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 β-carbon of α, β-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.
Footnotes
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↵1 Abbreviations used are: 2(3H)-furanone, 3-[2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5, 8a-dimethyl-2-methylene-1-napthalenyl]ethylidene] dihydro-4-hydroxy-; IR, infrared; HMBC, 1H-detected heteronuclear multiple-bond correlation; NOE, nuclear overhauser effect.
- Received November 4, 2002.
- Accepted April 16, 2003.
- The American Society for Pharmacology and Experimental Therapeutics
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