Antifungal Activity of Dihydrobenzofuran Neolignans

Dias, Herbert Júnior; Aquaroni, Nayara As; Pietro, Rosimeire Clr; Crotti, Antonio E. M.

doi:10.15406/mojpb.2017.06.00201

Cited by 5 publications

(7 citation statements)

References 26 publications

(31 reference statements)

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“…4 Over the years, the dermatomycosis has had a considerable increase, being that their treatment is still based on the use of triazoles (fluconazole, itraconazole, voriconazole), imidazoles (ketoconazole), allylamines (terbinafine), and griseofulvin. 5 However, due to the increase in the number of individuals immunocompromised by HIV, transplanted individuals and individuals undergoing cancer treatment, there was a reduction in the number of effective drugs against many dermatopathogens. 6 In Brazil, human fungal infections are prevalent, but these diseases caused by fungi are not officially reportable.…”

Section: Introductionmentioning

confidence: 99%

Antifungal activity of the essential oils of plectranthus neochilus (Lamiaceae) and tagetes erecta (Asteraceae) cultivated in brazil

Crevelin¹

2018

IJCAM

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The herbaceous and aromatic plant Plectranthus neochilus is popularly known as "boldo-rasteiro" in Brazil. 16 The essential oil of P. neochilus displays antimicrobial, 17 antischistosomal, 16 and insecticidal, 18 activities. On the other hand, Tagetes erecta L., commonly known as "marigold" in many countries and as "cravo-dedefunto" in Brazil, is an annual aromatic and branched herb native to Mexico. The essential oil from its leaves is utilized as antihelminthic in the Amazonia region. 19 Despite the different reported biological activities of these plants, the antifungal effects of its essential oil have not yet been investigated. Thus, as part of our ongoing interest in the biological activities of essential oils, in this work, we now report the chemical composition and the antifungal activity in vitro against fungi that cause dermatomycoses and aspergillosis of the essential oils obtained from leaves of P. neochilus (PN-EO) and T. erecta (TE-EO) grown in Brazil.

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Section: Introductionmentioning

confidence: 99%

Antifungal activity of the essential oils of plectranthus neochilus (Lamiaceae) and tagetes erecta (Asteraceae) cultivated in brazil

Crevelin¹

2018

IJCAM

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“…Recent studies on the cytotoxicity of DBNs to V79 cells demonstrated that acetylation of compound 1 (IC 50 = 232.00 AE 7.33 lM) to produce compound 4 (IC 50 = 67.97 AE 3.45 lM) increases cytotoxicity. [30] In contrast, hydrogenation of the double bond between C7 0 and C8 0 to produce compounds 6 and 7 from compounds 1 and 2, respectively, decreased the schistosomicidal activity drastically. Compound 9, which has a double bond between C7 and C8, exhibited less intense schistosomicidal action as compared to compound 1.…”

Section: Resultsmentioning

confidence: 99%

“…Similarly, acetylation of compound 2 to produce compound 5 increased the schistosomicidal activity. Recent studies on the cytotoxicity of DBNs to V79 cells demonstrated that acetylation of compound 1 (IC 50 = 232.00 ± 7.33 μ m ) to produce compound 4 (IC 50 = 67.97 ± 3.45 μ m ) increases cytotoxicity . In contrast, hydrogenation of the double bond between C7′ and C8′ to produce compounds 6 and 7 from compounds 1 and 2 , respectively, decreased the schistosomicidal activity drastically.…”

Section: Resultsmentioning

confidence: 99%

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Schistosomicidal Activity of Dihydrobenzofuran Neolignans

Dias

Patrocinio

Pagotti

et al. 2018

Chemistry & Biodiversity

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We have evaluated the antischistosomal activity of synthetic dihydrobenzofuran neolignans (DBNs) derived from (±)-trans-dehydrodicoumaric acid dimethyl ester (1) and (±)-trans-dehydrodiferulic acid dimethyl ester (2) against adult Schistosoma mansoni worms in vitro. Compound 4 ((±)-trans-4-O-acetyldehydrodiferulic acid dimethyl ester) displayed the most promising activity; at 200 μm, it kills 100 ± 0% of worms after 24 h, which resembles the result achieved with praziquantel (positive control) at 1.56 μm. The hydrogenation of the double bond between C7' and C8', the introduction of an additional methyl group at C3', and a double bond between C7 and C8 decreased the schistosomicidal activity of DBNs. On the other hand, the presence of the acetoxy group at C4 played an interesting role in this activity. These results demonstrated the interesting schistosomicidal potential of DBNs, which could be further exploited.

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“…The DBNs investigated in this study were synthesized as reported previously. 6,26,27 Briefly, the core structure of compounds 1 to 8 was obtained by oxidative coupling of coumaric (a), ferulic (b), and caffeic (c) methyl esters promoted by Ag 2 O in acetone/benzene (5:8) mixture.…”

Section: Synthesismentioning

confidence: 99%

Gas‐phase fragmentation reactions of protonated benzofuran‐ and dihydrobenzofuran‐type neolignans investigated by accurate‐mass electrospray ionization tandem mass spectrometry

et al. 2018

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We have investigated gas‐phase fragmentation reactions of protonated benzofuran neolignans (BNs) and dihydrobenzofuran neolignans (DBNs) by accurate‐mass electrospray ionization tandem and multiple‐stage (MSn) mass spectrometry combined with thermochemical data estimated by Computational Chemistry. Most of the protonated compounds fragment into product ions B ([M + H–MeOH]+), C ([B–MeOH]+), D ([C–CO]+), and E ([D–CO]+) upon collision‐induced dissociation (CID). However, we identified a series of diagnostic ions and associated them with specific structural features. In the case of compounds displaying an acetoxy group at C‐4, product ion C produces diagnostic ions K ([C–C2H2O]+), L ([K–CO]+), and P ([L–CO]+). Formation of product ions H ([D–H2O]+) and M ([H–CO]+) is associated with the hydroxyl group at C‐3 and C‐3′, whereas product ions N ([D–MeOH]+) and O ([N–MeOH]+) indicate a methoxyl group at the same positions. Finally, product ions F ([A–C2H2O]+), Q ([A–C3H6O2]+), I ([A–C6H6O]+), and J ([I–MeOH]+) for DBNs and product ion G ([B–C2H2O]+) for BNs diagnose a saturated bond between C‐7′ and C‐8′. We used these structure‐fragmentation relationships in combination with deuterium exchange experiments, MSn data, and Computational Chemistry to elucidate the gas‐phase fragmentation pathways of these compounds. These results could help to elucidate DBN and BN metabolites in in vivo and in vitro studies on the basis of electrospray ionization ESI‐CID‐MS/MS data only.

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Antifungal Activity of Dihydrobenzofuran Neolignans

Cited by 5 publications

References 26 publications

Antifungal activity of the essential oils of plectranthus neochilus (Lamiaceae) and tagetes erecta (Asteraceae) cultivated in brazil

Antifungal activity of the essential oils of plectranthus neochilus (Lamiaceae) and tagetes erecta (Asteraceae) cultivated in brazil

Schistosomicidal Activity of Dihydrobenzofuran Neolignans

Gas‐phase fragmentation reactions of protonated benzofuran‐ and dihydrobenzofuran‐type neolignans investigated by accurate‐mass electrospray ionization tandem mass spectrometry

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