Żyżelewicz D. Identification and quantification of free and bound phenolic compounds contained in the high-molecular weight melanoidin fractions derived from two different types of cocoa beans by UHPLC-DAD-ESI-HR-MSn. Food Res Int. 2019;115:135-149.

Oracz, J., Nebesny, E., & Żyżelewicz, D. (2019). Identification and quantification of free and bound phenolic compounds contained in the high-molecular weight melanoidin fractions derived from two different types of cocoa beans by UHPLC-DAD-ESI-HR-MSn. Food Research International (Ottawa, Ont.), 115, 135-149. https://doi.org/10.1016/j.foodres.2018.08.028

Oracz J, Nebesny E, Żyżelewicz D. Identification and Quantification of Free and Bound Phenolic Compounds Contained in the High-molecular Weight Melanoidin Fractions Derived From Two Different Types of Cocoa Beans By UHPLC-DAD-ESI-HR-MSn. Food Res Int. 2019;115:135-149. PubMed PMID: 30599925.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Identification and quantification of free and bound phenolic compounds contained in the high-molecular weight melanoidin fractions derived from two different types of cocoa beans by UHPLC-DAD-ESI-HR-MSn. AU - Oracz,Joanna, AU - Nebesny,Ewa, AU - Żyżelewicz,Dorota, Y1 - 2018/08/12/ PY - 2018/03/31/received PY - 2018/07/26/revised PY - 2018/08/10/accepted PY - 2019/1/3/entrez PY - 2019/1/3/pubmed PY - 2020/1/7/medline KW - Caffeic acid (PubChem CID: 689043) KW - Catechin (PubChem CID: 9064) KW - Cocoa beans KW - Ellagic acid (PubChem CID: 5281855) KW - Epicatechin (PubChem CID: 72276) KW - Ferulic acid (PubChem CID: 445858) KW - Flavan-3-ols KW - Gallic acid (PubChem CID: 370) KW - Maillard reaction KW - Melanoidins KW - N-[3′,4′-dihydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine (PubChem CID: 6506968) KW - N-[3′,4′-dihydroxy-(E)-cinnamoyl]-L-aspartic acid (PubChem CID: 24891368) KW - N-[4′-hydroxy-(E)-cinnamoyl]-L-aspartic acid (PubChem CID: 24891369) KW - N-[4′-hydroxy-(E)-cinnamoyl]-L-tyrosine (PubChem CID: 15825666) KW - N-phenylpropenoyl-L-amino acids KW - Phenolic acids KW - Phenolic aldehyde KW - Procyanidin B2 (PubChem CID: 122738) KW - Protocatechualdehyde (PubChem CID: 8768) KW - Protocatechuic acid (PubChem CID: 72) KW - Roasting KW - Sinapic acid (PubChem CID: 637775) KW - p-Coumaric acid (PubChem CID: 637542) SP - 135 EP - 149 JF - Food research international (Ottawa, Ont.) JO - Food Res Int VL - 115 N2 - The aim of the present study was to establish the profiles of soluble free phenolics (SFPs) and bound phenolics (BPs) in high molecular weight (HMW) melanoidin fractions isolated from raw and roasted beans of two Theobroma cacao L. varieties. Samples were prepared using three methods (saline treatment and acidic and alkaline hydrolysis) to obtain different forms of phenolic compounds. A total of fifteen phenolics, including three flavan-3-ols, seven phenolic acids, one phenolic aldehyde, and four N-phenylpropenoyl-L-amino acids (NPAs), were identified using ultra-high-performance liquid chromatography coupled to diode array detection and electrospray ionization high-resolution mass spectrometry (UHPLC-DAD-ESI-HR-MSn). In HMW fractions from both studied cocoa types, the main SFPs were N-caffeoyl-L-Asp and procyanidin B2, whereas the main BPs were catechin, epicatechin, ellagic acid, protocatechualdehyde, and N-caffeoyl-L-Asp. The concentrations of individual BPs were much higher than the content of total SFPs. It was also found that, as compared to alkaline hydrolysis, acid hydrolysis released a significantly higher amount of BPs from HMW melanoidin fractions. A comprehensive quantitative analysis indicated significant variation in the investigated phenolic compounds depending on the cocoa type and roasting conditions. An increase in treatment temperature from 110 to 150 °C led to a decline in SFPs and an increment in BPs. The HMW fractions of unroasted Criollo beans exhibited the highest content of SFPs and the lowest content of BPs. The highest BP concentrations were obtained for both cocoa bean varieties roasted at 150 °C. The present study revealed that HMW melanoidin fractions from cocoa beans of different varieties roasted at higher temperatures are a good source of phenolic compounds that can be released under both acidic and alkaline conditions. SN - 1873-7145 UR - https://www.unboundmedicine.com/medline/citation/30599925/Identification_and_quantification_of_free_and_bound_phenolic_compounds_contained_in_the_high_molecular_weight_melanoidin_fractions_derived_from_two_different_types_of_cocoa_beans_by_UHPLC_DAD_ESI_HR_MSn_ DB - PRIME DP - Unbound Medicine ER -

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Identification and quantification of free and bound phenolic compounds contained in the high-molecular weight melanoidin fractions derived from two different types of cocoa beans by UHPLC-DAD-ESI-HR-MSn.Food Res Int. 2019 01; 115:135-149.FR