title: Metabolic modifications of birch leaf phenolics by an herbivorous insect: detoxification of flavonoid aglycones via glycosylation.
abstract: The metabolic modifications of birch (Betula pubescens Ehrh.) leaf phenolics in the digestive tract of its major defoliator, larvae of the autumnal moth Epirrita autumnata, were studied. The main phenolic acids of birch, i.e. chlorogenic and p-coumaroylquinic acids, were isomerised in the alkaline digestive tract. Moreover, only 16 to 92% of the ingested amounts of chlorogenic acid were found in the faeces of individual larvae; the missing portion is possibly being used in the formation of reactive o-quinones. Water-soluble flavonoid glycosides were mostly excreted unaltered. In contrast, lipophilic flavonoid aglycones were not excreted as such, but as glycosides after being detoxified by E. autumnata via glycosylation. When the larvae were fed with leaf-painted acacetin and kaempferide, i.e. two naturally occurring birch leaf flavonoid aglycones, acacetin-7-O-glucoside and kaempferide-3-O-glucoside appeared in larval faeces as major metabolites. However, the efficiency of aglycone glycosylation varied-, ranging from 17 to 33%, depending on the aglycone and its dietary level. There was also large variation in the efficiency of glycosylation--from 2 to 57%--among individual larvae. These results demonstrate a compound-specific metabolism of phenolic compounds, leading to different phenolic profiles in the insect gut compared to its leaf diet.
authors.affiliation: Laboratory of Environmental Chemistry, Department of Chemistry, University of Turku, Turku, Finland. j-p.salminen@utu.fi
authors.forename: Juha-Pekka
authors.initials: JP
authors.lastname: Salminen
authors.forename: Maria
authors.initials: M
authors.lastname: Lahtinen
authors.forename: Kyösti
authors.initials: K
authors.lastname: Lempa
authors.forename: Lauri
authors.initials: L
authors.lastname: Kapari
authors.forename: Erkki
authors.initials: E
authors.lastname: Haukioja
authors.forename: Kalevi
authors.initials: K
authors.lastname: Pihlaja
mesh_terms: D000818:Animals; D029662:Betula / Q000469:parasitology*; D002851:Chromatography, High Pressure Liquid; D004317:Doxorubicin / Q000031:analogs & derivatives / Q000378:metabolism; D047309:Flavones / Q000378:metabolism; D005419:Flavonoids / Q000378:metabolism*; D006031:Glycosylation; D062385:Hydroxybenzoates / Q000378:metabolism*; D044949:Kaempferols / Q000378:metabolism; D007814:Larva / Q000378:metabolism; D013058:Mass Spectrometry; D009036:Moths / Q000254:growth & development / Q000472:pathogenicity*; D010935:Plant Diseases / Q000469:parasitology; D018515:Plant Leaves / Q000378:metabolism*
chemical_list: D047309:Flavones; D005419:Flavonoids; D062385:Hydroxybenzoates; D044949:Kaempferols; C449720:kaempferide; D004317:Doxorubicin; C017616:phenolic acid; C023717:acacetin