Isoflavones and coumarins from Milletia thonningii

Asomaning, William A.; Otoo, Emmanuel; Akoto, Osei; Oppong, Isaac V.; Addae‐Mensah, Ivan; Waibel, Reiner; Achenbach, Hans

doi:10.1016/s0031-9422(99)00019-9

Cited by 25 publications

(12 citation statements)

References 5 publications

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“…200–203 °C; IR ν max : 3288, 3093, 1716, 1658, 1620 cm −1 ; GC-MS m / z 437; 1 H-NMR (400 MHz, CDCl 3 ) δ: 10.23 (1H, s), 7.48 (1H, s), 7.45 (1H, d, J = 8 Hz), 7.00 (1H, s), 6.99 (1H, d, J = 8 Hz), 6.90 (1H, s), 6.89 (1H, m), 3.94 (1H, s), 3.91 (1H, s), 3.90 (1H, s), 3.85 (1H, s), 2.23 (1H, s); 13 C-NMR (100 MHz, CDCl 3 ) δ: 165.0, 160.1, 158.8, 158.5, 158.3, 143.8, 131.1, 122.1, 113.0, 110.4, 103.9, 102.1, 95.8, 64.7, 54.7, and 19.9. This is in agreement with published data [32].…”

Section: Methodssupporting

confidence: 94%

“…The isolation yielded robustic acid ( 1 ), thonningine-C ( 2 ), alpinumisoflavone ( 3 ), O , O -dimethylalpinumisoflavone ( 4 ) and 4’- O -methylalpinumisoflavone ( 5 ). These compounds are known constituents of the plant [20,30,31,32]. The yield of compound 5 was low but more was successfully synthesised via demethylation of 4 for biological testing.…”

Section: Resultsmentioning

confidence: 99%

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Coumarin Antifungal Lead Compounds from Millettia thonningii and Their Predicted Mechanism of Action

et al. 2016

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Fungal pathogens continue to pose challenges to humans and plants despite efforts to control them. Two coumarins, robustic acid and thonningine-C isolated from Millettia thonningii, show promising activity against the fungus Candida albicans with minimum fungicidal concentration of 1.0 and 0.5 mg/mL, respectively. Molecular modelling against the putative bio-molecular target, lanosterol 14α-demethylase (CYP51), revealed a plausible binding mode for the active compounds, in which the hydroxyl group binds with a methionine backbone carboxylic group blocking access to the iron catalytic site. This binding disrupts the synthesis of several important sterols for the survival of fungi.

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Section: Methodssupporting

confidence: 94%

Section: Resultsmentioning

confidence: 99%

Coumarin Antifungal Lead Compounds from Millettia thonningii and Their Predicted Mechanism of Action

et al. 2016

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“…Research geared towards the isolation of bioactive compounds from organisms thriving in these areas remain largely unexplored. Rather, a lot of attention has being focused on the terrestrial environment with most works dedicated to plant secondary metabolites (Adotey et al 2012 ; Asomaning et al 1999 ).…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial and antioxidant properties of the crude peptide extracts of Galatea paradoxa and Patella rustica

et al. 2015

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This study evaluated the antimicrobial and antioxidant activities of crude peptide extracted from Galatea paradoxa (G. paradoxa) and Patella rustica (P. rustica). The extracts were tested against eight strains of bacteria (Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Salmonella typhi, Enterococcus feacalis, Klebseilla pneumoniae, Streptococcus pneumoniae, Pseudomonas aeruginosa) and one strain of fungi (Candida albicans) using agar well diffusion and broth dilution assays. The extracts from G. paradoxa demonstrated a high degree of activity against the bacteria strains but were inactive towards the fungus. P. rustica, however, showed a markedly higher antifungal activity but little antibacterial effect. The minimum inhibitory concentrations (MIC) of the extracts determined by the broth tube dilution assay were 17 mg/mL of G. paradoxa against the entire spectrum of microorganisms tested except for C. albicans which was 20 mg/mL. The MIC of the extracts of P. rustica was 13 mg/mL against all the strains of microorganisms tested except for E. feacalis (17 mg/mL), K. pneumoniae (17 mg/mL) and C. albicans (13 mg/mL). Antioxidant activity using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay showed scavenging ability on the DPPH radical was 56.77 % at 0.39 mg/mL for G. paradoxa and 79.77 % at 0.39 mg/mL for P. rustica. The study indicates that the crude peptide extracts from the two molluscs have promising antimicrobial and antioxidant activities that can be harnessed as leads for potential bioactive compounds.

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“…Based on literature precedence, the signals at δ 4.59 (2H, br d, J = 6.6 Hz), 5.51 (1H, t, J = 7.0 Hz), 1.75 (3H, s), and 1.72 (3H, s) were assigned to a 3 ‴ -methyl-2 ‴ -butenyl moiety linked to C-4′ through an oxygen atom. 19,20 The foregoing suggested that the structure of pierreione C should be identical to the dimethoxy derivative of the previously known pyranoisoflavone, isoauriculasin. 20 Thus, pierreione C was identified as 3′,5-dimethoxy-4′- O -(3-methyl-2-butenyl)-3″,3″-dimethylpyrano-(6,7)-isoflavone ( 3 ).…”

mentioning

confidence: 99%

Pierreiones A−D, Solid Tumor Selective Pyranoisoflavones and Other Cytotoxic Constituents from Antheroporum pierrei

Gao

Valeriote

et al. 2011

J. Nat. Prod.

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Bioassay-guided fractionation of a solid tumor selective extract of the leaves and twigs of Antheroporum pierrei acquired from the U.S. National Cancer Institute extract repository afforded four new pyranoisoflavones, pierreiones A–D (1 – 4), together with rotenone (5), 12a-hydroxyrotenone (6), and tephrosin (7). The structures of all new compounds were determined on the basis of their spectroscopic data, and the absolute configuration of 1 was assigned with the help of 1H NMR analysis of its Mosher's ester derivatives. Compounds 1, and 5–7 accounted for the majority of the biological activity in terms of either cytotoxicity and/or selective toxicity to solid tumor cell lines. Pierreiones A (1) and B (2) demonstrated solid tumor selectivity with minimal cytotoxicity while pierreione C (3) exhibited no activity.

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Isoflavones and coumarins from Milletia thonningii

Cited by 25 publications

References 5 publications

Coumarin Antifungal Lead Compounds from Millettia thonningii and Their Predicted Mechanism of Action

Coumarin Antifungal Lead Compounds from Millettia thonningii and Their Predicted Mechanism of Action

Antimicrobial and antioxidant properties of the crude peptide extracts of Galatea paradoxa and Patella rustica

Pierreiones A−D, Solid Tumor Selective Pyranoisoflavones and Other Cytotoxic Constituents from Antheroporum pierrei

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