The isolation and structure analysis of 2-(2-cyanoethyl)-3-isoxazolin-5-one, 2-(β,D-glucopyranosyl)-3-isoxazolin-5-one and 2-carboxymethyl-3-isoxazolin-5-one from Lathyrus odoratus

Rompuy, Ludo Van; Lambein, Fernand; Gussem, R. De; Parijs, R. Van

doi:10.1016/s0006-291x(74)80334-7

Cited by 22 publications

(10 citation statements)

References 3 publications

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“…20−22 This approach requires complicated purification procedures and provides low yields because of the formation of many side products when applied to the synthesis of glucose derivatives. 22 Hence, Baldwin and co-workers developed an alternative method based on a 5-endo-dig cyclization reaction to synthesize amino acid derivatives of isoxazolin-5-one. 23−26 Herein we report a novel direct synthetic route for compound 1 based on a cascade reaction consisting of a 6exo-trig ring closure followed by a 5-endo-dig reaction.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis of Isoxazolin-5-one Glucosides by a Cascade Reaction

Becker

Goerls²,

Pauls

et al. 2013

J. Org. Chem.

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A novel synthetic route was developed for the construction of isoxazolin-5-one glucosides using a cascade reaction. An X-ray crystal structure analysis of a isoxazolin-5-one glucoside confirmed the structure and stereochemistry of the heterocycle. The properties of the α- and β-anomers of the isoxazolin-5-one glucosides were compared. The first synthesis of 2-[6'-(3″-nitropropanoyl)-β-D-glucopyranosyl]-3-isoxazolin-5-one was realized by direct enzymatic esterification without need of further protective groups.

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Section: ■ Introductionmentioning

confidence: 99%

Synthesis of Isoxazolin-5-one Glucosides by a Cascade Reaction

Becker

Goerls²,

Pauls

et al. 2013

J. Org. Chem.

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“…Although Nitropropanoyl glucosides have already been detected in leguminous plants (Stermitz et al, 1972;Harlow et al, 1975;Majak and Bose, 1976;Moyer et al, 1977), they were identified for the first time from animal sources in the present study. Isoxazolinone glucosides have also been previously identified in these plants (Van Rompuy et al, 1974;Lambein et al, 1976;Benn et al, 1997). Different amounts of each compound were present in the four species.…”

Section: Deterrent Effects Of the Secretionsmentioning

confidence: 82%

Adult secretions of four Japanese Chrysomelinae(Coleoptera: Chrysomelidae).

Sugeno

Matsuda

2002

Appl. Entomol. Zool.

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Adult secretions of four Japanese Chrysomelinae, Gastrophysa atrocyanea, Plagiodera versicolora distincta, Chrysomela vigintipunctata costella, and Gastrolina depressa (Coleoptera: Chrysomelidae) were analyzed by TLC, HPLC, NMR and FAB-MS. Three nitropropanoyl isoxazolinone glucosides, 2- (4) were found in all species. In addition, two nitropropanoyl glucosides, 1,6-di-(3Ј-nitropropanoyl)-b-D-glucopyranose (2) and 1,2,6-tri-(3Ј-nitropropanoyl)-b-Dglucopyranose (5) were also detected from these species. The secretions of the four species and compounds 3 and 5 showed strong deterrent effects against ants (Tetramorium caespitum), whereas compounds 2 and 4 exhibited low activity.

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“…This may be due to its high hydrophilic and neutral property. To the best of our knowledge, 2-CEIX was identified first in sweet pea (Van Rompuy et al, 1974a), and has only been found in Lathyrus plants (Ikegami et al, 1984;Lambein et al, 1976). Anthocyanins are pigments responsible for petal colors in sweet pea (Pecket, 1966).…”

Section: Discussionmentioning

confidence: 95%

“…Although 2-CEIX was previously identified in sweet pea (Ikegami et al, 1984;Van Rompuy et al, 1974a), it remains unclear whether 2-CEIX is the major nitrogenous compound in this plant. We, thus, investigated 2-CEIX and amino acid contents in various organs in sweet peas.…”

Section: Introductionmentioning

confidence: 98%

2-Cyanoethyl-isoxazolin-5-one Is a Major Low Molecular Weight Nitrogenous Compound in Sweet Pea (<i>Lathyrus odoratus</i> L.)

et al. 2016

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An unidentified compound was detected in sweet pea (Lathyrus odoratus L. ʻDianaʼ) petals by HPLC analysis using a cation-exchange column for soluble carbohydrate analysis. This compound was identified as 2-cyanoethyl-isoxazolin-5-one (2-CEIX) using 1 H-NMR, 13C-NMR, and CI-MS and ESIMS. 2-CEIX was detected in the petals, leaves and stem. Amino acid and other nitrogenous compound contents in these organs were compared with 2-CEIX. The content of asparagine was highest, followed by 2-CEIX in the petals, and 2-CEIX was highest among nitrogenous compounds in the stem and leaves. The 2-CEIX content in the petal decreased during flower opening, but those in the petals and the other floral parts increased during senescence regardless of sucrose treatment. These trends differed from those of monosaccharides, sucrose and cyclitols. Thus, the role of 2-CEIX appears to differ from those of soluble carbohydrates. 2-CEIX was not detected in phloem and xylem saps. The results suggest that 2-CEIX is a major nitrogenous compound of low molecular weight and is likely to be produced in situ in various organs in sweet pea.

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The isolation and structure analysis of 2-(2-cyanoethyl)-3-isoxazolin-5-one, 2-(β,D-glucopyranosyl)-3-isoxazolin-5-one and 2-carboxymethyl-3-isoxazolin-5-one from Lathyrus odoratus

Cited by 22 publications

References 3 publications

Synthesis of Isoxazolin-5-one Glucosides by a Cascade Reaction

Synthesis of Isoxazolin-5-one Glucosides by a Cascade Reaction

Adult secretions of four Japanese Chrysomelinae(Coleoptera: Chrysomelidae).

2-Cyanoethyl-isoxazolin-5-one Is a Major Low Molecular Weight Nitrogenous Compound in Sweet Pea (<i>Lathyrus odoratus</i> L.)

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