Quercetin-3-oleate

Abstract

Polyphenols are well-known health promoting agents, but they have some limitations due to their spontaneous oxidation. This evidence has limited their use as drugs in recent years. In this field, several chemical modifications have been proposed to overcome these restrictions; among these, esterification seems to be the preferred modification. Ester derivatives may be able to reduce the bioavailability problems connected to polyphenols. On the other hand, the presence of esterase enzymes in the body guarantees ester hydrolysis, which in turn frees the two molecules that make it up. Lipase-catalyzed esterifications gave birth to several derivatives of flavonoids glycosides, in green conditions. In this short paper, pancreatic porcine lipase was firstly used as a cheap bio-catalyst, to synthesize oleoyl derivatives of quercetin in aglycone form. The results demonstrated how the enzyme is able to promote a regioselective acylation on C-3 position, with high yields and easy purification processes.

Synthesis and characterization of a (+)-catechin and L-(+)-ascorbic acid cocrystal as a new functional ingredient for tea drinks

“…A typical feature of polyphenols, including flavonoids and flavan-3-ols is their poor bioavailability, requiring plasma concentrations prohibitively high to elicit their favourable health effects (Lambert et al., 2006). Over the years various strategies have been explored to overcome these limitations, including chemical modifications (Badolato et al., 2017; Tundis et al., 2019; Carullo et al., 2019a; Carullo and Aiello, 2018), polymerization processes (Restuccia et al., 2019; Carullo et al., 2019b) or cocrystallization. In particular, the latter has been proved to influence the solid state properties of a drug substance, in particular its solubility and hence bioavailability (Schultheiss and Newman, 2009; Aitipamula et al., 2012; Karimi-Jafari et al., 2018).…”

New Lipophenol Antioxidants Reduce Oxidative Damage in Retina Pigment Epithelial Cells

“…We validated for the first time the methodology using PUFA (LA, ALA and DHA). Only recently, Carullo et al [49] described another enzymatic pathway to access quercetin-3-oleate derivative in a single step from quercetin and oleic acid (C18: 1, ω-9) by using pancreatic porcine lipase. This methodology is a promising work and may be adapted in future to our derivatives using polyunsaturated fatty acids such as DHA.…”

Nanotechnologies: An Innovative Tool to Release Natural Extracts with Antimicrobial Properties

“…MCM-41 nanocarrier was fabricated by the co-condensation method using n-cetyl-n,n,n-trimethyl ammonium bromide as a template. In this view, different amounts of red propolis were embedded in silica mesoporous nanoparticles and tested against S. aureus at concentrations of 1050, 750, 500, 375, 225, and 150 µg/mL, finding an inhibition zone of approximately 19,20,21,17,16, and 17 mm in diameter, respectively. Poly(D,L-lactide-co-glycolide)/ poly(vinyl alcohol)…”

“…The search for new therapeutically active compounds has spurred researchers over the years to investigate natural compounds [ 12 , 13 , 14 , 15 , 16 , 17 ]. In particular, food and plant wastes represent interesting sources of biologically active molecules [ 18 , 19 , 20 , 21 , 22 , 23 , 24 ] and have been proposed as indigenous remedies [ 25 , 26 ].…”