8-Epi-9-epi-isolactarorufin, the first trans fused rings isolactarane sesquiterpene was synthesized. Its stereochemistry was determined by 1H NMR spectroscopy and X-ray analysis.
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.
Sesquiterpenoic analogues of TaxotereŽ i.e., N-BOC-phenylisoserinates of sesquiterpenoic alcohols, isolated from mushrooms of Lactarius genus, were synthesized. Cytotoxicity of compounds, thus obtained, was evaluated using Vero cells.
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