title: Hyperforin and deoxycohumulone as a larvicidal agent against Culex pipiens (Diptera: Culicidae).
abstract: The larvicidal effect of hyperforin (1), a bioactive compound of Hypericum perforatum, and deoxycohumulone (2) (biosynthetic precursor of hyperforin) were evaluated against Culex pipiens (Diptera: Culicidae) for the first time. All the acetate analogues (3-6) of hyperforin (1) and deoxycohumulone (2) were also synthesized and bioassayed to provide information on structural requirements for the tested compounds. Larvicidal results revealed that hyperforin (1) and deoxycohumulone (2) exhibited potent activity with LC50 value of 26.72 and 51.03 mg L(-1), respectively. The monoacetyl-deoxycohumulone (4) displayed lower activity with LC50 value of 135.92 mg L(-1), while all other acetate analogues were inactive at concentrations even as high as 150 mg L(-1), indicating that the free hydroxyl groups are essential for the larvicidal activity. The mortality values were increased, more than 80%, when 10 mg L(-1) piperonyl butoxide were added in hyperforin (1) or deoxycohumulone (2) bioassays. Finally, sub-lethal survival analysis is conducted for three doses of hyperforin (1) and deoxycohumulone (2) and results are discussed.
authors.affiliation: Natural Products Synthesis and Bioorganic Chemistry Laboratory, Institute of Advanced Materials, Physicochemical Processes, Nanotechnology and Microsystems, NCSR "Demokritos" 15310 Ag. Paraskevi, Attiki, POB 60228, Athens, Greece; Chemistry Laboratories, Agricultural University of Athens, 75 Iera Odos Str., 11855 Athens, Greece.
authors.forename: Kornilia P
authors.initials: KP
authors.lastname: Mitsopoulou
authors.affiliation: Natural Products Synthesis and Bioorganic Chemistry Laboratory, Institute of Advanced Materials, Physicochemical Processes, Nanotechnology and Microsystems, NCSR "Demokritos" 15310 Ag. Paraskevi, Attiki, POB 60228, Athens, Greece.
authors.forename: Veroniki P
authors.initials: VP
authors.lastname: Vidali
authors.affiliation: Laboratory of Biological Control of Pesticides, Benaki Phytopathological Institute, 8 S. Delta Str., 14561 Kifissia, Athens, Greece.
authors.forename: George
authors.initials: G
authors.lastname: Koliopoulos
authors.affiliation: Natural Products Synthesis and Bioorganic Chemistry Laboratory, Institute of Advanced Materials, Physicochemical Processes, Nanotechnology and Microsystems, NCSR "Demokritos" 15310 Ag. Paraskevi, Attiki, POB 60228, Athens, Greece; Chemistry Laboratories, Agricultural University of Athens, 75 Iera Odos Str., 11855 Athens, Greece.
authors.forename: Elias A
authors.initials: EA
authors.lastname: Couladouros
authors.affiliation: Laboratory of Agricultural Entomology, Department of Entomology and Agricultural Zoology, Benaki Phytopathological Institute, 8 S. Delta Str., 14561 Kifissia, Athens, Greece. Electronic address: a.michaelakis@bpi.gr.
authors.forename: Antonios
authors.initials: A
authors.lastname: Michaelakis
mesh_terms: D000818:Animals; D003465:Culex; D003512:Cyclohexanones / Q000138:chemical synthesis / Q000737:chemistry; D004305:Dose-Response Relationship, Drug; D004357:Drug Synergism; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry; D007814:Larva / Q000187:drug effects; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D010882:Piperonyl Butoxide; D013729:Terpenes / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D003512:Cyclohexanones; D007306:Insecticides; D013729:Terpenes; C000591672:deoxycohumulone; C442487:cohumulone; D010696:Phloroglucinol; D010882:Piperonyl Butoxide; C001654:hyperforin
keywords: Hypericum perforatum; Larvicidal activity; Piperonyl butoxide; Sub-lethal effect; West Nile virus (WNV)