Monoterpene hydroperoxides with trypanocidal activity from Chenopodium ambrosioides.
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.
Kiuchi
Fumiyuki
F
Graduate School of Pharmaceutical Sciences, Kyoto University, 46-29 Yoshida, Sakyo-ku, Kyoto, 606-8501, Japan. fkiuchi@pharm.kyoto-u.ac.jp
Itano
Yoshiaki
Y
Uchiyama
Nahoko
N
Honda
Gisho
G
Tsubouchi
Akiko
A
Nakajima-Shimada
Junko
J
Aoki
Takashi
T
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
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