Multimodal Carbon Monoxide Photorelease from Flavonoids
Andrea Ramundo, Martina Hurtová, Igor Božek, Zuzana Osifová, Marina Russo, Bokolombe P. Ngoy, Vladimı́r Křen, Petr Klán
Abstract
High Resolution Image Download MS PowerPoint Slide Photooxygenation of flavonoids leads to the release of carbon monoxide (CO). Our structure–photoreactivity study, employing several structurally different flavonoids, including their 13 C-labeled analogs, revealed that CO can be produced via two completely orthogonal pathways, depending on their hydroxy group substitution pattern and the reaction conditions. While photooxygenation of the enol 3-OH group has previously been established as the CO liberation channel, we show that the catechol-type hydroxy groups of ring B can predominantly participate in photodecarbonylation.
Topics & Concepts
ChemistryPhotooxygenationCarbon monoxideCatecholEnolPigmentPhotochemistryStereochemistryOrganic chemistrySinglet oxygenCatalysisOxygenHeme Oxygenase-1 and Carbon MonoxideCannabis and Cannabinoid ResearchNeonatal Health and Biochemistry