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

Weerasak Songoen,Dominik Wenisch,M. Jakupec,Witthawat Phanchai,Siriphan Sukkhaeng,Lothar Brecker,J. Schinnerl,S. Tharamak,W. Pluempanupat

Published 2024 in ACS Omega

ABSTRACT

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.

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