title: Sigillin A, a unique polychlorinated arthropod deterrent from the snow flea Ceratophysella sigillata.
abstract: The snow flea Ceratophysella sigillata, a winter-active species of springtail, produces unique polychlorinated octahydroisocoumarins to repel predators. The structure of the major compound, sigillin A, was elucidated through isolation, spectroscopic analysis, and X-ray crystallography. Sigillin A showed high repellent activity in a bioassay with predatory ants. A promising approach for the total synthesis of members of this new class of natural compounds was also developed.
authors.affiliation: Institut für Organische Chemie, TU Braunschweig, Hagenring 30, 38106 Braunschweig (Germany) http://www.oc.tu-bs.de/schulz/index.html.
authors.forename: Witali
authors.initials: W
authors.lastname: Schmidt
authors.affiliation: Institut für Organische Chemie, TU Braunschweig, Hagenring 30, 38106 Braunschweig (Germany) http://www.oc.tu-bs.de/schulz/index.html.
authors.forename: Thies M
authors.initials: TM
authors.lastname: Schulze
authors.affiliation: Institut für Organische Chemie, TU Braunschweig, Hagenring 30, 38106 Braunschweig (Germany) http://www.oc.tu-bs.de/schulz/index.html.
authors.forename: Gregor
authors.initials: G
authors.lastname: Brasse
authors.affiliation: Institut für Organische Chemie, TU Braunschweig, Hagenring 30, 38106 Braunschweig (Germany) http://www.oc.tu-bs.de/schulz/index.html.
authors.forename: Edyta
authors.initials: E
authors.lastname: Nagrodzka
authors.affiliation: Institut für Organische Chemie, TU Braunschweig, Hagenring 30, 38106 Braunschweig (Germany) http://www.oc.tu-bs.de/schulz/index.html.
authors.forename: Michael
authors.initials: M
authors.lastname: Maczka
authors.affiliation: Speichergasse 8, 3150 Schwarzenburg (Switzerland).
authors.forename: Jürg
authors.initials: J
authors.lastname: Zettel
authors.affiliation: Institut für Analytische und Anorganische Chemie, TU Braunschweig, Hagenring 30, 38106 Braunschweig (Germany).
authors.forename: Peter G
authors.initials: PG
authors.lastname: Jones
authors.affiliation: Institut für Organische Chemie, TU Braunschweig, Hagenring 30, 38106 Braunschweig (Germany) http://www.oc.tu-bs.de/schulz/index.html.
authors.forename: Jörg
authors.initials: J
authors.lastname: Grunenberg
authors.affiliation: Institut für Biologie, Freie Universität Berlin, Haderslebener Strasse 9, 12163 Berlin (Germany).
authors.forename: Monika
authors.initials: M
authors.lastname: Hilker
authors.affiliation: Institut für Biologie, Freie Universität Berlin, Haderslebener Strasse 9, 12163 Berlin (Germany).
authors.forename: Ute
authors.initials: U
authors.lastname: Trauer-Kizilelma
authors.affiliation: Institut für Biologie, Freie Universität Berlin, Haderslebener Strasse 9, 12163 Berlin (Germany).
authors.forename: Ute
authors.initials: U
authors.lastname: Braun
authors.affiliation: Institut für Organische Chemie, TU Braunschweig, Hagenring 30, 38106 Braunschweig (Germany) http://www.oc.tu-bs.de/schulz/index.html. stefan.schulz@tu-bs.de.
authors.forename: Stefan
authors.initials: S
authors.lastname: Schulz
mesh_terms: D000818:Animals; D001688:Biological Products / Q000737:chemistry*; D049934:Isocoumarins / Q000737:chemistry*; D015394:Molecular Structure; D005423:Siphonaptera
chemical_list: D001688:Biological Products; D049934:Isocoumarins
keywords: insect repellents; isocoumarine; natural products; organohalogen compounds; α-vinylation