title: Sex pheromone of the pink hibiscus mealybug, Maconellicoccus hirsutus, contains an unusual cyclobutanoid monoterpene.
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.
authors.affiliation: 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
authors.forename: Aijun
authors.initials: A
authors.lastname: Zhang
authors.forename: Divina
authors.initials: D
authors.lastname: Amalin
authors.forename: Shyam
authors.initials: S
authors.lastname: Shirali
authors.forename: Miguel S
authors.initials: MS
authors.lastname: Serrano
authors.forename: Rosa A
authors.initials: RA
authors.lastname: Franqui
authors.forename: James E
authors.initials: JE
authors.lastname: Oliver
authors.forename: Jerome A
authors.initials: JA
authors.lastname: Klun
authors.forename: Jeffrey R
authors.initials: JR
authors.lastname: Aldrich
authors.forename: Dale E
authors.initials: DE
authors.lastname: Meyerdirk
authors.forename: Stephen L
authors.initials: SL
authors.lastname: Lapointe
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000818:Animals; D001042:Aphids / Q000737:chemistry* / Q000187:drug effects / Q000502:physiology; D001681:Biological Assay; D001685:Biological Factors / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002087:Butyrates / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D003503:Cyclobutanes / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D004952:Esters / Q000737:chemistry; D005260:Female; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D015394:Molecular Structure; D039821:Monoterpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification*; D012724:Sex Attractants / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D012726:Sexual Behavior, Animal / Q000187:drug effects; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism
chemical_list: C488425:(2,2-dimethyl-3-(1-methylethylidene)cyclobutyl)methyl 2-methylbutanoate; C488424:2-isopropenyl-5-methyl-4-hexenyl 2-methylbutanoate; D000438:Alcohols; D001685:Biological Factors; D002087:Butyrates; D003503:Cyclobutanes; D004952:Esters; D039821:Monoterpenes; D012724:Sex Attractants; D013729:Terpenes; C488426:maconelliol