Flavan-Benzofurans from Artocarpus lacucha: Their Intracellular Antioxidant Activity and Molecular Docking to Glutathione Reductase

• Published in: ACS omega Vol. 9; no. 31; pp. 33888 - 33899
• Main Authors: Songoen, Weerasak, Wenisch, Dominik, Jakupec, Michael A., Phanchai, Witthawat, Sukkhaeng, Siriphan, Brecker, Lothar, Schinnerl, Johann, Tharamak, Sorachat, Pluempanupat, Wanchai
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 06.08.2024
• ISSN: 2470-1343; 2470-1343
• DOI: 10.1021/acsomega.4c03865

Phytochemical investigation of Artocarpus lacucha Buch.-Ham (Moraceae) leaves led to the identification of three of the rarely found flavan-benzofuranes named artocarpinol C (1), 3-epi-artocarpinol C (2), and artocarpinol D (6) along with six known flavan derivatives. Thus, a total of six artocarpinols are now described. All their chemical structures and absolute configurations were established by one dimensional (1D)- and two-dimensional (2D) NMR, infrared (IR), electronic circular dichroism (ECD), high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS), and optical rotation (OR). Density functional theory (DFT) calculations based on the B3LYP theory level were conducted to determine the stereochemistry at positions 2 and 3 in the C-ring. All compounds exhibited in vitro radical scavenging activities, and compounds 3 and 5 demonstrated pronounced intracellular antioxidative effects in colon carcinoma cells (SW480), as determined by the DCFH-DA assay. Compounds 3 and 5 exhibited further high affinities for binding to the active site of human glutathione reductase. These molecular properties are discussed with regard to possible applications.