Isolation and Identification of Indole-3-Ethanol (Tryptophol) from Cucumber Seedlings

Rayle, David L.; Purves, William K.

doi:10.1104/pp.42.4.520

Cited by 55 publications

(22 citation statements)

References 16 publications

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“…Indole-3-ethanol (tryptophol2) has been established as an endogenous plant constituent (6,19,23). It is also formed in vitro by preparations from bacteria, thallophytes, and seed plants from compounds supposed to participate in the biogenesis of IAA (e.g.…”

Section: Introductionmentioning

confidence: 99%

“…IAA, if detectable at all, was usually a minor metabolite, as should be expected, if tryptophol oxidase responds to feedback inhibition by IAA. Indole-3-carboxylic acid, formed by a few fungi and mosses, was the only tryptophol metabolite detected which is likely to be formed via IAA.Indole-3-ethanol (tryptophol2) has been established as an endogenous plant constituent (6,19,23). It is also formed in vitro by preparations from bacteria, thallophytes, and seed plants from compounds supposed to participate in the biogenesis of IAA (e.g.…”

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confidence: 99%

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Metabolism of Tryptophol in Higher and Lower Plants

Laćan¹,

Magnus²,

Šimaga³

et al. 1985

Plant Physiol.

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Bacteria, thallophytes, and seed plants (107 species), supplied with exogenous indole-3-ethanol (tryptophol), formed one or more of the following metabolites: O-acetyl tryptophoL an unknown tryptophol ester (or a set of structurally closely related esters), tryptophol glucoside, tryptophol plactoside, indole-3-acetic acid (IAA), and indole-3-carboxylic acid. The unknown ester was formed by all species exAmined; 0-acetyl tryptophol appeared sporadically in representatives of most major taxonomic groups. Tryptophol galactoside was found in the algae Chlorella, Euglena, and Ochromoaas. The glucoside was formed by many eucaryotic plants, but not by bacteria; it was a significant tryptophol metabolite in vascular plants. IAA, if detectable at all, was usually a minor metabolite, as should be expected, if tryptophol oxidase responds to feedback inhibition by IAA. Indole-3-carboxylic acid, formed by a few fungi and mosses, was the only tryptophol metabolite detected which is likely to be formed via IAA.Indole-3-ethanol (tryptophol2) has been established as an endogenous plant constituent (6,19,23). It is also formed in vitro by preparations from bacteria, thallophytes, and seed plants from compounds supposed to participate in the biogenesis of IAA (e.g. 18,23). In fact, tryptophol appears to be in an oxidase-reductasemediated equilibrium with the IAA precursor, indole-3-acetaldehyde (5, 16). The oxidase has been isolated and found to be feedback inhibited by IAA (16). This points to the involvement of tryptophol in a mechanism stabilizing auxin levels in plants. Its in vivo significance has, however, remained unclear, because IAA concentrations necessary to inhibit the isolated tryptophol oxidase are larger than bulk concentrations of the hormone in plant tissues (16).Local IAA concentrations at points ofregulation may be higher than bulk concentrations. Also, removal of tryptophol oxidase from its natural subcellular environment may render the enzyme less sensitive to feedback inhibitors. For these reasons, we were looking for indications of regulated IAA formation from tryptophol in systems containing nondisrupted cell structures. Suspensions of unicellular plants and sections of multicellular plants were supplied with a large excess of tryptophol. In the absence of regulatory mechanisms, this might reasonably be expected to lead to drastically enhanced IAA levels. However, the majority of plants examined did not accumulate substantial amounts of 2 Abbreviations: tryptophol, indole-3-ethanol or 3-(2-hydroxyethyl)indole; Ve, elution volume.The most abundant tryptophol metabolites in bacteria, thallophytes, and seed plants were conjugates: esters and glycosides.MATERIALS AND METHODS Instrumentation. 'H NMR spectra were recorded at 100 MHz on a JEOL FX-100 Fourier-transform spectrometer. Chemical shifts (a) were recorded relative to tetramethylsilane. GC-MS was on a Hewlett-Packard 5985a instrument, using helium at 30 ml/ min as the carrier gas and electron impact ionization at 70 ev. Columns and temperature pr...

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Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

Metabolism of Tryptophol in Higher and Lower Plants

Laćan¹,

Magnus²,

Šimaga³

et al. 1985

Plant Physiol.

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“…Therefore, compound 1 is thus unambiguously shown to be the 5-O-glucosyl derivative of tryptophol (indole-3-ethanol). Tryptophol has been isolated as a constituent of higher plants, fungi and marine organisms and is considered to be a plant auxin, 3 however its 5-Oglucosyl derivative 1 was hitherto unreported in the literature.…”

Section: Resultsmentioning

confidence: 99%

Indole alkaloid and other constituents from Ocotea minarum

Garcez¹,

Garcez²,

Silva³

et al. 2005

J. Braz. Chem. Soc.

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Dos frutos deA new alkyl phenol, 3-(1,4-dihydroxypentyl)-5-methoxyphenol, was obtained from the heartwood in addition to 5-propylresorcinol, trans-asarone, lyonyresinol, 3-O-β-D-glucopyranosyl stigmasterol and stigmasta-4,22-dien-3-one, whereas from the trunk bark the sesquiterpene lanceolic acid (as its methyl ester derivative after methylation procedures) and β-sitosterol were isolated. 5-propylresorcinol and lanceolic acid are reported for the first time as natural products.

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“…These spectral data are identical to previous literature values. 22) The indole-3-ethanol contents in FBS and buckwheat green juice are shown in Table 1. FBS showed higher antioxidative activity than buckwheat green juice.…”

Section: Sod-active Substance In Fbsmentioning

confidence: 99%