Further confirmation of the presence of indolylacrylic acid in lentil seedlings and identification of hypaphorine as its precursor

Hofinger, M.; Monseur, X.; Pais, M; Jarreau, F.‐X.

doi:10.1016/0031-9422(75)85112-0

Cited by 20 publications

(12 citation statements)

References 6 publications

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“…Hypaphorine was determined as follows: urine was twice extracted with n-butanol, combined organic layers evaporated, dissolved in the phosphate-citrate buffer pH 7.1 and incubated with urease (to prevent the overlapping of both HP and urea on TLC). The sample was then desalted on Dowex 50WX8, eluted with 2M ammonia and farther processed by TLC, as described by Hofinger et al (1975) for the vegetal material. The Ehrlich and Dragendorff reagents were used for detection.…”

Section: Methodsmentioning

confidence: 99%

“…A method for analysis of hypaphorine (N-trimethyltryptophan, lenthicine, HP) in plants (Hofinger et al, 1975) was introduced, and a number of foodstuff of vegetable origin has been processed. HP was found in eight types of plant fruits (e.g.…”

Section: Hypaphorinementioning

confidence: 99%

“…Another possible way of IAcrA production goes via hypaphorine (N-trimethyltryptophan). Conver-sion of Trp to this betaine has been so far demonstrated in some plants only (family Fabaceae) (Hofinger et al, 1975) (Fig. 1).…”

Section: Introductionmentioning

confidence: 97%

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Where does indolylacrylic acid come from

Marklová

1999

Amino Acids

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In addition to the main catabolic routes of tryptophan (Trp), there exist minor and less thoroughly investigated pathways; one of these leads to indolylacrylic acid (IAcrA). IAcrA is a plant growth hormone, whereas its biological role in animals is still obscure, as is the way and site where it is formed in the organism. A two-stage production is likely: Intestinal microorganisms catabolize Trp to indole derivatives which are then absorbed and converted to IAcrA and its glycine conjugate, indolylacryloylglycine (IAcrGly). Our finding of IAcrGly in the urine of proven germ-free piglets points to the possibility that Trp can be converted to IAcrA without the intervention of intestinal microorganisms. Seasonal and age variations, influence of light and connection with photodermatoses have been reported. Besides other pathological conditions the differences in IAcrGly excretion relative to normal controls were especially pronounced in some myopathies, namely in boys with Duchenne muscular dystrophy.

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Section: Methodsmentioning

confidence: 99%

Section: Hypaphorinementioning

confidence: 99%

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Where does indolylacrylic acid come from

Marklová

1999

Amino Acids

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“…A subgroup of eight participants underwent the fourth intervention with white beans, which was scheduled later. The subjects were on average 28 ± 6 years old (range: [19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] and had a BMI of 23.8 ± 3.6 kg m −2 (range: 18.6-28.9).…”

Section: Methodsmentioning

confidence: 99%

Discovery of Intake Biomarkers of Lentils, Chickpeas, and White Beans by Untargeted LC–MS Metabolomics in Serum and Urine

Ulaszewska¹,

Franceschi

Estruel-Amades

et al. 2020

Molecular Nutrition Food Res

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Scope To identify reliable biomarkers of food intake (BFIs) of pulses. Methods and results A randomized crossover postprandial intervention study is conducted on 11 volunteers who consumed lentils, chickpeas, and white beans. Urine and serum samples are collected at distinct postprandial time points up to 48 h, and analyzed by LC‐HR‐MS untargeted metabolomics. Hypaphorine, trigonelline, several small peptides, and polyphenol‐derived metabolites prove to be the most discriminating urinary metabolites. Two arginine‐related compounds, dopamine sulfate and epicatechin metabolites, with their microbial derivatives, are identified only after intake of lentils, whereas protocatechuic acid is identified only after consumption of chickpeas. Urinary hydroxyjasmonic and hydroxydihydrojasmonic acids, as well as serum pipecolic acid and methylcysteine, are found after white bean consumption. Most of the metabolites identified in the postprandial study are replicated as discriminants in 24 h urine samples, demonstrating that in this case the use of a single, noninvasive sample is suitable for revealing the consumption of pulses. Conclusions The results of the present untargeted metabolomics work reveals a broad list of metabolites that are candidates for use as biomarkers of pulse intake. Further studies are needed to validate these BFIs and to find the best combinations of them to boost their specificity.

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“…1). Since then, hypaphorine has been detected in several other higher plants: Desmodium trifolium (Ghosal et al 1971), Desmodium girans (Ghosal et al 1972), Sida cordifolia (Ghosal et al 1975), Lens culinaris (Hofinger et al 1975), Pterocarpus officinalis (Janzen et al 1982), South American Moraceae (Shrestha and Bisset 1991), Abrus precatorius (Dimetry et al 1992), Glycyrrhiza yunnanensis (Ohtani et al 1992) or Caragana species (Chen et al 2001). Recently, we detected hypaphorine in Eucalyptus globulus seedling shoot but not in roots (detection limit: 0.001 nmol g −1 FW) (unpublished data).…”

Section: Indole Alkaloid Hypaphorine In Plants and Fungimentioning

confidence: 99%