Antiprotozoal Activity of &amp;#945,&amp;#946-Unsaturated &amp;#948-Lactones: Promising Compounds for the Development of New Therapeutic Alternatives

Wilson, Cardona G; Jairo, Saez V

doi:10.4314/tjpr.v10i5.17

Cited by 5 publications

(3 citation statements)

References 42 publications

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“…In the early phases of drug discovery, computer‐aided techniques have often been used to discover and optimize novel hit or lead compounds of pharmaceutical interest [42] . Aligned to our in silico prediction results, the specialized literature indicated that some natural lactones displayed anti‐ Plasmodium falciparum effect, [24] and α,β‐unsaturated lactones presented antiprotozoal activity [43] . Following our in silico results, we investigated in vitro trypanocidal activities of (+)‐phomalactone ( 1 ), hydroxypestalopyrone ( 2 ), and pestalopyrone ( 3 ) against T. cruzi epimastigotes and trypomastigotes aiming to determine their inhibition activities (IC 50 ).…”

Section: Resultsmentioning

confidence: 75%

“…[42] Aligned to our in silico prediction results, the specialized literature indicated that some natural lactones displayed anti-Plasmodium falciparum effect, [24] and α,β-unsaturated lactones presented antiprotozoal activity. [43] Following our in silico results, we investigated in vitro trypanocidal activities of (+)-phomalactone (1), hydroxypestalopyrone (2), and pestalopyrone (3) against T. cruzi epimastigotes and trypomastigotes aiming to determine their inhibition activities (IC 50 ). Cytotoxicity assays toward Vero cells (CC 50 ) and selectivity index (SI, CC 50 /IC 50 ) values were also determined (Table 2).…”

Section: Resultsmentioning

confidence: 99%

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Computer‐Guided Trypanocidal Activity of Natural Lactones Produced by Endophytic Fungus of Euphorbia umbellata

Gusmão

Abreu

Tavares

et al. 2021

Chemistry & Biodiversity

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Hundreds of millions of people worldwide are affected by Chagas’ disease caused by Trypanosoma cruzi. Since the current treatment lack efficacy, specificity, and suffers from several side‐effects, novel therapeutics are mandatory. Natural products from endophytic fungi have been useful sources of lead compounds. In this study, three lactones isolated from an endophytic strain culture were in silico evaluated for rational guidance of their bioassay screening. All lactones displayed in vitro activity against T. cruzi epimastigote and trypomastigote forms. Notably, the IC50 values of (+)‐phomolactone were lower than benznidazole (0.86 vs. 30.78 μM against epimastigotes and 0.41 vs. 4.88 μM against trypomastigotes). Target‐based studies suggested that lactones displayed their trypanocidal activities due to T. cruzi glyceraldehyde‐3‐phosphate dehydrogenase (TcGAPDH) inhibition, and the binding free energy for all three TcGAPDH‐lactone complexes suggested that (+)‐phomolactone has a lower score value (−3.38), corroborating with IC50 assays. These results highlight the potential of these lactones for further anti‐T. cruzi drug development.

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Section: Resultsmentioning

confidence: 75%

Section: Resultsmentioning

confidence: 99%

Computer‐Guided Trypanocidal Activity of Natural Lactones Produced by Endophytic Fungus of Euphorbia umbellata

Gusmão

Abreu

Tavares

et al. 2021

Chemistry & Biodiversity

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“…γ-Decalactone and lactone analogs have been shown to be effective against Aspergillus species, C. albicans, Penicillium roqueforti, and Staphylococcus aureus, , Erwinia amylovora and Pantoae agglomerans, and even against protozoa . Effective antimicrobial volatiles include lipoxygenase pathway products against Alternaria alternata and Botrytis cinerea and against Colletotrichum acutatum .…”

Section: Introductionmentioning

confidence: 99%

Methyl Anthranilate and γ-Decalactone Inhibit Strawberry Pathogen Growth and Achene Germination

Chambers

Evans²,

Folta

2013

J. Agric. Food Chem.

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Plant volatile compounds have been shown to affect microbial growth and seed germination. Here two fruity volatiles found in strawberry ( Fragaria × ananassa ), γ-decalactone ("peachlike" aroma) and methyl anthranilate ("grapelike" aroma), were tested for effects on relevant pathogens and seedling emergence. Significant growth reduction was observed for Botrytis cinerea , Colletotrichum gloeosporioides , Colletotrichum acutatum , Phomopsis obscurans , and Gnomonia fragariae at 1 mM γ-decalactone or methyl anthranilate, and 5 mM γ-decalactone or methyl anthranilate supplemented medium resulted in complete cessation of fungal growth. Phytophthora cactorum was especially sensitive to 1 mM γ-decalactone, showing complete growth inhibition. Bacteriostatic effects were observed in Xanthamonas cultures. Postharvest infestations on store-bought strawberries were inhibited with volatile treatment. The γ-decalactone volatile inhibited strawberry and Arabidopsis thaliana germination. These findings show that two compounds contributing to strawberry flavor may also contribute to shelf life and suggest that γ-decalactone may play an ecological role by preventing premature germination.

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Total Synthesis of Coibacin D by Using Enantioselective Allylation and Metathesis Reactions

et al. 2016

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Thef irst asymmetric total synthesis of coibacin D, am etabolite isolated from the marine cyanobacterium cf. Oscillatoria sp.,w as achieved in six steps starting from simple hept-6-en-1-ol. The synthetic strategy was based on ac hiral Brønsted acid catalyzed enantioselective allylboration and aR u-carbene complex catalyzed sequential ring-closing and cross-metathesis strategy.T he recorded spectroscopic data and the sign of the opticalr otation of the synthesized coibacin Dw erei na greement with the published data for the isolated compound, which confirmed the proposed structure and absolute configuration. Figure 1. CoibacinsA-D and their antileishmanialactivity (in parentheses).Scheme4.One-potmetathesis of 5 to give 8a or 8b.Scheme5.Halogenolysis of 8 with NCS.Scheme6.Enantioselective synthesis of coibacinD(1b).

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Antiprotozoal Activity of &#945,&#946-Unsaturated &#948-Lactones: Promising Compounds for the Development of New Therapeutic Alternatives

Cited by 5 publications

References 42 publications

Computer‐Guided Trypanocidal Activity of Natural Lactones Produced by Endophytic Fungus of Euphorbia umbellata

Computer‐Guided Trypanocidal Activity of Natural Lactones Produced by Endophytic Fungus of Euphorbia umbellata

Methyl Anthranilate and γ-Decalactone Inhibit Strawberry Pathogen Growth and Achene Germination

Total Synthesis of Coibacin D by Using Enantioselective Allylation and Metathesis Reactions

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