Synthesis and Antifeedant Properties of N-Acylphenylisoserinates of lactarius Sesquiterpenoid Alcohols

• Autorzy: Kopczacki, P. , Gumułka, M. , Masnyk, M. , Sarosiek, A. , Barycki, R. , Ignacak, W. , Żochowski, S. , Grabarczyk, H. , Nowak, G. , Daniewski, W
• Języki publikacji: EN

Abstrakty

EN

The esterification of various sesquiterpenoid alcohols of Lactarius origin with Nbenzoyl-[ 2R,3S]-phenylisoserine (side chain of TaxolŽ), N-acetyl-[2R,3S]-phenylisoserine and N-tert-butoxy-[2R,3S]-phenylisoserine (side chain of TaxotereŽ) produced compounds whose antifeedant properties against storage pests Tribolium confusum, Trogoderma granarium, Sitophylus granarius and Rhizoperta dominica were measured. The introduction of the ester moiety in these molecules, in comparison to original compounds, moderately enhanced their antifeedant activities, as well as changed their selectivity of activity towards the test insects.

Słowa kluczowe

EN

sesquiterpenoid alcohols isolated from mushrooms of Lactarius genus; N-benzoylphenylisoserinates; N-tert-butoxyphenylisoserinates; N-acetylphenylisoserinates; Lactarius sesquiterpenoid; Taxotere; taxol; storage pests; Tribolium confusum; Trogoderma granarium; Sitophilus granarius; Rhizopertha dominica

• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2004
• Tom: Vol. 78 / nr 1
• Strony: 89-108
• Opis fizyczny: Bibliogr. 12 poz., rys.

Twórcy

autor

Kopczacki, P.

• Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

autor

Gumułka, M.

• Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

autor

Masnyk, M.

• Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

autor

Sarosiek, A.

• Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

autor

Barycki, R.

• Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

autor

Ignacak, W.

• Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

autor

Żochowski, S.

• Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

autor

Grabarczyk, H.

• Department of Medicinal Plants, Academy of Medicine, Mazowiecka 33, 60-623 Poznań, Poland

autor

Nowak, G.

• Department of Medicinal Plants, Academy of Medicine, Mazowiecka 33, 60-623 Poznań, Poland

autor

Daniewski, W

• Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

Bibliografia

• 1. Daniewski W.M., Gumułka M., Anczewski W., Masnyk M., Błoszyk E. and Gupta K.K., Phytochem., 49, 1279(1998).
• 2. Daniewski W.M., Gumułka M., Ptaszyńska K., Skibicki P., Błoszyk E., Drożdż B., Stromberg S., Norin T. and Hołub M., Eur. J. Entomol., 90, 65 (1993).
• 3. Daniewski W.M., Gumułka M., Przesmycka D., Ptaszyńska K., Błoszyk E. and Drożdż B., Phytochem 38, 1161 (1995).
• 4. Kopczacki P., Gumułka M., Masnyk M., Grabarczyk H., Nowak G. and Daniewski W.M., Phytochem 58, 775 (2001).
• 5. Daniewski W.M. and Vidari G., Progress in the Chemistry ofOrganic Natural Products, 77,69 (1999).
• 6. Daniewski W.M., Gumułka M., Kopczacki P. and Masnyk M., Polish J. Chem., 75, 1287 (2001).
• 7. Sarosiek A., Masnyk M., Gumulka M., Daniewski W.M., Kobus M., Krawczyk E. and Łuczak M., PolishJ. Chem., 76, 73 (2002).
• 8. Barycki R., Gumułka M., Masnyk M., Daniewski W.M., Kobus M. and Łuczak M., CoIIec Czech. Chem. Commun., 67, 75 (2002).
• 9. Mangatal L., Adeline M.-T., Guenard D., Guerite-Vogelein F. and Potier P., Tetrahedron, 45, 4177 (1989).
• 10. Bourzat J.D. and Commercon A., Tetraherdon Lett., 34, 6049 (1993).
• 11. Didier E., Fouque E., Taillepied 1. and Commercon A., Tetrahedron Lett., 35, 2349 (1994).
• 12. Błoszyk E., Szafrański F., Drożdż B. and Al-Shameri K., Journal of Herbs, Spices & Medicinal Plants 3,25 (1995).