Piperidinyl amides with insecticidal activity from the maritime plant Otanthus maritimus

J Agric Food Chem. 2005 Mar 9;53(5):1435-9. doi: 10.1021/jf0481857.

Abstract

Two new piperidine amides, N-[(2E,4E,8Z)-tetradecatrienoyl]piperidine (1) and N-[(2E,4E,8Z,11Z)-tetradecatetrenoyl]piperidine (2), along with the known metabolites N-[(2E,4E)-tetradecadienoyl]piperidine (3), N-isobutyl-(2E,4E,)-tetradecadienamide (4), N-isobutyl-(2E,4E,8Z)-tetradecatrienamide (5), N-isobutyl-(2E,4E,8Z,11Z)-tetradecatetraenamide (6), sesamine (7), pinoresinol (8), and espeletone (9), were isolated from the dichloromethane/methanol extracts of the plant Otanthus maritimus Hoffman & Link collected from coastal areas in Greece. Pinoresinol (8) and espeletone (9) are reported for the first time as metabolites of O. maritimus. The structures of the new natural products were elucidated by interpretation of their NMR and high-resolution mass spectral measurements. The insecticidal properties of the crude extracts, essential oil, and isolated metabolites 1-9 were evaluated on Crematogaster scutellaris (Olivier) ants and Reticulitermes balkanensis (Clement) termites, showing significant levels of activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Alkenes / isolation & purification
  • Amides / chemistry
  • Amides / isolation & purification*
  • Animals
  • Ants
  • Asteraceae / chemistry*
  • Insecticides / chemistry
  • Insecticides / isolation & purification*
  • Isoptera
  • Oils, Volatile / pharmacology
  • Piperidines / chemistry
  • Piperidines / isolation & purification*
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology

Substances

  • Alkenes
  • Amides
  • Insecticides
  • N-((2E,4E)-tetradecadienoyl)piperidine
  • Oils, Volatile
  • Piperidines
  • Plant Extracts