Chalcone Scaffolds, Bioprecursors of Flavonoids: Chemistry, Bioactivities, and Pharmacokinetics.

Atul Rupchand Bendale,Abdul Aziz Bin Dukhyil,Johra Khan,Mithun Rudrapal,Randa Mohammed Ibrahim Ismail Alarousy,Emmanuel Ifeanyi Attah,Shubham Jagdish Khairnar,Tripti Sharma

doi:10.3390/molecules26237177

Abstract

Chalcones are secondary metabolites belonging to the flavonoid (C6-C3-C6 system) family that are ubiquitous in edible and medicinal plants, and they are bioprecursors of plant flavonoids. Chalcones and their natural derivatives are important intermediates of the flavonoid biosynthetic pathway. Plants containing chalcones have been used in traditional medicines since antiquity. Chalcones are basically α,β-unsaturated ketones that exert great diversity in pharmacological activities such as antioxidant, anticancer, antimicrobial, antiviral, antitubercular, antiplasmodial, antileishmanial, immunosuppressive, anti-inflammatory, and so on. This review provides an insight into the chemistry, biosynthesis, and occurrence of chalcones from natural sources, particularly dietary and medicinal plants. Furthermore, the pharmacological, pharmacokinetics, and toxicological aspects of naturally occurring chalcone derivatives are also discussed herein. In view of having tremendous pharmacological potential, chalcone scaffolds/chalcone derivatives and bioflavonoids after subtle chemical modification could serve as a reliable platform for natural products-based drug discovery toward promising drug lead molecules/drug candidates.

Highlights

IntroductionChalcones (or 1,3-diaryl-2-propen-1-ones) are one of the major secondary metabolites of plants belonging to the flavonoid family
Chalcones are one of the major secondary metabolites of plants belonging to the flavonoid family
Representative examples of naturally occurring bioactive chalcones are cardamonin, a hydroxychalcone isolated from a Zingiberous plant species, which possesses antimutagenic, vasorelaxant, and anti-inflammatory properties, and xanthohumol, the principal prenylated flavonoid of the hop plant, which is characterized as a broad-spectrum cancer chemopreventing agent in vitro [3,4]

Summary

Introduction

Chalcones (or 1,3-diaryl-2-propen-1-ones) are one of the major secondary metabolites of plants belonging to the flavonoid family. These metabolites are abundantly present in edible plants. Chalconarngenin, phloretin, and its glucosidephloridzin (phloretin 2 -O-glucose) are some of the most common chalcones present in food [2] Chalcones and their structural analogues, either natural or synthetic, are known to exhibit diverse therapeutic and pharmacological activities such as antioxidant, antiinflammatory, antiplasmodial (antimalarial), antileishmanial, antitubercular, antimicrobial, antiviral, anticancer, modulation of P-glycoprotein (P-gp) mediated multi-drug resistance, and immunosupportive potential. Representative examples of naturally occurring bioactive chalcones are cardamonin, a hydroxychalcone isolated from a Zingiberous plant species, which possesses antimutagenic, vasorelaxant, and anti-inflammatory properties, and xanthohumol, the principal prenylated flavonoid of the hop plant, which is characterized as a broad-spectrum cancer chemopreventing agent in vitro [3,4]. All the relevant databases available in electronic search engines such as Web of Science, ScienceDirect, Pubmed, and Scopus were explored to collect relevant information for the terms such as chalcones, natural and dietary chalcones, chalcone derivatives, pharmacological activities, and the bioavailability or pharmacokinetics of naturally occurring chalcones

Chalcone

Chemical Structure

Nomenclature

Naturally Occurring Chalcones

Chalcones from Medicinal and Dietary Plants

Bioactivities of Naturally Occurring Chalcones

Conclusions and Future Directions