Resveratrol oligomer structure in Dipterocarpaceaeous plants

Abstract

Oligostilbenoids are a group of natural products derived from the oxidative coupling of C6–C2–C6 units found in some plant families. A structurally diverse chemical pool is produced after the successive regioselective and stereoselective oligomerization of resveratrol. This review describes the current status and knowledge of the structure of resveratrol oligomers (ROs) in Dipterocarpaceaeous plants (DPs). Beginning with the recently validated formation of ROs in DPs, each downstream conversion is described from the perspective of the resveratrol coupling mode. Particular emphasis is placed upon the regioselectivity of monomer- and dimer-derived radical–radical coupling processes, which are responsible for producing dimers, trimers, and tetramers with various cyclic frame skeletons, as well as related processes that result in highly condensed scaffolds, such as hexamers and octamers. Trimers in oxidized, dearomatized, and rearranged forms are also summarized, as well as the biogenic relationship between the compounds. Furthermore, emphasis is placed on the O- and C-glucosides of ROs, as well as on the hetero-coupled ROs. In addition, several stereoisomers that originate from asymmetric carbons and the stereochemistry with respect to the conformation due to the chiral axis are described. Besides, NMR spectroscopic properties such as coalescence and anisotropy are briefly described. Approaches to determine absolute configuration are also summarized.

Resveratrol: A potential therapeutic natural polyphenol for neurodegenerative diseases associated with mitochondrial dysfunction

“…Different biological activities are exhibited by plant families such as Cyperaceae, Vitaceae, Dipterocarpaceae and Gnetaceae, which contain RES oligomers (Ito, 2020).…”

Phytochemical and pharmacological profile of genus shorea: A review of the recent literature

“…Stilbenes are unique class of biologically active natural products produce primarily by plants [ 63 , 98 ]. A 14-carbon skeleton of two phenyl rings joined by an ethylene bridge forms the stilbene nucleus.…”

Antiviral Role of Phenolic Compounds against Dengue Virus: A Review

“…Resveratrol can be found in two stereoisomeric forms, trans- or cis-3 ,5,4′-trihydroxystilbene, but the trans -isomer changes into the cis -isomer in the presence of ultraviolet light. These differences could impact the different biological properties [ 103 , 104 , 105 ].…”