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Gallocatechin biosynthesis via a flavonoid 30,50-hydroxylase is a defense response in Norway spruce against infection by the bark beetle-associated sap-staining fungus Endoconidiophora polonica

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Hammerbacher,  Almuth
Department of Biochemistry, Prof. J. Gershenzon, MPI for Chemical Ecology, Max Planck Society;

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Raguschke,  Bettina
Department of Biochemistry, Prof. J. Gershenzon, MPI for Chemical Ecology, Max Planck Society;

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Wright,  Louwrance
Department of Biochemistry, Prof. J. Gershenzon, MPI for Chemical Ecology, Max Planck Society;

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Gershenzon,  Jonathan
Department of Biochemistry, Prof. J. Gershenzon, MPI for Chemical Ecology, Max Planck Society;

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Citation

Hammerbacher, A., Raguschke, B., Wright, L., & Gershenzon, J. (2018). Gallocatechin biosynthesis via a flavonoid 30,50-hydroxylase is a defense response in Norway spruce against infection by the bark beetle-associated sap-staining fungus Endoconidiophora polonica. Phytochemistry, 148, 78-86. doi:10.1016/j.phytochem.2018.01.017.


Cite as: http://hdl.handle.net/21.11116/0000-0001-291E-1
Abstract
One of the best-studied defense responses to fungal infection in Norway spruce (Picea abies) is the biosynthesis of flavan-3-ols, which accumulate as monomers or polymers known as proanthocyanidins. The individual flavan-3-ol units consist of compounds with a 30,40-dihydroxylated B ring [2,3-(trans)- (þ)-catechin or 2,3-(cis)-()-epicatechin] and compounds with a 30,40,50-trihydroxylated B ring [2,3 (trans)-(þ)-gallocatechin or 2,3-(cis)-()-epigallocatechin]. While much is known about the biosynthesis and biological activity of catechin in Norway spruce, there is little comparable information about gallocatechin or epigallocatechin.We found that there was a significant increase in the gallocatechin content of Norway spruce bark and wood after inoculation with the bark beetle-associated sap-staining fungus Endoconidiophora polonica. Gallocatechins increased proportionally more than catechins as both monomers and units of polymers. A flavonoid 30,50-hydroxylase gene identified in Norway spruce was shown by heterologous expression in Nicotiana benthamiana to be involved in the conversion of 2,3 (trans)-(þ)-catechin to 2,3 (trans)-(þ)-gallocatechin. The formation of the trihydroxylated B ring in Norway spruce occurs at the level of flavan-3-ols, rather than at the level of dihydroflavonols as in many angiosperms. The transcript abundance of the flavonoid 30,50- hydroxylase gene also increased significantly during fungal infection underlining its importance in gallocatechin biosynthesis. Comparisons of the effect of 2,3 (trans)-(þ)-catechin and 2,3 (trans)- (þ)-gallocatechin on fungal growth revealed that 2,3 (trans)-(þ)-catechin is a stronger inhibitor of fungal growth, while 2,3 (trans)-(þ)-gallocatechin is a stronger inhibitor of melanin biosynthesis.