Antibacterial chalcones––bioisosteric replacement of the 4′-hydroxy group

Nielsen, Simon Feldbæk; Boesen, Thomas; Larsen, Mona; Schønning, Kristian; Kromann, Hasse

doi:10.1016/j.bmc.2004.03.071

Cited by 163 publications

(95 citation statements)

References 27 publications

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“…Many of chalcones derivatives have been found to be also antioxidant (Miranda et Bioactivity and potential therapeutic benefits of some medicinal plants from the Caatinga (semi-arid) vegetation of Northeast Brazil: a review of the Maria I. G. Silva et al al., 2000), molluscicidal (Adewunmi et al, 1987) and antimicrobial (Nielsen et al, 2004). In addition to these pharmacological actions, in recent study carried out by researchers from our laboratory (Nobre-Junior et al, 2009), a chalcone-enriched fraction isolated from the stem bark of M. urundeuva presented neuroprotective action on 6-hydroxydopamine (6-OHDA)-induced neuronal cell death, in rat mesencephalic cells.…”

Section: Myracrodruon Urundeuva Allemão Anacardiaceae (Aroeira-do-sementioning

confidence: 94%

Bioactivity and potential therapeutic benefits of some medicinal plants from the Caatinga (semi-arid) vegetation of Northeast Brazil: a review of the literature

Silva¹,

Melo²,

Vasconcelos³

et al. 2012

Rev. bras. farmacogn.

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Abstract:Medicinal plants have been used in traditional medicine for several thousand years all over the world. In this sense, information from Brazilian ethnic groups on folk medicine have contributed to the discovery of pharmacological activities from various plant-derived agents potentially leading to the innovative drugs. The Caatinga (semi-arid) vegetation is a highly threatened biome, covering a vast area in northeastern Brazil and has suffered from strong human influence for many decades. Many plants species found in the Caatinga have been widely used in folk medicine and for commercial manufacturing of phytotherapeutic products. Thus, the present review aims to disseminate to the scientific community some known species of medicinal plants found in the Caatinga that have been studied and analyzed in pharmacological scientific assays. Among the species that stood out for their local importance and multiplicity of uses were: Amburana cearensisand Zingiber officinalis L. (gengibre). The present study shows that several herbal constituents from Caatinga plants, whose pharmacological actions have been well characterized, may be relevant candidates for future and innovative therapeutic development.

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Section: Myracrodruon Urundeuva Allemão Anacardiaceae (Aroeira-do-sementioning

confidence: 94%

Bioactivity and potential therapeutic benefits of some medicinal plants from the Caatinga (semi-arid) vegetation of Northeast Brazil: a review of the literature

Silva¹,

Melo²,

Vasconcelos³

et al. 2012

Rev. bras. farmacogn.

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“…Flavanonas e chalconas sintéticas e naturais são conhecidas por apresentarem várias atividades farmacológicas entre elas citotóxica, anti-inflamatória, antiangiogênica, antipirética, analgésica. 11,12 .…”

Section: Introductionunclassified

Avaliação das atividades antiproliferativa e antioxidante em frutos de Campomanesia pubescens

Cardoso

Salvador

Carvalho

et al. 2014

Rev. Inst. Adolfo Lutz

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Avaliação das atividades antiproliferativa e antioxidante em frutos de Campomanesia pubescensEvaluation of antioxidant and antiproliferative activities in fruits of Campomanesia pubescens RESUMO A investigação química dos extratos bioativos dos frutos de Campomanesia pubescens (Myrtaceae) resultou no isolamento de duas chalconas. Os compostos isolados foram identificados pelas análises espectroscópicas ( 1 H, 13C e 2D RMN) e, por comparação com os dados descritos na literatura. A capacidade antioxidante dos extratos e frações foi determinada utilizando-se os ensaios de capacidade de absorção de oxigênio radical (ORAC-FL) e de DPPH; e os teores de fenólicos solúveis foram medidos utilizando-se o reagente de Folin-Ciocalteau. Os efeitos antiproliferativos dos extratos e de isolados de chalconas 1 e 2 foram determinados in vitro contra as seguintes células cancerosas humanas U251 (glioma), UACC-62 (melanoma), MCF-7 (mama), NC1-ADR/RES (ovário resistente), 786,0 (rim), NCI-H460 (pulmão), PC-3 (próstata), OVCAR-3 (ovário), HT-29 (cólon) e K562 (leucemia), e contra linhagem celular não cancerígena VERO. O extrato hexânico e os compostos isolados de chalconas 1 e 2 demonstraram efeito antiproliferativo potente contra linhagens de células cancerosas com valores de inibição de crescimento total (TGI) menores dos aqueles observados na linhagem celular controle. A atividade mais elevada das chalconas 1 e 2 foi detectada nas células MCF-7, PC-3 e HT-29. Palavras-chave. guavira, Campomanesia pubescens, DPPH, antiproliferativa, chalconas. ABSTRACTChemical investigation on the bioactive extracts from fruits of Campomanesia pubescens (Myrtaceae) resulted in the isolation of two chalcones. The isolated compounds were identified by means of spectroscopic analysis ( 1 H, 13C and 2D NMR), and by comparing with the data reported in the specific literature. Antioxidant capacity of extracts and fractions was determined using the oxygen radical absorbance capacity (ORAC-FL) and DPPH assays; and the total soluble phenolic contents were measured by using Folin-Ciocalteau reagent. The anti-proliferative effects of the extracts and of the chalcone isolates 1 and 2 were determined in vitro against human cancer cells lineages U251 (glioma), UACC-62 (melanoma), MCF-7 (breast), NC1-ADR/RES (ovarian-resistant), 786.0 (kidney), NCI-H460 (lung), PC-3 (prostate), OVCAR-3 (ovarian), HT-29 (colon) and K562 (leukemia), and against non-cancerous cell line VERO. Hexanic extract and chalcone isolated compounds 1 and 2 showed potent antiproliferative effect against cancer cell lineages with lower total growth inhibition (TGI) values than those found in control cell line. The highest activity of the chalcones 1 and 2 was observed against the MCF-7, PC-3 and HT-29 cell lines.

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“…[1,2] These heterocyclic compounds have already been previously described as anticancer, antiviral, anti-inflammatory, antimicrobial, enzymatic inhibitory and antioxidant agents. [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] Taking in account the versatility of the coumarin moiety one can thoroughly modify it to best serve one purposes. In this work, our group fused two other classes of natural products onto the coumarin skeleton, the chalcones (figure 1 -A) and the resveratrol derivatives ( figure 1 -B).…”

Section: Introductionmentioning

confidence: 99%

Structural Modifications on Natural-based Products: Synthetic Strategies and Biological Applications

Fonseca

Matos

Vázquez-Rodríguez

et al. 2014

Proceedings of the 18th International Electronic Conference on Synthetic Organic Chemistry

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Coumarins are a class of heterocyclic compounds present in a significant quantity in several plants. The simplest coumarin, a benzene ring fused with a pyran-2-one heterocycle, was first discovered in the 19 th century and since then, due to the synthetic accessibility and the biological properties of its derivatives, has been playing an important role in the Medicinal Chemistry field. In fact, coumarins have been previously described as anticancer, antiviral, anti-inflammatory, antimicrobial, enzymatic inhibitory and antioxidant agents.Another two interesting compounds found widely in nature are resveratrol derivatives and chalcones. Both families of compounds are known for having remarkable antioxidant activity, cardio-and neuroprotective effects, among other relevant biological properties. Therefore, we devised several synthetic strategies to incorporate these natural products in one compound, combining their potential as promising agents for the treatment of several illnesses.In our group, we have already synthesised multiple novel compounds incorporating into the coumarin scaffold the resveratrol or chalcones moieties with remarkable activities towards different pharmacological targets. In this work, we continue exploiting this strategy by incorporating different linkers at coumarin position 3, thus giving us a wide range of possibilities for new compounds.

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Antibacterial chalcones––bioisosteric replacement of the 4′-hydroxy group

Cited by 163 publications

References 27 publications

Bioactivity and potential therapeutic benefits of some medicinal plants from the Caatinga (semi-arid) vegetation of Northeast Brazil: a review of the literature

Bioactivity and potential therapeutic benefits of some medicinal plants from the Caatinga (semi-arid) vegetation of Northeast Brazil: a review of the literature

Avaliação das atividades antiproliferativa e antioxidante em frutos de Campomanesia pubescens

Structural Modifications on Natural-based Products: Synthetic Strategies and Biological Applications

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