| Title: | "Sex pheromone of the pink hibiscus mealybug, Maconellicoccus hirsutus, contains an unusual cyclobutanoid monoterpene" |
| Author(s): | Zhang A; Amalin D; Shirali S; Serrano MS; Franqui RA; Oliver JE; Klun JA; Aldrich JR; Meyerdirk DE; Lapointe SL; |
| Address: | "Chemicals Affecting Insect Behavior Laboratory, Beltsville Agriculture Research Center West, Agricultural Research Service, United States Department of Agriculture, Beltsville, MD 20705, USA. zhanga@bars.ars.usda.gov" |
| ISSN/ISBN: | 0027-8424 (Print) 1091-6490 (Electronic) 0027-8424 (Linking) |
| Abstract: | "Two compounds that together constitute the female sex pheromone of the pink hibiscus mealybug (PHM), Maconellicoccus hirsutus, were isolated, identified, and synthesized. They are (R)-2-isopropenyl-5-methyl-4-hexenyl (S)-2-methylbutanoate [common name is (R)-lavandulyl (S)-2-methylbutanoate] and [(R)-2,2-dimethyl-3-(1-methylethylidene)cyclobutyl]methyl (S)-2-methylbutanoate [which we refer to as (R)-maconelliyl (S)-2-methylbutanoate]. Maconelliol is an unusual cyclobutanoid monoterpene, and its structure has been established by enantioselective synthesis from precursors of known structure and configuration. A 1:5 synthetic mixture of the two RS esters (1 microg per rubber septum) proved to be a potent attractant of males in field bioassays. The pheromone component, maconelliyl 2-methylbutanoate, represents a heretofore undescribed natural product" |
| Keywords: | Alcohols/chemistry Animals Aphids/*chemistry/drug effects/physiology Biological Assay Biological Factors/chemical synthesis/chemistry/isolation & purification/pharmacology Butyrates/chemical synthesis/chemistry/isolation & purification Cyclobutanes/chemic; |
| Notes: | "MedlineZhang, Aijun Amalin, Divina Shirali, Shyam Serrano, Miguel S Franqui, Rosa A Oliver, James E Klun, Jerome A Aldrich, Jeffrey R Meyerdirk, Dale E Lapointe, Stephen L eng 2004/06/16 Proc Natl Acad Sci U S A. 2004 Jun 29; 101(26):9601-6. doi: 10.1073/pnas.0401298101. Epub 2004 Jun 14" |
