The Antioxidant Activity of Coumarins and Flavonoids

Bubols, Guilherme Borges; Vianna, Débora Renz Barreto; Medina‐Remón, Alexander; Poser, Gilsane von; Lamuela‐Raventós, Rosa M.; Eifler‐Lima, Vera Lucia; Garcia, Solange Cristina

doi:10.2174/138955713804999775

Cited by 117 publications

(64 citation statements)

References 144 publications

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“…However, CHCl 3 , SLG, and n -hexane extracts significantly reduced the lipid peroxidation. The phytochemical screening revealed the presence of low polarity compounds, such as coumarins and alkaloids, both inhibitors of lipid peroxidation [53, 54]. These results are in accordance with previous studies on antioxidant activity of Smilax species extracts, which presented diverse mechanisms of action, such as quenching of superoxide anion, lipid peroxidation inhibition, deoxyribose degradation inhibition, and reducing power [29, 55].…”

Section: Discussionsupporting

confidence: 86%

Phytochemical and Antinociceptive, Anti‐Inflammatory, and Antioxidant Studies of Smilax larvata (Smilacaceae)

Hirota

Paula

Oliveira

et al. 2016

Evidence-Based Complementary and Alternative Medicine

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The tea of aerial parts of Smilax larvata Griseb. (Smilacaceae) has been ethnopharmacologically used in Southern Brazil due to its anti-inflammatory action. In this study, ethanolic and organic extracts from aerial parts of S. larvata were phytochemically and pharmacologically characterized. The phytochemical analysis of EtOAc extract of S. larvata revealed the presence of three flavonoids, drabanemoroside, kaempferol 3-O-α-L-rhamnopyranosyl(1→2)-α-L-rhamnopyranoside, and kaempferol, the first two being isolated for the first time in this genus, two phenolic compounds p-hydroxybenzoic acid and p-coumaric acid, and alkaloids. In vitro assays demonstrated a potential antioxidant property of SLG. The treatment with SLG induced a significant reduction of the formalin-evoked flinches in rats, an effect reversed by opioid antagonist naloxone. Treatment with SLG also induced a significant increase in the hot plate latency and a decrease of intestinal motility by 45%. No effect was observed over nociceptive responses induced by a TRPA1 agonist mustard oil or over acetic acid-induced writhing in mice. Together, our data suggested that SLG has an in vivo antinociceptive effect, which seems to be associated with the opioid system activation. These findings support previous claims of medical use of Smilax larvata in the treatment of pain conditions.

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Section: Discussionsupporting

confidence: 86%

Phytochemical and Antinociceptive, Anti‐Inflammatory, and Antioxidant Studies of Smilax larvata (Smilacaceae)

Hirota

Paula

Oliveira

et al. 2016

Evidence-Based Complementary and Alternative Medicine

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“…2C). The lack of effect under control conditions is surprising because flavonoids are well known for their antioxidant properties (Bubols et al, 2013) and they have been shown to be protective against a variety of excitotoxic insults by reducing oxidative stress (Cho and Lee, 2004, Silva et al, 2008, Campos-Esparza et al, 2009). However, the neuroprotective effects of rhamnetin during EWD suggest that the mechanism of enhanced excitotoxicity following ethanol exposure is a target for rhamnetin.…”

Section: Discussionmentioning

confidence: 99%

The Dietary Flavonoid Rhamnetin Inhibits Both Inflammation and Excitotoxicity During Ethanol Withdrawal in Rat Organotypic Hippocampal Slice Cultures

Lutz

Carter

Fields

et al. 2015

Alcoholism Clin & Exp Res

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Background Ethanol causes neurotoxicity via several mechanisms including neuroinflammation (during ethanol exposure), and excitotoxicity (during ethanol withdrawal – EWD). Alpha7 nicotinic acetylcholine receptor (nAChR) selective agonists have the potential to reduce both. The aim of this study was to evaluate the anti-inflammatory and neuroprotective potential of rhamnetin, a dietary flavonoid with alpha7 nAChR selective activity, in an in vitro model of ethanol-induced neurotoxicity. Methods The anti-inflammatory and neuroprotective properties of rhamnetin were assessed in neonatal organotypic hippocampal slice cultures (OHSC) undergoing EWD (or not) and challenged with N-methyl-D-aspartate (NMDA) and/or lipopolysaccharide (LPS). Neurotoxicity was determined using propidium iodide uptake and the inflammatory response was evaluated by measuring the release of TNF-alpha (quantified by ELISA) and nitric oxide (quantified by the Griess reaction) into culture media. Results As predicted, rhamnetin reduced LPS-induced release of TNF-alpha and nitric oxide both under control conditions and during EWD. Additionally, rhamnetin had no effect on NMDA induced neurotoxicity under control conditions but significantly reduced NMDA toxicity during EWD. In contrast, rhamnetin had no effect on neurotoxicity induced by NMDA and LPS combined despite reducing TNF-alpha and nitric oxide levels under these conditions. Conclusions Rhamnetin is anti-inflammatory and neuroprotective during EWD and therefore has potential value in treating neurotoxicity caused by ethanol.

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“…Moreover, coumarins are considered as a privileged scaffold in the design of compounds with several biological targets. Coumarin derivatives displayed a wide range of pharmacological activities like anti-cancer [188], among others [189][190][191][192][193].…”

Section: Coumarin Derivativesmentioning

confidence: 99%

Synthesis of Biologically Active Molecules through Multicomponent Reactions

et al. 2020

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Focusing on the literature progress since 2002, the present review explores the highly significant role that multicomponent reactions (MCRs) have played as a very important tool for expedite synthesis of a vast number of organic molecules, but also, highlights the fact that many of such molecules are biologically active or at least have been submitted to any biological screen. The selected papers covered in this review must meet two mandatory requirements: (1) the reported products should be obtained via a multicomponent reaction; (2) the reported products should be biologically actives or at least tested for any biological property. Given the diversity of synthetic approaches utilized in MCRs, the highly diverse nature of the biological activities evaluated for the synthesized compounds, and considering their huge structural variability, much of the reported data are organized into concise schemes and tables to facilitate comparison, and to underscore the key points of this review.Molecules 2020, 25, 505 2 of 71 acetylcholinesterase inhibitors, anti-HIV, antimicrobial, antioxidant, anti-mycobacterial and anticancer activities ( Figure 1). It is noteworthy that 64% and 16% of the supporting literature found for this review correspond to heterocyclic structures with anticancer and antimicrobial activities, respectively. Scheme 2. Three-component synthesis of 3,4-dihydropyrimidinones/thiones type 7 under microwave irradiation, for anti-inflammatory activity.Patil et al., reported a one-pot pseudo-five-component synthesis of highly functionalized tetrahydropyridines 9 using Cu(OTf) 2 as catalyst, Scheme 3. In vitro anti-inflammatory activity of the obtained compounds 9 was determined against matrix metalloproteinases (MMPs) as MMP-2 and MMP-9 by using gelatin zymography [29]. Scheme 3. Multicomponent Cu(OTf) 2 catalyzed synthesis of substituted tetrahydropyridines 9 for anti-inflammatory activity.A highly diastereoselective synthesis (exclusively the cis isomer is formed), of chromeno β-lactam hybrids 13/14 was also achieved by an efficient one-pot three-component reaction between either 5,5-dimethylcyclohexane-1,3-dione (10a) or 4-hydroxycoumarin (10b), diverse benzaldehydes 11 and malononitrile (12), in the presence of DABCO under reflux conditions (Scheme 4). Scheme 4. Three-component synthesis of β-lactam hybrids 13/14 for anti-inflammatory activity.The synthesized compounds (13 in 80-95% yield) and (14 in 82-95% yield) were screened for anti-inflammatory activity (as well as for anticancer activity, please see Section 3.13.13. Compound 13b (Ar = 4-ClC 6 H 4 , Ar 1 = 4-MeC 6 H 4 ) was the most active of all the chromeno β-lactam hybrids 13/14 tested, with a 19.8 anti-inflammatory ratio, although, it resulted less active than the reference drug dexamethasone corticosteroid used for the treatment of rheumatoid and skin inflammation [30].

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The Antioxidant Activity of Coumarins and Flavonoids

Cited by 117 publications

References 144 publications

Phytochemical and Antinociceptive, Anti‐Inflammatory, and Antioxidant Studies of Smilax larvata (Smilacaceae)

Phytochemical and Antinociceptive, Anti‐Inflammatory, and Antioxidant Studies of Smilax larvata (Smilacaceae)

The Dietary Flavonoid Rhamnetin Inhibits Both Inflammation and Excitotoxicity During Ethanol Withdrawal in Rat Organotypic Hippocampal Slice Cultures

Synthesis of Biologically Active Molecules through Multicomponent Reactions

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