Finding more active antioxidants and cancer chemoprevention agents by elongating the conjugated links of resveratrol

Tang, Jiang‐Jiang; Fan, Guijuan; Dai, Fang; Ding, Dejun; Wang, Qi; Lu, Dongliang; Li, Ranran; Li, Xiu-Zhuang; Hu, Limei; Jin, Xiaoling; Zhou, Bo

doi:10.1016/j.freeradbiomed.2011.02.028

Cited by 46 publications

(29 citation statements)

References 80 publications

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“…In the second position, 3‐GR (with the retained 4′‐OH) exhibited a electron‐donating capability comparable to that of RES ( n =1.06 and 1.45, respectively), thus highlighting the importance of 4′‐OH in the electron‐donating capability of RES. This result also supports the previous conclusion that 4′‐OH is more active than 3‐OH and 5‐OH in the antioxidant reaction of RES 5e,g. 13 In contrast, impairment of the conjugated links, such as hydrogenation of the aliphatic double bond, could significantly decrease its electron‐donating ability, as exemplified by DHR and RES ( n =0.55 and 1.45, respectively).…”

Section: Resultssupporting

confidence: 88%

Influence of Glucuronidation and Reduction Modifications of Resveratrol on its Biological Activities

Ding

Yan

et al. 2013

ChemBioChem

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Resveratrol (3,5,4'-trihydroxystilbene, RES), a star among dietary polyphenols, shows a wide range of biological activities, but it is rapidly and extensively metabolized into its glucuronide and sulfate conjugates as well as to the corresponding reduced products. This begs the question of whether the metabolites of RES contribute to its in vivo biological activity. To explore this possibility, we synthesized its glucuronidation (3-GR and 4'-GR) and reduction (DHR) metabolites, and evaluated the effect of these structure modifications on biological activities, including binding ability with human serum albumin (HSA), antioxidant activity in homogeneous solutions and heterogeneous media, anti-inflammatory activity, and cytotoxicity against various cancer cell lines. We found that 1) 4'-GR, DHR and RES show nearly equal binding to HSA, mainly through hydrogen bonding, whereas 3-GR adopts a quite different orientation mode upon binding, thereby resulting in reduced ability; 2) 3-GR shows comparable (even equal) ability to RES in FRAP- and AAPH-induced DNA strand breakage assays; DHR, 3-GR, and 4'-GR exhibit anti-hemolysis activity comparable to that of RES; additionally, 3-GR and DHR retain some degree activity of the parent molecule in DPPH.-scavenging and cupric ion-initiated oxidation of LDL assays, respectively; 3) compared to RES, 4'-GR displays equipotent ability in the inhibition of COX-2, and DHR presents comparable activity in inhibiting NO production and growth of SMMC-7721 cells. Relative to RES, its glucuronidation and reduction metabolites showed equal, comparable, or some degree of activity in the above assays, depending on the specific compound and test model, which probably supports their roles in contributing to the in vivo biological activities of the parent molecule.

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Section: Resultssupporting

confidence: 88%

Influence of Glucuronidation and Reduction Modifications of Resveratrol on its Biological Activities

Ding

Yan

et al. 2013

ChemBioChem

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“…The structural simplicity of this molecule has prompted interest in designing novel analogues with improved antioxidant potency (Amorati et al, 2004;Fukuhara et al, 2008;Murias et al, 2005). In this connection, we have also demonstrated that the introduction of electron-donating groups at positions ortho and para to the 4-OH or 4 0 -OH group in the stilbene scaffold (Fang & Zhou, 2008;Shang et al, 2009), construction of the hydroxylated stilbene-chroman hybrids (Yang et al, 2010), the insertion of additional double bonds between two aromatic rings (Tang et al, 2011) and the substitution of 4-SH for 4-OH in the stilbene scaffold (Cao et al, 2012) could effectively improve antioxidant activity of this parent molecule.…”

Section: Introductionmentioning

confidence: 88%

“…FRAP assay (Benzie & Strain, 1996) was used to evaluate the reducing capacity of hydroxylated phenanthrenes and the related procedure was described in our previous work (Tang et al, 2011).…”

Section: Assay For Ferric Reducing/antioxidant Power (Frap)mentioning

confidence: 99%

Synthesis and antioxidant activity of hydroxylated phenanthrenes as cis-restricted resveratrol analogues

et al. 2012

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“…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.…”

Section: Introductionmentioning

confidence: 99%

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

Wei

Zhang

et al. 2012

Food Chemistry

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Finding more active antioxidants and cancer chemoprevention agents by elongating the conjugated links of resveratrol

Cited by 46 publications

References 80 publications

Influence of Glucuronidation and Reduction Modifications of Resveratrol on its Biological Activities

Influence of Glucuronidation and Reduction Modifications of Resveratrol on its Biological Activities

Synthesis and antioxidant activity of hydroxylated phenanthrenes as cis-restricted resveratrol analogues

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

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