Dihydrochalcones: Methods of Acquisition and Pharmacological Properties—A First Systematic Review

Abstract

Dihydrochalcones are a class of secondary metabolites, for which demand in biological and pharmacological applications is still growing. They posses several health-endorsing properties and, therefore, are promising candidates for further research and development. However, low content of dihydrochalcones in plants along with their low solubility and bioavailability restrict the development of these compounds as clinical therapeutics. Therefore, chemomicrobial and enzymatic modifications are required to expand their application. This review aims at analyzing and summarizing the methods of obtaining dihydrochalcones and of presenting their pharmacological actions that have been described in the literature to support potential future development of this group of compounds as novel therapeutic drugs. We have also performed an evaluation of the available literature on beneficial effects of dihydrochalcones with potent antioxidant activity and multifactorial pharmacological effects, including antidiabetic, antitumor, lipometabolism regulating, antioxidant, anti-inflammatory, antibacterial, antiviral, and immunomodulatory ones. In addition, we provide useful information on their properties, sources, and usefulness in medicinal chemistry.

Transfer Hydrogenation of Flavanones and ortho‐Hydroxychalcones to 1,3‐Diarylpropanols Catalyzed by CNN Pincer Ruthenium Complexes

“…[3] Flavanones can be reduced at the C=O group affording flavan-4-ols (Scheme 1, left), whereas ortho-hydroxychalcones are hydrogenated to dihydrochalcones, 1,3-diarylpropanols and 1,3-diarylpropanes (Scheme 1, right), which are compounds of high biological relevance. [4] While the syntheses of flavan-4ols, [5] dihydrochalcones [6] and 1,3-diarylpropanes [7][8][9] have been widely described in the literature, the preparation of orthohydroxy 1,3-diarylpropanols has not been properly covered yet. Interestingly, compounds containing this motif have shown to display inhibitory properties in the transcription factor NF-kB, [10] anti-cholinesterase, [11] anti-inflammatory activity [12] and P-glycoprotein-inhibitory effects (GP-88) [13] (Figure 1).…”

From Preclinical Stroke Models to Humans: Polyphenols in the Prevention and Treatment of Stroke

“…A few dihydrochalcones, a family of bicyclic flavonoids, have shown antioxidant properties [ 213 ]. In particular, phloretin, a dihydrochalcone abundant in apples and apple-derived products, displayed a neuroprotective effect by activating the Nrf2 pathway in rats subjected to tMCAO [ 214 ].…”

Antiviral properties of chalcones and their synthetic derivatives: a mini review

“…The anti-herpes effect showed was mostly moderate or low, except for three of the compounds which express high antiviral activity due to the presence of electron-donating groups in the p-position of the phenyl group (CH 3 , OCH 3 , and NMe 2 ). Dihydrochalcones (obtained by double bond reduction of chalcone) especially Trilobatin (effective in inhibiting HSV-2 at the concetration of 458 µM) derived from Millettia leucantha (Leguminosae) were shown also to possess anti-herpes simplex effect (Stompor et al 2019).…”