Caffeates and Caffeamides: Synthetic Methodologies and Their Antioxidant Properties

Abstract

Polyphenols are secondary metabolites of plants and include a variety of chemical structures, from simple molecules such as phenolic acids to condensed tannins and highly polymerized compounds. Caffeic acid (3,4-dihydroxycinnamic acid) is one of the hydroxycinnamate metabolites more widely distributed in plant tissues. It is present in many food sources, including coffee drinks, blueberries, apples, and cider, and also in several medications of popular use, mainly those based on propolis. Its derivatives are also known to possess anti-inflammatory, antioxidant, antitumor, and antibacterial activities, and can contribute to the prevention of atherosclerosis and other cardiovascular diseases. This review is an overview of the available information about the chemical synthesis and antioxidant activity of caffeic acid derivatives. Considering the relevance of these compounds in human health, many of them have been the focus of reviews, taking as a center their obtaining from the plants. There are few revisions that compile the chemical synthesis methods, in this way, we consider that this review does an important contribution.

Phytochemical Profile, Mineral Content, and Bioactive Compounds in Leaves of Seed-Propagated Artichoke Hybrid Cultivars

“…This compound has been reported to have a cytotoxicity against cancer cell lines (HL-60 and U-937), even stronger than quercetin, probably the best-studied flavonoid [ 21 ]. Caffeic acid derivatives are known to possess anti-inflammatory, antioxidant, anti-tumor, and antibacterial activities, and can contribute to the prevention of atherosclerosis and other cardiovascular diseases [ 22 ]. The most abundant sesquiterpene lactones were anthemolide B, ixerisoside K, and chlorohyssopifolin B, together with its isomer chlorochrymorin ( Supplementary Table S1 ).…”

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“…Thymol has antiaggregant ability and it is able to inhibit platelet aggregation induced by thrombin, collagen, adenosine diphosphate and arachidonic acid [62].…”

Natural and Synthetic Derivatives of Hydroxycinnamic Acid Modulating the Pathological Transformation of Amyloidogenic Proteins

“…Both compounds showed anticancer activity against P388 murine leukemia cells. Other coupling reagents, i.e., benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate(BOP), 1-(bis(dimethylamino)methylene)-1 H -[1,2,3]triazolo[4,5- b ]pyridine-1-ium 3-oxide hexafluorophosphate (HATU), and dicyclohexylcarbodiimide (DCC) have been used for the preparation of ferulic [ 88 ] and caffeic acid esters and amides [ 89 ]. The nucleophilic hydroxyl groups were often protected via acetylation by acetic anhydride in the presence of pyridine [ 87 , 90 , 91 ] or other bases [ 92 , 93 ].…”

“…The nucleophilic hydroxyl groups were often protected via acetylation by acetic anhydride in the presence of pyridine [ 87 , 90 , 91 ] or other bases [ 92 , 93 ]. Other methods for the preparation of HCA esters and amides have been used and were thoroughly reviewed by de Armas-Ricard and co-authors in 2019 [ 89 ].…”

“…As previously described, esters and amides of coumaric, ferulic and caffeic acid possess numerous biological activities, e.g., antioxidant [ 82 , 83 , 86 , 89 , 94 , 95 , 96 ], anticancer [ 78 , 87 , 92 ], antibacterial [ 82 , 97 , 98 , 99 ], antifungal [ 100 , 101 , 102 ], antiviral [ 82 , 90 , 103 ], anti-inflammatory [ 104 , 105 , 106 ], and many other activities [ 84 , 107 , 108 ]. The most commonly described health beneficial properties of HCAs and their derivatives is antioxidant activity due to the phenolic hydroxyl group(s) on the main aromatic ring, which possess(es) the ability to react with free radicals and reactive oxygen species forming a resonance-stabilized phenoxyl radical.…”