Sex pheromone of the pink hibiscus mealybug, Maconellicoccus hirsutus, contains an unusual cyclobutanoid monoterpene.
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.
Zhang
Aijun
A
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
Amalin
Divina
D
Shirali
Shyam
S
Serrano
Miguel S
MS
Franqui
Rosa A
RA
Oliver
James E
JE
Klun
Jerome A
JA
Aldrich
Jeffrey R
JR
Meyerdirk
Dale E
DE
Lapointe
Stephen L
SL
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
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