Synthesis and antifeedant properties of N-benzoylphenylisoserinates of Lactarius sesquiterpenoid alcohols.
The esterification of various sesquiterpenoid alcohols of Lactarius origin with N-benzoyl-[2R,3S]-phenylisoserine (side chain of Taxol) produced compounds whose antifeedant properties against storage pests Tribolium confusum, Trogoderma granarium and Sitophylus granarius were measured. The introduction of the taxol side chain 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.
Kopczacki
P
P
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
Gumulka
M
M
Masnyk
M
M
Grabarczyk
H
H
Nowak
G
G
Daniewski
W M
WM
D000363:Agaricales / Q000737:chemistry*; D000818:Animals; D005247:Feeding Behavior / Q000187:drug effects; D017239:Paclitaxel / Q000737:chemistry; D012694:Serine / Q000031:analogs & derivatives / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry / Q000494:pharmacology*; D014200:Trematoda / Q000187:drug effects*; D014231:Tribolium / Q000187:drug effects*
D012717:Sesquiterpenes; D012694:Serine; C010286:beta-phenylisoserine; D017239:Paclitaxel