Antioxidant Activity of Synthetic Resveratrol Analogs: A Structure- Activity Insight

Calil, Natalia Oliveira; Carvalho, Gustavo Senra Gonçalves de; Silva, Annelisa Farah da; Silva, Adilson David da; Raposo, Nádia Rezende Barbosa

doi:10.2174/157018012801319508

Cited by 9 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Resveratrol analogs may be important compounds to provide skin whitening and some analogs tested ( A , D and E ) showed lower IC 50 values than resveratrol, the natural compound. Some of these aza-stilbenes were evaluated in recent studies for their antioxidant [21,32] and antituberculous effects [30] and together with the present results, indicate that these molecules may have pharmacological utility in a near future. Studies of the ratio between the in vitro behavior of the new analogs and their in vivo activity may contribute to the development of more effective skin whitening treatments.…”

Section: Discussionsupporting

confidence: 71%

“…Utilizing the classical method of imine formation, the six azaresveratrol derivates A – F were synthesized through condensation between aniline with a variety of aromatic aldehydes in ethanol [31,32] (Scheme 1). All compounds were characterized by 1 H- and 13 C-NMR, recorded on a BRUKER AVANCE DRX300, infrared (IR, BOMEM-FTIR MB-102) and melting point values (Table 2) which were in accord with literature data [21,40,41,42,43,44,45].…”

Section: Methodsmentioning

confidence: 99%

“…Such compounds have shown good antitubercular and antioxidant activity [21,31,32], which encouraged us to test the potential of this class of compounds in other areas, such as depigmenting action. Thus, this paper presents a study of the in vitro inhibitory activity of six aza-stilbenes or azaresveratrols analogs on tyrosinase activity.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Inhibitory Effects of Resveratrol Analogs on Mushroom Tyrosinase Activity

et al. 2012

View full text Add to dashboard Cite

Skin pigmentation disorders typically involve an overproduction or uneven distribution of melanin, which results in skin spots. Resveratrol can inhibit tyrosinase, the active enzyme in the synthesis of melanin, but it does not inhibit the synthesis of melanin to an extent that enables its use alone as a skin whitening agent in pharmaceutical formulations, so its use as a coadjuvant in treatment of hyperpigmentation is suggested. Six resveratrol analogs were tested for tyrosinase inhibitory activity in vitro. Among the analogs tested, compound D was the most powerful tyrosinase inhibitor (IC50 = 28.66 µg/mL), two times more active than resveratrol (IC50 = 57.05 µg/mL), followed by the analogs A, E, B, F and C, respectively. This demonstrated that the hydroxylation at C4' on the phenolic ring was the molecular modification with most importance for the observed activity.

show abstract

Section: Discussionsupporting

confidence: 71%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Inhibitory Effects of Resveratrol Analogs on Mushroom Tyrosinase Activity

et al. 2012

View full text Add to dashboard Cite

show abstract

“…Phenolic acids and their derivatives scavenge reactive oxygen species, showing antioxidant behavior. Compounds with one, two or three free hydroxyl groups on their aromatic ring exhibit low, medium and high antioxidant activity, respectively [51]. The highest antioxidant activity was observed in compounds with an -OH-group-oriented ortho or para position to the COOH group.…”

Section: Discussionmentioning

confidence: 99%

Phytochemical Profiling, Antioxidant, Anti-Inflammatory, Thrombolytic, Hemolytic Activity In Vitro and In Silico Potential of Portulacaria afra

et al. 2022

View full text Add to dashboard Cite

The use of complementary herbal medicines has recently increased in an attempt to find effective alternative therapies that reduce the adverse effects of chemical drugs. Portulacaria afra is a rich source of phytochemicals with high antioxidant activity, and thus may possess health benefits. This study used the latest developments in GC-MS coupling with molecular docking techniques to identify and quantify the phytoconstituents in P. afra tissue extracts. The results revealed that n-butanol P. afra (BUT-PA) dry extracts contained total phenolic and flavonoids contents of 21.69 ± 0.28 mgGAE/g and 196.58 ± 6.29 mgGAE/g, respectively. The significant potential of antioxidants was observed through CUPRIC, FRAP, and ABTS methods while the DPPH method showed a moderate antioxidants potential for P. afra. Enzymatic antioxidants, superoxide dismutase, peroxidase and catalase also showed a better response in the BUT-PA dry extracts. The thrombolytic activity of the BUT-PA extracts ranged from 0.4 ± 0.32 to 11.2 ± 0.05%. Similarly, hemolytic activity ranged from 5.76 ± 0.15 to 9.26 ± 0.15% using the standard (triton x) method. The BUTPA and CHPA showed moderate acetylcholinesterase and butrylcholinesterase inhibition, ranging from 40.78 ± 0.52 to 58.97 ± 0.33, compared to galantamine. The carrageenan induced hind-paw edema assay, while BUT-PA extracts showed anti-inflammatory properties in a dose-dependent manner. Furthermore, 20 compounds were identified in the BUTPA extracts by GC-MS. Molecular docking was performed to explore the synergistic effect of the GC-MS-identified compounds on COX-1 and COX-2 inhibition. A high binding affinity was observed for Stigmastan-3, 5-diene, Phthalic acid, 3. Alpha-Hydroxy-5, 16-androstenol. The computed binding energies of the compounds revealed that all the compounds have a synergistic effect, preventing inflammation. It was concluded that active phytochemicals were present in P. afra, with the potential for multiple pharmacological applications as a latent source of pharmaceutically important compounds. This should be further explored to isolate secondary metabolites that can be employed in the treatment of different diseases.

show abstract

Resveratrol: a review of plant sources, synthesis, stability, modification and food application

2019

View full text Add to dashboard Cite

Resveratrol, a stilbene molecule belonging to the polyphenol family, is usually extracted from a great many natural plants. The technologies of preparation and extraction methods are developing rapidly. As resveratrol has many beneficial properties, it has been widely utilized in food and medicine industry. In terms of its structure, it is susceptible to degradation and can undergo chemical changes during food processing. Different studies have therefore given more attention to various aspects of resveratrol, including anti-aging, anti-oxidant, and anti-cancer activity. This review classifies the study of resveratrol, considers plant sources, synthesis, stability, common reactions, and food applications, and provides references to boost its food and medical utilization. SYNTHESISSince the discovery of natural resveratrol by researchers, chemist have made many attempts at the chemical synthesis / biosynthesis of resveratrol (Fig. 2). 15

show abstract

Antioxidant Activity of Synthetic Resveratrol Analogs: A Structure- Activity Insight

Cited by 9 publications

References 0 publications

Inhibitory Effects of Resveratrol Analogs on Mushroom Tyrosinase Activity

Inhibitory Effects of Resveratrol Analogs on Mushroom Tyrosinase Activity

Phytochemical Profiling, Antioxidant, Anti-Inflammatory, Thrombolytic, Hemolytic Activity In Vitro and In Silico Potential of Portulacaria afra

Resveratrol: a review of plant sources, synthesis, stability, modification and food application

Contact Info

Product

Resources

About