A theoretical antioxidant pharmacophore for resveratrol

Queiroz, Auriekson N.; Gomes, Bruno Alexandre Quadros; Moraes, Waldir M.; Borges, Rosivaldo S.

doi:10.1016/j.ejmech.2008.09.023

Cited by 167 publications

(121 citation statements)

References 22 publications

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“…e previous article focused on the study of the transformation of transresveratrol into the cis under UV irradiation [34]. e reason of this change was that resveratrol was an unstable polyphenol which was easily damaged by UV irradiation [19,35]. In addition, comparable results were obtained when resveratrol formed inclusion complex with CM-β-CD.…”

Section: Photostability Studymentioning

confidence: 51%

Resveratrol Functionalized Carboxymethyl-β-Cyclodextrin: Synthesis, Characterization, and Photostability

Cheng

Tian

Huang

et al. 2018

Journal of Chemistry

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e resveratrol functionalized carboxymethyl-β-cyclodextrin conjugate was synthesized by two simple steps. e conjugate was successfully demonstrated by 1 H NMR, 13 C NMR, UV, and FTIR. e photostability of the conjugate was studied by ultraviolet absorption spectrum. After 360 min of UV light irradiation, the conjugate showed a total loss in absorbance of only 12.54%, while the resveratrol and its CM-β-CD inclusion complex showed a total loss in absorbance of 32.15% and 24.05%, respectively. e results indicate that the conjugate was more stable than resveratrol and its CM-β-CD inclusion complex.

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Section: Photostability Studymentioning

confidence: 51%

Resveratrol Functionalized Carboxymethyl-β-Cyclodextrin: Synthesis, Characterization, and Photostability

Cheng

Tian

Huang

et al. 2018

Journal of Chemistry

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“…This is despite the fact that there is no consensus as to its modes of action (Bhullar & Hubbard, 2015; Bitterman & Chung, 2015). In particular, RSV might act as an antioxidant, but other redox effects have also been documented (e.g., Miura et al ., 2000; Stivala et al ., 2001; Galati et al ., 2002; Ahmad et al ., 2003, 2005; Zheng et al ., 2006; de la Lastra & Villegas, 2007; Gadacha et al ., 2009; Queiroz et al ., 2009; Gueguen et al ., 2015). In addition, numerous distinct specific targets have been identified and characterized (reviewed in Bhullar & Hubbard, 2015; Bitterman & Chung, 2015).…”

Section: Introductionmentioning

confidence: 99%

Antioxidants reveal an inverted U‐shaped dose‐response relationship between reactive oxygen species levels and the rate of aging in Caenorhabditis elegans

et al. 2016

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SummaryReactive oxygen species (ROS) are potentially toxic, but they are also signaling molecules that modulate aging. Recent observations that ROS can promote longevity have to be reconciled with the numerous claims about the benefits of antioxidants on lifespan. Here, three antioxidants [N‐acetylcysteine (NAC), vitamin C, and resveratrol (RSV)] were tested on Caenorhabditis elegans mutants that alter drug uptake, mitochondrial function, and ROS metabolism. We observed that like pro‐oxidants, antioxidants can both lengthen and shorten lifespan, dependent on concentration, genotypes, and conditions. The effects of antioxidants thus reveal an inverted U‐shaped dose–response relationship between ROS levels and lifespan. In addition, we observed that RSV can act additively to both NAC and paraquat, to dramatically increase lifespan. This suggests that the effect of compounds that modulate ROS levels can be additive when their loci of action or mechanisms of action are sufficiently distinct.

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“…Similarly, the antioxidative activity of pinosylvin may be involved to a lesser extent, because both pinosylvin hydroxyl groups are located in the meta position (with respect to the ethylene bridge of the stilbene molecule), ie, in an arrangement that is less favorable for both electron abstraction and the distribution of the unpaired electron [18,33] . The assessment of lipid peroxyl radical formation [34] and the measurement of human low-density lipoprotein peroxidation [35] confirmed pinosylvin to be a less potent scavenger than resveratrol.…”

Section: Discussionmentioning

confidence: 99%

The natural stilbenoid pinosylvin and activated neutrophils: effects on oxidative burst, protein kinase C, apoptosis and efficiency in adjuvant arthritis

et al. 2012

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Aim: To investigate the effects of the naturally occurring stilbenoid pinosylvin on neutrophil activity in vitro and in experimental arthritis, and to examine whether protein kinase C (PKC) activation served as an assumed target of pinosylvin action. Methods: Fresh human blood neutrophils were isolated. The oxidative burst of neutrophils was evaluated on the basis of enhanced chemiluminescence. Neutrophil viability was evaluated with flow cytometry, and PKC phosphorylation was assessed by Western blotting analysis. Adjuvant arthritis was induced in Lewis rats with heat-killed Mycobacterium butyricum, and the animals were administered with pinosylvin (30 mg/kg, po) daily for 21 d after arthritis induction. Results: In isolated human neutrophils, pinosylvin (10 and 100 µmol/L) significantly decreased the formation of oxidants, both extraand intracellularly, and effectively inhibited PKC activation stimulated by phorbol myristate acetate (0.05 µmol/L). The inhibition was not due to neutrophil damage or increased apoptosis. In arthritic rats, the number of neutrophils in blood was dramatically increased, and whole blood chemiluminescence (spontaneous and PMA-stimulated) was markedly enhanced. Pinosylvin administration decreased the number of neutrophils (from 69 671±5588/µL to 51 293±3947/µL, P=0.0198) and significantly reduced the amount of reactive oxygen species in blood. Conclusion: Pinosylvin is an effective inhibitor of neutrophil activity, and is potentially useful as a complementary medicine in states associated with persistent inflammation.

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A theoretical antioxidant pharmacophore for resveratrol

Cited by 167 publications

References 22 publications

Resveratrol Functionalized Carboxymethyl-β-Cyclodextrin: Synthesis, Characterization, and Photostability

Resveratrol Functionalized Carboxymethyl-β-Cyclodextrin: Synthesis, Characterization, and Photostability

Antioxidants reveal an inverted U‐shaped dose‐response relationship between reactive oxygen species levels and the rate of aging in Caenorhabditis elegans

The natural stilbenoid pinosylvin and activated neutrophils: effects on oxidative burst, protein kinase C, apoptosis and efficiency in adjuvant arthritis

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