Xanthones from Gentianella amarella ssp. acuta with Acetylcholinesterase and Monoamine Oxidase Inhibitory Activities

• Published in: Journal of natural products (Washington, D.C.) Vol. 71; no. 5; pp. 895 - 897
• Main Authors: Urbain, A., Marston, A., Grilo, L. Sintra, Bravo, J., Purev, O., Purevsuren, B., Batsuren, D., Reist, M., Carrupt, P.-A., Hostettmann, K.
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society and American Society of Pharmacognosy 01-05-2008; Glendale, AZ American Society of Pharmacognosy; American Chemical Society
• Subjects: acetylcholinesterase; amine oxidase (flavin-containing); Biological and medical sciences; chemical structure; Cholinesterase Inhibitors - chemistry; Cholinesterase Inhibitors - isolation & purification; Cholinesterase Inhibitors - pharmacology; corymbiferin 3-O-β-D-glucopyranoside; enzyme inhibition; General pharmacology; Gentianaceae; Gentianella - chemistry; Gentianella amarella ssp. acuta; Glucosides; Glycosides - chemistry; Glycosides - isolation & purification; Glycosides - pharmacology; Medical sciences; medicinal plants; Molecular Structure; Mongolia; Monoamine Oxidase Inhibitors - chemistry; Monoamine Oxidase Inhibitors - isolation & purification; Monoamine Oxidase Inhibitors - pharmacology; Nuclear Magnetic Resonance, Biomolecular; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; phytochemicals; Plants, Medicinal - chemistry; spectral analysis; stereochemistry; swertiabisxanthone-I 8'-O-β-D-glucopyranoside; xanthones; Xanthones - chemistry; Xanthones - isolation & purification; Xanthones - pharmacology; Mongolia; Enzyme; Pharmacognosy; Whole plant; Oriental medicine; Enzyme inhibitor; Esterases; Acetylcholinesterase; In vitro; Biological activity; Amine oxidase (flavin-containing); Carboxylic ester hydrolases; Medicinal plant; Dicotyledones; Angiospermae; Gentianaceae; Plant origin; Phenols; Hydrolases; Isolation; Spermatophyta; Oxidoreductases; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np070690l

Two new xanthone glycosides, corymbiferin 3-O-β-d-glucopyranoside (1) and swertiabisxanthone-I 8′-O-β-d-glucopyranoside (2), were isolated from Gentianella amarella ssp. acuta, along with eight known xanthones: triptexanthoside C, veratriloside, corymbiferin 1-O-glucoside, swertianolin, norswertianolin, swertiabisxanthone-I, bellidin, and bellidifolin, four of them identified for the first time in G. amarella ssp. acuta. The isolation was conducted mainly by centrifugal partition chromatography, and the structures of the isolated compounds were established on the basis of spectrometric data including 2D NMR and mass spectrometry. Xanthones were weakly active against acetylcholinesterase (AChE), except triptexanthoside C, which inhibited AChE with an IC50 of 13.8 ± 1.6 µM. Some compounds were active against monoamine oxidases (MAO): bellidin and bellidifolin showed interesting inhibitory activity of MAO A, while swertianolin, the 8-O-glucopyranoside form of bellidifolin, gave 93.6% inhibition of MAO B activity at 10−5 M.