Monoterpene hydroperoxides with trypanocidal activity from Chenopodium ambrosioides

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

Research output: Contribution to journalArticle

98 Citations (Scopus)

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 (-)-(28,4S)- 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 μM, 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.

Original languageEnglish
Pages (from-to)509-512
Number of pages4
JournalJournal of Natural Products
Volume65
Issue number4
DOIs
Publication statusPublished - 2002 May 11
Externally publishedYes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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  • Cite this

    Kiuchi, F., Itano, Y., Uchiyama, N., Honda, G., Tsubouchi, A., Nakajima-Shimada, J., & Aoki, T. (2002). Monoterpene hydroperoxides with trypanocidal activity from Chenopodium ambrosioides. Journal of Natural Products, 65(4), 509-512. https://doi.org/10.1021/np010445g