Diverting phenylpropanoid pathway flux from sinapine to produce industrially useful 4-vinyl derivatives of hydroxycinnamic acids in Brassicaceous oilseeds

A - Papers appearing in refereed journals

Menard, G. N., Langdon, M., Bhunia, R., Shankhapal, A., Noleto-Dias, C., Lomax, C., Ward, J. L., Kurup, S. and Eastmond, P. J. 2022. Diverting phenylpropanoid pathway flux from sinapine to produce industrially useful 4-vinyl derivatives of hydroxycinnamic acids in Brassicaceous oilseeds. Metabolic Engineering. 70, pp. 196-205. https://doi.org/10.1016/j.ymben.2022.01.016

AuthorsMenard, G. N., Langdon, M., Bhunia, R., Shankhapal, A., Noleto-Dias, C., Lomax, C., Ward, J. L., Kurup, S. and Eastmond, P. J.
Abstract

Sinapine (sinapoylcholine) is an antinutritive phenolic compound that can account for up to 2% of seed weight in brassicaceous oilseed crops and reduces the suitability of their protein-rich seed meal for use as animal feed. Sinapine biosynthesis draws on hydroxycinnamic acid precursors produced by the phenylpropanoid pathway. The 4-vinyl derivatives of several hydroxycinnamic acids have industrial applications. For example, 4-vinyl phenol (4-hydroxystyrene) is a building block for a range of synthetic polymers applied in resins, inks, elastomers, and coatings. Here we have expressed a modified bacterial phenolic acid decarboxylase (PAD) in developing seed of Camelina sativa to redirect phenylpropanoid pathway flux from sinapine biosynthesis to the production of 4-vinyl phenols. PAD expression led to a ∼95% reduction in sinapine content in seeds of both glasshouse and field grown C. sativa and to an accumulation of 4-vinyl derivatives of hydroxycinnamic acids, primarily as glycosides. The most prevalent aglycone was 4-vinyl phenol, but 4-vinyl guaiacol, 6-hydroxy-4-vinyl guaiacol and 4-vinylsyringol (Canolol) were also detected. The molar quantity of 4-vinyl phenol glycosides was more than twice that of sinapine in wild type seeds. PAD expression was not associated with an adverse effect on seed yield, harvest index, seed morphology, storage oil content or germination in either glasshouse or field experiments. Our data show that expression of PAD in brassicaceous oilseeds can supress sinapine accumulation, diverting phenylpropanoid pathway flux into 4-vinyl phenol derivatives, thereby also providing a non-petrochemical source of this class of industrial chemicals.

KeywordsMetabolic engineering; Plant; Oilseed; 4-Vinyl phenol; 4-Vinyl guaiacol; 4-Vinylsyringol
Year of Publication2022
JournalMetabolic Engineering
Journal citation70, pp. 196-205
Digital Object Identifier (DOI)https://doi.org/10.1016/j.ymben.2022.01.016
Open accessPublished as ‘gold’ (paid) open access
FunderBiotechnology and Biological Sciences Research Council
Funder project or codeTPM - Tailoring Plant Metabolism - Work package 1 (WP1) - High value lipids for health and industry
TPM - Tailoring Plant Metabolism - Work package 2 (WP2) - Designer Willows: high value phenolic glycosides for health and industry
Publisher's version
Supplemental file
Output statusPublished
Publication dates
Online01 Feb 2022
Publication process dates
Accepted29 Jan 2022
PublisherAcademic Press Inc Elsevier Science
ISSN1096-7176

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