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

92 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
Externally publishedYes

Fingerprint

Chenopodium ambrosioides
Monoterpenes
hydroperoxides
monoterpenoids
Hydrogen Peroxide
Mentha
Singlet Oxygen
Anthelmintics
Trypanosoma cruzi
epimastigotes
singlet oxygen
Antennas
anthelmintics
Oxidation
aerial parts
oxidation

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

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

Monoterpene hydroperoxides with trypanocidal activity from Chenopodium ambrosioides. / Kiuchi, Fumiyuki; Itano, Yoshiaki; Uchiyama, Nahoko; Honda, Gisho; Tsubouchi, Akiko; Nakajima-Shimada, Junko; Aoki, Takashi.

In: Journal of Natural Products, Vol. 65, No. 4, 2002, p. 509-512.

Research output: Contribution to journalArticle

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, vol. 65, no. 4, pp. 509-512. https://doi.org/10.1021/np010445g
Kiuchi, Fumiyuki ; Itano, Yoshiaki ; Uchiyama, Nahoko ; Honda, Gisho ; Tsubouchi, Akiko ; Nakajima-Shimada, Junko ; Aoki, Takashi. / Monoterpene hydroperoxides with trypanocidal activity from Chenopodium ambrosioides. In: Journal of Natural Products. 2002 ; Vol. 65, No. 4. pp. 509-512.
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