Antinociceptive activity of the pyranocoumarin seselin in mice

Lima, Vilma; Silva, Caio B.; Mafezoli, Jair; Bezerra, Mirna Marques; Moraes, Manoel Odoríco de; Mourão, Guilherme S.M.M.; Silva, J. Nunes; Oliveira, Maria C. F. de

doi:10.1016/j.fitote.2006.09.005

Cited by 35 publications

(20 citation statements)

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“…It has been isolated from plants particularly those belonging to the Rutaceae family (Keating and O'Kennedy, 1997;Borges et al, 2005). It has several activities including vasodilatory (Lima et al, 2006); antitumor and anti-HIV (Huang et al, 1994);antifungal (Bandara et al, 1991;Cardenas-Ortega et al, 2007); ovicidal against Tetranynchus urticae (red spider mite) (Tanaka et al, 1985); weak to moderate cytotoxicity (Gunatilaka et al, 1994); peripheral anti-inflammatory and antinociceptive (Lima et al, 2006); inhibits phytohemagglutinin-stimulated cell proliferation in human blood mononuclear cells (Tsai et al, 2008); inhibitory activity in both indole acetic acid oxidase and peroxidase enzyme systems (Goren and Tomer, 1971) and autotoxicity in citrus trees (Singh et al, 1999). However this is the first report on seselin having mosquito larvicidal activity.…”

Section: Discussionmentioning

confidence: 99%

Larvicidal activity of leaf extracts and seselin from Clausena anisata (Rutaceae) against Aedes aegypti

Mukandiwa

Eloff

Naidoo

2015

South African Journal of Botany

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Highlights• Hexane leaf extracts of Clausena anisata cause A. eagypti mosquito larval mortality.• The larvicidal activity is partially attributed to the pyranocoumarin, seselin.• The hexane leaf extract retains larvicidal activity after 2 months of storage. AbstractThe Aedes aegypti mosquito is a vector of various diseases in both humans and livestock.Mosquito control focuses on reducing the longevity as well as the population of mosquitoes to lessen their damage on human and animal health. It entails several strategies such as environmental management, insecticide treatments, and molecular entomological approaches.Environmental management centres on elimination of breeding sites, however mosquitoes can breed in sites that cannot be eliminated. Resultantly, focus is turned onto mosquito larvae control. The objective of this study was to evaluate the larvicidal activity of extracts and compounds from Clausena anisata against A. aegypti. The World Health Organization guidelines for testing of mosquito larvicides were used. The acetone, dichloromethane and hexane crude leaf extracts were evaluated in a preliminary screening for larvicidal activity at 2 the concentrations of 12.5, 25, 50, 100 and 200 ppm. Batches of 25 third-instar larvae were transferred into cups each containing test solutions and larval mortality was recorded 24 h and 48 h after exposure. Acetone was used as the solvent control while permethrin was used as a positive control. Only the n-hexane extract caused mortality at the tested concentrations, thus it was further tested at 40, 60, 80, 100, and 120 ppm and had LC 50 values of 68.30 and 59.65 ppm after 24h and 48h respectively. A stored hexane extract, of 2 months, was also evaluated under simulated field conditions to establish stability of extract. It caused about 90% mortality when tested at 100 ppm. The n-hexane extract was subjected to open column chromatography on silica gel to isolate the active compound. The isolated compound was identified as the pyranocoumarin, seselin. Dose dependent mortality was observed in the larvae exposed to seselin. The LC 50 values at 24 and 48 h were 13.90 and 9.96 ppm respectively. Results obtained from this study indicate a potential of the incorporation of C.anisata extracts into the control of mosquito populations.

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Section: Discussionmentioning

confidence: 99%

Larvicidal activity of leaf extracts and seselin from Clausena anisata (Rutaceae) against Aedes aegypti

Mukandiwa

Eloff

Naidoo

2015

South African Journal of Botany

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“…However, considering that pain therapies from natural sources date back thousands of years owing to a variety of painful conditions and inflammatory injuries, studies aimed at discovering new compounds of natural origin with potential therapeutic effects and minimal side effects have been pursued vigorously. 1) It has been proposed that inflammatory pain mediators should be classified in two groups: direct activators of nociceptors and nociceptor upregulators that directly sensitize the nociceptors. Therefore, considering both these mechanisms of nociceptor activation (excitation and upregulation), it is possible to define some classes of peripheral analgesics.…”

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confidence: 99%

Antinociceptive and Anti-inflammatory Activities of Lectin from Marine Red Alga Pterocladiella capillacea

Silva

Lima

Araújo

et al. 2010

Biological & Pharmaceutical Bulletin

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Researchers see algae as a promising tool to discover both efficient and safe agents for pain therapy. We evaluated the antinociceptive and anti-inflammatory activities of lectin from the marine alga Pterocladiella capillacea lectin (PcL). PcL was purified and tested in classical models of nociception and inflammation. Male Swiss mice received PcL 30 min prior to receiving 0.8% acetic acid (10 m ml/10 g, i.p.), 1% formalin (20 m ml/intraplantar) or the hot plate test, and were compared to untreated animals or animals pretreated with indomethacin or morphine. PcL (0.9, 8.1 or 72.9 mg/kg, i.v.) significantly reduced the number of writhes (30%, 39%, and 52%, respectively). PcL (72.9 mg/kg, i.v.) also reduced (pϽ Ͻ0.05) both the first and second phases of the formalin test by 58% and 87%, respectively. However, PcL (72.9 mg/kg) did not present significant antinociceptive effects in the hot plate test when compared to morphine, suggesting that its antinociceptive action occurs via peripheral rather than a central-acting mechanism. It was also observed that leukocyte migration was induced by carrageenan (500 m mg/cavity) in male Wistar rats and that PcL (8.1 mg/kg, i.v.) significantly reduced neutrophil migration by 84%, as compared to untreated animals, suggesting inhibition of inflammatory mediators. The data indicated that PcL has peripheral actions with both anti-inflammatory and antinociceptive properties.

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“…A solution of 7-hydroxy-6-(3-methyl-but-2-enyl)-chromen-2-one (31.7 mg, 0.14 mmol) in CH2Cl2 (3 mL) was added dropwise to an ice-cooled solution of 4-bromobenzyl chloride (33.26 mg, 0.15 mmol) and triethylamine (0.04 mL, 0.28 mmol). The mixture was stirred at room temperature for 18 h, basified with saturated aqueous NaHCO 3 , extracted with dichloromethane, dried over MgSO 4 and concentrated under reduced pressure. The residue was purified by flash column chromatography (EtOAc:n-Hexane = 1:5) to provide the product (23.4 mg, 74% yield).…”

Section: -Nitro-benzoic Acid 6-(3-methyl-but-2-enyl)-2-oxo-2h-chromementioning

confidence: 99%

“…1 Especially, coumarins isolated from Angelica gigas exhibit neuroprotective, 2 antitumor, 3 antinociceptive, 4 antibacterial, 5 platelet antiaggregatory 6 and protein kinase C (PKC) activation activities. 7 Coumarins of A. gigas contain a series of dihydropyranocoumarins, including (+)-decursin, (+)-decursinol angelate, (-)-prantschimgin, (+)-decursinol, and (-)-marmesin.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Decursin, Prantschimgin and Their Derivatives

Xia¹,

Min²,

Lee³

2009

Bulletin of the Korean Chemical Society

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The synthesis of coumarin-based natural products and their derivatives is described. In vitro MDR reversal activities of the synthesized compounds were evaluated in P-glycoprotein over-expressing human sarcoma cell line MES-SA/DX5. Some of the coumarin derivatives were found to show potent MDR reversal activity. In particular, pyridyl derivative (15e) exhibited more potency than verapamil. 9 In view of such diverse biological activities, it is of interest to construct a coumarin library in order to generate biologically interesting lead compounds. Accordingly, it has driven us to synthesize the coumarin derivatives and investigate their biological activities.As part of our program for development of novel multidrug resistance (MDR) modulators, we have screened a library of natural products including coumarins and synthetic molecules. Multidrug resistance (MDR) that disables most potent anticancer drugs is one of major problems in chemotherapy. 10 Intensive biochemical and clinical studies have demonstrated that overexpression of P-glycoprotein (Pgp), an ATP-binding cassette transporter, is largely responsible for MDR and clinically more significant than other mechanisms. Although a number of compounds with the effect of inhibiting Pgp have been developed, no useful drug is available so far. There is still high unmet clinical need for novel Pgp inhibitors. For the excavation of Pgp-selective MDR modulators, we have established image based high-throughput screening system and identified a series of coumarins that reverse Pgp-mediated MDR. We herein report an efficient synthesis of coumarins and their MDR reversal activity. Results and DiscussionChemistry. The syntheses of the target compounds were accomplished as indicated in Scheme 1 and 2. The intermediate, ortho-prenylated phenol 4 was readily prepared as described in the literature, 11 starting from 2,4-dihydroxybenzaldehyde 1. Boc protection of 1, followed by NaBH 4 reduction, gave alcohol 3 in 63% yield (2 steps). Addition of excess of Grignard reagent to the alcohol 3 afforded ortho-prenylated phenol 4. Benzyl protection of this phenol 4 and subsequent removal of the Boc group under acidic condition afforded benzyloxy prenylated phenol 6. Then treatment of triethylorthoformate in the presence of AlCl 3 introduced formyl group in 35% yield. Heating the aldehyde 7 with (carbethoxymethylene)-triphenylphosphorane in diethylaniline gave prenylated coumarin 8 in 84% yield. Debenzylation of 8 with Raney nickel furnished demethylsuberosin (9), which was converted into racemic marmesin (10) and decursinol (11) under basic and acidic conditions, respectively. Decursinol angelate (12) and decursin (13) were obtained by coupling of decursinol with angelic acid and senecioyl chloride, respectively. DCC mediated coupling of marmesin (10) with angelic acid provided prantschimgin (14). Naturally occurring coumarins, marmesin (10), decursinol (11), decursinol angelate (12), decursin (13) and prantschimgin (14) were efficiently obtained from intermediate 9. We next turned o...

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Antinociceptive activity of the pyranocoumarin seselin in mice

Cited by 35 publications

References 11 publications

Larvicidal activity of leaf extracts and seselin from Clausena anisata (Rutaceae) against Aedes aegypti

Larvicidal activity of leaf extracts and seselin from Clausena anisata (Rutaceae) against Aedes aegypti

Antinociceptive and Anti-inflammatory Activities of Lectin from Marine Red Alga Pterocladiella capillacea

Synthesis and Biological Evaluation of Decursin, Prantschimgin and Their Derivatives

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