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Identification of a new metabolite of astilbin, 3'-O-methylastilbin, and its immunosuppressive activity against contact dermatitis.

Guo J, Qian F, Li J, Xu Q, Chen T

State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Key Laboratory of Analytical Chemistry for Life Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.

BACKGROUND: Astilbin is a flavonoid isolated from the rhizome of Smilax glabra. In a previous study, we revealed its unique immunosuppressive activity, a selective inhibition against activated T lymphocytes. This characteristic of astilbin is beneficial for the treatment of human immune diseases. METHODS: We incubated astilbin with rat liver microsomal/cytosolic fractions and isolated the metabolite of astilbin, which was fully characterized by mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy. We administered astilbin orally via a gastric tube to rats at 0.22 mmol/kg and collected whole blood samples after 30 min and urine samples after 0 to 12 h. We applied HPLC and liquid chromatography/MS to measure the metabolite in the samples, and we assayed cytokine expression by reverse-transcription PCR. RESULTS: After incubation of astilbin with rat liver microsomal/cytosolic fractions, we detected a new metabolite of astilbin and isolated it from the culture solution. We characterized this metabolite by MS and NMR techniques as 3'-O-methylated astilbin. We detected the metabolite in both blood and urine samples after oral administration of astilbin, and the metabolite inhibited picryl chloride-induced ear swelling in mice and suppressed the expression of tumor necrosis factor-alpha and interferon-gamma, similarly to astilbin. CONCLUSION: This is the first identification of 3'-O-methylastilbin as a new flavonoid, as well as an active metabolite of astilbin in vivo, and is helpful for studying the kinetics of astilbin and its clinical applications.

Published 28 February 2007 in Clin Chem, 53(3): 465-71.
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