On the Nature of the Enzymatically Catalyzed Oxidation Products of Indoleacetic Acid.

Manning, David T.; Galston, Arthur W.

doi:10.1104/pp.30.3.225

Cited by 36 publications

(12 citation statements)

References 14 publications

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“…With respect to the primary, site of action of IAA oxidase, the observations are in harmony with the results of other laboratories (7,10,11); the ring system is altered by the primary attack. Further work will be required to unravel the reaction sequence and identity of the products.…”

Section: Stutz-indole-3-carboxaldehyde From Iaa Oxidation2supporting

confidence: 88%

Enzymatic Formation of Indole-3-Carboxaldehyde from Indole-3-Acetic Acid.

Stutz

1958

Plant Physiol.

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It was first suggested by Tang and Bonner (14) that indole-3-carboxaldehyde is the product of the oxidative degradation of indole-3-acetic acid (IAA) by crude enzyme preparations from etiolated pea seedlings. Using the more active bean root enzyme, Wagenknecht and Burris (15) attempted without success to obtain the 2,4-dinitropheny1hydrazone of the aldehyde. On the basis of chromatographic data, Racusen (9) reports that the pea enzyme forms small amounts of the aldehyde. More MIanningf and Galston (7) have reported the formation in the pea system of two products having high Rf values and giving qualitative color tests which indicate a similarity to our products # 4 and # 5 (see below). They were unable to demonstrate the formation of indole-3-carboxaldehyde, and also ruled out ortho-formamidoacetophenone, ortho-aminoacetophenone, and 4-hydroxyquinoline as major end products, although they believe that the indole ring is ruptured.Chromatographic separation and spectrophotometric examination of the products of the IAA oxidase-peroxidase system from Lupinus albus L. (13) gave no indication that the aldehyde was formed; likewise, the results obtained when the chromatograms were tested with 2,4-dinitrophenylhydrazine hydrochloride, modified Salkowski (3), and Ehrlich reagent suggested the absence of the aldehyde. In view of the conflicting results, attempts were made to suplement the purified IAA oxidase with the auxiliary enzyme systems presumed to be present in the crude enzyme preparations employed in the early investigations. The present report is concerned with the coupling of the oxidase system to the cytochrome oxidase system. Under these conditions the formation of indole-3-carboxaldehyde as a major reaction product was observed.Subsequent reexamination of the reaction products from the oxidase-peroxidase system, particularly those freshly prepared from etiolated lupine hypocotyls, the oxidation mechanism, indole-3-carboxylic acid and a number of substituted indole-3-acetic acid derivatives were tested both with the oxidase-peroxidase system alone and with the added cytochrome system. It is of interest to note that since this paper was submitted, Jones and Taylor (5) have reported the isolation of both indole-3-carboxaldehyde and indole-3-carboxvlic acid from cabbage extracts. MATERIALS AND METHODSPreparation and purification of the IAA oxidase from Lupinus albus L. has been previously described (13). The course of the oxidation of IAA was followed with the Warburg manometric apparatus under the conditions outlined earlier (13) except where 0.4 M tris-(hy-droxymethyl)-aminomethane buffer at pH 7.2 was uised in an attempt to approach the pH optimum of the cytochrome oxidase system and still maintain IAA oxidase activity. Under these conditions a small amount of phosphate, 4 micromoles per flask, was added for optimum IAA oxidase activity. The normal 3-ml reaction mixture was enzyme; 1 ml 0.4 M orthophosphate buffer, pH 6.3; 0.3 micromole MInCl,; 0.3 micromole soditim-2,4-dichlorophenolate; (in the main com...

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Section: Stutz-indole-3-carboxaldehyde From Iaa Oxidation2supporting

confidence: 88%

Enzymatic Formation of Indole-3-Carboxaldehyde from Indole-3-Acetic Acid.

Stutz

1958

Plant Physiol.

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“…IAA labeled in the 2-and 7-positions fed to pea root tips was conjugated, or converted to C14 Ehrlich negative substances, but only very minute C1402 yields were observed (2). This informationi could support earlier observations on in vitro systems (10,15) which indicated ring opening may precede loss of the carboxvl carbon during enzymnatic destruction of IAA.…”

supporting

confidence: 78%

“…It has been found that an extra-cellular IAAoxidase was excreted into the nutrient medium by Picea glauca and pea root callus (13), as well as by crown gall induced callus tissue of Partheniocissus tricuspidata (10). An 3 Present address: Botany Department, University of Chicago, Chicago 37, Illinois. from Ephedra callus (14) was found in both the tissue and( culture medium.…”

mentioning

confidence: 99%

The Metabolism of Indole-3-acetic Acid by Geranium Stem Callus Cultures

Troxler

Hamilton

1965

Plant Physiol.

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“…Since in this experiment no effort was made to remove the TAA solution from the surface of the basal ends of the cuttings after treatment, and since the cuttings were placed under intermittent mist, much of the loss in the first 24 Although much work has been done to determine the mechanism whereby IAA is oxidized by IAA oxidase, the results have been conflicting. The same situation exists regarding the identity of the products of IAA metabolism (11,16,17,19,22,23,27). According to Ray (18), the lack of agreement as to the products of IAA oxidation is due to the fact that an unstable intermediate is formed which subseauently yields two or more -substances.…”

Section: Methodsmentioning

confidence: 97%

Absorption, Distribution, and Destruction of Indoleacetic Acid in Plum Stem Cuttings

Strydom

Hartmann

1960

Plant Physiol.

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Rooting of greenwood cuttings of Marianna 2624plum (Priunus cerasifera Ehrh. X P. munsoniana Wight & Hedr.) taken in spring or summer is dependent on the presence of a certain minimum leaf area.Treatment of the basal portion of the cuttings with indoleacetic (IAA) or indolebutyric acid (IBA) sub-stantially increases the number of roots per cutting (20). The site of the auxin action is not known. Perhaps there is a direct effect at the site of application wlhere roots appear. Another possibility is that auxin stimulates mobilization of root-promoting substances from the leaves; these substances would then presumably be translocated basipetally to the site of root initiation.Although much study has been given to the absorption and translocation of auxins in intact plants, very few workers have investigated these phenomena in detached parts of woody plants. Cooper (4), using the standard Avena curvature test to follow movement of IAA in the bark of leafless lemon cuttings found initially relatively large amounts of IAA in the region of treatment; however, 95 per cent of the auxin disappeared during the 1st day, and little auxin was translocated to the apices of the cuttings. Turetskaya (24) followed the distribution of I-13 in soft and hardwood cuttings of various species treated with I'31-labeled-p-iodophenoxyacetic acid. In the hardwood cuttings the maximum I13' accumulation occurred in the base of the stem where the roots were formed. Decreasing amounts of f131 were found in xylem, bark, and buds, in that order. Turetskaya (25) followed the movement of C14-carboxyl-labeled naphthaleneacetic acid in leafy cuttings of balsam, cherry, and currant, and found some evidence that the NAA was metabolized.The present study was designed to follow the absorption, translocation, and persistence of C14 from alpha-labeled IAA in cuttings of Marianna 2624 plum. MATERIALS AND METHODS

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On the Nature of the Enzymatically Catalyzed Oxidation Products of Indoleacetic Acid.

Cited by 36 publications

References 14 publications

Enzymatic Formation of Indole-3-Carboxaldehyde from Indole-3-Acetic Acid.

Enzymatic Formation of Indole-3-Carboxaldehyde from Indole-3-Acetic Acid.

The Metabolism of Indole-3-acetic Acid by Geranium Stem Callus Cultures

Absorption, Distribution, and Destruction of Indoleacetic Acid in Plum Stem Cuttings

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