The major metabolic pathway for profenofos in cotton involves cleavage of the phosphorothioate ester to yield 4-bromo-2-chlorophenol followed by conjugation with sugars. This investigation found a unique sugar conjugate in cotton stalks and seed. The unique metabolite is identified as a glucosylsulfate conjugate of 4-bromo-2-chlorophenol, and its isolation and structure elucidation are reported. Keywords: Organophosphate metabolism; cotton plants; conjugation reactions; O-glucosylsulfate formation
Since polyribonucleotides are susceptible to base-catalyzed hydrolysis of the phosphodiester bonds, one might suppose that the peroxodisulfate oxidation would be chiefly useful for polydeoxyribonucleotides. However, the hydrolysis is quite slow at pH values suitable for the oxidation. For example, using the data of one can calculate an approximate half-time of 850 hr for the hydrolysis of RNA a t pH 9, 40'.The structures of five new alkaloids are reported. Sceletium alkaloid A4 (3) is a new type of Sceletium alkaloid containing a tetracyclic ring system and N-formyltortuosamine (8) is a ring C seco derivative of 3. Three additional members of the 3a-aryloctahydroindole class are described by the structures of the phenolic base, 4'-O-demethylmesembrenone (12), A7-mesembrenone (71, and sceletenone (15). The latter constitutes the prototype of a monooxyaryl member of this class. A unified biogenetic scheme which accounts for the origins of the various ring systems of the different classes of Sceletium alkaloids is presented.
The biosynthesis of berberine and hydrastine (in Hydrastis canadensis), corydaline and protopine (in Corydalis solida), and ochotensimine and protopine (in C. ochotensis), has been investigated by the administration of [3-14C]-3′,4′-dihydroxyphenylalanine ([3-14C]DOPA). In all cases, incorporation of label was predominantly into the isoquinoline portion of the alkaloid. The role of DOPA in the early stages of isoquinoline alkaloid biosynthesis in these plants is discussed in the light of this and other relevant data. In addition, the later stages of corydaline biosynthesis have been studied by the administration of [9-methoxy-14C]palmatine and -tetrahydropalmatine to C. solida, and the origin of the exocyclic carbons of ochotensimine further verified by feeding [methyl-14C,3H]methionine to C. ochotensis.
The structures of five new alkaloids are reported. These include N-acetyltortuosamine (6), the dihydropyridone base (5) related to Sceletium alkaloid At (3), and three new alkaloids with the joubertiamine (2) skeleton represented by 4-(3,4-dimethoxyphenyl)-4-[2-(acetylmethylamino)ethyl]cyclohexanone (20), 4-(3-methoxy-4-hydroxyphenyl)-4-[2-(acetylmethylamino)ethyl]cyclohexadienone (24), and (-)-3,-methoxy-4'-0-methyljoubertiaminol (13). The stereochemistry of joubertinamine ( 18) is suggested by !H NMR spectral data.
[(1)(4)C]Prometryn, 2, 4-bis(isopropylamino)-6-(methylthio)-s-triazine, was orally administered to male and female rats at approximately 0.5 and 500 mg/kg; daily urine and feces were collected. After 3 or 7 days rats were sacrificed, and blood and selected tissues were isolated. The urine and feces extracts were characterized for metabolite similarity as well as for metabolite identification. Over 30 metabolites were observed, and of these, 28 were identified mostly by mass spectrometry and/or cochromatography with available reference standards. The metabolism of prometryn was shown to occur by N-demethylation, S-oxidation, S-S dimerization, OH substitution for NH(2) and SCH(3), and conjugation with glutathione or glucuronic acid. Rat liver microsomal incubations of prometryn were conducted and compared to the in vivo metabolism. Both in vivo and in vitro phase I metabolisms of prometryn were similar, with S-oxidation and N-dealkylation predominating. The involvement of cytochrome P-450 and flavin-containing monooxidase in the in vitro metabolism of prometryn was investigated.
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