Flavan-Benzofurans from <i>Artocarpus lacucha</i>: Their Intracellular Antioxidant Activity and Molecular Docking to Glutathione Reductase
- Author(s)
- Weerasak Songoen, Dominik Wenisch, Michael A. Jakupec, Witthawat Phanchai, Siriphan Sukkhaeng, Lothar Brecker, Johann Schinnerl, Sorachat Tharamak, Wanchai Pluempanupat
- 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.
- Organisation(s)
- Department of Inorganic Chemistry, Department of Organic Chemistry, Department of Botany and Biodiversity Research
- External organisation(s)
- Kasetsart University, Khon Kaen University
- Journal
- ACS Omega
- Volume
- 9
- Pages
- 33888-33899
- No. of pages
- 12
- ISSN
- 2470-1343
- DOI
- https://doi.org/10.1021/acsomega.4c03865
- Publication date
- 08-2024
- Peer reviewed
- Yes
- Austrian Fields of Science 2012
- 106034 Phytochemistry
- ASJC Scopus subject areas
- General Chemistry, General Chemical Engineering
- Portal url
- https://ucrisportal.univie.ac.at/en/publications/2d162288-1fdf-4335-93c6-6f3cae61e61c