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Total Synthesis, Absolute Configuration, and Phytotoxic Activity of Foeniculoxin
Akane Yamagishi1, Yuki Egoshi1, Makoto T Fujiwara2
1Organic Chemistry Laboratory, Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo, 102-8554, Japan.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 10, 2022
Summary
Researchers synthesized foeniculoxin, a phytotoxin from Phomopsis foeniculi. This study details its synthesis and reveals its role in plant cell death by damaging chloroplasts and mitochondria in Arabidopsis thaliana.
Area of Science:
- Natural Product Synthesis
- Plant Pathology
- Cell Biology
Background:
- Foeniculoxin is a significant phytotoxin identified in Italian Phomopsis foeniculi strains.
- Understanding its structure and biological activity is crucial for plant disease research.
Purpose of the Study:
- To achieve the first total synthesis of foeniculoxin.
- To elucidate the phytotoxicity and cellular mechanisms of foeniculoxin action.
- To determine the absolute configuration of foeniculoxin.
Main Methods:
- Total synthesis employing ene reaction and Sonogashira cross-coupling.
- Chiral separation and advanced Mosher's method for absolute configuration determination.
- Syringe-based infiltration assays in Chenopodium album and Arabidopsis thaliana.
Main Results:
- Successful total synthesis of foeniculoxin was accomplished.
- Phytotoxicity was confirmed, with foeniculoxin inducing cellular defects in Arabidopsis thaliana leaves prior to lesion development.
- Observed defects included protein leakage from chloroplasts and mitochondria, and mitochondrial morphological changes.
- Foeniculoxin induced mitochondrial agglomeration around chloroplasts, a phenomenon also observed with hygromycin B.
Conclusions:
- The total synthesis provides access to foeniculoxin for further study.
- Foeniculoxin disrupts plant cell integrity, particularly affecting chloroplasts and mitochondria.
- Mitochondrial-chloroplast interactions are implicated as an early event in foeniculoxin-induced plant cell death.
