Madyastha K M, Raj C P
Department of Organic Chemistry, Indian Institute of Science, Bangalore.
Biochem Biophys Res Commun. 1991 May 31;177(1):440-6. doi: 10.1016/0006-291x(91)92003-3.
Menthofuran (II, 4,5,6,7-tetrahydro-3,6-dimethyl benzofuran), the proximate toxin of R-(+)-pulegone (I), was administered orally to rats (200 mg/kg of body weight/day) for three days and the urinary metabolites were investigated. Among the several metabolites formed, two of them viz. 4-Hydroxy-4-methyl-2-cyclohexenone (VII) and p-cresol (VIII) were identified. In support of the formation of these metabolites, it has been demonstrated that phenobarbital induced rat liver microsomes readily convert 4-methyl-2-cyclohexenone (V) to 4-hydroxy-4-methyl-2-cyclohexenone (VII) and p-cresol (VIII) in the presence of NADPH and O2. Possible mechanism for the formation of these two metabolites (VII, VIII) from menthofuran (II) has been proposed.
薄荷呋喃（II，4,5,6,7-四氢-3,6-二甲基苯并呋喃）是R-（+）-长叶薄荷酮（I）的直接毒素，以口服方式给予大鼠（200毫克/千克体重/天），持续三天，并对尿液代谢物进行了研究。在所形成的几种代谢物中，鉴定出其中两种，即4-羟基-4-甲基-2-环己烯酮（VII）和对甲酚（VIII）。为了支持这些代谢物的形成，已经证明苯巴比妥诱导的大鼠肝微粒体在NADPH和O2存在下很容易将4-甲基-2-环己烯酮（V）转化为4-羟基-4-甲基-2-环己烯酮（VII）和对甲酚（VIII）。已经提出了从薄荷呋喃（II）形成这两种代谢物（VII，VIII）的可能机制。
