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Transient Expression in Nicotiana Benthamiana Leaves for Triterpene Production at a Preparative Scale

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Veratrole biosynthesis in white campion.

Tariq A Akhtar¹, Eran Pichersky

¹Department of Molecular, Cellular, and Developmental Biology, University of Michigan, Ann Arbor, Michigan 48109, USA.

Plant Physiology

|April 3, 2013

Summary

White campion flowers produce veratrole, a pollinator attractant, from phenylalanine. This study reveals veratrole biosynthesis involves guaiacol methylation, originating from phenylalanine via benzoic acid and salicylic acid.

Area of Science:

Plant biochemistry
Chemical ecology
Biosynthesis pathways

Background:

White campion (Silene latifolia) emits 1,2-dimethoxybenzene (veratrole), a pollinator attractant for the moth Hadena bicruris.
The biosynthesis of veratrole, a key floral volatile, is not well understood.
Methylation of guaiacol has been proposed as a step in veratrole production.

Purpose of the Study:

To elucidate the biosynthetic pathway of veratrole in white campion flowers.
To identify the precursors and enzymes involved in veratrole synthesis.
To investigate the genetic basis and variability of veratrole emission in white campion populations.

Main Methods:

Stable isotope feeding studies using [(13)C9]l-phenylalanine, [(2)H5]benzoic acid, and [(2)H6]salicylic acid.

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Enzyme inhibition assays using phenylalanine ammonia lyase inhibitor 2-aminoindan-2-phosphonic acid.

Purification and characterization of guaiacol O-methyltransferase (GOMT) activity and identification of the corresponding gene (SlGOMT1).

Analysis of floral volatile emissions and SlGOMT1 gene expression in different white campion plants.

Main Results:

Feeding with l-phenylalanine increased guaiacol and veratrole emission, with stable isotopes incorporated into both compounds.
Inhibition of phenylalanine ammonia lyase significantly reduced guaiacol and veratrole levels.
Benzoic acid and salicylic acid feeding increased veratrole emission, and isotope labeling confirmed their role as precursors via salicylic acid.
Guaiacol O-methyltransferase (GOMT) was purified, and its gene (SlGOMT1) was identified and found to be expressed only in veratrole-emitting plants.
Variability in veratrole emission and GOMT activity was observed among white campion populations.

Conclusions:

Veratrole biosynthesis in white campion flowers proceeds via the methylation of guaiacol.
Guaiacol originates from l-phenylalanine, through benzoic acid and salicylic acid intermediates.
This pathway represents a novel branch point in the general phenylpropanoid pathway.
The genetic basis for veratrole production is variable within white campion populations.