title: Piperidinyl amides with insecticidal activity from the maritime plant Otanthus maritimus.
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.
authors.affiliation: Department of Pharmacy, Division of Pharmacognosy and Chemistry of Natural Products, University of Athens, Panepistimiopolis Zografou, 15771 Athens, Greece.
authors.forename: Lito
authors.initials: L
authors.lastname: Christodoulopoulou
authors.forename: Maria
authors.initials: M
authors.lastname: Tsoukatou
authors.forename: Leto A
authors.initials: LA
authors.lastname: Tziveleka
authors.forename: Constantinos
authors.initials: C
authors.lastname: Vagias
authors.forename: Panos V
authors.initials: PV
authors.lastname: Petrakis
authors.forename: Vassilios
authors.initials: V
authors.lastname: Roussis
mesh_terms: D000475:Alkenes / Q000737:chemistry / Q000302:isolation & purification; D000577:Amides / Q000737:chemistry / Q000302:isolation & purification*; D000818:Animals; D001000:Ants; D019659:Asteraceae / Q000737:chemistry*; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification*; D020049:Isoptera; D009822:Oils, Volatile / Q000494:pharmacology; D010880:Piperidines / Q000737:chemistry / Q000302:isolation & purification*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000475:Alkenes; D000577:Amides; D007306:Insecticides; C499939:N-((2E,4E)-tetradecadienoyl)piperidine; D009822:Oils, Volatile; D010880:Piperidines; D010936:Plant Extracts