Chlorogenic acids and the acyl-quinic acids: discovery, biosynthesis, bioavailability and bioactivity

Abstract

Covering: 2000 up to late 2017This review is focussed upon the acyl-quinic acids, the most studied group within the ca. 400 chlorogenic acids so far reported. The acyl-quinic acids, the first of which was characterised in 1846, are a diverse group of plant-derived compounds produced principally through esterification of an hydroxycinnamic acid and 1l-(-)-quinic acid. Topics addressed in this review include the confusing nomenclature, quantification and characterisation by NMR and MS, biosynthesis and role in planta, and the occurrence of acyl-quinic acids in coffee, their transformation during roasting and delivery to the beverage. Coffee is the major human dietary source world-wide of acyl-quinic acids and consideration is given to their absorption and metabolism in the upper gastrointestinal tract, and the colon where the microbiota play a key role in the formation of catabolites. Evidence on the potential of the in vivo metabolites and catabolites of acyl-quinic acids to promote the consumer's health is evaluated.

Where to Look into the Puzzle of Polyphenols and Health? The Postbiotics and Gut Microbiota Associated with Human Metabotypes

“…[ 149,150,152 ] The final metabolites in this catabolic pathway are not specific to proanthocyanidin catabolism, but they are also common to the gut microbial catabolism of many other polyphenols (flavonoids and non‐flavonoids). [ 153 ] Therefore, the binary response of metabotypes is not accomplished, that is, the presence versus absence of unique metabolites. Although phenylvalerolactones have been proposed as biomarkers of proanthocyanidin intake, [ 154,155 ] these metabolites are intermediates in the catabolic pathway, being further metabolized to unspecific final metabolites.…”

The Bioavailability, Transport, and Bioactivity of Dietary Flavonoids: A Review from a Historical Perspective

“…When ileostomists were fed raspberries, blueberries, lingonberries, and grapes up to 40% of the ingested anthocyanins remained in the ileal fluid (Brown et al., ; González‐Barrio, Borges; Mullen, & Crozier, ; Kahle et al., ; Stalmach et al., ; McDougall et al., ). In volunteers with a functioning colon this portion of anthocyanins would pass into the large intestine where it would be deglycosylated and the resulting aglycones broken down by fission of the C‐ring, with the A‐ and B‐ring fragments being converted to a diversity of phenolic constituents (Feliciano et al., ; González‐Barrio et al., ; Rodriguez‐Mateos et al., ), some of which are also produced by catabolism of other classes of flavonoids and related dietary (poly)phenols, such as chlorogenic acids (Clifford, Jaganath, Ludwig, & Crozier, ; Williamson & Clifford, , ).…”

Caffeoylquinic Acids: Separation Method, Antiradical Properties and Cytotoxicity

“…[22] Analyzing the isolated compounds, flavones (1, 2) presented a low activity, less than 32 % Tx activity. However, chlorogenic acid derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) were more active than flavones showing higher ability to trapping DPPH radicals. CQAs are already known for their potent antioxidant capacity because they have a greater capacity to stabilize radicals due to the presence of catechol group in their structures.…”

“…In vitro assays frequently have shown CGA's as powerful antioxidants. [6] However, due to the complexity of isolation of the isomers from caffeoylquinic acids, the most studied and tested compound from this class is 5-CQA. Chlorogenic acid has been heavily studied on several assays of biological activities like antioxidant and anti-inflammatory activities, enzyme inhibitors, etc., which have encouraged many researchers to work with this chemical class of phenolic compounds.…”