Metabolism of (-)-grandisin from Piper solmsianum in Coleoptera and Lepidoptera species.
The biotransformation of the major Piper solmsianum leaf phenylpropanoids, such as the tetrahydrofuran lignan grandisin and derivatives was investigated in the beetle Naupactus bipes as well as in the caterpillars Heraclides hectorides and Quadrus u-lucida. Analysis of fecal material indicated that metabolism occurred mainly through mono- and di-O-demethylation at para positions of 3,4,5-trimethoxyphenyl rings of tetrahydrofuran lignans during digestion by these insects. Additionally, 3-hydroxy-4,5-dimethoxycinnamyl and 3,4,5-trimethoxycinnamyl alcohols were identified in fecal extracts of N. bipes.
Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, 05508-900 São Paulo, SP, Brazil.
Clécio S
CS
Ramos
Sérgio A
SA
Vanin
Massuo J
MJ
Kato
D000818:Animals; D001517:Coleoptera / Q000378:metabolism*; D005663:Furans / Q000737:chemistry* / Q000378:metabolism*; D007915:Lepidoptera / Q000378:metabolism*; D017705:Lignans / Q000737:chemistry* / Q000378:metabolism*; D015394:Molecular Structure; D031701:Piper / Q000378:metabolism*; D020005:Propanols / Q000737:chemistry / Q000378:metabolism
D005663:Furans; D017705:Lignans; D020005:Propanols; C439395:1-phenylpropanol; C074346:grandisin