Radical coupling reactions of piceatannol and monolignols: A density functional theory studyAuthor(s): Thomas Elder; José Carlos del Río; John Ralph; Jorge Rencoret; Hoon Kim; Gregg T. Beckham
Publication Series: Scientific Journal (JRNL)
Station: Southern Research Station
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DescriptionRecent experimental work has revealed that the hydroxystilbene piceatannol can function as a monomeric unit in the lignification of palm fruit endocarp tissues. Results indicated that piceatannol homo-couples and crosscouples with monolignols through radical reactions and is integrally incorporated into the lignin polymer. The current work reports on the thermodynamics of the proposed reactions using density functional theory calculations. The results indicated that, in general, the energetics of both homo-coupling and cross-coupling are not dissimilar from those of the monolignol coupling, demonstrating the compatibility of piceatannol with the lignification process. Moreover, the DFT methods appear to predict the correct courses of post-coupling rearomatization reactions.
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CitationElder, Thomas; Carlos del Río, José; Ralph, John; Rencoret, Jorge; Kim, Hoon; Beckham, Gregg T. 2019. Radical coupling reactions of piceatannol and monolignols: A density functional theory study. Phytochemistry. 164: 12-23. https://doi.org/10.1016/j.phytochem.2019.04.003.
KeywordsStilbene, Piceatannol, Coniferyl alcohol, Sinapyl alcohol, p-coumaryl alcohol, Quinone methide, Density functional theory (DFT)
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