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Structure Activity Relationship for Fumonisin Phytotoxicity.

Justin B Renaud¹, Natasha DesRochers¹, Shawn Hoogstra¹

¹London Research and Development Centre, Agriculture and Agri-Food Canada, 1391 Sandford Street, London, Ontario N5V 4T3, Canada.

Chemical Research in Toxicology

|April 23, 2021

Summary

This summary is machine-generated.

Fumonisins are mycotoxins that inhibit ceramide synthase. This study shows the amine group, not just the tricarballylic acid side chains, is crucial for fumonisin toxicity in plants.

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Area of Science:

Mycology
Plant Science
Biochemistry

Background:

Fumonisins are polyketide mycotoxins produced by Fusarium and Aspergillus species.
They inhibit Ceramide Synthase (CerS), disrupting sphingolipid metabolism.
The roles of fumonisin's tricarballylic acid side chains and amine group in toxicity are not fully elucidated.

Purpose of the Study:

To investigate the individual contributions of tricarballylic acid side chains and the amine group to fumonisin toxicity.
To compare the toxicity of fumonisin B1 (FB1) with its hydrolyzed, deaminated, and hydrolyzed/deaminated analogues.
To analyze the effects of these fumonisins on plant lipid and metabolite profiles.

Main Methods:

Structure/function activity assay using Lemna minor (duckweed) exposed to FB1 and its analogues (hFB1, FPy1, hFPy1) at 40 μM.
Monitoring of plant dry weight and frond surface area.
Lipidomic and metabolomic profiling to assess biochemical changes.

Main Results:

Hydrolyzed FB1 (hFB1) and deaminated FB1 (FPy1) were less toxic than FB1.
Hydrolyzed/deaminated FB1 (hFPy1) showed reduced toxicity compared to FB1 and hFB1, but not significantly less than FPy1.
FB1 altered lipid profiles (increasing phosphotidylcholines, ceramides; decreasing chlorophyll) and metabolite levels (e.g., phenylalanine, ADMA).
hFB1 uniquely elevated citrulline, N-acetylornithine, and ornithine.

Conclusions:

Removal of tricarballylic acid side chains significantly reduces fumonisin toxicity.
The amine functional group is a key contributor to fumonisin toxicity in Lemna minor.
Findings support further investigation of fumonisin toxicity mechanisms in mammalian systems.