Two Novel Antioxidative Stilbene Tetramers from Parthenocissus laetevirens

Abstract

Laetevirenols F (1) and G (2), two novel stilbene tetramers with an unprecedented skeleton, were isolated from Parthenocissus laetevirens. Their structures were elucidated by spectroscopic analysis, including 1D-and 2D-NMR experiments, and their possible biogenetic pathway was discussed. In addition, both compounds were determined to be potent singlet-oxygen quenchers by electron paramagnetic resonance (EPR) experiments, which highlights their potential pharmacological applications in singlet oxygen mediated diseases.

Resveratrol and Its Oligomers from Wine Grapes Are Selective 1O2 Quenchers: Mechanistic Implication by High-Performance Liquid Chromatography−Electrospray Ionization−Tandem Mass Spectrometry and Theoretical Calculation

“…In essence, the performance of oligomers' multiple activities could be traced back to their inhibitory effects on ROS involving 1 O 2 . In our previous work (17), pallidol (Figure 1), a resveratrol dimer reported to be present at levels (0.5-4.8 mg L -1 ) equivalent to those of resveratrol in 19 French red wines (9), has been isolated and exhibited a selective quenching effect on 1 O 2 , whereas no potent scavenging activities on hydroxyl radical resveratrol tetramers (18) and one hexamer (19). All of these observations prompted us to further investigate the quenching mechanism of resveratrol and its oligomers on 1 O 2 .…”

Natural stilbenoids: distribution in the plant kingdom and chemotaxonomic interest in Vitaceae

“…Whereas the parthenocissin A-type trimers (38-42) 234,249 and tetramers (64-67), 246,250 are only found in Parthenocissus or Cayratia species. Outside of a-viniferin (37) 11,251 and gnetin E (34), 66,238 the remaining known trimers are only found in Vitis and Ampelopsis species (see ESI † Tables S2-S12).…”

Stilbene profiles in different tissues ofVitis viniferaL. cv. Cabernet Sauvignon and a comparison of their antioxidant activity

“…Stilbenes include trans ‐resveratrol, piceid (a 3‐O‐β‐ d ‐glucoside of resveratrol), pterostilbene (a dimethylated resveratrol derivative), ε‐viniferin (a resveratrol dipolymer) and vitisin B (a resveratrol tetramer). Two novel stilbene tetramers were previously extracted and analysed for antioxidant capacity (He et al ). The direct generation of hydroxyl radicals (·OH) and 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) as well as other models are used to evaluate the scavenging capacity of various free radicals.…”