A cytochrome P450 from juvenile mustard leaf beetles hydroxylates geraniol, a 
key step in iridoid biosynthesis

Fu, Nanxia; Yang, Zhi-ling; Pauchet, Yannick; Paetz, Christian; Brandt, Wolfgang; Boland, Wilhelm; Burse, Antje

doi:10.1016/j.ibmb.2019.103212

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A cytochrome P450 from juvenile mustard leaf beetles hydroxylates geraniol, a key step in iridoid biosynthesis

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Fu, Nanxia
Research Group Dr. A. Burse, Chemical Defense of Leaf Beetles, Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;
IMPRS on Ecological Interactions, MPI for Chemical Ecology, Max Planck Society;

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Yang, Zhi-ling
Research Group Dr. F. Beran, Detoxification in Insects, MPI for Chemical Ecology, Max Planck Society;

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Pauchet, Yannick
Department of Entomology, Prof. D. G. Heckel, MPI for Chemical Ecology, Max Planck Society;

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Paetz, Christian
Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society;

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Boland, Wilhelm
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;

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Burse, Antje
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;

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Citation

Fu, N., Yang, Z.-l., Pauchet, Y., Paetz, C., Brandt, W., Boland, W., et al. (2019). A cytochrome P450 from juvenile mustard leaf beetles hydroxylates geraniol, a key step in iridoid biosynthesis. Insect Biochemistry and Molecular Biology, 113: 103212. doi:10.1016/j.ibmb.2019.103212.

Cite as: https://hdl.handle.net/21.11116/0000-0003-9712-E

Abstract

Juveniles of the leaf beetle Phaedon cochleariae synthesize iridoid via the mevalonate pathway to repel predators. The normal terpenoid biosynthesis is integrated into the dedicated defensive pathway by the ω-hydroxylation of geraniol to 8-hydroxygeraniol. Here we identify and characterize the geraniol 8-hydroxylase as a P450 monooxygenase using integrated transcriptomic and proteomic analyses. In the fat body, 73 individual cytochrome P450s were identified. The double stranded RNA (dsRNA)-mediated knock down of CYP6BH5 led to a significant reduction of 8-hydroxygeraniol-glucoside in the hemolymph and, later, of the chrysomelidial in the defensive secretion. Heterologously expressed CYP6BH5 converted geraniol to 8-hydroxygeraniol. In addition to geraniol, CYP6BH5 also catalyzes other monoterpenols, such as nerol and citronellol, into the corresponding α, ω-dihydroxy compounds.