Synthesis and Cytotoxicity Evaluation of a Series of 3-Alkenyl-2-Hydroxy1,4-Naphthoquinones Obtained by an Efficient Knoevenagel Condensation

David, Cibelle C.; Lins, Antonio C. S.; Silva, Tania M. S.; Campos, Júlia Furtado; Silva, Teresinha G.; Militão, Gardênia Carmen Gadelha; Câmara, Celso A.

doi:10.21577/0103-5053.20180146

Cited by 3 publications

(1 citation statement)

References 14 publications

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“…Among all quinones, 1,4-NQ and its secondary products are of particular interest because of their occurrence as natural chemicals and/or products [12,13]. These compounds have diverse pharmacological properties, such as antimicrobial [14], antiviral [15], antiprotozoal and anthelmintic [16,17], also presenting cytotoxic effects on cancer cell lines [18]. Moreover, 2-hydroxy-1,4-naphthoquinone (lawsone) (2-OH-NQ), a photochemical reaction product of 1,4-naphthoquinones, can also be extracted from the leaves of Lawsonia inermis.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of the Toxicity on Lung Cells of By-Products Present in Naphthalene Secondary Organic Aerosols

Albuquerque

Berger

Tomaz

et al. 2021

Life

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In 2018, seven million people died prematurely due to exposure to pollution. Polycyclic aromatic hydrocarbons (PAHs) are a significant source of secondary organic aerosol (SOA) in urban areas. We investigated the toxic effects of by-products of naphthalene SOA on lung cells. These by-products were 1,4-naphthoquinone (1,4-NQ), 2-hydroxy-1,4-naphthoquinone (2-OH-NQ), phthalic acid (PA) and phthaldialdehyde (OPA). Two different assessment methodologies were used to monitor the toxic effects: real-time cell analysis (RTCA) and the Holomonitor, a quantitative phase contrast microscope. The chemicals were tested in concentrations of 12.5 to 100 µM for 1,4-NQ and 1 to 10 mM for 2-OH-NQ, PA and OPA. We found that 1,4-NQ is toxic to cells from 25 to 100 µM (EC50: 38.7 µM ± 5.2); 2-OH-NQ is toxic from 1 to 10mM (EC50: 5.3 mM ± 0.6); PA is toxic from 5 to 10 mM (EC50: 5.2 mM ± 0.3) and OPA is toxic from 2.5 to 10 mM (EC50: 4.2 mM ± 0.5). Only 1,4-NQ and OPA affected cell parameters (migration, motility, motility speed and optical volume). Furthermore, 1,4-NQ is the most toxic by-product of naphthalene, with an EC50 value that was one hundred times higher than those of the other compounds. RTCA and Holomonitor analysis showed a complementarity when studying the toxicity induced by chemicals.

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Section: Introductionmentioning

confidence: 99%

Evaluation of the Toxicity on Lung Cells of By-Products Present in Naphthalene Secondary Organic Aerosols

Albuquerque

Berger

Tomaz

et al. 2021

Life

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NaCl as an eco-friendly and efficient promoter for Knoevenagel condensation at room temperature

Abrantes

Ferreira

et al. 2022

Synthetic Communications

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Chemical Constituents of Moringa oleifera Leaves of Ethanol Extract and its Cytotoxicity against Enterococcus faecalis of Root Canal Isolate

Soraya

Alibasyah

Nazar

et al. 2022

RJPT

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Moringa oleifera has been famous as a natural medicine due to its rich vitamins, minerals, and flavonoids. However, the study of its effect on Enterococcus faecalis (E. faecalis) is limited. This study analyzes the chemical constituents of the ethanol extract of Moringa leaves using GC-MS and assessing the toxicity against E. faecalis. Moringa oleifera leaves were extracted by ethanol, evaporated, and the concentrated extract was analyzed using GC-MS instruments. The effect of cytotoxic of Moringa oleifera against E. faecalis was investigated by morphological and coagulation cells; also, the toxicity area was evaluated by ImageJ software. The GC-MS Spectrum was confirmed by NIST databased resulted in 17 different compounds including Alpha-butyrolactone, 1,3-cyclopentanedione, Glycerin, Cis-1,2,6-trimethylpiperidine, 1,2-epoxy cyclohexane, benzeneacetaldehyde, Isobutyraldehyde, propylhydrazone, 2-pyrrolidinone, 2-butenamide,2-cyano-3-hydroxy, 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one, 2-trideuteromethoxy-3-methyl pyrazine, Benzeneacetonitrile,4-hydroxy-, 1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole, 1,3,4,5-tetrahydroxy-cyclohexane carboxylic acid, Hexadecanoic acid, n-cbz-beta-alanine, and 3-(2,2-dimethyltetrahydrofuran-3-yl)phenol. These active compounds are involved in the cytotoxicity against E. faecalis. The Moringa oleifera leaves have better toxicity at lower concentrations (12.5% and 6.25%) with 24 hours of incubating.: At least 17 chemical components were detected in the ethanol extract of Moringa oleifera leaves with quinic acid, glycerol, and DDMP as the most abundant compound. They probably affect the toxicity of E. faecalis cells.

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Synthesis and Cytotoxicity Evaluation of a Series of 3-Alkenyl-2-Hydroxy1,4-Naphthoquinones Obtained by an Efficient Knoevenagel Condensation

Cited by 3 publications

References 14 publications

Evaluation of the Toxicity on Lung Cells of By-Products Present in Naphthalene Secondary Organic Aerosols

Evaluation of the Toxicity on Lung Cells of By-Products Present in Naphthalene Secondary Organic Aerosols

NaCl as an eco-friendly and efficient promoter for Knoevenagel condensation at room temperature

Chemical Constituents of Moringa oleifera Leaves of Ethanol Extract and its Cytotoxicity against Enterococcus faecalis of Root Canal Isolate

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