A new uv-sensitive heterocyclic amino acid frott pea seedlings : 2-alanyl-3-isoxazoliin-5-one

Lambein, Fernand; Schamp, N.; Vandendriessche, L.; Parijs, R. Van

doi:10.1016/0006-291x(69)90925-5

Cited by 28 publications

(11 citation statements)

References 4 publications

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“…The peak presumably containing y-Glu-BAPN was collected and analyzed by two-dimensional TLC. um, similar to the spectra of isoxazolin-5-one derivatives (14). The concentrations of the UV-absorbing products in the exudates increase during the growth period examined.…”

supporting

confidence: 55%

Isoxazolin-5-ones and Amino Acids in Root Exudates of Pea and Sweet Pea Seedlings

Kuo

Lambein²,

Ikegami³

et al. 1982

Plant Physiol.

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Seeds of Pisum sativum L. cv Finale and Lathyrs odoratus L. cv Spencer were germinated asepticafly in moistened sand in the dark. At several stages, the amino acid composition of the exudate and of the corresponding roots was analyzed. A number of common amino acids, including homoserine, were exuded by the growing seeding root in an early stage and were partly reabsorbed later. A number of uncommon amino acids, including several isoxazolin-5-one derivatives, uracil alanines, ia-yglutamyl-D-alanine, and a-aminoadipic acid were exuded at different rates.The range of compounds exuded by the roots of higher plants includes sugars, amino acids, enzymes, vitamins, nucleotides, growth hormones, terpenoids, flavanones, organic acids, and inorganic ions (22,24). By means of these exudates, the plants can affect the microflora in the rhizosphere by selective stimulation or inhibition of certain bacteria, fungi, or nematodes. There is also evidence that the root exudates of some plants inhibit the germination of some seeds or are toxic to roots of neighboring plants (22). It is generally believed that this root exudation is an uncontrolled process caused by damage to the cells at the root cap, at the sites where lateral roots emerge, and by infection of the root by microorganisms (23).Pea root exudates have been investigated in several laboratories (1,2,5,20,21,25). Some authors mentioned the presence of unknown amino acids (1,2,25). Rovira (20) showed the presence of UV-absorbing substances in 10-d-old and 21-d-old pea root exudates. Fries and Forsman (5) found some low mol wt UVabsorbing substances in the exudate from excised pea roots, besides adenine, guanine, uridine, and cytidine.A group of heterocyclic products, mostly amino acids, was isolated in our laboratory from pea seedlings and sweet pea seedlings: the uracil alanines willardiine and isowillardiine (15) and eight derivatives of the isoxazolin-5-one ring (13). (See Fig. 1 for the chemical structures.) Possibly, these products are the unknown compounds mentioned earlier by other authors (1, 2, 25).A preliminary study has shown the presence of some of these heterocycic products in root exudates of both pea and sweet pea seedlings (11). The differences in amino acid composition of the exudate and the corresponding root extract suggest that in some cases this exudation may be a specific phenomenon. This paper presents more detailed information on the exudation ofisoxazolin-5-one derivatives and other amino acids by intact roots ofetiolated pea and sweet pea seedlings under axenic conditions. MATERIALS AND METHODS Culture Conditions. Pea (Pisum sativum L. cv Finale) and sweet pea (Lathyrus odoratus L. cv Spencer) seeds were surface-sterilized with ethanol and were washed thoroughly with sterile distilled H20. After imbibing in sterile H20 for 16 h, the seeds were germinated in individual autoclaved glass tubes (20 x 2.8 cm), containing sterile quartz sand (5-cm height) moistened with distilled H20. The tubes were incubated at 25°C in the dark.Preparation...

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supporting

confidence: 55%

Isoxazolin-5-ones and Amino Acids in Root Exudates of Pea and Sweet Pea Seedlings

Kuo

Lambein²,

Ikegami³

et al. 1982

Plant Physiol.

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“…It has been pointed out that the 2,3-enediol tautomer may become stabilized in the form of a pseudo-isoxazoline structure (Berrens,i971a). The above conclusions may then be linked up with the findings of Lambein et al (1969)., who reported UV-sensitivity of 2-aianyl-3-isoxazolin-5-one and derivatives.…”

Section: Discussionmentioning

confidence: 54%

Photo‐inactivated allergens I. Preparation, physicochemical and biological properties

Berrens¹,

Hénocq²,

Radermecker³

1973

Clin Experimental Allergy

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Summary A method is described for the preparation of inactive atopic allergens by irradiation with ultraviolet light. From an analysis of the absorption and fluorescence emission spectra, and with the aid of synthetic model compounds, it is concluded that the allergenic determinant of lysine‐sugar conjugation is extremely sensitive to ultraviolet light. Considerable reduction of allergenicity in vitro (diminished capacity to inactivate human complement in fluid phase) and in vivo (impressive reduction of skin‐reactivity in atopic patients and, by passive transfer, in monkeys) was demonstrated. Only slight modification of the antigenic characteristics was detected.

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“…Three contiguous peaks were recorded (fractions 65-71, 71-78 and 78-86). By using the chromatographic, electrophoretic and spectrophotometric methods described previously (Brown & Silver, 1966;Brown & Mangat, 1969), comparisons with authentic samples showed that peak (1) consisted largely of willardiine, peak (2) of isowillardiine and peak (3) of ,-(isoxazolin-5-oxo-2-yl)alanine (Lambein et al, 1969). For routine extraction of willardiine and isowillardiine, peaks (1) and (2) were separately evaporated in vacuo and sequentially chromatographed on Whatman no.…”

Section: Methodsmentioning

confidence: 97%

“…During cation-exchange chromatography of an extract from pea seedlings, Lambein et al (1969) identified a peak, contiguous with that of isowillardiine, as #-(isoxazolin-5-oxo-2-yl)alanine. The simul-taneous appearance of this compound with the uracilylalanines during germination led these authors to suggest a possible biogenetic relationship.…”

Section: Biosynthetic Interrelationship Of Willardiine and Isowillardmentioning

confidence: 99%

Biosynthesis of willardiine and isowillardiine in germinating pea seeds and seedlings

Ashworth

Brown

Roberts

1972

Biochemical Journal

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The synthesis of the pyrimidinyl amino acids willardiine and isowillardiine was studied in vivo and in vitro. Uracil derivatives stimulate the biosynthesis of both compounds; the free base is the most effective. Significant incorporation of [2-(14)C]uracil and [6-(14)C]orotate into willardiine and isowillardiine was found. Incorporation of [6-(14)C]orotate was substantially decreased in the presence of uracil, and to a lesser extent by uridine and UMP. [3-(14)C]Serine was incorporated into the alanine side chain of the two uracilylalanines but not into the ring. The effect of a number of uracil analogues and inhibitors of pyrimidine metabolism was examined. Some were shown to stimulate the biosynthesis; the most noticeable effects were obtained with 6-azauracil and 2-thiouracil. Attempts to obtain extracts capable of synthesizing the uracilylalanines from uracil and serine were unsuccessful, but weak activity was observed when serine was replaced by O-acetylserine.

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A new uv-sensitive heterocyclic amino acid frott pea seedlings : 2-alanyl-3-isoxazoliin-5-one

Cited by 28 publications

References 4 publications

Isoxazolin-5-ones and Amino Acids in Root Exudates of Pea and Sweet Pea Seedlings

Isoxazolin-5-ones and Amino Acids in Root Exudates of Pea and Sweet Pea Seedlings

Photo‐inactivated allergens I. Preparation, physicochemical and biological properties

Biosynthesis of willardiine and isowillardiine in germinating pea seeds and seedlings

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