Improved synthesis of seven aromatic Baylis–Hillman adducts (BHA): Evaluation against Artemia salina Leach. and Leishmania chagasi

Barbosa, Ticiano P.; G.L., Cláudio; Silva, Fábio P.L.; Lopes, Horacimone M.; Figueiredo, Lucas R. F.; Sousa, Suervy C.O.; Batista, Guilherme N.; Silva, Thiago G. da; Silva, Tania M. S.; Oliveira, Márcia Rosa de; Vasconcellos, Mário L. A. A.

doi:10.1016/j.ejmech.2008.03.016

Cited by 30 publications

(21 citation statements)

References 22 publications

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“…Barbosa et al (2009) demonstrated that the A. salina assay was efficient in the search for antileishmanial substances. The evaluation of plant extract toxicity by the brine shrimp bioassay, an LC 50 value lower than 1000 μg/mL is considered bioactive (Meyer et al, 1982).…”

Section: Resultsmentioning

confidence: 99%

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Different susceptibilities of Leishmania spp. promastigotes to the Annona muricata acetogenins annonacinone and corossolone, and the Platymiscium floribundum coumarin scoparone

Vila-Nova

Morais

Falcão

et al. 2013

Experimental Parasitology

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Leishmaniasis is a zoonotic disease that can manifest itself in visceral and cutaneous form. The aim of this study was to search for new leishmanicidal compounds. Preliminarily, Artemia salina assay was applied to compounds from two plants found in Northeastern Brazil, Platymiscium floribundum and Annona muricata. Then these compounds were tested against three Leishmania species (Leishmania donovani, Leishmania mexicana and Leishmania major). A screening assay using luciferase-expressing promastigote form were used to measure the viability of promastigote One coumarin, scoparone, isolated from P. floribundum and two acetogenins, annonacinone and corossolone isolated from A. muricata showed leishmanicidal activity in all species tested. Nevertheless, Leishmania species indicated different susceptibilities in relation to the tested compounds: L. mexicana was more sensitive to scoparone followed by L. major and L. donovani. The three species presented similar inhibition to corossolone and annonacinone. Acetogenin annonacinone (EC50 = 6.72 8.00 μg/mL) indicated high leishmanicidal activity; corossolone (EC50 = 16.14 18.73 μg/mL) and scoparone (EC50 = 9.11 27.51 μg/mL) moderate activity. A. saline larvae were less sensitive to the coumarin scoparone and acetogenin corossolone was the most toxic. In conclusion, the leishmanicidal activity demonstrated by the coumarin and acetogenins indicate these compounds for further studies aiming the development of new leishmanicidal agents.

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Section: Resultsmentioning

confidence: 99%

“…A. salina (Artemiidae), also known as brine shrimp larva, is an invertebrate normally used as a safe, practical and economic substitute assay to determine toxicity of compounds from natural products (Barbosa et al, 2009). The toxicity tests were developed using A. salina assay by Vanhaecke et al (1981) with modifications.…”

Section: Methodsmentioning

confidence: 99%

Different susceptibilities of Leishmania spp. promastigotes to the Annona muricata acetogenins annonacinone and corossolone, and the Platymiscium floribundum coumarin scoparone

Vila-Nova

Morais

Falcão

et al. 2013

Experimental Parasitology

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“…The product was obtained using 2,6-dichlorobenzaldehyde in 66 h. The crude product was purified by FC eluting with PE/EtOAc from 9.5/ 0.5 to 8/2 to afford 29 as a colorless oil (0.210 mmol, 47 2-((2,4-Dichlorophenyl)(hydroxy)methyl)acrylonitrile (30). The product was obtained using 2,4-dichlorobenzaldehyde in 68 h. The crude product was purified by FC eluting with PE/EtOAc from 9.9/ 0.1 to 7/3 to afford 30 as a yellowish oil (0.370 mmol, 84.4 mg, 37% yield).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Electrophilic Warhead-Based Design of Compounds Preventing NLRP3 Inflammasome-Dependent Pyroptosis

et al. 2014

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Pyroptosis is a caspase-1-dependent pro-inflammatory form of programmed cell death implicated in the pathogenesis of autoinflammatory diseases as well as in disorders characterized by excessive cell death and inflammation. Activation of NLRP3 inflammasome is a key event in the pyroptotic cascade. In this study, we describe the synthesis and chemical tuning of α,β-unsaturated electrophilic warheads toward the development of antipyroptotic compounds. Their pharmacological evaluation and structure-activity relationships are also described. Compound 9 was selected as a model of this series, and it proved to be a reactive Michael acceptor, irreversibly trapping thiol nucleophiles, which prevented both ATP- and nigericin-triggered pyroptosis of human THP-1 cells in a time- and concentration-dependent manner. Moreover, 9 and other structurally related compounds, inhibited caspase-1 and NLRP3 ATPase activities. Our findings can contribute to the development of covalent, multitarget antipyroptotic compounds targeting molecular components of the NLRP3 inflammasome regulatory pathway.

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“…30 Brine shrimp eggs of A. salina were hatched in artificial sea water prepared from commercial sea salt (40 g/L). A plastic chamber with two compartments (one dark, one light) separated by a partition plate with small holes for the hatching was used.…”

Section: Cytotoxic Activitymentioning

confidence: 99%

Fungal hydroxylation of (-)-α-santonin

Pacciaroni¹,

Sosa²,

Bustos³

2012

ROC

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Functionalization of organic compounds using enzymes present in microorganisms is a very useful tool for organic chemists, since it is a method carried out under milder conditions than chemical ones and allows the introduction of functional groups in a nonreactive carbon in a regioselective and stereoselective way. In order to look for new compounds derived from natural products with antioxidant and cytotoxic activity, the sesquiterpene lactone (-)-α-santonin was transformed using a pure strain of Cunninghamella spp. A two-stage standard protocol with growing cells was followed, which led to 8β-hydroxy-α-santonin. The structure of the product was unequivocally elucidated by spectroscopic methods. Both the starting material and metabolite were tested in vitro for antioxidant activity using the 1,1-diphenyl-2-picrylhydrazyl method, and cytotoxic activity was tested using the Artemia salina (brine shrimp) method. In both assays, the new compound was less active than substrate and reference compounds, which means that the introduction of a hydroxyl group on carbon-8 of (-)-α-santonin with β stereochemistry did not improve the tested biological activities.

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Improved synthesis of seven aromatic Baylis–Hillman adducts (BHA): Evaluation against Artemia salina Leach. and Leishmania chagasi

Cited by 30 publications

References 22 publications

Different susceptibilities of Leishmania spp. promastigotes to the Annona muricata acetogenins annonacinone and corossolone, and the Platymiscium floribundum coumarin scoparone

Different susceptibilities of Leishmania spp. promastigotes to the Annona muricata acetogenins annonacinone and corossolone, and the Platymiscium floribundum coumarin scoparone

Electrophilic Warhead-Based Design of Compounds Preventing NLRP3 Inflammasome-Dependent Pyroptosis

Fungal hydroxylation of (-)-α-santonin

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Improved synthesis of seven aromatic Baylis–Hillman adducts (BHA): Evaluation against Artemia salina Leach. and Leishmania chagasi

Cited by 30 publications

References 22 publications

Different susceptibilities of Leishmania spp. promastigotes to the Annona muricata acetogenins annonacinone and corossolone, and the Platymiscium floribundum coumarin scoparone

Different susceptibilities of Leishmania spp. promastigotes to the Annona muricata acetogenins annonacinone and corossolone, and the Platymiscium floribundum coumarin scoparone

Electrophilic Warhead-Based Design of Compounds Preventing NLRP3 Inflammasome-Dependent Pyroptosis

Fungal hydroxylation of (-)-&alpha;-santonin

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Fungal hydroxylation of (-)-α-santonin