2-Pyrrolidinones and 3-Pyrrolin-2-ones: A Study on the Chemical Reactivity of These Structural Moieties

Alves, José C. F.

doi:10.1155/2011/803120

Cited by 2 publications

(3 citation statements)

References 19 publications

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“…In the presence of strong acids and bases, a tautomeric equilibrium of the pyrrolin-2-one-derivatives was previously observed [ 35 ]. The opening of the pyrrolin-2-one ring structure under basic conditions has already been discussed by Alves et al as a possible mechanism [ 36 ]. This is probably the reason why lyophilization under acidic conditions led to rearrangement of the desired compound and necessitated a solvent change after purification (first preparative HPLC run).…”

Section: Resultsmentioning

confidence: 99%

“…Storage at pH 10 resulted in significant losses of Lys-BDA and AcLys-BDA in the urine samples after only 4 weeks, and their levels continued to decrease thereafter. A possible mechanism for rearrangement of the pyrrolin-2-one ring structure has been discussed previously [ 36 ]. In contrast, storage at a slightly acidic pH of 5.4 did not result in significant reductions.…”

Section: Resultsmentioning

confidence: 99%

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Stable Isotope Dilution Analysis (SIDA) to Determine Metabolites of Furan and 2-Methylfuran in Human Urine Samples: A Pilot Study

Kremer,

Karlstetter,

Kirsch

et al. 2023

Metabolites

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Furan and 2-methylfuran (2-MF) are food contaminants that are classified as potentially carcinogenic to humans. The main source of exposure for adults via food is coffee consumption. Furan and 2-MF are volatile, which complicates exposure assessment because their content measured in food prior to consumption does not afford a reliable dosimetry. Therefore, other ways of exposure assessment need to be developed, preferably by monitoring exposure biomarkers, e.g., selected metabolites excreted in urine. In this study, cis-2-buten-1,4-dial (BDA)-derived urinary furan metabolites Lys-BDA (l-2-amino-6-(2,5-dihydro-2-oxo-1H-pyrrol-1-yl)hexanoic acid), AcLys-BDA (l-2-(acetylamino)-6-(2,5-dihydro-2-oxo-1H-pyrrol-1-yl)hexanoic acid) and GSH-BDA (N-[4-carboxy-4-(3-mercapto-1H-pyrrol-1-yl)-1-oxobutyl]-l-cysteinyl-glycine cyclic sulfide), as well as acetyl acrolein (AcA, 2-oxo-pent-2-enal)-derived metabolites Lys-AcA (l-2-(acetylamino)-6-(2,5-dihydro-5-methyl-2-oxo-1H-pyrrol-1-yl)-hexanoic acid) and AcLys-AcA (l-2-amino-6-(2,5-dihydro-5-methyl-2-oxo-1H-pyrrol-1-yl)-hexanoic acid) and their stable isotopically labeled analogs, were synthesized and characterized through NMR and MS, and a stable isotope dilution analysis (SIDA) with UPLC-ESI-MS/MS was established. As a proof of concept, urinary samples of a four-day human intervention study were used. In the frame of this study, ten subjects ingested 500 mL of coffee containing 0.648 µmol furan and 1.059 µmol 2-MF. Among the furan metabolites, AcLys-BDA was the most abundant, followed by Lys-BDA and GSH-BDA. Exposure to 2-MF via the coffee brew led to the formation of Lys-AcA and AcLys-AcA. Within 24 h, 89.1% of the ingested amount of furan and 15.4% of the ingested amount of 2-MF were detected in the urine in the form of the investigated metabolites. Therefore, GSH-BDA, Lys-BDA, AcLys-BDA, Lys-AcA and AcLys-AcA may be suitable as short-term-exposure biomarkers of furan and 2-MF exposure.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Stable Isotope Dilution Analysis (SIDA) to Determine Metabolites of Furan and 2-Methylfuran in Human Urine Samples: A Pilot Study

Kremer,

Karlstetter,

Kirsch

et al. 2023

Metabolites

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“…Elemanolides represent a small group of sesquiterpene lactones that are biogenetically derived from germacranolides. 17 Additionally, twenty-nine known compounds were identified as N-acetylanonaine (5), 18 N-acetylnornuciferin (6), 19 tuliferoline ( 7), 20 N-acetyl-3-methoxynornantenine (8), 21 lysicamine (9), 22 liriodenine (10), 23 atherospermidine (11), 24 liridine (12), 25 oxoglaucine (13), 23 oxophoebine ( 14), 23 (±)-virolongin A (15), 26 (±)-virolongin B (16), 27 (−)-virolongin C (17), 28 (+)-syringaresinol (18), 29 (−)(7′S,8R,8′R)-4,4′-dihydroxy-3,3′,5,5′-tetramethoxy-7′,9-epoxylignan-9′-ol-7-one (19), 30 (7′S,8R,8′R)-lariciresinol (20), 31 (2S,3R)-dihydrodehydrodiconiferyl alcohol (21), 32 costunolide ( 22), 33 eupatolide ( 23), 34 epi-tulipinolide (24), 35 trans-N-feruloyl tyramine (25), 36 trans-N-feruloyl-3-methoxytyramine (26), 36 sakuranetin (27), 37 5,6,7-trimethoxycoumarin (28), 38 methoxyeugenol (29), 39 N-phenethylbenzamide (30), 40 N-phenethyl-N-methylacetamide (31), vanillin (32), 41 and 4-hydroxybenzaldehyde (33) 42 by the comparison of their spectroscopic and physical data with published values for the structures (see the Supporting Information file). This is the first report on the isolation of virolongins A−C (15−17, respectively), dehydrotemisin (4), sakuranetin (27), and N-phenethyl-N-methylacetamide (31) from this plant.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Tulipiferamide A, an Alkamide from Liriodendron tulipifera, Exhibits an Anti-Inflammatory Effect via Targeting IKKβ Phosphorylation

et al. 2021

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Three new alkamides, tulipiferamides A–C (1–3, respectively), and 30 known compounds (4–33) were obtained from the roots of Liriodendron tulipifera (Magnoliaceae). Dehydrotemisin (4), an elemane sesquiterpene lactone, was isolated for the first time from nature. The structures were deduced by the interpretation of NMR spectroscopic and MS spectral data. The geometries of the double bonds in tulipiferamides A–C (1–3, respectively) were determined on the basis of 1H–1H coupling constants and 13C chemical shifts. The presence of the alkamide type in this plant is reported for the first time. An analysis of the inflammatory response revealed that seven compounds (1, 4, 7, 9, 14, 23, and 27) suppressed the nitric oxide production induced by LPS in RAW264.7 macrophages. Furthermore, tulipiferamide A (1) inhibits NF-κB activation by selectively targeting IKKβ, an upstream kinase of NF-κB, resulting in the suppression of inflammatory mediators, including iNOS, COX-2, IL-1β, TNFα, and IL-6. Our results provide a rationale for the further development of tulipiferamide A as a selective IKKβ inhibitor to modulate inflammatory diseases.

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2-Pyrrolidinones and 3-Pyrrolin-2-ones: A Study on the Chemical Reactivity of These Structural Moieties

Abstract: The chemical reactivity of 2-pyrrolidinones and 3-pyrrolin-2-ones was evaluated in reactions of addition, nucleophilic substitution, elimination, and reduction as well as the protection of the lactamic nitrogen.

Cited by 2 publications

References 19 publications

Stable Isotope Dilution Analysis (SIDA) to Determine Metabolites of Furan and 2-Methylfuran in Human Urine Samples: A Pilot Study

Stable Isotope Dilution Analysis (SIDA) to Determine Metabolites of Furan and 2-Methylfuran in Human Urine Samples: A Pilot Study

Tulipiferamide A, an Alkamide from Liriodendron tulipifera, Exhibits an Anti-Inflammatory Effect via Targeting IKKβ Phosphorylation

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