Piperidinyl amides with insecticidal activity from the maritime plant Otanthus maritimus.
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.
Christodoulopoulou
Lito
L
Department of Pharmacy, Division of Pharmacognosy and Chemistry of Natural Products, University of Athens, Panepistimiopolis Zografou, 15771 Athens, Greece.
Tsoukatou
Maria
M
Tziveleka
Leto A
LA
Vagias
Constantinos
C
Petrakis
Panos V
PV
Roussis
Vassilios
V
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
D000475:Alkenes; D000577:Amides; D007306:Insecticides; C499939:N-((2E,4E)-tetradecadienoyl)piperidine; D009822:Oils, Volatile; D010880:Piperidines; D010936:Plant Extracts