?-? Conjugation Enhances Oligostilbene's Antioxidant Capacity: Evidence from ?-Viniferin and Caraphenol A.

ABSTRACT: ?-Viniferin and caraphenol A, the two oligostilbenes, have the sole difference of the presence or absence of an exocyclic double bond at the ?-? conjugative site. In this study, the antioxidant capacity and relevant mechanisms for ?-viniferin and caraphenol A were comparatively explored using spectrophotometry, UV-visible spectral analysis, and electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-Q-TOF-MS/MS) analysis. The spectrophotometric results suggested that caraphenol A always gave lower IC50 values than ?-viniferin in cupric ion-reducing antioxidant capacity assay, ferric-reducing antioxidant power assay, 1,1-diphenyl-2-picryl-hydrazl radical (DPPH•)-scavenging, and 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide radical-scavenging assays. In UV-visible spectra analysis, caraphenol A was observed to show enhanced peaks at 250-350 nm when mixed with Fe2+, but ?-viniferin exhibited no similar effects. UPLC-ESI-Q-TOF-MS/MS analysis revealed that ?-viniferin mixed with DPPH• produced radical adduct formation (RAF) peak (m/z = 1070-1072). We conclude that the antioxidant action of ?-viniferin and caraphenol A may involve both redox-mediated mechanisms (especially electron transfer and H?-transfer) and non-redox-mediated mechanisms (including Fe2+-chelating or RAF). The ?-? conjugation of the exocyclic double bond in caraphenol A can greatly enhance the redox-mediated antioxidant mechanisms and partially promote the Fe2+-chelating mechanism. This makes caraphenol A far superior to ?-viniferin in total antioxidant levels.

SUBMITTER: Li X 

PROVIDER: S-EPMC6017043 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature