Neoglucobrassicin, ein zweiter SCN-Precursor vom Indoltyp in Brassica-Arten.

Gmelin, Rolf; Virtanen, Artturi I.; Salmenperä, A.; Block-Bolten, A.; Toguri, J. M.; Flood, H.

doi:10.3891/acta.chem.scand.16-1378

Cited by 78 publications

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“…In previous papers (9,10) we have reported the isolation from woad (Isatis tinctoria L.) of crystalline salts of 3-indolylmethylglucosinolate (glucobrassicin [14]), 1-methoxy-3-indolylmethylglucosinolate (neoglucobrassicin [15]), and a new indole glucosinolate which we identified as 1-sulfo-3-indolylmethylglucosinolate (glucobrassicin sulfonate [9]), (Fig. 1).…”

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Distribution and Variation of Indole Glucosinolates in Woad (Isatis tinctoria L.)

Elliott

Stowe

1971

Plant Physiol.

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The exceptionally high levels in woad (Isatis tinctoria L.) of three indolic goitrogens, namely glucobrassicin, neoglucobrassicin, and glucobrassicin-l-sulfonate, permit the facile study of their distribution in the plant and their changes during its development. Woad seeds contain as much as 0.23 % fresh weight of glucobrassicin but no other indole glucosinolate, while 1-week-old seedlings also contain substantial amounts of neoglucobrassicin and glucobrassicin-l-sulfonate in their shoots whether grown in the light or dark. The sulfonate is not found in roots, and light depresses neoglucobrassicin levels in shoots. Sterile root cultures synthesize glucobrassicin and neoglucobrassicin, and significant quantities of these were even found to be excreted by the roots of intact sterile seedlings in culture. This may explain the long known deleterious effect of woad and other cruciferous crops on subsequent plantings and the observation could be of ecological importance. Long term changes in levels of all three substances in the plant are similar and are compatible with earlier suggestions that the compounds could be auxin precursors at the time of flower stem elongation. Since sterile seedlings readily incorporate 3SO42-into indole glucosinolates and relative specific radioactivities suggest that glucobrassicin is the precursor of the other two compounds, pathways of goitrogen biosynthesis should be relatively easily determined in this material.In previous papers (9, 10) of the plant (e.g., during very rapid growth such as "bolting" of the flower shoot).Animal nutrition is influenced by indole glucosinolates due to the fact that the enzyme myrosinase (which is released from special cells in the plant tissues upon crushing) acts to release the goitrogenic thiocyanate ion from them (10, 41). In areas where large quantities of brassicaceous crops are eaten or fed to cows (which transfer part of the thiocyanate to their milk) these thiocyanate ions are at least partially responsible for endemic goiter in the human population (Ref. 28 and references therein).Finally, the distribution of indole glucosinolates in the plant kingdom has provided useful information for chemotaxonomic considerations (1 1. 31, 33).As the woad plant has exceptionally high levels of three indole glucosinolates, its study should cast light on these topics. We have examined the changes which occur in the levels of each of the indole glucosinolates in the shoots and roots of woad plants during germination, growth, and flowering. A similar study with the mustard plant (Sinapis alba L.) has recently been published by Bergmann (3). MATERIALS AND METHODSPlant Material. Seeds of woad (l. tinctoria L.) were collected from plants which had flowered in Yale University's Marsh Botanic Garden in 1967 and had been stored at room temperature over the winter. The field-grown woad plants were obtained from the crop produced by sowing these seeds in the spring of 1968.For sterile culture, seeds were dissected out of the fruits, sterilized as described pr...

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Distribution and Variation of Indole Glucosinolates in Woad (Isatis tinctoria L.)

Elliott

Stowe

1971

Plant Physiol.

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“…The R, values of compounds 3 and 4 suggested that they might be neoglucobrassicin and glucobrassicin (15) respectively, and their chromogenic reactions also supported these identifications (11,33).…”

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confidence: 50%

“…Interest in these topics was heightened by the fact that one degradation product, indole-3-acetonitrile, has high auxin activity in some growth hormone assays (17), whereas other substances formed by glucobrassicin decomposition, notably thiocyanate, have high goiter-inducing activity when plants in the Cruciferae are included in animal diets and can even enter their milk (44). At first, it was thought that glucobrassicin was the only natural indole occurring in large amounts in Brassica plants, but in 1962 Gmelin and Virtanen (15) isolated another indole glucosinolate, neoglucobrassicin, which was described as the 1-methoxy derivative of glucobrassicin (Fig. lb).…”

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Indole Compounds Related to Auxins and Goitrogens of Woad (Isatis tinctoria L.)

Elliott

Stowe

1971

Plant Physiol.

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Five conspicuous indole derivatives are present in leaves and other tissues of woad (Isatis tinctoria L.). They were identified as tryptophan, isatan B, glucobrassicin, neoglucobrassicin, and glucobrassicin-l-sulfonate. The Following the demonstration by Linser (25) that Brassica plants were rich sources of indole compounds, a large number of simple indole derivatives were detected in extracts of Brassica and other Cruciferae (1, 5, 10, 17-19, 26-28, 31, 34, 35). In 1960 Gmelin et al. (12) reported the isolation of the crystalline TMA+ salt' of an indole glucosinolate which was shown (14) to be 3-indolylmethylglucosinolate (glucobrassicin, Fig. la). They also demonstrated that the enzyme myrosinase, as well as exposure to acids or bases, caused degradation of glucobrassicin to yield a range of indolic products which included those described as natural endogenous indoles by the earlier workers. Virtanen (44) proposed that the presence of these compounds in the extracts was a consequence of the failure of the earlier workers to inactivate myrosinase before extraction, since it is present in special cells in the same tissues. Simple indole compounds could also have been produced as a consequence of the breakdown of glucobrassicin ( (15) isolated another indole glucosinolate, neoglucobrassicin, which was described as the 1-methoxy derivative of glucobrassicin (Fig. lb). This structure has not been considered conclusive (9).Previous studies in this laboratory (8, 40, 41) have established that the precursor of indigo in the woad plant is an unusual indoxyl derivative (isatan B), different from indoxyl-,f-D-glucoside which is the precursor of indigo in Indigofera plants. The present paper identifies other natural indole compounds present in high concentration in the woad plant, establishes this plant as particularly suitable for studies of higher plant indole metabolism related to auxin and goitrogen formation, and describes techniques useful to these ends. MATERIAILS AND METHODSPlant Material. Woad plants (Isatis tinctoria L.) were grown in Yale University's Marsh Botanic Garden from seed collected from plants of the previous year. The original sources of seed were the herb garden of Sissinghurst Castle, Kent, and Thompson and Morgan (Ipswich) Ltd. The plants were harvested and extracted when they were about 7 months old.For sterile culture, seeds were sterilized by rinsing in 90% ethanol for 1 min and then soaking in 0.5% calcium hypochlorite solution for 4 hr. After washing with sterile water, the seeds were transferred to autoclaved 14-cm Petri dishes (about 130 seeds per dish) containing the inorganic solution used by Danckwardt-Lilliestrbm (3) modified to include an Fe-EDTA preparation (43), 11 ml/liter, instead of ferric tartrate. The germinated seeds were allowed to grow in this solution in a constant temperature room at 25 C under 16-hr photoperiods of approximately 1000 ft-c of mixed incandescent and fluorescent light. After 7 days the seedlings were rinsed thoroughly with distilled water, then...

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“…33 Experimental results have shown that the urinary and salivary SCNconcentration is higher for smokers than nonsmokers, and so the assay can be used to detect whether or not a person is smoking. However, the SCN -level may vary widely, 34 depending on the dietary ingestion of the ion. When consumed in excess, some foods contribute to slight elevations in SCN -concentration and these elevations may make it difficult to separation nonsmokers from smokers.…”

Section: Resultsmentioning

confidence: 99%

Determination of SCN– in Urine and Saliva of Smokers and Non-Smokers by SCN–-Selective Polymeric Membrane Containing a Nickel(II)-Azamacrocycle Complex Coated on a Graphite Electrode

et al. 2002

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The conventional anion-selective electrodes based on quaternary ammonium or phosphonium salts always display the so-called Hofmeister selectivity pattern. 1 Since the 1980's, research interest in anti-Hofmeister anion selective membrane electrodes has increased more and more. Recently, electrodes based on derivatives of vitamin B12 and transitional metal complexes of porphyrins, and phthalocyanines have been reported. [2][3][4][5][6] These electrodes demonstrated potentiometric anion selectivity sequences apparently deviating from the Hofmeister sequences. Such deviations result from the unique interaction of the central metals with an anion rather than from the hydration free energy and the relative solubility of the individual anions in the solvent mediator.Due to the vital importance of selective SCN -determination, especially in food, biological and water samples, there are several reports on the preparation of SCN -selective membrane electrodes based on a variety of ion carriers.5,7-13 However, most of these SCN -sensors have one, two or, in some cases, all of the following problems: a) high detection limit, b) narrow working concentration range and/or c) serious interfering effect of such anions as ClO4 -, I -and IO4 -.In this work we report a coated graphite membrane electrode based on Ni(II)-2,2′,4,9,9′,11-hexamethyltetraazacyclotetradecanediene perchlorate (NiL) for potentiometric monitoring of ultra trace amounts of SCN -. Experimental ReagentsReagent grade dibutyl phthalate (DBP), benzyl acetate (BA), acetophenone (AP), hexadecyltrimethylammonium bromide (HTAB), tetrahydrofuran (THF), and high relative molecular weight (PVC) were purchased from Aldrich and used as received. Nickel(II)-2,2′,4,9,9′,11-hexamethyltetraazacyclotetradecanediene perchlorate (NiL) was synthesized and purified as described elsewhere.14 Potassium salts of all anions used (all from Merck) were of the highest purity available; they were used without any further purification except for vacuum drying The construction, performance characteristics, and application of a novel polymeric membrane coated on a graphite electrode with unique selectivity towards SCN -are reported. The electrode was prepared by incorporating Ni(II)-2,2,4,9,9,11-hexamethyltetraazacyclotetradecanediene perchlorate into a plasticized poly(vinyl chloride) membrane. The influences of membrane composition, pH and foreign ions were investigated. The electrode displays a near Nernstian slope (-57.8 mV decade -1 ) over a wide concentration range of 1 × 10 -7 -1 × 10 -1 M of SCN -ion. The electrode has a detection limit of 4.8 × 10 -8 M (2.8 ng/cm 3 ) SCN -and shows response times of about 15 s and 120 s for low to high and high to low concentration sequences, respectively. The proposed sensor shows high selectivity towards SCN -over several common organic and inorganic anions. The electrode revealed a great enhancement in selectivity coefficients and detection limit for SCN -, in comparison with the previously reported electrodes. It was successfully applied to the d...

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Neoglucobrassicin, ein zweiter SCN-Precursor vom Indoltyp in Brassica-Arten.

Cited by 78 publications

References 0 publications

Distribution and Variation of Indole Glucosinolates in Woad (Isatis tinctoria L.)

Distribution and Variation of Indole Glucosinolates in Woad (Isatis tinctoria L.)

Indole Compounds Related to Auxins and Goitrogens of Woad (Isatis tinctoria L.)

Determination of SCN– in Urine and Saliva of Smokers and Non-Smokers by SCN–-Selective Polymeric Membrane Containing a Nickel(II)-Azamacrocycle Complex Coated on a Graphite Electrode

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