Previous work by this laboratory showed that under anaerobic conditions
and the presence of a
polyunsaturated fatty acid, soybean (Glycine max L.)
lipoxygenase isoenzymes converted a
lipoxygenase-catalyzed oxidation product of linolenic acid,
13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid, into 1-penten-3-ol, 2(Z)-penten-1-ol,
and 13-oxo-9(Z),11(E)-tridecadienoic
acid.
It seemed plausible that the “raw bean odor”, ethyl vinyl
ketone, previously isolated from soybean
homogenates by other workers could arise from oxidation of
1-penten-3-ol by alcohol dehydrogenase.
It is shown here that both ethyl vinyl ketone and 2-pentenal are
produced by a soybean preparation
after anaerobic incubation with
13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic
acid and linolenic acid and that NAD+ stimulated the formation of
2-pentenal. In the presence of NAD+,
two
separable isoenzymes of soybean alcohol dehydrogenase were capable of
utilizing as substrates both
1-penten-3-ol and 2(Z)-penten-1-ol, as well as
(2E)-hexen-1-ol. In terms of substrate
preference
indicated by K
m, the order was
2(E)-hexen-1-ol > 2(Z)-penten-1-ol >
1-penten-3-ol. Because ethyl
vinyl ketone formed in the presence of only
13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic
acid
and linolenic acid in the absence of NAD+, another
pathway also seemed possible.
Keywords: Lipoxygenase; 1-penten-3-ol; 2(Z)-penten-1-ol; alcohol
dehydrogenase; ethyl vinyl ketone;
2-pentenal; linolenic acid; hydroperoxide; flavor