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Handbook of Phytochemical Constituents of GRAS Herbs and Other Economic Plants
Published in James A. Duke, Handbook of Phytochemical Constituents of GRAS Herbs and Other Economic Plants, 2017
“Pyrethrum”BETA-AMYRIN FL CRCASH 71,000 SH CRCCALCIUM 5,300 SH CRCCARBOHYDRATES 794,000 SH CRCCHOLINE PL HHBCHRYSANIN FL CRCCHRYSANOLEDE FL CRCCHRYSANTHEMIC-ACID-ESTER FL 411/CHRYSANTHEMINE PL JSGCINERINS FL 411/BETA-CYCLOPYRETHROSIN FL HHBFAT 5,000 SH CRCFIBER 236,000 SH CRCJASMOLINS FL 411/PHOSPHORUS 2,400 SH CRCPROTEIN 130,000 SH CRCPYRETHRIN 7,000–20,000 FL CRCPYRETHRIC-ACID FL 411/PYRETHROL FL 411/PYRETHROSIN PL JAGPYRETHROTOXIC-ACID FL CRC(+)-SESAMIN FL HHBSTACHYDRINE PL HHB
Metabolism of metofluthrin in rats: II. Excretion, distribution and amount of metabolites
Published in Xenobiotica, 2018
Jun Abe, Yoshitaka Tomigahara, Hirokazu Tarui, Hirohisa Nagahori, Motohiro Kurosawa, Kenji Sugimoto, Naohiko Isobe
Since metofluthrin has a unique structure on its alcohol side that is unlike that of existing pyrethroids, its metabolic fate and behaviour in mammals need to be elucidated. As the first step to elucidate the whole metabolic fate of metofluthrin RTE and metofluthrin RTZ, we conducted in vivo studies to identify their metabolites and elucidate their metabolic pathways (Abe et al., 2017). In that research, we identified a total of 42 metabolites recovered from the urine and faeces of rats dosed with RTE and RTZ and found that the major metabolic reactions were ester cleavage, O-demethylation, hydroxylation, double-bond epoxidation or reduction, glutathione conjugation and its further metabolism, epoxide hydroxylation, and lactone ring formation. As notable observations, we reported that the metabolism of the acid moiety of metofluthrin, 2,2-dimethyl-3-(1-propenyl)-cyclopropanecarboxylic acid, was much more varied than that of chrysanthemic acid, a common acid moiety of the known pyrethroids, and the extent of epoxidation and hydroxylation differed between the isomers, with the Z-isomer being more easily epoxidated and hydroxylated. Also, novel metabolic pathways including isomerisation of the ω-carboxylic acid group, reduction or hydration of double bond and cleavage of the cyclopropane ring via epoxidation were suggested in the article.
Metabolism of metofluthrin in rats: I. Identification of metabolites
Published in Xenobiotica, 2018
Jun Abe, Hirohisa Nagahori, Hirokazu Tarui, Yoshitaka Tomigahara, Naohiko Isobe
As we can see in many pyrethroid compounds, such as prallethrin, phenothrin, tetramethrin and imiprothrin, chrysanthemic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropanecarboxylic acid, is the most common substructure of their acid side. Mammalian metabolism of the chrysanthemic acid is well identified, and the major metabolic pathway is ω-oxidation to yield alcohol or carboxylic acid (Kaneko, 2011; Kaneko & Ohkawa, 1981b; Kaneko et al., 1984; Tomigahara et al., 1994c). In the present research, the metabolic pathways of 2,2-dimethyl-3-(1-propenyl)-cyclopropanecarboxylic acid were identified for the first time. ω-Oxidation was one of the major pathways, similar to that of chrysanthemic acid, but several unique reactions of epoxidation of the double bond and 2-methyl oxidation followed by some other reactions were found on this metabolite. It was suggested that the reactivity of the acid side was gained by the removal of a methyl moiety to produce initial epoxide/oxide metabolites.