Possible metabolic intermediates from IAA to .BETA.-acid in rice bran.

Identification of 3-(O-β-Glucosyl)-2-Indolone-3-Acetylaspartic Acid as a New Indole-3-Acetic Acid Metabolite in Vicia Seedlings

“…The quinolone ring formation proceeds via the dicarboxylic acid formed by hydrolysis of the amide bond and its recyclization to form a new amide bond. This conversion is analogous to the formation of the ,B-acid from 5-hydroxydioxindole-3-acetic acid (17 (Fig. 4).…”

A Novel Metabolic Pathway for Indole-3-Acetic Acid in Apical Shoots of Populus tremula (L.) x Populus tremuloides (Michx.)

“…OxIAA, DiOxIAA, and their 5-hydroxy derivatives have been isolated and characterized in rice bran (Kinashi et al, 1976). The amide conjugate IAAsp is probably the most common product formed after feeds with exogenous IAA (eg.…”

Four new indole alkaloids from Plantago asiatica

“…Comparisons of these characteristic IR and UV absorptions with those of 1 indicated that 2 was also an oxindole-type compound. 33,34 The NMR data (Tables 1 and 2) suggested that 2 had the same oxindole moiety as that in (+)-(R)-3-cyanomethyl-3-hydroxyoxindole (5). 30,31 The structural difference between 2 and 5 was an additional hydroxy at C-5 in 2, which was further confirmed by the HMBC correlations (Figure 1).…”

“…These characteristic IR and UV absorptions indicated 1 was an oxindole-type compound. 33,34 The 1 H NMR spectroscopic data (Table 1) showed one set of 1,3,4-trisubstituted benzene protons, one oxygenated methine group connecting with a methyl, and two methylene protons neighboring a carbonyl group. The 13 C NMR and DEPT spectra ( Table 2) showed one methyl, one methylene, four methines (one oxygenated and three olefinic), and six quarternary carbons (two carbonyls and three olefinic ones).…”