RT Journal Article
SR Electronic
T1 ISOLATION AND IDENTIFICATION OF SEVEN GLUCURONIDE CONJUGATES OF ANDROGRAPHOLIDE IN HUMAN URINE
JF Drug Metabolism and Disposition
JO Drug Metab Dispos
FD American Society for Pharmacology and Experimental Therapeutics
SP 555
OP 562
DO 10.1124/dmd.104.001958
VO 33
IS 4
A1 Liang Cui
A1 Feng Qiu
A1 Xinsheng Yao
YR 2005
UL http://dmd.aspetjournals.org/content/33/4/555.abstract
AB Andrographolide is one of the principal components of a famous traditional Chinese herbal medicine, Andrographis paniculate (Burm) Nees, and has been widely used in the clinic for the treatment of infectious diseases. In this paper, metabolites of andrographolide in the urine of eight healthy volunteers after oral administration were further investigated. Building on previous findings, an additional seven phase II metabolites were isolated by liquid-liquid extraction, open-column chromatography, medium-pressure liquid chromatography, and, finally, preparative high-performance liquid chromatography. Structural elucidation was carried out by mass spectra and NMR spectroscopy including 1H NMR, 13C NMR and two-dimensional NMR (distortionless enhancement by polarization transfer, heteronuclear multiple-quantum correlation, heteronuclear multiple-bond correlation, 1H-1H correlated spectroscopy, and nuclear Overhauser enhancement spectroscopy). All of the metabolites were characterized as glucuronide conjugates, and the structures were determined to be andrographolide-19-O-β-d-glucuronide (M-1), isoandrographolide-19-O-β-d-glucuronide (M-2), 14-deoxy-12-hydroxy-andrographolide-19-O-β-d-glucuronide (M-3), andrographolide-19-O-[6′-methyl-β-d-glucuronide] (M-4), 14-deoxy-12(13)-en-andrographolide-19-O-β-d-glucuronide (M-5), 14-deoxyandrographolide-19-O-β-d-glucuronide (M-6), and 3-oxoandrographolide-19-O-β-d-glucuronide (M-7), respectively. The American Society for Pharmacology and Experimental Therapeutics