Exploring the Potential of Compounds Isolated from Laranthus micranthus for the Treatment of Benign Prostatic Hyperplasia: Comprehensive Studies on Spectroscopic, Reactivity, and Biological Activity

• Published in: Chemistry Africa Vol. 7; no. 2; pp. 671 - 687
• Main Authors: Ukpanukpong, Richard U., Azubuike, Adindu E., Agwupuye, Eyuwa I., Ajen, Michael U., Boco, Hogan M., Chukwuneke, Chibueze P., Benjamin, Innocent, Louis, Hitler
• Format: Journal Article
• Language: English
• Published: Cham Springer International Publishing 01.03.2024
• Subjects: Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Inorganic Chemistry; Organometallic Chemistry; Original Article; Benign prostatic hyperplasia (BPH); Spectroscopy; DFT; ADMET; Molecular docking
• ISSN: 2522-5758; 2522-5766
• DOI: 10.1007/s42250-023-00778-1

Owing to the significant challenges encountered in the diagnosis, management, and treatment of benign prostatic hyperplasia (BPH), which have emerged as essential clinical issues requiring objective study and focus. Hence, this study satisfactorily investigates both theoretical and experimental calculations on three compounds: comp01 = 7 β 15α-dihydroxy-lup-20-(29)-en-3 β -O-palmitate; comp02 = 7 β , 15 α-dihydroxy-lup-20(29)-en-3 β , -O-stearate; and comp03 = 7, 15-dihydroxy-lup-20(29)-en β -O-eicosanoate) isolated from Laranthus micranthus . Theoretical investigations were rigorously undertaken using density functional theory at the advanced B3LYP-GD3BJ/6-311++G (d,p) level of theory. This comprehensive approach aimed to elucidate the intricate electronic, structural, and spectroscopic (FT-IR, UV, and NMR) properties of the compounds under scrutiny. The reactivity indices show that comp03 with the highest energy gap possess a low chemical reactivity, while comp02 with the least energy gap possess a high chemical reactivity. The HOMO and LUMO energy values of comp02 are − 6.623 and − 0.604 eV respectively, implying maximum charge transfer within the complex, hence improving the biological activity. Additionally, results from pharmacokinetics study, revealed that the compounds exhibited a clean bill of health with regard to hepatotoxicity, carcinogenicity, mutagenicity, and cytotoxicity. Notably, they displayed reactivity to immunotoxicity, indicated by a probability score of 0.99, underscoring the significance of considering potential immunological responses in their application. Examining molecular docking results revealed distinct patterns. Comp01, comp02, and comp03 exhibited varying binding affinities in interactions with 1AFS, ranging from − 6.7 to − 6.4 kcal/mol. Docking with protein 5VBU yielded even more compelling results, with comp01, comp02, and comp03 demonstrating binding affinities of − 8.4 kcal/mol, − 8.3 kcal/mol, and − 8.5 kcal/mol, respectively. Importantly, in these interactions with 5VBU, the studied compounds displayed superior binding affinities compared to the standard drug doxazosin. This study concludes that comp01, comp02, and comp03 exhibit significantly enhanced biological activity against proteins associated with BPH, particularly 5VBU. Consequently, this investigation strongly recommends further research and development of these compounds for potential therapeutic applications.