Azastilbene Analogs as Tyrosinase Inhibitors: New Molecules with Depigmenting Potential

• Published in: TheScientificWorld Vol. 2013; no. 2013; pp. 1 - 7
• Main Authors: Barbosa Raposo, Nádia R., Silva, Adilson David da, Carmo, Antônio Márcio Resende do, Silva, Annelisa Farah da, Lima, Rebeca Mól, Lima, Larissa Lavorato
• Format: Journal Article
• Language: English
• Published: Cairo, Egypt Hindawi Publishing Corporation 01.01.2013; Hindawi Limited; Wiley
• Subjects: Acids; Agaricales - chemistry; Agaricales - enzymology; Analogs; Antioxidants - chemistry; Aqueous solutions; Biosynthesis; Chemical properties; Chemical synthesis; Enzyme Inhibitors - chemical synthesis; Enzyme Inhibitors - chemistry; Enzymes; Fungal Proteins - chemistry; Health aspects; Methods; Molecular Conformation; Monophenol Monooxygenase - antagonists & inhibitors; Phenols - chemistry; Phosphotransferases; Production processes; Pyrones - chemistry; Resveratrol; Skin; Stilbenes - chemistry; Structure-Activity Relationship; Studies; Time Factors; Tyrosinase; Tyrosine
• ISSN: 2356-6140; 1537-744X; 1537-744X
• DOI: 10.1155/2013/274643

This research has been an effort to develop synthetic resveratrol analogs in order to improve the depigmenting potential of natural resveratrol. Six resveratrol analogs were synthesized and tested for tyrosinase inhibitory activity in vitro, by qualitative and quantitative steps. The results showed the analog C as being the most powerful tyrosinase inhibitor (IA50 = 65.67 ± 0.60 μg/mL), followed by the analogs B, E, F, A, and D, respectively. The analog C presented a tyrosinase inhibition potential better than natural resveratrol (P<0.001). The best depigmenting activity was provided by the presence of hydroxyl in the orthoposition on the second phenolic ring.