Novel 4,5-Diaryl-3-hydroxy-2(5H)-furanones as Anti-Oxidants and Anti-Inflammatory Agents

Weber, Valérie

doi:10.1016/s0968-0896(02)00053-6

Cited by 50 publications

(24 citation statements)

References 42 publications

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“…Mushrooms are rich in the reactants of the Maillard reaction such as carbohydrates, proteins, and lipids [6]. Moreover, some furanones are found in fruits and their antioxidant and anti-inflammatory activities are also reported [34]. 2-Methoxy-4-vinylphenol (0.49 mg/kg) and 2,6-dimetoxy-4-vinylphenol (0.33 mg/kg), which are found in coffee [35], possess antioxidant activity as well as anti-inflammatory activity [36].…”

Section: Chemicals Identified and Their Relationships To Antioxidant mentioning

confidence: 99%

Antioxidant/Anti-Inflammatory Activities and Chemical Composition of Extracts from the Mushroom Trametes Versicolor

Kamiyama¹,

Shibamoto

Horiuchi³

et al. 2013

IJNFS

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Abstract:The mushroom, Trametes versicolor is commonly used as a traditional Chinese medicine and is known to exhibit various biological activities. However, its antioxidant activity has remained unknown. In the present study, various extracts obtained from the Trametes versicolor mushroom were examined for antioxidant and anti-inflammatory activities. Among the extracts obtained with Soxhlet extraction, the extract from acetone exhibited the highest antioxidant activity (50.9%), followed by the extracts from methanol (33.9%), n-hexane (29.5%), and chloroform (15.2%) at the level of 500 µg/mL. This acetone fraction displayed a dose-dependent anti-inflammatory activity or lipoxygenase inhibitory activity by 76.4% at 500 µg/mL, 55.6% at 200 µg/mL, and 37.0% at 100 µg/mL. Among a total of 76 compounds identified in this acetone extract, hexadecanoic acid was the largest component (18.11 mg/kg), followed by 5-hydroxy-2-pentanone (17.33 mg/kg), lactic acid (3.25 mg/kg), and acetic acid (3.21 mg/kg). The following possible principles of antioxidant activity were identified: furfural (1.48 mg/kg), γ-butyrolactone (0.51 mg/kg), furfuryl alcohol (0.49 mg/kg), 2-methoxy-4-vinylphenol (0.49 mg/kg), and 2,6-dimetoxy-4-vinylphenol (0.33 mg/kg), and benzaldehyde (0.15 mg/kg).

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Section: Chemicals Identified and Their Relationships To Antioxidant mentioning

confidence: 99%

Antioxidant/Anti-Inflammatory Activities and Chemical Composition of Extracts from the Mushroom Trametes Versicolor

Kamiyama¹,

Shibamoto

Horiuchi³

et al. 2013

IJNFS

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“…Phospholipids containing polyunsaturated fatty acids are predominantly susceptible to peroxidation. ROS are produced during the inflammation process by phagocytic leukocytes at the inflamed site and they are involved in the biosynthesis of prostaglandins and in the cycloxygenase-and lipoxygenase-mediated conversion of arachidonic acid into proinflammatory intermediates 7,8 . LO products are regulators of platelet [Ca 2þ ] mobilization and aggregation in response to some agonists.…”

Section: Biological Studiesmentioning

confidence: 99%

“…Persistently high levels of reactive oxygen species (ROS) are believed to produce pathological conditions. ROS, like superoxide radical anion, hydrogen peroxide and hydroxyl radical, are produced during the inflammation process by phagocytic leukocytes at the inflamed site and they are involved in the biosynthesis of prostaglandins and in the cycloxygenase (COX)-and lipoxygenase (LO)-mediated conversion of arachidonic acid into proinflammatory intermediates 7,8 . Initial studies of the effects of adenosine on human neutrophiles 9 indicated that adenosine inhibits stimulated O À 2 or H 2 O 2 generation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of modified purine homo-N-nucleosides containing pyrazole or 2-pyrazoline moiety

Thalassitis

Katsori

Dimas

et al. 2013

Journal of Enzyme Inhibition and Medicinal Chemistry

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9-Substituted (pyrazol-5-yl)methyl-or (2-pyrazolin-5-yl)methyl-9H-purines were synthesized from 9-allyl-6-chloro-9H-purine through the 1,3-dipolar cycloaddition reaction with nitrile imines, prepared in situ from the corresponding hydrazone and NBS/Et 3 N under MW or from hydrazinoylchloride and Et 3 N under reflux. The coupling of new 6-chloropurines with amines in H 2 O under microwaves resulted quantitatively to modified pyrazol-5-yl-or 2-pyrazolin-5-yl adenine homo-N-nucleosides. The new compounds were tested in vitro for their ability to: (i) interact with 1,1-diphenyl-2-picryl-hydrazyl (DPPH), (ii) inhibit lipid peroxidation, (iii) inhibit the activity of soybean lipoxygenase, (iv) inhibit in vitro thrombin and for (v) their antiproliferative and cytotoxic activity. Pyrazolines were found to be more potent in vitro. Compound 7a exhibited satisfactory combined antioxidant and anti-lipid peroxidation activity, inhibition of lipoxygenase (89%) and thrombin inhibitory ability, whereas compound 7b exhibited high lipoxygenase inhibitory activity in combination to significant anti-thrombin activity. No compound exhibited a significant cytotoxic activity, while all showed moderate antiproliferative activity.

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“…As shown in Figure 2, l-ascorbic acid (1) and penicillic acid (2) are two important derivatives of the butenolide. 17 Also, butenolide rings are present in a number of natural compounds. 18 Chemical structures of some known butenolides that are separated from natural compounds like bipinnatin J (3), 19 asteriscunolide D (4), 20 gymnodimine (5), 21 lambertellol C (6) and spirofragilide (7) are also shown in Figure 2.…”

Section: Introductionmentioning

confidence: 99%

Tetramethylguanidine-functionalized silica-coated iron oxide magnetic nanoparticles catalyzed one-pot three-component synthesis of furanone derivatives

et al. 2018

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Tetramethylguanidine-functionalized silica-coated iron oxide magnetic nanoparticles as a productive and reusable catalyst have been applied for the one-pot three-component synthesis of furanone derivatives (4a-o). In addition to the characterization of all products by FT-IR, 1 HNMR and 13 CNMR spectroscopy, single-crystal X-ray analysis of ethyl 5-oxo-2-phenyl-4-(phenylamino)-2,5-dihydrofuran-3carboxylate product has been made. Easy recrystallization and good-to-excellent yields (81-92%) of furanone derivatives are notable characteristics of this procedure. The catalyst identification was performed using FT-IR, XRD, SEM, TEM and TGA techniques. It is worth noting that the nanocatalyst can be recycled with an external magnet and reused for several times.

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Novel 4,5-Diaryl-3-hydroxy-2(5H)-furanones as Anti-Oxidants and Anti-Inflammatory Agents

Cited by 50 publications

References 42 publications

Antioxidant/Anti-Inflammatory Activities and Chemical Composition of Extracts from the Mushroom Trametes Versicolor

Antioxidant/Anti-Inflammatory Activities and Chemical Composition of Extracts from the Mushroom Trametes Versicolor

Synthesis and biological evaluation of modified purine homo-N-nucleosides containing pyrazole or 2-pyrazoline moiety

Tetramethylguanidine-functionalized silica-coated iron oxide magnetic nanoparticles catalyzed one-pot three-component synthesis of furanone derivatives

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