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Preparation of Retinoyl-Flavonolignan Hybrids and Their Antioxidant Properties

Christopher S. Chambers, David Biedermann, Kateřina Valentová, Lucie Petrásková, Jitka Viktorová, Marek Kuzma, Vladimír Křen
Published: 23 July 2019
 by  MDPI
Antioxidants , Volume 8; doi:10.3390/antiox8070236

Abstract: Antioxidants protect the structural and functional components in organisms against oxidative stress. Most antioxidants are of plant origin as the plants are permanently exposed to oxidative stress (UV radiation, photosynthetic reactions). Both carotenoids and flavonoids are prominent antioxidant and anti-radical agents often occurring together in the plant tissues and acting in lipophilic and hydrophilic milieu, respectively. They are complementary in their anti-radical activity. This study describes the synthesis of a series of hybrid ester conjugates of retinoic acid with various flavonolignans, such as silybin, 2,3-dehydrosilybin and isosilybin. Antioxidant/anti-radical activities and bio-physical properties of novel covalent carotenoid-flavonoid hybrids, as well as various mixtures of the respective parent components, were investigated. Retinoyl conjugates with silybin—which is the most important flavonolignan in silymarin complex—(and its pure diastereomers) displayed better 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity than both the parent compounds and their equimolar mixtures.
Keywords: antioxidant / carotenoids / retinol / Esterification / Vitamin A / retinoic acid / conjugate / silymarin / Flavonolignans / Anti-radical

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