Procyanidin A2 and Its Degradation Products in Raw, Fermented, and Roasted Cocoa

Taeye, Cédric De; Caullet, Gilles; Evina, Victor Jos Eyamo; Collin, Sonia

doi:10.1021/acs.jafc.6b05262

Cited by 32 publications

(27 citation statements)

References 39 publications

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“…This reaction is carried out by polyphenol oxidase (Figure 5), which is released because of cotyledon changes affected by fermentation. The results of this process are reduced bitterness and astringency and increased brown color [5,35]. During oxidation, polyphenols react with proteins and are converted into insoluble forms [8].…”

Section: Polyphenolsmentioning

confidence: 99%

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The Chemistry behind Chocolate Production

et al. 2019

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Chocolate production is a complex process during which numerous chemical reactions occur. The most important processes, involving most of the reactions important for development of the proper chocolate flavor, are fermentation, drying and roasting of cocoa bean, and chocolate conching. During fermentation, formation of important precursors occurs, which are essential for further chemical reactions in the following processes of chocolate production. Roasting is one of the most important processes due to the occurrence of Maillard’s reactions, during which aroma compounds are formed. In this paper, we have reviewed the most important chemical reactions that occur with proteins, carbohydrates, lipids, and polyphenols. Additionally, we present other components that may be naturally present or form during the production process, such as methylxanthines, aldehydes, esters, ketones, pyrazines, acids, and alcohols.

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Section: Polyphenolsmentioning

confidence: 99%

“…During fermentation, procyanidin A2 epimerizes to procyanidin F2. F1 and F2 procyanidins are specific to fermented cocoa beans [35].…”

Section: Polyphenolsmentioning

confidence: 99%

The Chemistry behind Chocolate Production

et al. 2019

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“…On the contrary, pole 4 seems to present a higher amount of catechin, an unknown procyanidin dimer, and an unknown compound. As explained above, a temperature elevation can cause the epimerization of the main flavan-3-ols (i.e., (-)-epicatechin, dimer B2 and dimer B5), leading to the formation of (-)-catechin and dimers containing (-)-catechin units, as shown earlier for procyanidin A2 [53]. Our data suggests that these reactions, which have been reported to occur under conditions mimicking conching, may also take place during fermentation.…”

Section: Exploring the Link Between Cocoa And Chocolate Polyphenols Cmentioning

confidence: 57%

Multiblock Analysis to Relate Polyphenol Targeted Mass Spectrometry and Sensory Properties of Chocolates and Cocoa Beans

Fayeulle

Preys²,

Roger

et al. 2020

Metabolites

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Chocolate quality is largely due to the presence of polyphenols and especially of flavan-3-ols and their derivatives that contribute to bitterness and astringency. The aim of the present work was to assess the potential of a quantitative polyphenol targeted metabolomics analysis based on mass spectrometry for relating cocoa bean polyphenol composition corresponding chocolate polyphenol composition and sensory properties. One-hundred cocoa bean samples were transformed to chocolates using a standard process, and the latter were attributed to four different groups by sensory analysis. Polyphenols were analyzed by an ultra-high-performance liquid chromatography (UPLC) system hyphenated to a triple quadrupole mass spectrometer. A multiblock method called a Common Component and Specific Weights Analysis (CCSWA) was used to study relationships between the three datasets, i.e., cocoa polyphenols, chocolate polyphenols and sensory profiles. The CCSWA multiblock method coupling sensory and chocolate polyphenols differentiated the four sensory poles. It showed that polyphenolic and sensory data both contained information enabling the sensory poles’ separation, even if they can be also complementary. A large amount of variance in the cocoa bean and corresponding chocolate polyphenols has been linked. The cocoa bean phenolic composition turned out to be a major factor in explaining the sensory pole separation.

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“…Commonly, the biosynthesis of these compounds is due to electrophilic substitution by acetaldehyde on the nucleophilic C6 or C8 positions of catechins A-ring [28]. Compounds 21, 28, and 32 were tentatively identified as A-type procyanidins [29]. In particular, procyanidin A2, which was commonly found in unfermented red beans, was likely compound 28, which showed the [M-H] − ion at m/z 575.1198 and TOF-MS/MS fragment ions at m/z 557.1144 and 539.1008, which were attributable to the sequential loss of two water molecules.…”

Section: Uhplc-esi-qqtof-ms/ms Analyses Of Hydroalcoholic Extractsmentioning

confidence: 99%

Theobromacacao Criollo var. Beans: Biological Properties and Chemical Profile

Lavorgna

Pacifico

Nugnes

et al. 2021

Foods

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Theobroma cacao provides precious products such as polyphenol-rich beans that are useful for nutraceutical purposes. The geographical area may influence the chemical composition of raw cocoa beans in terms of the polyphenols and biological qualities of the products. This work aimed to investigate the biological properties and the chemical composition of two different samples of Criollo var. cocoa raw beans coming from two areas (Indonesia; Peru). Beans underwent biphasic extraction obtaining lipophilic and hydroalcoholic extracts. The extracts were tested for antiradical, antimutagenic, and antigenotoxic effects. Cell viability inhibition toward breast, gastric/esophageal colorectal adenocarcinoma, and hepatoblastoma human cell lines was evaluated. Extracts were chemically investigated through UV-Vis spectroscopy and ultra-high-pressure liquid chromatography electrospray ionization quadrupole time-of-flight mass spectrometry (UHPLC-ESI-QqTOF MS/MS). Results showed that the Indonesian bean hydroalcoholic extracts were able to scavenge 2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS) cation radical better than the Peruvian hydroalcoholic extracts (ECs50: 72.63 vs. 322.20 μg/mL). Extracts showed antimutagenic and antigenotoxic activity. The viability inhibitory effect on breast and hepatic cancer cells was reached only for the Indonesian hydroalcoholic extracts at hundreds of μg/mL. Phenylpropenoyl-L-amino acids, hydroxycinnamoyl aminoacids conjugates, and procyanidin compounds were found mainly in the hydroalcoholic extracts, whereas fatty acids and lyso-phospholipids were found mainly in lipophilic fractions. Fatty acid and (epi)catechins appeared to be affected by different environmental conditions of the geographical areas.

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Procyanidin A2 and Its Degradation Products in Raw, Fermented, and Roasted Cocoa

Cited by 32 publications

References 39 publications

The Chemistry behind Chocolate Production

The Chemistry behind Chocolate Production

Multiblock Analysis to Relate Polyphenol Targeted Mass Spectrometry and Sensory Properties of Chocolates and Cocoa Beans

Theobromacacao Criollo var. Beans: Biological Properties and Chemical Profile

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