Bio-active compound isolated from Aegle marmelos fruit pulp and semi-synthetic modifications: a Biological potential

The Aegle marmelos (AM) is a deciduous tree recognized in traditional medicine for the treatment of various illnesses due to the presence of phytoconstituents such as coumarin component of imperatorin. The current investigation, obtained three end products, such as (1b) 9-hydroxy-7H-furo[3,2 g]chromen-7-one, (2b) N-(8-hydroxy-2,6-dimethyloctan-2-yl)acetamide, and (Z) N-(2-(4-methylcyclohex-3-en-1-yl)propan-2-yl)acetamide due to modification in isoprenyl group. Interestingly, in the case of four mono terpenes, Geraniol, Linalool, alpha-Pinene, and Limonene, are single reaction products (Z) yielded from the Ritter reaction. The obtained compounds are to test in vitro anti-microbial, were subjected to molecular docking, mosquito larvicidal, pupicidal, and brine shrimp activities were accompanied against Staphylococcus aureus, Klebsiella pneumonia, dengue vector Aedes aegypti and Brine shrimp lethality assay (BSLA) on Artemia nauplii. The imperatorin (1a), isoprene contains compounds (2a-6a) and semi-synthetic modified compounds (1b), (2b), and (Z) exhibited potential pharmacological activities. The highest-level zone of inhibition was present in imperatorin (1a), modified compounds (1b), (2b), and (Z) against Staphylococcus aureus, Klebsiella pneumonia (17.8, 18.9, 17, and 18.2 mm) (17.2, 21.2, 20, and 22.1 mm), and antibiotics chloramphenicol (CP) inhibit (24.2 and 27.4 mm). In comparison to the reference drug Ciprofloxacin, compound (1b) showed the best potency against both bacterial strains. To ascertain the potential binding orientation of PDB ID: 3OZU, docking research was used. In accordance with the docking data, compound (1b) had a greater binding affinity and an energy of 7.62 kcal/mol. These findings shed light on the process of binding development and offer a prestigious route for designing and structurally modifying Ritter reactions as a cutting-edge class of antibacterial agents, respectively. 100% potential larvicidal and pupicidal was observed in imperatorin (1a), derivatives (1b), (2b), and (Z) against larvae of A. aegypti (LC50 = 42.37, 57.07, 42.89, and 45.08 ppm) and pupicidal with LC50= 37.20, 49.82, 46.76, and 41.65 ppm, respectively at 24 h observation. Isolated and all the modified compounds revealed a low toxic effect on Artemia nauplii with the viability of 96, 96.2, 97, 85, 98, 85, 87, 86, 85.4, and 98% at 500 ppm, respectively at 24 h treatments. The findings clearly support the prospective usage of these compounds in the pharmaceutical industry.

Automated summary

The study found that imperatorin and its derivatives have potential pharmacological and insecticidal activities, showing good inhibitory effects against Staphylococcus aureus and Klebsiella pneumoniae. The modified compounds of imperatorin showed the best antibacterial activity and exhibited high larvicidal and pupicidal activities against larvae and pupae of Aedes aegypti.