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Analysis of the Solvent Accessibility of Cysteine Residues on Maize rayado fino virus Virus-like Particles Produced in Nicotiana benthamiana Plants and Cross-linking of Peptides to VLPs

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Absolute configuration of volicitin from the regurgitant of lepidopteran caterpillars and biological activity of

Yoshitsugu Sawada¹, Naoko Yoshinaga, Kenji Fujisaki

¹Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Sakyo, Kyoto, Japan.

Bioscience, Biotechnology, and Biochemistry

|September 9, 2006

Summary

This summary is machine-generated.

Insect-produced plant volatile elicitors, volicitin and N-linolenoyl-L-glutamine, were studied. The L-glutamine part of volicitin is more crucial for volatile release than the hydroxyl group.

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Area of Science:

Plant Science
Insect Chemical Ecology
Organic Chemistry

Background:

Volicitin, an N-(17-hydroxylinolenoyl)-L-glutamine conjugate, and N-linolenoyl-L-glutamine are insect-derived compounds that elicit plant volatile release.
Understanding the structure-activity relationship of these elicitors is key to plant defense signaling.

Purpose of the Study:

To determine the absolute configuration of the hydroxylinolenoyl moiety in volicitin from three noctuid moth species.
To investigate the role of the hydroxyl and L-glutamine moieties in volicitin's elicitor activity.

Main Methods:

Chiral analysis to determine the absolute configuration of the hydroxylinolenoyl group.
Treatment of corn seedlings with synthesized volicitin isomers and N-linolenoyl-L-glutamine.
Quantification of volatile organic compounds released by treated seedlings.

Main Results:

The absolute configuration of the hydroxylinolenoyl moiety in volicitin from Helicoverpa armigera, Mythimna separata, and Spodoptera litura was confirmed as 17S with high enantiomeric excess.
Both (17S)- and (17R)-volicitin isomers induced volatile release in corn seedlings without significant difference.
N-linolenoyl-L-glutamine showed approximately 30% of volicitin's activity, and only the L-glutamine conjugate among synthesized analogs induced volatile emission.

Conclusions:

The L-glutamine moiety is more critical for volicitin's elicitor activity than the hydroxyl moiety.
Both structural components contribute to the induction of plant volatile release by volicitin.