Modified approach for preparing (E)-stilbenes related to resveratrol, and evaluation of their potential immunobiological effects

Šmidrkal, Ján; Harmatha, Juraj; Budêšínský, Miloś; Vokáč, Karel; Zı́dek, Zdeňek; Kmoníčková, Eva; Merkl, Roman; Filip, V.

doi:10.1135/cccc2009531

Cited by 17 publications

(17 citation statements)

References 36 publications

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“…Resveratrol (RES) was prepared by targeted regioselective synthesis purely as transisomer [ 20 ] and was diluted in 1 : 50 (v/v) of 1 M NaOH in water.…”

Section: Methodsmentioning

confidence: 99%

On the Molecular Pharmacology of Resveratrol on Oxidative Burst Inhibition in Professional Phagocytes

Nosáľ

Drábiková

Jančinová

et al. 2014

Oxidative Medicine and Cellular Longevity

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Resveratrol—3,5,4′-trihydroxystilbene—possesses antioxidant activities in vitro. It dose-dependently inhibited the generation of peroxyl, hydroxyl, peroxides, and lipid peroxidation products in cell free systems. Oxidative burst of whole human blood stimulated with PMA, fMLP, OpZ, and A23187 was inhibited in a concentration-dependent way, indicating suppression of both receptor and nonreceptor activated chemiluminescence by resveratrol. Results from isolated human neutrophils revealed that resveratrol was active extracellularly as well as intracellularly in inhibiting the generation of reactive oxygen species. Liberation of ATP and analysis of apoptosis showed that in the concentration of 100 μM, resveratrol did not change the viability and integrity of isolated neutrophils. Western blot analysis documented that resveratrol in concentrations of 10 and 100 μM significantly decreased PMA-induced phosphorylation of PKC α/βII. Dose-dependent inhibition of nitrite production and iNOS protein expression in RAW 264.7 cells indicated possible interference of resveratrol with reactive nitrogen radical generation in professional phagocytes. The results suggest that resveratrol represents an effective naturally occurring substance with potent pharmacological effect on oxidative burst of human neutrophils and nitric oxide production by macrophages. It should be further investigated for its pharmacological activity against oxidative stress in ischaemia reperfusion, inflammation, and other pathological conditions, particularly neoplasia.

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“…Resveratrol (RES) was prepared by targeted regioselective synthesis purely as transisomer [ 20 ] and was diluted in 1 : 50 (v/v) of 1 M NaOH in water.…”

Section: Methodsmentioning

confidence: 99%

On the Molecular Pharmacology of Resveratrol on Oxidative Burst Inhibition in Professional Phagocytes

Nosáľ

Drábiková

Jančinová

et al. 2014

Oxidative Medicine and Cellular Longevity

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“…Pterostilbene (precisely specified as trans -pterostilbene in this paper) was synthesised at the Institute of Chemical Technology, Prague, Czech Republic, and structurally characterised as (E)-4′-hydroxy-3,5-dimethoxystilbene in the Institute of Organic Chemistry and Biochemistry, Prague, Czech Republic [22]. TLC, RP-HPLC, and 1 H-NMR spectroscopy were used for standardisation before and during the experiments.…”

Section: Methodsmentioning

confidence: 99%

The Effects of Pterostilbene on Neutrophil Activity in Experimental Model of Arthritis

Perečko

Drábiková

Lojek

et al. 2013

BioMed Research International

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It has been demonstrated that pterostilbene inhibits reactive oxygen species production in neutrophils in vitro. However, little is known about its effects on neutrophils during inflammation in vivo. In this study, the effect of pterostilbene on neutrophil activity was investigated in experimental arthritis model. Lewis rats were injected by a single intradermal injection of heat-killed Mycobacterium butyricum in Freund's adjuvant to develop arthritis. Another group of arthritic animals received pterostilbene 30 mg/kg, daily, p.o. The number and activity of neutrophils in blood were measured on a weekly basis during the whole experiment. Moreover, the total radical trapping potential in plasma was measured at the end of the experiment. In the pterostilbene treated arthritic group, the treatment significantly lowered the number of neutrophils in blood on days 14 and 21 without significant downregulation of neutrophil oxidative burst. Pterostilbene nonsignificantly increased total radical trapping potential in arthritic animals. These results indicate that the promising effects of pterostilbene on reactive oxygen species operate by different mechanisms in vitro and in the animal model of inflammation. In conclusion, the positive effects of pterostilbene in the model of arthritis may be attributed to regulation of neutrophil number.

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“…These compounds were prepared by chemical synthesis using an original approach (Šmidrkal et al ., 2010). Their structural differences are obvious, varying only by different type and position of substituents in compounds 1–8 , or by additional internal bonding, as in lactones 9, 10 .…”

Section: Stilbenoids With Immunoactive Propertiesmentioning

confidence: 99%

Immunobiological properties of selected natural and chemically modified phenylpropanoids

Harmatha¹,

Zı́dek²,

Kmoníčková³

et al. 2011

Interdisciplinary Toxicology

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Effects of natural and structurally transformed lignans compared with stilbenes or stilbenoids on production of nitric oxide (NO) triggered by lipopolysaccharide (LPS) and interferon-γ (IFN-γ), tested under in vitro conditions using murine resident peritoneal macrophages, are reviewed. Relation between the molecular structure and immunobiological activity was investigated, and implication of substituents, double bond stereochemistry, or cyclic attachments (double bond geometry fixation) was assessed. The focus was on lignans and stilbenoids because they were originally selected for a joint project of common interest to phytochemical and pharmacological investigation and because they represent well interesting and universally attractive groups of polyphenols with a feasible potential for therapeutic or nutraceutic utilization.

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Modified approach for preparing (E)-stilbenes related to resveratrol, and evaluation of their potential immunobiological effects

Cited by 17 publications

References 36 publications

On the Molecular Pharmacology of Resveratrol on Oxidative Burst Inhibition in Professional Phagocytes

On the Molecular Pharmacology of Resveratrol on Oxidative Burst Inhibition in Professional Phagocytes

The Effects of Pterostilbene on Neutrophil Activity in Experimental Model of Arthritis

Immunobiological properties of selected natural and chemically modified phenylpropanoids

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