4,4′-Dihydroxy-trans-stilbene, a resveratrol analogue, exhibited enhanced antioxidant activity and cytotoxicity

Hypohalous acid-mediated halogenation of resveratrol and its role in antioxidant and antimicrobial activities

“…However, the reaction products of resveratrol with hypohalous acids (HOCl and HOBr) and their biological activities, are yet to be determined. As part of our laboratory's continuous effort to find resveratrol-inspired antioxidants and cancer chemopreventive agents (Cao et al, 2012;Fan et al, 2009;Shang et al, 2009;Tang et al, 2011;Yang et al, 2010), we initiated the current study on the reaction of resveratrol with hypohalous acids under physiological conditions to mimic MPO-mediated fate of this molecule and to investigate antioxidant, antimicrobial and antiproliferative activities of the related products.…”

Resveratrol analogue 3,4,4′-trihydroxy-trans-stilbene induces apoptosis and autophagy in human non-small-cell lung cancer cells in vitro

“…For example, 3,4,5-trihydroxytrans-stilbene (3,4,5-THS) has been shown to exhibit a potent cytotoxic effect on human leukemia Jurkat cells by inducing extensive cell apoptosis at lower concentrations than resveratrol [13] . The anti-proliferative effects and cytotoxicity of 4,4′-dihydroxy-trans-stilbene (4,4'-DHS), which were attributed to the inhibition of DNA polymerase delta activity and DNA replication, have been shown to be more efficient than those of resveratrol [14,15] . Changing the 5-hydroxy group in resveratrol to 4-hydroxy (3,4,4'-trihydroxy-trans-stilbene, 3,4,4'-THS; Figure 1) dramatically increases the protective effects of the resveratrol analogues against free radical-induced lipid peroxidation, photo-sensitized DNA oxidative damage, and the free radical-induced hemolysis of human red blood cells [16] .…”

Hybrid‐Increased Radical‐Scavenging Activity of Resveratrol Derivatives by Incorporating a Chroman Moiety of Vitamin E

“…[4a, 6] Recently, we found that introduction of electron-donating substituents in the ortho-or para-position of the 4'-OH could significantly enhance its antioxidant activity, [7] prooxidant activity on DNA damage in the presence of Cu II ions, [8] and cytotoxicity on human promeolocytic leukemia cells. [9] The hybrid approach has recently attracted much attention in medicinal chemistry and design of hybrid molecules encompassing two pharmacophores in one molecular scaffold is a niche area in a large field of drug discovery. [10] In view of the fact that a-tocopherol (vitamin E) (Scheme 1) is known as a natural and chroman-based antioxidant of lipoproteins and biomembranes, [11] Koufaki and co-workers reported the synthesis of a trihydroxydihydrostilbene-chroman hybrid, which was proven to be a strong neuroprotectant against oxidative stress.…”