Inhibition of anthocyanin formation in seedlings and flowers by the enantiomers of ?-aminooxy-?-phenylpropionic acid and their N-benzyloxycarbonyl derivatives

Abstract

Both enantiomers of α-aminooxy-β-phenylpropionic acid (AOPP), potent inhibitors of L-phenylalanine ammonia-lyase, and their N-benzyloxycarbonyl (N-BOC) derivatives inhibit anthocyanin formation in developing flowers of Ipomoea tricolor Cav. and Catharanthus roseus Don. as well as in seedlings of Brassica oleracea var. caulo-rapa DC (kohlrabi) and B. oleracea var. capitata L. (red cabbage) with little interference with their normal development. Kohlrabi seedlings tolerate up to 0.3 mM L-AOPP and N-BOC-L-AOPP without a reduction of fresh weight or chlorophyll content, while anthocyanin is reduced to less than 20%.

Lignins: A Twenty‐First Century Challenge

“…would thus be expected to have negative consequences on either all aspects of phenylpropanoid metabolism or on specific elements, depending upon which PAL gene(s) is (are) affected. This was facilely demonstrated first using the PAL inhibitor, L-AOPP (57, Figure 7.11), as early as in 1977 and in subsequent studies extending through 1985 (200)(201)(202)(203)(204)(205). This resulted, depending upon the plant species investigated, in reductions in formation/accumulation of anthocyanins, isoflavones, hydroxycinnamic acids, and lignins, respectively.…”

Phenylalanine Ammonia-Lyase

“…It is sufficient here to consider ratios K 2 /K x for inhibition or protection constants, bearing in mind that free energy values refer to log Κ values. The compounds have proved to be important tools for studying phenylpropanoid metabolism (Amrhein and Godeke, 1977;Amrhein and Hollander, 1979). One may also assume that K m values are dissociation constants.…”

Suppression of Elongation and Growth of Tomato Seedlings by Auxin Biosynthesis Inhibitors and Modeling of the Growth and Environmental Response

“…To develop a more practical application method, we applied the inhibitor by spraying the leaves and stem. Although AOPP inhibits auxin biosynthesis, AOPP is known as an inhibitor of phenylalanine ammonia-lyase (PAL)234. We have targeted to develop a new inhibitor that inhibits only auxin biosynthesis.…”