title: Ring-fluorinated analog of methyl eugenol: attractiveness to and metabolism in the oriental fruit fly, Bactrocera dorsalis (Hendel).
abstract: Oriental fruit fly, Bactrocera dorsalis (Hendel), males are highly attracted to the natural phenylpropanoid methyl eugenol (ME). They compulsively feed on ME and metabolize it to ring and side-chain hydroxylated compounds that have both pheromonal and allomonal functions. Side-chain metabolic activation of ME leading to (E)-coniferyl alcohol has long been recognized as a primary reason for hepatocarcinogenicity of this compound in rodents. Earlier, we demonstrated that introduction of a fluorine atom at the terminal carbon of the ME side chain significantly depressed metabolism and specifically reduced formation of coniferyl alcohol but had little effect on field attractiveness to B. dorsalis. In the current paper, we demonstrate that fluorination of ME at the 4 position of the aromatic ring blocks metabolic ring-hydroxylation but overall enhances side-chain metabolism by increasing production of fluorinated (E)-coniferyl alcohol. In laboratory experiments, oriental fruit fly males were attracted to and readily consumed 1,2-dimethoxy-4-fluoro-5-(2-propenyl)benzene (I) at rates similar to ME but metabolized it faster. Flies that consumed the fluorine analog were as healthy post feeding as ones fed on methyl eugenol. In field trials, the fluorine analog I was approximately 50% less attractive to male B. dorsalis than ME.
authors.affiliation: Beltsville Agricultural Research Center, USDA-ARS, MD 20705, USA. ashot.khrimian@ars.usda.gov
authors.forename: Ashot
authors.initials: A
authors.lastname: Khrimian
authors.forename: Matthew S
authors.initials: MS
authors.lastname: Siderhurst
authors.forename: Grant T
authors.initials: GT
authors.lastname: Mcquate
authors.forename: Nicanor J
authors.initials: NJ
authors.lastname: Liquido
authors.forename: Janice
authors.initials: J
authors.lastname: Nagata
authors.forename: Lori
authors.initials: L
authors.lastname: Carvalho
authors.forename: Filadelfo
authors.initials: F
authors.lastname: Guzman
authors.forename: Eric B
authors.initials: EB
authors.lastname: Jang
mesh_terms: D000818:Animals; D005054:Eugenol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D005247:Feeding Behavior; D054879:Halogenation; D006900:Hydroxylation; D008297:Male; D010636:Phenols / Q000737:chemistry; D033621:Tephritidae / Q000378:metabolism*
chemical_list: C541424:1,2-dimethoxy-4-fluoro-5-(2-propenyl)benzene; D010636:Phenols; C005223:methyleugenol; D005054:Eugenol; C010559:coniferyl alcohol