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

Armando Alcazar Magaña; Naofumi Kamimura; Amala Soumyanath; Jan F. Stevens; Claudia S. Maier

doi:10.1111/tpj.15390

journal article Jul 23, 2021

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

Armando Alcazar Magaña

Naofumi Kamimura Amala Soumyanath Jan F. Stevens Claudia S. Maier

The Plant Journal Vol. 107 No. 5 pp. 1299-1319 · Wiley

View at Publisher Save 10.1111/tpj.15390

Abstract

SUMMARYCaffeoylquinic acids (CQAs) are specialized plant metabolites we encounter in our daily life. Humans consume CQAs in mg‐to‐gram quantities through dietary consumption of plant products. CQAs are considered beneficial for human health, mainly due to their anti‐inflammatory and antioxidant properties. Recently, new biosynthetic pathways via a peroxidase‐type p‐coumaric acid 3‐hydroxylase enzyme were discovered. More recently, a new GDSL lipase‐like enzyme able to transform monoCQAs into diCQA was identified in Ipomoea batatas. CQAs were recently linked to memory improvement; they seem to be strong indirect antioxidants via Nrf2 activation. However, there is a prevalent confusion in the designation and nomenclature of different CQA isomers. Such inconsistencies are critical and complicate bioactivity assessment since different isomers differ in bioactivity and potency. A detailed explanation regarding the origin of such confusion is provided, and a recommendation to unify nomenclature is suggested. Furthermore, for studies on CQA bioactivity, plant‐based laboratory animal diets contain CQAs, which makes it difficult to include proper control groups for comparison. Therefore, a synthetic diet free of CQAs is advised to avoid interferences since some CQAs may produce bioactivity even at nanomolar levels. Biotransformation of CQAs by gut microbiota, the discovery of new enzymatic biosynthetic and metabolic pathways, dietary assessment, and assessment of biological properties with potential for drug development are areas of active, ongoing research. This review is focused on the chemistry, biosynthesis, occurrence, analytical challenges, and bioactivity recently reported for mono‐, di‐, tri‐, and tetraCQAs.

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Details

Published: Jul 23, 2021
Vol/Issue: 107(5)
Pages: 1299-1319
License: View

Authors

A

Armando Alcazar Magaña

Department of Chemistry Oregon State University Corvallis OR USA; Linus Pauling Institute Oregon State University Corvallis OR USA; BENFRA Botanical Dietary Supplements Research Center Oregon Health and Science University Portland OR USA

N

Naofumi Kamimura

Department of Bioengineering Nagaoka University of Technology Nagaoka, Niigata Japan

A

Amala Soumyanath

BENFRA Botanical Dietary Supplements Research Center Oregon Health and Science University Portland OR USA; Department of Neurology Oregon Health and Science University Portland OR USA

J

Jan F. Stevens

Linus Pauling Institute Oregon State University Corvallis OR USA; BENFRA Botanical Dietary Supplements Research Center Oregon Health and Science University Portland OR USA; Department of Pharmaceutical Sciences Oregon State University Corvallis OR USA

C

Claudia S. Maier

Department of Chemistry Oregon State University Corvallis OR USA; Linus Pauling Institute Oregon State University Corvallis OR USA; BENFRA Botanical Dietary Supplements Research Center Oregon Health and Science University Portland OR USA

Funding

National Institutes of Health Award: S10RR027878

National Center for Complementary and Integrative Health Award: U19AT010829

Cite This Article

Armando Alcazar Magaña, Naofumi Kamimura, Amala Soumyanath, et al. (2021). Caffeoylquinic acids: chemistry, biosynthesis, occurrence, analytical challenges, and bioactivity. The Plant Journal, 107(5), 1299-1319. https://doi.org/10.1111/tpj.15390

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

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