Antifungal and antibacterial naphthoquinones from Newbouldia laevis roots

Gafner, Stefan; Wolfender, Jean‐Luc; Nianga, Malo; Stœckli-Evans, Helen; Hostettmann, Kurt

doi:10.1016/0031-9422(96)00135-5

Cited by 140 publications

(87 citation statements)

References 14 publications

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“…Another study of the antimicrobial activity of 1,4-naphthoquinones indicated that active compounds must possess at least a substitution at position 2 or 3, which is either an electron-releasing or weaker electron with drawing group [32]. Consequently, the hydrogen bonding capacity is enhanced and allows the compound to bind more strongly to its site of action.…”

Section: Discussionmentioning

confidence: 99%

Antimicrobial Activities of the Henna Extract and Some Synthetic Naphthoquinones Derivatives

Rahmoun¹,

Boucherit-Atmani²,

Benabdallah³

et al. 2013

AJMBR

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Naphthoquinones are compounds widely distributed in the environment, both as natural products and as pharmaceutical agents. They have been the subject of much research due to their pharmacological activities. In this study, methanol extract of henna and a series of synthesized structural analogue of lawsone have been assessed for their antimicrobial activities. Methanol extract of henna and eight naphthoquinones derivatives were tested as potential antimicrobial agents against twelve bacteria and three Candida species using the agar disc diffusion and broth microdilution methods according to guidelines recommended by the Clinical and Laboratory Standards Institute. Besides 2b and 3b, methanol extract and all the synthesized compounds 1a, 2a, 1b and 1c, 2c and 3c showed weakto-strong activity against at least one tested strain. However, the compounds 1c and 1b were found to have the most effective activity against pathogenic bacteria and displayed an activity 8 to 64 fold higher than that othe structural analogue, lawsone. Their MICs ranged from 8-64 µg ml -1. Henna extract was found to have an interesting activity. Our results indicate an effective in vitro activity of 1,4-naphthoquinone derivatives and suggest the benefits of further studies for its application in antibiotherapy.

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Section: Discussionmentioning

confidence: 99%

Antimicrobial Activities of the Henna Extract and Some Synthetic Naphthoquinones Derivatives

Rahmoun¹,

Boucherit-Atmani²,

Benabdallah³

et al. 2013

AJMBR

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“…13 O lapachol (1) e seus derivados, como, por exemplo, a α-xiloidona (deidro-α-lapachona) (2) e a deidro-iso-α-lapachona (3), são naftoquinonas naturais isoladas das cascas das árvores da família Bignoneacea, como a Tabebuia spp., [1][2][3] Haplophragma adenophylum, 14 Oroxylum indicum (L.) Vent, 15 Newbouldia laevis Seem., 16 Radermachera sinica Hemsl 17 e mais recentemente da Catalpa ovata; 18 enquanto a rinacantina-A (4) foi isolada em 1988 da Rhinacanthus nasutus (L.) Kurz (Acanthaceae). 19 Lapachol (1), α-xiloidona (2) e a deidro-iso-α-lapachona (3) possuem atividades biológicas comuns a esta classe de substâncias, como as descritas acima, [1][2][3][4][5][6][7][8][9][10][11][12][13]18,[20][21][22]23 e a rinacantina-A (4) não apresentou citotoxicidade 19 (Figura 1).…”

Section: Introductionunclassified

Ciclização do lapachol induzida por sais de tálio III

Ribeiro¹,

Souza²,

Ferreira³

et al. 2008

Quím. Nova

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Recebido em 29/11/07; aceito em 7/3/08; publicado na web em 9/4/08 CYCLIZATION OF LAPACHOL INDUCED BY THALLIUM SALTS. This work describes the cyclization of lapachol (1) induced by thallium triacetate (TTA) and thallium trinitrate (TTN) in several solvents using magnetic stirring and under microwave irradiation. α-Xyloidone (2) -dehydro-α-lapachone -was obtained as the main product in these reactions in 20 -75% yield. However, rhinacanthin-A (4) was isolated as main product in a 40% yield, using TTA and acetic anhydride:water (1:1) as solvent, and dehydroiso-α-lapachone (3) in 21% yield, using TTA and dichloromethane as solvent. The reaction time decreased drastically under microwave conditions, but the yields of these reactions were not the expected.

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“…The degree of purity was determined by standard procedures (thin layer chromatography, melting point, elemental analysis). The structures were confirmed by proton nuclear magnetic resonance ( 1 H-NMR), 13 C-NMR, infrared spectroscopy, UV-visible spectroscopy, and mass spectrometry.…”

Section: Naphthoquinonesmentioning

confidence: 97%

“…Antibacterial activity has been described for isoxazolylnaphthoquinones (10), and some hydroxyquinones and their metal complexes (11,12). The fungitoxicity of naphthoquinones (8), particularly against several species of Candida (13)(14)(15), and the inhibitory activity of some naphthoquinones on HIV-1 protease have also been described (16,17).…”

Section: Introductionmentioning

confidence: 99%

In vitro antimicrobial activity of a new series of 1,4-naphthoquinones

Riffel

Medina

Stéfani

et al. 2002

Braz J Med Biol Res

126

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The antibacterial activity of a series of 1,4-naphthoquinones was demonstrated. Disk diffusion tests were carried out against several Gram-positive and Gram-negative bacteria. The compound 5-amino-8-hydroxy-1,4-naphthoquinone was the most effective, presenting inhibition zones measuring 20 mm against staphylococci, streptococci and bacilli at 50 µg/ml. Methicillin-resistant Staphylococcus aureus and several clinical isolates of this bacterium were also inhibited. Naphthazarin, 5-acetamido-8-hydroxy-1,4-naphthoquinone, and 2,3-diamino-1,4-naphthoquinone were the next most active compounds. The minimal inhibitory concentration of the active compounds was determined against S. aureus, ranging from 30 to 125 µg/ml. All compounds presented a minimal bactericidal concentration higher than 500 µg/ml, indicating that their effect was bacteriostatic. The EC 50 , defined as the drug concentration that produces 50% of maximal effect, was 8 µg/ml for 5-amino-8-hydroxy-1,4-naphthoquinone against S. aureus, S. intermedius, and S. epidermidis. These results indicate an effective in vitro activity of 5-amino-8-hydroxy-1,4-naphthoquinone and encourage further studies for its application in antibiotic therapy.

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Antifungal and antibacterial naphthoquinones from Newbouldia laevis roots

Cited by 140 publications

References 14 publications

Antimicrobial Activities of the Henna Extract and Some Synthetic Naphthoquinones Derivatives

Antimicrobial Activities of the Henna Extract and Some Synthetic Naphthoquinones Derivatives

Ciclização do lapachol induzida por sais de tálio III

In vitro antimicrobial activity of a new series of 1,4-naphthoquinones

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