Monoterpene hydroperoxides with trypanocidal activity from Chenopodium ambrosioides.

Fumiyuki Kiuchi, Yoshiaki Itano, Nahoko Uchiyama, Gisho Honda, Akiko Tsubouchi, Junko Nakajima-Shimada, Takashi Aoki

Graduate School of Pharmaceutical Sciences, Kyoto University, 46-29 Yoshida, Sakyo-ku, Kyoto, 606-8501, Japan. fkiuchi@pharm.kyoto-u.ac.jp

Journal of natural products 2002 Apr

filter terms:

Four monoterpene hydroperoxides were isolated from aerial parts of Chenopodium ambrosioides along with ascaridole (1), the anthelmintic principle of this plant, as anti-trypanosomal compounds. The structures of these monoterpenes were determined to be (-)-(2S,4S)- and (-)-(2R,4S)-p-mentha-1(7),8-dien-2-hydroperoxide (2a and 3a) and (-)-(1R,4S)- and (-)-(1S,4S)-p-mentha-2,8-dien-1-hydroperoxide (4a and 5a) on the basis of spectroscopic methods and chemical correlations. In vitro trypanocidal activities of ascaridole (1) and these hydroperoxides (2a-5a) against epimastigotes of Trypanosoma cruzi were 23, 1.2, 1.6, 3.1, and 0.8 microM, respectively. Fresh leaves of C. ambrosioides also contained isomeric hydroperoxides 6a and 7a, and the content ratio of 2a-7a suggested that these hydroperoxides were formed through the singlet-oxygen oxidation of limonene.

Citation

Fumiyuki Kiuchi, Yoshiaki Itano, Nahoko Uchiyama, Gisho Honda, Akiko Tsubouchi, Junko Nakajima-Shimada, Takashi Aoki. Monoterpene hydroperoxides with trypanocidal activity from Chenopodium ambrosioides. Journal of natural products. 2002 Apr;65(4):509-12