Chemical apparatus and process disinfecting – deodorizing – preser – Process disinfecting – preserving – deodorizing – or sterilizing
Patent
1988-08-04
1992-02-11
Johnson, Jill
Chemical apparatus and process disinfecting, deodorizing, preser
Process disinfecting, preserving, deodorizing, or sterilizing
47 58, 71 68, 71 84, 422 40, A01N 302
Patent
active
050874179
DESCRIPTION:
BRIEF SUMMARY
FIELD OF INVENTION
The present invention relates to the inhibition of ethylene formation from perishable fruits, vegetables and flowers, thereby inhibiting the onset of senescence therein.
BACKGROUND TO THE INVENTION
Once fruits, vegetables and flowers are harvested, they are vulnerable to spoilage and must be consumed within a certain period of time. Some fruits and vegetables, for example, apples, can be stored under cold conditions for long periods without spoilage. Most fruits and vegetables, however, are perishable and cannot be stored for protracted periods.
Studies have been made of the mechanism of senescence and post-harvest deterioration. Membrane deterioration mediated by lipoxygenase has been identified as an early manifestation of the onset of senescence. Senescence is accompanied by the evolution of ethylene and once ethylene evolution commences, the process of deterioration is accelerated.
The biosynthetic path to ethylene formation has been identified as initial conversion of methionine to S-adenosyl methionine (SAM), the conversion of SAM to 1-amino-cyclopropane-1-carboxylic acid (ACC), and thence to ethylene.
It has previously been observed that the cytosol fraction from extraction of the petals of senescing carnation flowers inhibited ACC to ethylene conversion activity of membranes isolated from the petals (Mayak et al, Planta (1981) 153:49-55).
We have now been able to isolate and identify the active material which provides the inhibition and have identified a class of compounds which are useful in the inhibition of ethylene production in vitro and in situ from harvested fruits, vegetables and flowers.
SUMMARY OF INVENTION
In accordance with the present invention, there is provided a method of inhibiting senescence in perishable plant tissue, including fruits, vegetables and flowers, by the application thereto of an effective amount of a compound of the formula: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each hydrogen, --OH or --OR.sub.7 provided that at least one of R.sub.1 to R.sub.5 is a hydroxyl group, R.sub.6 is --OH, --OR.sub.8 or --NHR.sub.9, R.sub.7 is a substituent group, usually an alkyl group, or a sugar via an ether linkage, R.sub.8 is the residue of an ester-forming compound, and R.sub.9 is the residue of an amide-forming compound.
BRIEF DESCRIPTION OF DRAWING
The sole FIGURE of the drawing is a schematic flow sheet of the procedure used to effect isolation of the active component and as set forth in detail in Example 1 below.
GENERAL DESCRIPTION OF INVENTION
As noted above, the present invention resides in the application to perishable plant tissue of an effective amount of a compound of formula (I). In the compounds of formula (I), R.sub.7 usually is a methyl or an ethyl group. Usually one only of the R.sub.1 to R.sub.5 groups is hydroxyl, while another of the R.sub.1 to R.sub.5 groups is alkoxy. Preferably, the organic acid, esterified or otherwise, is ferulic acid, i.e. the compound of formula (I) wherein R.sub.1, R.sub.2 and R.sub.5 are hydrogen, R.sub.3 is --OH and R.sub.4 is --OCH.sub.3. The organic acid also may be a benzoic acid derived by side-chain degradation of respective hydroxycinnamic acid precursors.
In the compounds of formula (I), the free acid may be used, i.e. R.sub.8 is hydrogen, but it has been found that esters of the acids are preferred, especially esters having a plurality of hydroxyl groups. In one embodiment, R.sub.8 may be a glycosyl ester, such as a glucose ester, for example, the compound wherein R.sub.8 is B-D-glucose, i.e.: ##STR3##
Multiples and mixtures of sugars may comprise the glycosyl group. Another example of an R.sub.8 group is the ester of quinic acid.
The compounds used in the present invention may be isolated from natural sources. For example, the glucose ester of ferulic acid may be isolated from carnation petals by conventional isolation procedures involving chromatography. Such compound has been identified as the active compound achieving the inhibition reported in the previous work.
Some
REFERENCES:
patent: 3169849 (1965-02-01), Lemin
patent: 4388473 (1983-06-01), Richter et al.
Dumbroff Erwin B.
Shih Ching Y.
Thompson John E.
Johnson Jill
University of Waterloo
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