Hesperitin Esters: Highly Stable Flavanones with Both Free Radical Scavenging and Anti-Elastase Activities

Abstract

In targeting molecules, destinated for treatment of skin ageing, we synthesized esters of hesperitin (4'-methoxy-5,7,3'-trihydroxyflavanone). Esterification with lauric acid was used with the aim to overcome the flavonoid instability and to improve the therapeutic usefulness. Stability, free radical scavenging activity and anti-elastase potency of the prepared compounds were studied and compared to those of hesperitin (natural compound). Compounds obtained are more stable than hesperitin and display similar or higher antielastolytic and free radical scavenging activities.

Elucidation of the Kinetic Behavior of Quercetin, Isoquercitrin, and Rutin Solubility by Physicochemical and Thermodynamic Investigations

“…Flavonoids are powerful antioxidants and have been reported to possess a wide range of biological effects: free radical scavenging, inhibition of cellular proliferation, antibiotic, antiallergic, antiulcer, or anti-inflammatory activities . For these properties, plant-extracted flavonoids are increasingly used as nutritional, cosmetic, and pharmaceutical active ingredients. − However, the solubility of flavonoids in different media (water, organic solvent, hydrophobic media) is a complex and important process. It is a key factor in extraction, formulation, and biocatalysis processes of flavonoids.…”

Solubility of Flavonoids in Organic Solvents

“…[1][2][3][4][5][6][7] Many of these compounds are already used in pharmaceutical, cosmetic, and food preparations. 4,[8][9][10][11][12][13] However, their solubility is very low in water, 8,10,[14][15][16] being about (0.12, 0.5, < 0.01, and 0.4) g‚L -1 at 20 °C for rutin, naringin, quercetin, and neohesperidine dihydrochalcone, respectively. [17][18][19] The solubility also depends on the pH.…”

“…Flavonoids are frequently present in nature and easily extracted from many different plants. Their protective effect against lipid peroxidation of membranes, involved in several physiological and pathological disorders, such as inflammation, atherosclerosis, ischemia, toxicity of oxygen, and chemical substances, has been largely studied. − Many of these compounds are already used in pharmaceutical, cosmetic, and food preparations. ,− However, their solubility is very low in water, ,,− being about (0.12, 0.5, < 0.01, and 0.4) g·L -1 at 20 °C for rutin, naringin, quercetin, and neohesperidine dihydrochalcone, respectively. − The solubility also depends on the pH . At pH 1.5, the solubilities of hesperetin and naringenin are (0.06·10 -3 and 0.025·10 -3 ) g·L -1 , respectively, whereas at pH 8, they increase 4-fold.…”

Ziziphorins A and B. New Flavonoids from Ziziphora tenuior

“…The signals of rings A and C were similar to those of 1, the only notable difference being observed for ring B. Flavonoids carrying long-chain acyl groups are not commonly reported in literature. Previously such compounds have also been synthesized from hesperitin and shown to posses free radical scavenging, anti-elastase and hypocholesterolemic activities [8,9]. Pharmacological screening of the isolated compounds could not be carried out due to paucity of material.…”