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Panduratin A is a prenylated flavonoid derivative from Boesenbergia pandurata with many potential biological activities. The biogenesis of this compound and its derivatives is believed to involve a Diels-Alder reaction between monoterpenoid and chalcone derivatives. This study provides insight into modeling biogenesis through the Diels-Alder reaction for Panduratin A and derivatives biosynthesis. We are using M06-2X/6-31G(d)//PM6 level of theory to explore the potential energy surfaces, asynchronicity degree, and global electron density transfer. Explicit water was applied to mimic physiological conditions. Contrary to the fact that water accelerates this reaction through hydrogen bonding catalysis, we found that water could slow this reaction. These results suggest that this reaction proceeds very slowly under physiological conditions, and enzymes catalyze this reaction. [ABSTRACT FROM AUTHOR]

Bergenin is a polyphenolic compound that contains isocoumarin skeletal derived from C -glycosylated 4- O -methylgallic acid. The biological activities of this compound and its derivatives are quite diverse. Recent studies reveal neuroprotective effects in vitro and in vivo in Alzheimer's. Norbergenin is a demethylated form of bergenin, known for better antioxidant capacity and associated with neuroprotective properties through oxidative stress inhibition. This study focused on investigating the scavenging mechanism of norbergenin with the • OH, • OOH, and O 2 ∙ - as a radical model under physiological and lipid environments. The thermodynamic and kinetic parameters of the hydrogen transfer (HT), single electron transfer (SET), sequential proton lost-electron transfer (SPLET) and radical adduct formation (RAF) mechanisms were determined theoretically by the density functional theory (DFT) at M06-2X/6-311 + + G(d,p) level of theory. Based on the computational results, this compound has proved as an excellent • OOH and • OH scavenger under physiological conditions better than Trolox and vitamin C, whereas its radical demonstrated as an efficient O 2 ∙ - scavenger., (© 2022 The Authors.)