title: Monoterpene hydroperoxides with trypanocidal activity from Chenopodium ambrosioides.
abstract: 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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, 46-29 Yoshida, Sakyo-ku, Kyoto, 606-8501, Japan. fkiuchi@pharm.kyoto-u.ac.jp
authors.forename: Fumiyuki
authors.initials: F
authors.lastname: Kiuchi
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Itano
authors.forename: Nahoko
authors.initials: N
authors.lastname: Uchiyama
authors.forename: Gisho
authors.initials: G
authors.lastname: Honda
authors.forename: Akiko
authors.initials: A
authors.lastname: Tsubouchi
authors.forename: Junko
authors.initials: J
authors.lastname: Nakajima-Shimada
authors.forename: Takashi
authors.initials: T
authors.lastname: Aoki
mesh_terms: D000818:Animals; D019663:Chenopodiaceae / Q000737:chemistry*; D000081005:Cyclohexane Monoterpenes; D005260:Female; D006367:HeLa Cells / Q000187:drug effects; D006801:Humans; D006861:Hydrogen Peroxide / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007564:Japan; D015394:Molecular Structure; D039821:Monoterpenes; D019906:Nuclear Magnetic Resonance, Biomolecular; D010545:Peroxides; D010946:Plants, Medicinal / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014344:Trypanocidal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014349:Trypanosoma cruzi / Q000187:drug effects*; D014407:Tumor Cells, Cultured / Q000187:drug effects; D002583:Uterine Cervical Neoplasms
chemical_list: D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; D010545:Peroxides; D013729:Terpenes; D014344:Trypanocidal Agents; C457140:p-mentha-1(7),8-dien-2-hydroperoxide; C457139:p-mentha-2,8-dien-1-hydroperoxide; C043372:ascaridole; D006861:Hydrogen Peroxide