Remarkable substrate-specificity of CYP6AB3 in Depressaria pastinacella, a highly specialized caterpillar

Insect Molecular Biology
W MaoM R Berenbaum

Abstract

The parsnip webworm, Depressaria pastinacella, a specialist on two genera in Apiaceae, feeds exclusively on the furanocoumarin-containing reproductive structures of its host plants. This caterpillar relies principally on cytochrome P450-mediated detoxification for coping with the high concentrations of furanocoumarins in its diet. A cDNA encoding the furanocoumarin-inducible P450 CYP6AB3 from this species was coexpressed with house-fly NADPH P450 reductase in baculovirus-infected Sf9 cells and tested for binding and metabolism of the six furanocoumarins typically encountered in host plant tissues. Only imperatorin and bergapten bind in close proximity to the catalytic haem and only imperatorin is metabolized (V(max) and K(m) of 2.412 pmol/min per pmol P450 and 94.28 microm, respectively). Purification of the imperatorin metabolite by normal phase HPLC and characterization of its structure by MS-MS analysis indicate that CYP6AB3 initially epoxidizes the carbon-carbon pi-bond on the isoprenyl side chain on imperatorin. An improved molecular model for the CYP6AB3 protein based on this biochemical characterization and the recently defined mammalian CYP3A4 crystal structure provides insight into the remarkable substrate specificity ...Continue Reading

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Citations

Sep 1, 2012·Journal of Toxicology and Environmental Health. Part B, Critical Reviews·Michael Murray
Mar 5, 2008·Plant Physiology·May R Berenbaum, Arthur R Zangerl
Jul 21, 2012·Journal of Economic Entomology·Yue-E ZhangZe Zhang
Sep 25, 2015·Plant Cell Reports·Andrew Maxwell P JonesPraveen K Saxena
Oct 5, 2010·Biochimica Et Biophysica Acta·Mary A Schuler
May 31, 2008·Insect Biochemistry and Molecular Biology·Wenfu MaoMary A Schuler
Feb 28, 2007·Trends in Ecology & Evolution·Laurence DesprésChristiane Gallet
Nov 10, 2009·Evolution; International Journal of Organic Evolution·Steph B J MenkenErik J van Nieukerken
Feb 20, 2010·Insect Molecular Biology·J G OakeshottC Claudianos
Feb 5, 2013·Insect Biochemistry and Molecular Biology·Minmin SongClaus Tittiger
Feb 22, 2017·Annals of the New York Academy of Sciences·Kim L Vertacnik, Catherine R Linnen
Feb 22, 2012·Journal of Chemical Ecology·Arthur R ZangerlMay R Berenbaum
Dec 15, 2016·Frontiers in Plant Science·Julie A PetersonJames D Harwood
Jan 3, 2021·Current Opinion in Insect Science·Kai LuRensen Zeng
May 23, 2019·Current Opinion in Insect Science·Paul J Ode

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