Glycosides and xanthine oxidase inhibitors from Conyza bonariensis

• Published in: Phytochemistry (Oxford) Vol. 58; no. 4; pp. 645 - 651
• Main Authors: Kong, L.D., Abliz, Z., Zhou, C.X., Li, L.J., Cheng, C.H.K., Tan, R.X.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.10.2001; Elsevier
• Subjects: 4-Hydroxypyridin-3-carboxylic acid 4- O-glucopyranoside; 8-Hydroxy-6,7-dihydrolinalool 8- O-glucopyranoside; Asteraceae; Asteraceae - chemistry; Biochemistry & Molecular Biology; Biological and medical sciences; Bonaroside; Carbohydrate Conformation; Chemical constitution; Conyza bonariensis; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - isolation & purification; Fundamental and applied biological sciences. Psychology; Glucosides - chemistry; Glucosides - isolation & purification; Life Sciences & Biomedicine; Plant physiology and development; Plant Sciences; Science & Technology; Spectrum Analysis; Syringic acid; Takakin 8- O-glucuronide; Xanthine Oxidase - antagonists & inhibitors; Conyza bonariensis; 8-Hydroxy-6,7-dihydrolinalool 8- O-glucopyranoside; Syringic acid; Asteraceae; Bonaroside; Takakin 8- O-glucuronide; 4-Hydroxypyridin-3-carboxylic acid 4- O-glucopyranoside; syringic acid; bonaroside; STILBENOIDS; ACIDS; 4-hydroxypyridin-3-carboxylic acid 4-O-glucopyranoside; takakin 8-O-glucuronide; FLAVONOIDS; 8-hydroxy-6,7-dihydrolinalool 8-O-glucopyranoside; CONSTITUENTS; Weed; Molecular structure; Enzyme; Enzyme inhibitor; Compositae; Biological activity; Sitosterol; Enzymatic activity; Structure activity relation; Carboxylic acid; Apigenin; Dicotyledones; Angiospermae; Isolation; Xanthine oxidase; Spermatophyta; Glycoside; Oxidoreductases; Luteolin
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(01)00176-5

Fractionation of the xanthine oxidase inhibitory methanol extract of Conyza bonariensis afforded three glycosides, in addition to nine known compounds including amyrin, β-sitostero1 daucosterol, syringic acid 3-hydroxy-5-methoxybenzoic acid, eugenol 4- O-glucopyranoside, and luteolin, apigenin and takakin 8- O-glucuronide. The structures of the glycosides were established by a combination of spectroscopic methods (IR, MS, 1H and 13C NMR, DEPT, COSY, HMQC and HMBC) as 4-hydroxypyridin-3-carboxylic acid 4- O-glucopyranoside, 8-hydroxy-6,7-dihydrolinalool 8- O-glucopyranoside and bonaroside [viz. 1,3,4,12-tetrahydroxy-2-(9-hexadecenoylamino)octadecane 1- O-glucopyranoside]. The in vitro enzyme assay showed that syringic acid and takakin 8- O-glucuronide displayed weak inhibitory activity against xanthine oxidase with IC 50 values of 500±41 μM and 170±12 μM, respectively. Three glycosides, such as bonaroside, and four xanthine oxidase inhibitors were isolated from Conyza bonariensis.