Farinomalein Explained

Farinomalein is a natural maleimide with formula C₁₀H₁₃NO₄ - was first isolated from the entomopathogenic fungus Isaria farinosa (Paecilomyces farinosus) - source H599 (Japan).^[1]

Farinomalein has shown potent and selective inhibition (0.15-5 μg/disk) against eight isolates of plant pathogenic Phytophthora sojae.^[2] These results suggest that farinomalein might be useful as a candidate pesticide for the treatment of Phytophthora stem rot in soybean.

Synthesis

A simple two-stage synthesis from the γ-hydroxybutenolide compound, 5-hydroxy-4-methyl-2-5(H)-furanone, has been reported.^[3] Firstly, the furanone is oxidized to 3-isopropylfuran-2,5-dione by Dess–Martin periodinane, followed by acetic acid reflux with beta-alanine. The white powdered product has a melting point of 75-77 °C.

Notes and References

1. 10.1021/np9002806. 19670877. Farinomalein, a Maleimide-Bearing Compound from the Entomopathogenic Fungus Paecilomyces farinosus. Journal of Natural Products. 72. 8. 1544–6. 2009. Putri. Sastia P. Kinoshita. Hiroshi. Ihara. Fumio. Igarashi. Yasuhiro. Nihira. Takuya.
2. Sastia Prama Putri, Hiroshi Kinoshita, Masayasu Kato and Takuya Nihira. Antimicrobial and antioomycete activities of the novel antibiotic farinomalein. Poster Presentation 2P-2124, Annual Conference, The Society for Bioscience and Bioengineering, Japan, 28 October 2010.
3. 10.1016/j.tetlet.2010.01.083. Synthesis of farinomalein. Tetrahedron Letters. 51. 13. 1710. 2010. Miles. William H. Yan. Ming.