Senfölglukoside als genuine Muttersubstanzen von natürlich vorkommenden antithyreoiden Stoffen. XIII. Mitteilung über Senfölglukoside

Schultz, Otto-Erich; Wagner, Werner

doi:10.1002/ardp.19562890912

Cited by 21 publications

(3 citation statements)

References 12 publications

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“…To test the hypothesis that UGT74B1 functions in glucosinolate biosynthesis, we first studied its enzymatic properties in vitro . We used phenylacetothiohydroximate (PATH) as a test substrate because it is readily synthesized (Ettlinger and Lundeen, 1957), occurs naturally as a glucosinolate precursor (Schultz and Wagner, 1956), and has been used for previous biochemical studies of thiohydroximate glucosyltransferase activity (Matsuo and Underhill, 1969). The reaction to be assayed is shown in Figure 1(a).…”

Section: Recombinant Ugt74b1 Catalyzes Thiohydroximate‐specific Glucomentioning

confidence: 99%

Arabidopsis glucosyltransferase UGT74B1 functions in glucosinolate biosynthesis and auxin homeostasis

et al. 2004

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SummaryGlucosinolates are a class of secondary metabolites with important roles in plant defense and human nutrition. Here, we characterize a putative UDP-glucose:thiohydroximate S-glucosyltransferase, UGT74B1, to determine its role in the Arabidopsis glucosinolate pathway. Biochemical analyses demonstrate that recombinant UGT74B1 specifically glucosylates the thiohydroximate functional group. Low K m values for phenylacetothiohydroximic acid (approximately 6 lM) and UDP-glucose (approximately 50 lM) strongly suggest that thiohydroximates are in vivo substrates of UGT74B1. Insertional loss-of-function ugt74b1 mutants exhibit significantly decreased, but not abolished, glucosinolate accumulation. In addition, ugt74b1 mutants display phenotypes reminiscent of auxin overproduction, such as epinastic cotyledons, elongated hypocotyls in lightgrown plants, excess adventitious rooting and incomplete leaf vascularization. Indeed, during early plant development, mutant ugt74b1 seedlings accumulate nearly threefold more indole-3-acetic acid than the wild type. Other phenotypes, however, such as chlorosis along the leaf veins, are likely caused by thiohydroximate toxicity. Analysis of UGT74B1 promoter activity during plant development reveals expression patterns consistent with glucosinolate metabolism and induction by auxin treatment. The results are discussed in the context of known mutations in glucosinolate pathway genes and their effects on auxin homeostasis. Taken together, our work provides complementary in vitro and in vivo evidence for a primary role of UGT74B1 in glucosinolate biosynthesis.

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Section: Recombinant Ugt74b1 Catalyzes Thiohydroximate‐specific Glucomentioning

confidence: 99%

Arabidopsis glucosyltransferase UGT74B1 functions in glucosinolate biosynthesis and auxin homeostasis

et al. 2004

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“…Marine, Baumann, Spence, and Cipra (1931) stated that allyl, ethyl, and phenyl isothiocyanates had no goitrogenic activity when tested on rabbits. According to Schultz and Wagner (1956) 5-methylsulphinylpentenyl isothiocyanate is nongoitrogenic, while Jensen, Conti, and Kjaer (1953) observed that isothiocyanates generally had little or no antithyroid activity, but the compounds tested were not listed. On the other hand, Clements (1957) stated that benzyl isothiocyanate is goitrogenic to rats, while Wagner-Jauregg and Koch (1947) found solutions of the thioglucoside sinalbin, after treatment wIth the enzyme myrosinase, active when administered to rabbits.…”

Section: Introductionmentioning

confidence: 99%

Studies on Endemic Goitre III an Investigation of the Antithyroid Aotivities of Isothiocyanates and Derivatives With Observations on Fractions of Milk From Goitrous Areas

Hs¹,

McQuillan²,

Trikojus³

1963

Aust. Jnl. Of Bio. Sci.

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Certain isothiocyanates and thioureas, in particular 3-methylsulphonylpropyl isothiocyanate (cheirolin) and dicheirolin thiourea, were tested for their antithyroid activity by an acute 1311 test and by chronic administration to rats. Cheirolin proved more active in the acute test than n-propyl isothiocyanate, but dicheirolin thiourea, the major product resulting from the incubation of cheirolin with rumen liquor, was without activity, whereas di-n-propylthiourea had a marked effect. Dicheirolin thiourea was also inactive when tested in the human. The response to cheirolin when chronically administered, either as such or in the form of its thioglucoside present in turnip weed fruit, appeared to be less than in the acute test. Its possible mode of action is discussed.

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“…of many Brassica species (turnip, cabbage, kale, and rape) (9), whereas the epimeric (S)-glucosinolate (3), giving rise to (R) (+)-5-vinyloxazolidine-2thione ( 5), has been encountered previously only in seeds of Crambe abyssinica (10). Reported rotation values of the penta-O-acetyl derivative of the (R)-glucosinolate (2), ([«po -9.5°) (11), and the (S)-glucosinolate (3),…”

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confidence: 99%

Glucosinolates in the Genus Zilla (Brassicaceae)

El-Menshawi¹,

Karawya²,

Wassel³

et al. 1980

J. Nat. Prod.

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Senfölglukoside als genuine Muttersubstanzen von natürlich vorkommenden antithyreoiden Stoffen. XIII. Mitteilung über Senfölglukoside

Cited by 21 publications

References 12 publications

Arabidopsis glucosyltransferase UGT74B1 functions in glucosinolate biosynthesis and auxin homeostasis

Arabidopsis glucosyltransferase UGT74B1 functions in glucosinolate biosynthesis and auxin homeostasis

Studies on Endemic Goitre III an Investigation of the Antithyroid Aotivities of Isothiocyanates and Derivatives With Observations on Fractions of Milk From Goitrous Areas

Glucosinolates in the Genus Zilla (Brassicaceae)

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