Inhibitory effect of γ-ray-modified hydroxymethylated baicalins on NO production
- Bioorg Med Chem Lett. 2023 Nov 15:96:129491. doi: 10.1016/j.bmcl.2023.129491.
- 1. Research Division for Biotechnology, Advanced Radiation Technology Institute (ARTI), Korea Atomic Energy Research Institute (KAERI), Jeongeup 56212, Republic of Korea; Center for Companion Animal New Drug Development, Korea Institute of Toxicology (KIT), Jeongeup 56212, Republic of Korea.
- 2. Center for Companion Animal New Drug Development, Korea Institute of Toxicology (KIT), Jeongeup 56212, Republic of Korea.
- 3. Medical Device Development Center, Daegu-Gyeongbuk Medical Innovation Foundation (K-MEDI Hub), 80 Cheombok‑Ro, Dong‑Gu, Daegu 41061, Republic of Korea.
- 4. Research Division for Biotechnology, Advanced Radiation Technology Institute (ARTI), Korea Atomic Energy Research Institute (KAERI), Jeongeup 56212, Republic of Korea. Electronic address: [email protected].
- 5. Research Division for Biotechnology, Advanced Radiation Technology Institute (ARTI), Korea Atomic Energy Research Institute (KAERI), Jeongeup 56212, Republic of Korea; Center for Companion Animal New Drug Development, Korea Institute of Toxicology (KIT), Jeongeup 56212, Republic of Korea; Radiation Biotechnology and Applied Radioisotope Science, University of Science and Technology (UST), Daejeon 34113, Republic of Korea. Electronic address: [email protected].
Baicalin, a glucuronic flavone, is the major active component in the medicinal plant Scutellaria baicalensis. Herein, baicalin was irradiated by γ-rays to afford four unusual flavanones, baicalinols A (2), B (3), and C (4) and peroxybaicaleinol (5), and two known Flavones, oroxylin A (6) and baicalein (7). The structures of the hydroxymethylated products were elucidated using nuclear magnetic resonance spectroscopy and mass spectrometry, and their absolute configuration was established using electronic circular dichroism spectroscopy. Novel hydroxymethylated flavanones 2 and 3 suppressed both nitric oxide (NO) production and the expression of inducible NO Synthase and showed significantly higher anti-inflammatory activities in lipopolysaccharide-stimulated macrophages than the parent compound. These newly generated hydroxymethylated flavanones can be potentially used for treating inflammatory diseases.