title: Identification of a rare sulfonic acid metabolite of andrographolide in rats.
abstract: Andrographolide is widely used in clinic as an anti-inflammatory and antibiotic drug. In this paper, the metabolites of andrographolide in rats after single oral doses of 120 mg/kg were investigated. The structures of the metabolites were elucidated by high-resolution mass spectra, NMR spectroscopy including 1H NMR, 13C NMR, and two-dimensional NMR, through comparison to a synthetic standard. The main metabolite of andrographolide in rats was 14-deoxy-12(R)-sulfo andrographolide. In the proposed mechanism, the beta-carbon of alpha, beta-unsaturated carbonyl was attacked by sulfonic acid, to form the sulfonate compound. This was a rare metabolic reaction. It may be the main metabolic pathway of andrographolide in rats. The polarity of the sulfonate metabolite increased greatly and could be easily eliminated from body.
authors.affiliation: Department of Natural Products Chemistry, Shenyang Pharmaceutical University, Shenyang, China, 110016.
authors.forename: Xiangjiu
authors.initials: X
authors.lastname: He
authors.forename: Jiankuan
authors.initials: J
authors.lastname: Li
authors.forename: Hao
authors.initials: H
authors.lastname: Gao
authors.forename: Feng
authors.initials: F
authors.lastname: Qiu
authors.forename: Ke
authors.initials: K
authors.lastname: Hu
authors.forename: Xiangmin
authors.initials: X
authors.lastname: Cui
authors.forename: Xinsheng
authors.initials: X
authors.lastname: Yao
mesh_terms: D000284:Administration, Oral; D000818:Animals; D002247:Carbon Isotopes; D004224:Diterpenes / Q000737:chemistry* / Q000378:metabolism* / Q000493:pharmacokinetics; D007421:Intestine, Small / Q000737:chemistry / Q000187:drug effects / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D015394:Molecular Structure; D051381:Rats / Q000378:metabolism*; D017208:Rats, Wistar; D013451:Sulfonic Acids / Q000737:chemistry* / Q000302:isolation & purification* / Q000652:urine
chemical_list: C487001:14-deoxy-12-sulfoandrographolide; D002247:Carbon Isotopes; D004224:Diterpenes; D013451:Sulfonic Acids; C030419:andrographolide