Synthesis and biological evaluation of novel benzyl-substituted flavones as free radical (DPPH) scavengers and α-glucosidase inhibitors

• Published in: Journal of asian natural products research 2010-11, Vol.12 (11), p.978-984
• Main Authors: Kumar, G. Suresh, Tiwari, Ashok K., Rao, V. Rama Subba, Prasad, K. Rajendra, Ali, A. Zehra, Babu, K. Suresh
• Format: Article
• Language: English
• Subjects: Benzene Derivatives - chemical synthesis; Benzene Derivatives - chemistry; Benzene Derivatives - pharmacology; benzyl-substituted flavones; Bignoniaceae - chemistry; Biological and medical sciences; Biphenyl Compounds - pharmacology; cinnamic acids; DPPH free radical scavenging activity; Flavanones; flavones; Flavonoids - chemical synthesis; Flavonoids - chemistry; Flavonoids - pharmacology; Free Radical Scavengers - chemical synthesis; Free Radical Scavengers - chemistry; Free Radical Scavengers - pharmacology; General and cellular metabolism. Vitamins; Glycoside Hydrolase Inhibitors; Hypoglycemic Agents - chemical synthesis; Hypoglycemic Agents - chemistry; Hypoglycemic Agents - pharmacology; India; Medical sciences; Molecular Structure; Pharmacology. Drug treatments; Picrates - pharmacology; Plant Roots - chemistry; Plants, Medicinal - chemistry; α-glucosidase inhibitory activity
• ISSN: 1028-6020; 1477-2213
• DOI: 10.1080/10286020.2010.511190

Pharmacologically motivated natural product investigations have yielded a large variety of structurally unique lead compounds with interesting biomedical properties, but the natural roles of these molecules often remain unknown. In the present investigation, a series of benzyl substituted-flavone derivatives have been synthesized from the lead compounds and were screened against 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging and α-glucosidase inhibitory properties. The resulting activity profiles of these flavone derivatives were compared for degree of similarity to the profile of 1-3. Most of the synthesized derivatives displayed potent activities when compared to the parent compounds. Maximum potencies for DPPH free radical scavenging activity were observed only in compounds containing the 4-hydroxyl substitution and 3-methoxyl group on the phenyl ring. While the 2- and 4-hydroxyl group substitutions on the phenyl ring seem to be crucial for the intestinal α-glucosidase inhibitory activity.