Generation of primary amide glucosides from cyanogenic glucosides.
The cyanogenic glucoside-related compound prunasinamide, (2R)-beta-d-glucopyranosyloxyacetamide, has been detected in dried, but not in fresh leaves of the prunasin-containing species Olinia ventosa, Prunus laurocerasus, Pteridium aquilinium and Holocalyx balansae. Experiments with leaves of O. ventosa indicated a connection between amide generation and an excessive production of reactive oxygen species. In vitro, the Radziszewski reaction with H(2)O(2) has been performed to yield high amounts of prunasinamide from prunasin. This reaction is suggested to produce primary amides from cyanogenic glycosides in drying and decaying leaves. Two different benzoic acid esters which may be connected to prunasin metabolism were isolated and identified as the main constituents of chlorotic leaves from O. ventosa and P. laurocerasus.
Sendker
Jandirk
J
Institute of Pharmaceutical Biology and Phytochemistry, Westfälische Wilhelms-Universität, Hittorfstr. 56, 48149 Münster, Germany.
Nahrstedt
Adolf
A
D002851:Chromatography, High Pressure Liquid; D055864:Droughts; D005960:Glucosides / Q000737:chemistry* / Q000378:metabolism*; D006027:Glycosides / Q000737:chemistry* / Q000378:metabolism*; D006861:Hydrogen Peroxide / Q000737:chemistry; D008027:Light; D008315:Malondialdehyde / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D018515:Plant Leaves / Q000378:metabolism; D027861:Prunus / Q000378:metabolism / Q000528:radiation effects; D032498:Pteridium / Q000378:metabolism / Q000528:radiation effects; D017382:Reactive Oxygen Species / Q000378:metabolism
D005960:Glucosides; D006027:Glycosides; D009570:Nitriles; D017382:Reactive Oxygen Species; C007173:cyanogenic glycosides; C019063:prunasin; D008315:Malondialdehyde; D006861:Hydrogen Peroxide