In-vitro biosynthesis of 1-(4'-hydroxyphenyl)-2-nitroethane and production of cyanogenic compounds in osmotically stressed cell suspension cultures of Eschscholtzia californica Cham.

Cell suspension cultures of Eschscholtzia californica produce one or more cyanogenic compounds when placed under osmotic stress. The nature of the compound(s) has not yet been established but they are not identical with the cyanogenic glucosides triglochinin and dhurrin, which occur in the intact plant. Microsomal fractions isolated from stressed cell cultures catalyze the synthesis of 1-(4'-hydroxyphenyl)-2-nitroethane from L-tyrosine. Both NADPH and molecular oxygen are required as cosubstrates, and 4-hydroxyphenylacetaldoxime is an intermediate in the synthesis of the nitrocompound. This observation indicates that the biosynthetic pathways leading from L-tyrosine to 1-(4'-hydroxyphenyl)-2-nitroethane and to the L-tyrosine-derived cyanogenic glucosides are closely related. A glucosyltransferase which glucosylates the nitrocompound in the presence of uridine diphosphate glucose appears in the osmotically stressed cultures in a time pattern similar to that for production of the nitrocompound.