Studies on Crude Drugs Effective on Visceral Larva Migrans. IV.1) Isolation and Identification of Larvicidal Principles in Pepper

Fumiyuki Kiuchi, Norio Nakamura, Yoshisuke Tsuda, Kaoru Kondo, Hiroyuki Yoshimura

Research output: Contribution to journalArticlepeer-review

85 Citations (Scopus)

Abstract

Eight new amide constituents together with seven known amides were isolated from pepper and their structures were determined by spectroscopic means. They are piperamide-C5:1(2E) (2), -C7:1(6E) (3), -C7:2(2E, 6E) (4), -C9:1(8E) (5), -C9:2(2E, 8E) (6), -C9:3(2E, 4E, 8E) (7), 1-[(2E, 4E)-2, 4-decadienoyl]pyrrolidine (8), and 1-[(2E, 4E)-2, 4-dodecadienoyl]pyrrolidine (9). Among all of the amides isolated, seven (3, 4, 5, 6, 8, 9, and 15) showed larvicidal activity against second-stage larva of Toxocara canis and the others were inactive. The assay results suggested that the strongest activity was exhibited by the tertiary amides (piperidin- and pyrrolidin-amides) possessing a nine-carbon chain between the aromatic group and the amine moiety [for example, piperamide-C9: 1(8E), MLC: 0.05 mM after 24h of incubation]. The aliphatic amides 8 and 9 were also larvicidal. Mass spectra of piperamides are also discussed.

Original languageEnglish
Pages (from-to)2452-2465
Number of pages14
JournalChemical and Pharmaceutical Bulletin
Volume36
Issue number7
DOIs
Publication statusPublished - 1988
Externally publishedYes

Keywords

  • Piper nigrum
  • Piperaceous amide
  • Toxocara canis
  • larvicidal activity
  • mass spectrum
  • pepper
  • piperamide
  • pyrrolidin-amide
  • structure–activity relationship
  • visceral larva migrans

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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