title: Chromone derivatives from Halenia elliptica and their anti-HBV activities.
abstract: Nine water-soluble chromone derivatives, including chromone-2-carboxylic acids, 2-methylchromones and their structural hybrids, were isolated from aerial tissues of Halenia elliptica (Gentianaceae), six of which were previously unknown. Their structures were elucidated by comprehensive mass, 1D and 2D NMR spectroscopic analyses and chemical derivatization. Two unstable structural hybrids of chromone-2-carboxylic acids and 2-methylchromones, viz. 3-acetyl-8-hydroxy-4H-1-benzopyran-4-one-2-carboxylic acid (halenic acid C) and 2-(8-hydroxy-2-methyl-4H-1-benzopyran-4-one-3-yl)-2-oxoacetic acid (halenichromone A), were isomers and were interconvertible. The proposed mechanism of their acid-catalyzed isomerization in aqueous solvent is described. In addition, 2-methylchromones, 8-hydroxy-2-methyl-4H-1-benzopyran-4-one, and 8-methoxy-2-methyl-4H-1-benzopyran-4-one, were found to exhibit a strong inhibitory effect towards hepatitis B virus (HBV) in vitro without showing significant cytotoxicity.
authors.affiliation: Department of Natural Products Chemistry, School of Pharmacy, Fudan University, Shanghai 201203, PR China.
authors.forename: Yu-wei
authors.initials: YW
authors.lastname: Sun
authors.forename: Guang-ming
authors.initials: GM
authors.lastname: Liu
authors.forename: Hai
authors.initials: H
authors.lastname: Huang
authors.forename: Pei-zhong
authors.initials: PZ
authors.lastname: Yu
mesh_terms: D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002460:Cell Line; D002867:Chromones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D029965:Gentianaceae / Q000737:chemistry*; D006515:Hepatitis B virus / Q000187:drug effects*; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000998:Antiviral Agents; D002867:Chromones