Work

An efficient approach to flavan-4-ols via radiolysis and their inhibitory activity against cytokine production

Year: 2025

Type: article

Abstract: Facile structural modification of naringin ( 1 ) induced by γ-irradiation produced five novel hydroxymethylated flavan-4-ols, namely, narinflavans A ( 2 ), B ( 3 ), C ( 4 ), D ( 5 ), and E ( 6 ). The structures of the newly synthesized flavan derivatives were determined through comprehensive one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) analyses, whereas their absolute configurations were confirmed by electronic circular dichroism (ECD) spectroscopy. The new unusual flavan derivatives 4 and 5 containing a hydroxymethyl, instead of a ketone moiety, exhibited significantly modulated inhibitory effects on cytokine production than the parent compound. These results highlight γ-irradiation as an efficient one-step approach to generate structurally novel flavan-4-ols with biological functions. • γ-Irradiation generates structurally novel flavan-4-ols with biological functions. • These included narinflavans A ( 2 ), B ( 3 ), C ( 4 ), D ( 5 ), and E ( 6 ). • NMR, HRESIMS, and ECD were used to study their chemical structures. • They inhibited IL-6 and TNF-α production in LPS-stimulated RAW 264.7 macrophages. • γ-Rays can be used to develop bioactive natural product analogs.

Source: Bioorganic & Medicinal Chemistry Letters

DOI: 10.1016/j.bmcl.2025.130464

Authors: Gyeong Han Jeong, Ha-Yeon Song, Hanui Lee, Byung Yeoup Chung, Kyung-Bon Lee, Hyoung-Woo Bai

Institutions: Korea Atomic Energy Research Institute, Chonnam National University, Korea University of Science and Technology

Language: English

Topic: Synthesis of Organic Compounds

Subfield: Pharmacology

Field: Medicine

Domain: Health Sciences

SDG: Good health and well-being

Open Access status: hybrid

Estimated APC paid: $3,880