Monoterpene hydroperoxides with trypanocidal activity from Chenopodium ambrosioides

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

研究成果: Article査読

100 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)509-512
ページ数4
ジャーナルJournal of Natural Products
65
4
DOI
出版ステータスPublished - 2002 5 11
外部発表はい

ASJC Scopus subject areas

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

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