New Semi-Synthetic Rosmarinic Acid-Based Amide Derivatives as Effective Antioxidants

Abstract

Rosmarinic acid (RA), a bioactive compound isolated from Rosmarinus officinalis exhibits multiple pharmacological activities, including antioxidant, anti‐allergic and anti‐inflammatory effects. Herein, we report the synthesis of new series of amide analogs of rosmarinic acid along with their antioxidant potential. Highest DPPH scavenging effect was observed in case of (E)‐3‐(3,4‐dihydroxy‐phenyl)‐1‐((4‐fluorophenyl)amino)‐1‐oxopropan‐2‐yl‐3‐(3,4dihydroxy phenyl)acrylate (RA‐15) displaying an IC50 of 3.19 μg/ml compared to standard ascorbic acid (IC50=4.09 μg/ml). However (E)‐3‐(3,4‐dihydroxyphenyl)‐1‐((4‐hydroxyphenyl)amino)‐1‐oxopropan‐2‐yl‐3‐(3, 4‐dihydroxyphenyl)acrylate (RA‐10) displayed the highest hydroxy radical scavenging effect exhibiting an IC50 of 8.98 μg/ml compared to standard ascorbic acid (IC50=9.00 μg/ml). This study thus, provides an important aspect with regard to the use of these rosmarinic acid‐based antioxidants in food industry as dietary supplements.

Nanoantioxidant–Based Silica Particles as Flavonoid Carrier for Drug Delivery Applications

“…In the present work, we evaluated the antiradical activity expressed as radical scavenging activity percentage (%RSA) versus RA concentration of free RA and nano-RA, in the concentration range of 0.43-10.8 µg/mL ( Figure 5). As the concentration of free RA increases, the %RSA increases, reaching a 50% of DPPH • deactivation approximately at a concentration of 2.5-3 µg/mL, which is consistent with literature reports [55][56][57]. 0.43-10.8 µ g/mL ( Figure 5).…”

“…0.43-10.8 µ g/mL ( Figure 5). As the concentration of free RA increases, the %RSA increases, reaching a 50% of DPPH • deactivation approximately at a concentration of 2.5-3 µ g/mL, which is consistent with literature reports [55][56][57]. Xie and Schaich studied the kinetics patterns of different phenol reactions with DPPH • , and classified them into five groups.…”

Synthesis of an unusual quinazoline alkaloid: theoretical and experimental investigations of its structural, electronic, molecular and biological properties

“…8,9 In general alkaloids possess a range of biological activities which include analgesic, antiviral, antimalarial, antineoplastic, antimicrobial, anti-inammatory, antioxidant antifungal, antibacterial, hemoglobinization agents of human leukemia cells, effects on the CNS, estrogenic effects etc. [10][11][12][13][14][15][16][17][18][19][20][21][22][23][24] Based on these literature reports of alkaloids and our previous work on the isolation, and synthesis of bioactive compounds, [25][26][27][28][29][30][31][32][33][34][35][36][37] we carried out the synthesis of an unusual selfcondensation product of 2-aminobenzaldehyde by a method reported by Seidal and coworkers. 38 In order to get deeper insights in to the molecular, structural and biological properties of the synthesized compound, we resorted to spectral, X-ray and DFT analysis.…”

Microwave-Assisted Synthesis of Andrographolide Analogues as Potent β-Glycosidase Inhibitors

“…1 minute at r.t. in a microwave synthesiser. 48 To this mixture, suitably substituted aromatic amine (1.2 equiv) was then added and the reaction mixture was allowed to react for 3 minutes. Progress of the reaction was monitored using TLC in EtOAc/hexane (30:70).…”