Metabolic, toxicological, chemical, and commercial perspectives on esterification of dietary polyphenols: a review

Abstract

Molecular modifications have been practiced for more than a century and nowadays they are widely applied in food, pharmaceutical, or other industries to manipulate the physicochemical, bioactivity, metabolic/catabolic, and pharmacokinetic properties. Among various structural modifications, the esterification/O-acylation has been well-established in altering lipophilicity and bioactivity of parent bioactive compounds, especially natural polyphenolics, while maintaining their high biocompatibility. Meanwhile, various classic chemical and enzymatic protocols and other recently emerged cell factory technology are being employed as viable esterification strategies. In this contribution, the main motivations of phenolic esterification, including the tendency to replace synthetic alkyl phenolics with safer alternatives in the food industry to improve the bioavailability of phenolics as dietary supplements/pharmaceuticals, are discussed. In addition, the toxicity, metabolism, and commercial application of synthetic and natural phenolics are briefly introduced. Under these contexts, the mechanisms and reaction features of several most prevalent chemical and enzymatic esterification pathways are demonstrated. In addition, insights into the studies of esterification modification of natural phenolic compounds and specific pros/cons of various reaction systems with regard to their practical application are provided.

Keywords:

• Chemoselectivity
• esterification/O-acylation
• lipidic phenolic esters
• phenolic modification
• synthetic phenolic antioxidants
• toxicology/metabolism/bioavailability

Disclosure statement

The authors declare no competing financial interest.

Additional information

Funding

We thank the Natural Science and Engineering Research Council (NSERC) of Canada and Mitacs – Canada, for financial support. Han Peng acknowledges the scholarship support from China Scholarship Council (CSC).