Thermally-induced formation of taste-active 2,5-diketopiperazines from short-chain peptide precursors in cocoa

Andruszkiewicz, Paweł J.; Dsouza, Roy N.; Altun, Irem; Corno, Marcello; Kuhnert, Nikolai

doi:10.1016/j.foodres.2019.03.015

Cited by 27 publications

(20 citation statements)

References 38 publications

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“…Additionally, polymerization reactions produce melanoidin pigments that are responsible for the brown colour. 2,5-Diketopiperazines (bitter taste) are semi-volatile cyclic dipeptides formed from specific peptide precursors during roasting (Andruszkiewicz et al 2019). The most abundant Strecker aldehydes that contribute to chocolate notes are acetaldehyde (originating from alanine; fruity notes), benzaldehyde (phenylalanine; sweet, bitter and almond notes), 3-methylbutanal (leucine; malty/chocolate notes), 2-methylbutanal (isoleucine; malty/chocolate notes), 2-methylpropanal (valine; malty/nutty/chocolate notes) and phenylacetaldehyde (phenylalanine; floral/honey notes).…”

Section: Cocoa Bean Flavour Formationmentioning

confidence: 99%

Functional role of yeasts, lactic acid bacteria and acetic acid bacteria in cocoa fermentation processes

Vuyst

Leroy

2020

FEMS Microbiology Reviews

145

175

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Cured cocoa beans are obtained through a post-harvest, batchwise process of fermentation and drying carried out on farms in the equatorial zone. Fermentation of cocoa pulp-bean mass is performed mainly in heaps or boxes. It is made possible by a succession of yeast, lactic acid bacteria (LAB) and acetic acid bacteria (AAB) activities. Yeasts ferment the glucose of the cocoa pulp into ethanol, perform pectinolysis and produce flavour compounds, such as (higher) alcohols, aldehydes, organic acids and esters. LAB ferment the glucose, fructose and citric acid of the cocoa pulp into lactic acid, acetic acid, mannitol and pyruvate, generate a microbiologically stable fermentation environment, provide lactate as carbon source for the indispensable growth of AAB, and contribute to the cocoa and chocolate flavours by the production of sugar alcohols, organic acids, (higher) alcohols and aldehydes. AAB oxidize the ethanol into acetic acid, which penetrates into the bean cotyledons to prevent seed germination. Destruction of the subcellular seed structure in turn initiates enzymatic and non-enzymatic conversions inside the cocoa beans, which provides the necessary colour and flavour precursor molecules (hydrophilic peptides, hydrophobic amino acids and reducing sugars) for later roasting of the cured cocoa beans, the first step of the chocolate-making.

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Section: Cocoa Bean Flavour Formationmentioning

confidence: 99%

Functional role of yeasts, lactic acid bacteria and acetic acid bacteria in cocoa fermentation processes

Vuyst

Leroy

2020

FEMS Microbiology Reviews

145

175

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“…In addition to bioactive peptides, other structures have been documented to form during cocoa processing: diketopiperazines. These compounds are cyclic dipeptides that have been partially associated with the bitter taste of cocoa, and also with different functional effects (Andruszkiewicz D'Souza, Altun, Corno, and Kuhnert, 2019). Although these molecules have not been studied during alkalization, they might form as a result of treatment, and may contribute to the flavour and functional effects of cocoa.…”

Section: Proteins Peptides Amino Acids and Maillard Reaction Productsmentioning

confidence: 99%

Changes in cocoa properties induced by the alkalization process: A review

García

Pérez‐Esteve

Baviera

2020

Comp Rev Food Sci Food Safe

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Alkalization, also known as "Dutching", is an optional, but very useful, step taken in the production chain of cocoa to darken its colour, modify its taste and increase natural cocoa solubility. Over the years, various attempts have been made to design new and more effective alkalization methods. Moreover, different authors have attempted to elucidate the impact of alkalization on the physico-chemical, nutritional, functional, microbiological and sensory characteristics of alkalised cocoa. The aim of this review is to provide a clear guide about not only the conditions that can be applied to alkalize cocoa, but also the reported effects of alkalization on the nutritional, functional, microbiological and sensory characteristics of cocoa.The first part of this review describes different cocoa alkalization systems and how they can be tuned to induce specific changes in cocoa properties. The second part is a holistic analysis of the effects of the alkalization process on different cocoa features, performed by emphasising the biochemistry behind all these transformations.

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“…Also, the nutrigenomic effects of CP against white adipose tissue (WAT) dysfunction with reduction in inflammatory factors, triglyceride levels, and non-esterified fatty acids (NEFAs) in serum, as well as decrease in body weight and different WATs have been shown [ 18 ]. Also, other investigations have suggested the contribution of CP to the release of flavor precursor peptides [ 10 , 19 ]. However, there are no data about the PL inhibitory effects of CP and its relation to the decrease in body weight.…”

Section: Introductionmentioning

confidence: 99%

Cocoa (Theobroma cacao L.) Seed Proteins’ Anti-Obesity Potential through Lipase Inhibition Using In Silico, In Vitro and In Vivo Models

Coronado-Cáceres

Rabadán-Chávez

Mojica

et al. 2020

Foods

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The aim of this study was to determine the pancreatic lipase (PL) inhibitory effect of cocoa protein (CP) hydrolysates (CPH) using in silico and in vitro approaches, and an in vivo high-fat diet (HF) obese rat model. The results showed better theoretical affinity on PL for cocoa peptides EEQR, GGER, QTGVQ, and VSTDVNIE released from vicilin and albumins (−6.5, −6.3, −6.2, and −6.1 kcal/mol, respectively). Absorption, distribution, metabolism, and excretion (ADMET) prediction showed the human intestinal absorption (HIA) capacity of orlistat and eight cocoa peptides, demonstrating that they presented a low probability of toxicity with values lower than 0.6, while the orlistat has a high probability of hepatotoxicity with a mean value of 0.9. CPH (degree of hydrolysis of 55%) inhibited PL with an IC50 (concentration needed to inhibit 50% of enzyme activity) value of 1.38 mg/mL. The intragastric administration of 150 mg CP/kg/day to rats increased total lipids and triglycerides excretion in feces, ranging from 11% to 15% compared to the HF-diet. The HF + CP-diet also significantly decreased (p < 0.05) the apparent rate of fat absorption compared with the HF group. These results suggest that CP has anti-obesity potential by inhibiting PL, thus helping to prevent the development of non-communicable diseases.

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Thermally-induced formation of taste-active 2,5-diketopiperazines from short-chain peptide precursors in cocoa

Cited by 27 publications

References 38 publications

Functional role of yeasts, lactic acid bacteria and acetic acid bacteria in cocoa fermentation processes

Functional role of yeasts, lactic acid bacteria and acetic acid bacteria in cocoa fermentation processes

Changes in cocoa properties induced by the alkalization process: A review

Cocoa (Theobroma cacao L.) Seed Proteins’ Anti-Obesity Potential through Lipase Inhibition Using In Silico, In Vitro and In Vivo Models

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