title: Five new eudesmane-type sesquiterpenoid lactones biotransformed from atractylenolide I by rat hepatic microsomes.
abstract: The work presented here is the first study performed on the biotransformation and/or metabolism of atractylenolide I (1) as a valuable anti-inflammatory and chemopreventive agent, using liver microsomes from rats pre-treated with sodium phenobarbital. Two known eudesmane-type sesquiterpenoid lactones, namely 1β-acetoxyatractylenolide I (2) and 1β-hydroxy-atractylenolide I (3), and five new ones, namely 3β-hydroxy-atractylenolide I (4), 1β,13-dihydroxy-atractylenolide I (5), 1β,2α-dihydroxy-atractylenolide I (6), 1β,3α-dihydroxy-atractylenolide I (7), and 1β,3β-dihydroxy-atractylenolide I (8) were obtained. Their chemical structures were unambiguously established by both 1D and 2D NMR as well as mass spectroscopic techniques. The result indicated that the parent prototype compound 1 could be specifically oxidized at C-1, C-2 and C-3 of A-ring, suggesting that the oxidizable of 1 may contribute to its in vivo anti-inflammatory and chemopreventive effects. And the result also provided valuable information for further investigation of relationship among metabolic activation and liver microsomal cytochrome P450 enzyme isoforms.
authors: State Key Laboratory of Natural and Biomimetic Drugs (Peking University), Department of Natural Medicines, School of Pharmaceutical Sciences, Peking University Health Science Center, Peking University, Beijing 100191, PR China. girlinred@126.com
authors: Ying
authors: Y
authors: Li
authors: Xiu-Wei
authors: XW
authors: Yang
mesh_terms: D000818:Animals; D031174:Atractylodes / Q000737:chemistry; D001711:Biotransformation; D007783:Lactones / Q000032:analysis / Q000302:isolation & purification / Q000378:metabolism* / Q000493:pharmacokinetics; D008862:Microsomes, Liver; D010634:Phenobarbital; D010946:Plants, Medicinal / Q000737:chemistry; D051381:Rats; D012717:Sesquiterpenes / Q000302:isolation & purification / Q000378:metabolism* / Q000493:pharmacokinetics; D045787:Sesquiterpenes, Eudesmane / Q000032:analysis / Q000378:metabolism
chemical_list: D007783:Lactones; D012717:Sesquiterpenes; D045787:Sesquiterpenes, Eudesmane; C424804:atractylenolide I; D010634:Phenobarbital