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 language | English |
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Pages (from-to) | 2452-2465 |
Number of pages | 14 |
Journal | Chemical and Pharmaceutical Bulletin |
Volume | 36 |
Issue number | 7 |
DOIs | |
Publication status | Published - 1988 |
Externally published | Yes |
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