Current Advances in Naturally Occurring Caffeoylquinic Acids: Structure, Bioactivity, and Synthesis

Abstract

Caffeoylquinic acids (CQAs) are a broad class of secondary metabolites that have been found in edible and medicinal plants from various families. It has been 100 years since the discovery of chlorogenic acid in 1920. In recent years, a number of naturally derived CQAs have been isolated and structurally elucidated. Accumulated evidence demonstrate that CQAs have a wide range of biological activities, such as antioxidation, antibacterial, antiparasitic, neuroprotective, anti-inflammatory, anticancer, antiviral, and antidiabetic effects. Up to date, some meaningful progresses on the biosynthesis and total synthesis of CQAs have also been made. Therefore, it is necessary to comprehensively summarize the structure, biological activity, biosynthesis, and chemical synthesis of CQAs. This review provides extensive coverage of naturally occurring CQAs discovered from 1990 until 2020. Modern isolation techniques, chemical data (including structure, biosynthesis, and total synthesis), and bioactivity are summarized. This would be helpful for further research of CQAs as potential pharmaceutical agents.

Screening of Antioxidative Properties and Inhibition of Inflammation-Linked Enzymes by Aqueous and Ethanolic Extracts of Plants Traditionally Used in Wound Healing in Poland

“…Therefore, these constituents might affect the activity of extracts in a significant manner. Antioxidant and anti-inflammatory properties are demonstrated by derivatives of phenolic acids, such as caffeoylquinic acids, and their succinic and malonyl esters, identified in All EtOH and K EtOH [47], as well as rosmarinic acid and salvianolic acids, which were found in Th EtOH [48,49]. In addition, compounds from the group of flavonoids, derivatives of apigenin, quercetin, and luteolin, present in K and Th extracts, apart from other activities, exert the free radical scavenging effect and anti-inflammatory activity confirmed by previous research [50].…”

Persea Americana Agro-Industrial Waste Biorefinery for Sustainable High-Value-Added Products

“…Furthermore, caffeoylquinic acid, a high-interest product, is present in the fruit as well. This substance possesses therapeutic properties due to its pharmacological activity as an anti-inflammatory, antiviral, anticancer, and antidiabetic molecule [112,113]. These properties, combined with the possibility of obtaining biopolymer from avocado wastes, represent a great opportunity for developing advanced drug delivery systems that can improve the bioavailability of these compounds and, thus, their therapeutic effect [17].…”

Caffeoylquinic acids: chemistry, biosynthesis, occurrence, analytical challenges, and bioactivity

“…Despite the diversity of reported qualitative and quantitative methodologies for the study of CQAs (Liu, Li, Zu, et al. , 2020; Wianowska and Gil, 2019), comprehensive characterization methods for CQAs are still in an early stage of development. There are several challenges associated with the reliable characterization of individual CQAs, including degradation and transformation through sample processing, a lack of commercially available authentic standards, matrix interferences, and the presence of multiple isomers with similar physicochemical properties that make the unambiguous characterization of isomers challenging.…”

“…Some current advances for other substituents are reported elsewhere (Liu, Li, Zu, et al. , 2020; Wianowska and Gil, 2019).…”