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.
Highlights
Quercetin, 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one, is one of the secondary metabolites of plants, representative of the flavonoid family [1]
In recent years regioselective syntheses emerged as very important chemical processes; various researchers have proposed enzymatic reactions as very selective and high yielding methods, often in the case of flavonoids glycosides [4]
Two studies [5,6] reported the enzymatic synthesis of cinnamate and oleate esters of quercetin, demonstrating how in particular reaction’s conditions it is possible to obtain a mixture of three main products, 40 -monoester, 30,40 -diester and 7,30,40 -triester
Summary
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one, is one of the secondary metabolites of plants, representative of the flavonoid family [1] It has several biological activities, including antioxidant, anti-proliferative, anti-diabetic, vasodilating, anti-inflammatory and others. Two studies [5,6] reported the enzymatic synthesis of cinnamate and oleate esters of quercetin, demonstrating how in particular reaction’s conditions it is possible to obtain a mixture of three main products, 40 -monoester, 30 ,40 -diester and 7,30 ,40 -triester. In this short paper, an ecofriendly, bio-catalytic process has been proposed to synthesize the C-3-oleate of quercetin in only one step. This study demonstrates the regioselectivity of PPL towards the C3-hydroxyl group
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