Profiles of Phenolic Compounds and Purine Alkaloids during the Development of Seeds of Theobroma cacao cv. Trinitario

Abstract

Changes occurring in phenolic compounds and purine alkaloids, during the growth of seeds of cacao (Theobroma cacao) cv. Trinitario, were investigated using HPLC-MS/MS. Extracts of seeds with a fresh weight of 125, 700, 1550, and 2050 mg (stages 1-4, respectively) were analyzed. The phenolic compounds present in highest concentrations in developing and mature seeds (stages 3 and 4) were flavonols and flavan-3-ols. Flavan-3-ols existed as monomers of epicatechin and catechin and as procyanidins. Type B procyanidins were major components and varied from dimers to pentadecamer. Two anthocyanins, cyanidin-3-O-arabinoside and cyanidin-3-O-galactoside, along with the N-phenylpropernoyl-l-amino acids, N-caffeoyl-l-aspartate, N-coumaroyl-l-aspartate, N-coumaroyl-3-hydroxytyrosine (clovamide), and N-coumaroyltyrosine (deoxyclovamide), and the purine alkaloids theobromine and caffeine, were present in stage 3 and 4 seeds. Other purine alkaloids, such as theophylline and additional methylxanthines, did not occur in detectable quantities. Flavan-3-ols were the only components to accumulate in detectable quantities in young seeds at developmental stages 1 and 2.

Changes in the flavan-3-ols, anthocyanins, and flavanols composition of cocoa beans of different Theobroma cacao L. groups affected by roasting conditions

“…We showed that all of the analyzed groups contain monomeric flavan-3-ols (epicatechin and catechin) and dimeric and trimeric procyanidins, which are composed of catechin and epicatechin as monomeric units. These findings are in accordance with the results presented by other authors [5,6,9,20]. In this study, the procyanidins detected and quantified were the procyanidin dimer B2 and procyanidin trimer C1.…”

“…The literature on individual flavanols contents in raw cocoa beans is very limited. The Qu-3-ara and Qu-3-glu contents of raw cocoa beans in the present study are much lower than those of the values reported by Pereira-Caro et al [20] for fresh unfermented cocoa seeds of the Trinitario type. The variation in the levels of individual quercetin glycosides is probably related to the s degradation during the fermentation and drying of cocoa beans.flavanol The studies were also conducted to evaluate the changes in the levels of flavanols that occur during roasting of cocoa beans.…”

“…32 µg/g ff-dw) and 9.7-10.7 % (9.57 ± 0.09-33.84 ± 0.10 µg/g ff-dw) of the total flavanol content, respectively, whereas quercetin was present in very low quantities in raw cocoa beans representing less than 1.7 % (0.60 ± 0.09-2.79 ± 0.09 µg/g ff-dw) of the total flavanol levels. The presence of these same flavanols has been previously reported in the cocoa beans and different cocoaderived products by Andres-Lacueva et al [5], Ortega et al [8], and Pereira-Caro et al [20]. It was demonstrated that all of the cocoa types had similar qualitative profiles but different amounts of the individual flavanols.…”

“…Identification and peak assignment of phenolic compounds were based on the comparison of their retention times, UV-visible absorbance spectra characteristics, fullscan mass spectra (ionization modes positive or negative), and MS/MS fragmentation patterns with those of authentic standards analyzed under identical conditions, as well as the bibliographic references used in the characterization process [20,21]. Quantification of individual phenolic compounds was carried out using external standard method.…”

Evaluación de epicatequina, teobromina y cafeína en cáscaras de cacao (<i>Theobroma cacao</i> L.), determinación de su capacidad antioxidante

“…En determinadas situaciones las defensas antioxidantes pueden verse desbordadas por la excesiva generación de EROS. Este desequilibrio entre especies oxidantes y antioxidantes se conoce como estrés oxidativo, el cual está asociado a numerosas enfermedades y al proceso normal de envejecimiento Pereira et al, (2013). La dieta desempeña un papel importante en la prevención de enfermedades relacionadas con el estrés oxidativo, fundamentalmente a través del aporte de compuestos bioactivos de origen vegetal, entre ellos, las vitaminas hidrosolubles y liposolubles, carotenoides y una gran variedad de compuestos fenólicos, cuya ac-tividad antioxidante y potenciales efectos beneficiosos están siendo ampliamente investigados en los últimos años (Díaz, 2011).…”