Hydroxycinnamoyl Amino Acids Conjugates: A Chiral Pool to Distinguish Commercially Exploited Coffea spp.

Abstract

The synthesis of five hydroxycinnamoyl amides (HCAs) was accomplished and their identification and quantification in the green coffee bean samples of Coffea arabica, Coffea canephora, and Coffea liberica was performed. The HCAs p-coumaroyl-N-tyrosine 1b, caffeoyl-N-phenylalanine 2b, caffeoyl-N-tyrosine 3b, and p-coumaroyl-N-tryptophan 4b were characteristic of the C. canephora species while caffeoyl-N-tryptophan 5b was present in both C. canephora and C. arabica, but with higher content in C. canephora. The HCAs presence was also analyzed in C. liberica for the first time and none of the targeted compounds was found, indicating that this species is very similar to C. arabica species. Between C. canephora samples from various origins, significant differences were observed regarding the presence of all the HCAs, with C. canephora from Tanzania containing all five derivatives.

How Does LC/MS Compare to UV in Coffee Authentication and Determination of Antioxidant Effects? Brazilian and Middle Eastern Coffee as Case Studies

“…The MN ( Figure 1 C) showed most of the identified hydroxycinnamoyl amides, as identified in Table 2 , indicating their structural similarities. The results were in agreement with the previous literature distinguishing C. robusta products from other Coffea species-containing analogues [ 46 ].…”

Metabolomics Combined with Sensory Analysis Reveals the Impact of Different Extraction Methods on Coffee Beverages from Coffea arabica and Coffea canephora var. Robusta

“…Overall, the amino acid conjugates of hydroxycinnamic acids (e.g., Na- p -hydroxy-coumaroyl-tryptophan) have been previously reported as potential marker compounds to discriminate among coffee cultivars [ 29 ]. In this regard, [ 30 ] showed that p -coumaroyl-N-tryptophan was a characteristic marker compound of the C. canephora species, thus confirming our findings. Also, the compound coffeasterene belongs to the class of organic compounds known as stigmastanes and derivatives.…”

Metabolomics-Based Approach for Coffee Beverage Improvement in the Context of Processing, Brewing Methods, and Quality Attributes

“…Chlorogenic acids were annotated in various green coffee specimens based on LC-MS 4 patterns of fragmentation, including derivatives of dimethoxycinnamoylquinic acids, caffeoyl-dimethoxycinnamoylquinic acids, and diferuloylquinic acids [ 46 ], in addition to hydroxycinnamoyl amides [ 47 ]. Additionally, roasting changes the coffee chemical profile and increases its complexity, due to the formation of quinides, chlorogenic derivatives, and shikimates.…”

“…LC/MS has been applied for studying the non-volatile metabolites associated with coffee brewing, including polyphenolics, alkaloids, and diterpenes. Compared to roasting effects, the effects of brewing on phytochemical composition, particularly chlorogenic acid and hydroxycinnamoyl amide derivatives, has not been extensively reported [ 46 , 47 ]. LC/MS showed potential in detecting health-related metabolites, either undesirable as acrylamide and furans, or desirable as the antioxidant phenolics, providing a good readout of coffee safety and efficacy of coffee prepared by cold methods [ 64 , 82 ].…”