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Consumption of Chlorogenic Acids Through Coffee and Health Implications

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Consumption of Chlorogenic Acids Through Coffee and Health Implications beverages Review Consumption of Chlorogenic Acids through Coffee and Health Implications Adriana Farah * and Juliana dePaula Lima Laboratório de Química e Bioatividade de Alimentos e Núcleo de Pesquisa em Café (NUPECAFÉ), Instituto de Nutrição, Universidade Federal do Rio de Janeiro, Avenida Carlos Chagas Filho, 373, CCS, Bl. J, Rio de Janeiro 21941-902, Brazil; [email protected] * Correspondence: [email protected]; Tel.: +55-21-39386449 Received: 11 December 2018; Accepted: 15 January 2019; Published: 1 February 2019 Abstract: Chlorogenic acids (CGA) are the main antioxidant compounds in the Western diet, due to their high concentrations in coffee associated with the high consumption of the beverage. Until about 10 years ago, like many other phenolic compounds, CGA were thought to be poorly absorbed in the human digestive system. Along the years, large amounts of information on the absorption and metabolism of these compounds have been unveiled, and today, it is known that, on average, about one third of the consumed CGA from coffee is absorbed in the human gastrointestinal tract, although large inter-individual variation exists. Considering results from in vitro animal and human studies, it is possible to conclude that the antioxidant and anti-inflammatory effects of coffee CGA are responsible for, at least to a certain extent, the association between coffee consumption and lower incidence of various degenerative and non-degenerative diseases, in addition to higher longevity. Keywords: chlorogenic acids; coffee beverages; consumption; health effects 1. Introduction Chlorogenic acids (CGA), esters of trans-hydroxycinnamic acids and quinic acid (Figure1), were discovered in 1837 [1]. They were first thought to be caffetannic acid [2], which was in fact a mixture of different acids. Later, CGA were found to be distinct from tannic acid, the latest only found in green coffee. In 1908, 5-caffeoylquinic acid (5-CQA) or chlorogenic acid, numbered according to the International Union of Pure and Applied Chemistry (IUPAC) recommendations [3], was first isolated from a cristaline potassium–caffeine chlorogenate complex by Gorter [2,4], who discovered that this compound was widely distributed in leaves and seeds of numerous plants [5] including phytotherapeutic ones. But at least until the early 1920s substances in coffee other than caffeine were considered to have no biological effects [6]. In 1950, the term isochlorogenic acid was given to another CGA fraction found in coffee which was purified by Corse et al. [7] in 1965 and came to be the mixture of the three main dicaffeoylquinic acids (diCQA) [8]. By the end of the 60s, the neochlorogenic and cryptochlorogenic acids, corresponding to 3-caffeylquinic (3-CQA) and 4-caffeoylquinic (4-CQA) acids, respectively, according to IUPAC [3] as well as the three main feruloylquinic acids (3-FQA, 4-FQA, and 5-FQA) had already been isolated and identified by Nuclear Magnetic Resonance (NMR) spectroscopy [8]. In the late 70s and early 80s, the use of liquid chromatography enabled the identification of nine major CGA and other minor compounds in the coffee matrix [8]. From the beginning of the 90s and on, a new field of research laid in the study of CGA antioxidant attributes and their physiological significance stimulated studies with decaffeinated coffee. Discovered and isolated in the 80s [9], quinic acid lactones or quinides formed by dehydration of the quinic acid moiety during roasting (Figure2) also gained physiological importance in the 90s [10–14]. Currently, more than 300 major and Beverages 2019, 5, 11; doi:10.3390/beverages5010011 www.mdpi.com/journal/beverages Beverages 2019, 5, x FOR PEER REVIEW 2 of 29 compoundsBeverages 2019 such, 5, x FOR as PEERdicaffeoylquinic REVIEW acids (diCQA), diferuloylquinic acids, caffeoylferuloylquinic2 of 29 Beverages 2019, 5, 11 2 of 29 acids, dimethoxycinnamoylquinic acids, caffeoyldimethoxycinnamoylquinic acids, compounds such as dicaffeoylquinic acids (diCQA), diferuloylquinic acids, caffeoylferuloylquinic trimetoxycinnamoylcaffeoylquinic acids; feruloyldimethoxycinnamoylquinic acid, sinapoylquinic acids, dimethoxycinnamoylquinic acids, caffeoyldimethoxycinnamoylquinic acids, minoracids, CGAsinapoylcaffeoylquinic and related compounds acids, such sinapoylfe as dicaffeoylquinicruloylquinic acidsacids, (diCQA), and related diferuloylquinic compounds, acids, in trimetoxycinnamoylcaffeoylquinic acids; feruloyldimethoxycinnamoylquinic acid, sinapoylquinic caffeoylferuloylquinicaddition to a number acids,of new dimethoxycinnamoylquinic minor p-coumaric acid-containing acids, caffeoyldimethoxycinnamoylquinic compounds have been described acids, sinapoylcaffeoylquinic acids, sinapoylferuloylquinic acids, and related compounds, in acids,both in trimetoxycinnamoylcaffeoylquinic coffee [15–24] and in other plant acids; materi feruloyldimethoxycinnamoylquinicals [25,26], and a number of acid,potential sinapoylquinic beneficial addition to a number of new minor p-coumaric acid-containing compounds have been described acids,effects sinapoylcaffeoylquinic of CGA have been acids,revealed sinapoylferuloylquinic in vitro and in animal acids, andstudies, related corroborating compounds, inresults addition of both in coffee [15–24] and in other plant materials [25,26], and a number of potential beneficial toepidemiological a number of newstudies. minor Thep aim-coumaric of this review acid-containing was to raise compounds the awareness have of been coffee described consumers both and in effects of CGA have been revealed in vitro and in animal studies, corroborating results of coffeenot consumers [15–24] and for inthe other high plantintake materials of CGA [through25,26], and coffee a number and for oftheir potential potential beneficial beneficial effects health of epidemiological studies. The aim of this review was to raise the awareness of coffee consumers and CGAeffects have on health. been revealed in vitro and in animal studies, corroborating results of epidemiological studies. not consumers for the high intake of CGA through coffee and for their potential beneficial health The aim of this review was to raise the awareness of coffee consumers and not consumers for the high effects on health. intake of CGA through coffee and for their potential beneficial health effects on health. Figure 1. Major chlorogenic acids found in coffee. CQA: caffeoylquinic acids; FQA: feruloylquinic Figureacids; p 1.-CoQA:Major p chlorogenic-coumaroylquinic acids foundacids; indiCQA: coffee. dicaffeoylq CQA: caffeoylquinicuinic acids. acids;When FQA:citing feruloylquinicother authors, Figure 1. Major chlorogenic acids found in coffee. CQA: caffeoylquinic acids; FQA: feruloylquinic acids;their numberingp-CoQA: p -coumaroylquinichas been changed acids; for consistency. diCQA: dicaffeoylquinic Numbering follows acids. Whenthe International citing other Union authors, of acids; p-CoQA: p-coumaroylquinic acids; diCQA: dicaffeoylquinic acids. When citing other authors, theirPure numberingand Applied has Chemistry been changed (IUPAC for consistency.) numbering Numbering system [3], followswhich has the Internationalbeen recently Union discussed, of Pure in their numbering has been changed for consistency. Numbering follows the International Union of andother Applied reviews Chemistry [23,24]. (IUPAC) numbering system [3], which has been recently discussed, in other reviewsPure and [23 ,Applied24]. Chemistry (IUPAC) numbering system [3], which has been recently discussed, in other reviews [23,24]. O O COOH O O HO 3 OH 1 Δ HO 3 O 1 OO COOHOH OO OH HO 4 35 OH 1 H2ΔO HO 4 35O 1 O OH O OH HO OH HO OH 4 5 H2O 4 5 HFigureO 2. Formation of 1,5-quinolactoneOH during coffee roasting,HO exemplified by 3-caffeoylquinide-OH Figure 2. Formation of 1,5-quinolactone during coffee roasting, exemplified by 3-caffeoylquinide- 3CQL. Note: Although under IUPAC rules the numbering system [3] for the lactones is different from 3CQL. Note: Although under IUPAC rules the numbering system [3] for the lactones is different theFigure acids, 2. to Formation avoid confusion, of 1,5-quinolactone the authors used during for lactones coffee theroasting, same numberingexemplified of by the 3-caffeoylquinide- carbon atoms as from the acids, to avoid confusion, the authors used for lactones the same numbering of the carbon for3CQL. the acid Note: precursors. Although under IUPAC rules the numbering system [3] for the lactones is different atoms as for the acid precursors. 2. Chlorogenicfrom the acids, Acids to Levels avoid confusio in Coffeen, the Beverages authors used and for Estimated lactones Dailythe same Consumption numbering of the carbon atoms as for the acid precursors. through2. Chlorogenic Coffee Acids Levels in Coffee Beverages and Estimated Daily Consumption through Coffee 2. ChlorogenicTogether with Acids mate Levels (Ilex paraguariensis in Coffee Beve) greenrages coffee and Estimated seed is the Daily main Consumption known source through of CGA in nature,CoffeeTogether especially with in mateCoffea (Ilex canephora, paraguariensiscultivars) green (Robusta coffee and seed Conilon), is the main in which known contents source commonlyof CGA in reachnature, 7–8 especially g/100 g (dryin Coffea matter-dm), canephora, while cultivars in C. (Robusta arabica cultivars and Conilon), 4–6 g/100 in which g (dm) contents are more commonly common. Together with mate (Ilex paraguariensis) green coffee seed is the main known source of CGA in However,reach 7–8 g/100 coffee g is(dry mostly matter-dm),
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