Efeito antifúngico de α-pineno isolado e em associação com antifúngicos frente às cepas de Candida albicans

Barros, Daniela Bomfim; Lima, Luanna de Oliveira e; Silva, Larissa Alves; Fonseca, Mariana Cavalcante; Neto, Hermes Diniz; Rocha, Walicyranison Plínio da Silva; Beltrão, Gheorgia Victoria de Medeiros; Castellano, Lúcio Roberto Cançado; Guerra, Felipe Queiroga Sarmento; Silva, Márcia Vanusa da

doi:10.33448/rsd-v11i4.27748

Cited by 4 publications

(4 citation statements)

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“…It was seen that α-pinene presents a fungicidal effect, and that this effect occurs after 4 h of exposure to the drug, corroborating what was observed in our previous study [ 19 ], which demonstrated a fungicidal effect through the determination of MIC and MFC.…”

Section: Discussionsupporting

confidence: 90%

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α-Pinene: Docking Study, Cytotoxicity, Mechanism of Action, and Anti-Biofilm Effect against Candida albicans

et al. 2023

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Candida albicans is associated with serious infections in immunocompromised patients. Terpenes are natural-product derivatives, widely studied as antifungal alternatives. In a previous study reported by our group, the antifungal activity of α-pinene against C. albicans was verified; α-pinene presented an MIC between 128–512 µg/mL. In this study, we evaluate time-kill, a mechanism of action using in silico and in vitro tests, anti-biofilm activity against the Candida albicans, and toxicity against human cells (HaCaT). Results from the molecular-docking simulation demonstrated that thymidylate synthase (−52 kcal mol−1), and δ-14-sterol reductase (−44 kcal mol−1) presented the best interactions. Our in vitro results suggest that α-pinene’s antifungal activity involves binding to ergosterol in the cellular membrane. In the time-kill assay, the antifungal activity was not time-dependent, and also inhibited biofilm formation, while rupturing up to 88% of existing biofilm. It was non-cytotoxic to human keratinocytes. Our study supports α-pinene as a candidate to treat fungal infections caused by C. albicans.

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Section: Discussionsupporting

confidence: 90%

“…As reported by our group [ 19 ], the antifungal activity of α-pinene against planktonic strains of C. albicans has been verified, whether alone or in association with other drugs. A-pinene presented an MIC between 128–512 µg/mL and the MFC presented the same values, which demonstrated its fungicidal effect.…”

Section: Introductionsupporting

confidence: 63%

α-Pinene: Docking Study, Cytotoxicity, Mechanism of Action, and Anti-Biofilm Effect against Candida albicans

et al. 2023

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“…The hydrocarbon monoterpene α-pinene showed significant antifungal activity against Candida parapsilosis [ 39 ] and C . albicans [ 40 ]. Antifungal activity of caryophyllene oxide was reported in a previous study [ 41 ].…”

Section: Resultsmentioning

confidence: 99%

Exploring the chemical composition, in vitro and in silico study of the anticandidal properties of annonaceae species essential oils from the Amazon

Cascaes,

Marques da Silva,

de Oliveira

et al. 2023

PLoS ONE

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Chemical composition of the essential oils (EOs) from the leaves of five Annonaceae species found in the amazon region was analyzed by Gas chromatography coupled to mass spectrometry. The antifungal activity of theses EOs was tested against Candida albicans, Candida auris, Candida famata, Candida krusei and Candida tropicalis. In addition, an in silico study of the molecular interactions was performed using molecular modeling approaches. Spathulenol (29.88%), α-pinene (15.73%), germacra-4(15),5,10(14)-trien-1-α-ol (6.65%), and caryophylene oxide (6.28%) where the major constitents from the EO of Anaxagorea dolichocarpa. The EO of Duguetia echinophora was characterized by β-phellanderene (24.55%), cryptone (12.43%), spathulenol (12.30%), and sabinene (7.54%). The major compounds of the EO of Guatteria scandens where β-pinene (46.71%), α-pinene (9.14%), bicyclogermacrene (9.33%), and E-caryophyllene (8.98%). The EO of Xylopia frutescens was characterized by α-pinene (40.12%) and β-pinene (36.46%). Spathulenol (13.8%), allo-aromadendrene epoxide (8.99%), thujopsan-2-α-ol (7.74%), and muurola-4,10(14)-dien-1-β-ol (7.14%) were the main chemical constituents reported in Xylopia emarginata EO. All EOs were active against the strains tested and the lowest inhibitory concentrations were observed for the EOs of D. echinophora, X. emarginata, and X. frutescens against C. famata the Minimum Inhibitory Concentration values of 0.07, 0.019 and 0.62 μL.mL-1, respectively. The fungicidal action was based on results of minimum fungicidal concentration and showed that the EOs showed fungicide activity against C. tropicalis (2.5 μL.mL-1), C. krusei (2.5 μL.mL-1) and C. auris (5 μL.mL-1), respectively. The computer simulation results indicated that the major compounds of the EOs can interact with molecular targets of Candida spp.

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“…Docking maps of (E)-3-benzylidene-chroman-4-one with the analyzed targets indicated the presence of hydrogen bonds, which are stronger bonds that result from the electrostatic attraction between a negatively charged atom and a hydrogen atom; steric interactions, which are internal bonds; and electrostatic interactions, resulting from the electrostatic attraction between ionized groups with opposite charges, characterized as weak bonds [ 39 ]. The target Thymidylate kinase (5UIV), a phosphotransferase crucial for synthesizing genetic material and parasite survival [ 40 ], exhibited the highest affinity with the test compound.…”

Section: Discussionmentioning

confidence: 99%

In Silico and In Vitro Evaluation of the Antifungal Activity of a New Chromone Derivative against Candida spp.

Araújo,

Costa,

Nogueira

et al. 2024

BioTech

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Candida species are frequently implicated in the development of both superficial and invasive fungal infections, which can impact vital organs. In the quest for novel strategies to combat fungal infections, there has been growing interest in exploring synthetic and semi-synthetic products, particularly chromone derivatives, renowned for their antimicrobial properties. In the analysis of the antifungal activity of the compound (E)-benzylidene-chroman-4-one against Candida, in silico and laboratory tests were performed to predict possible mechanisms of action pathways, and in vitro tests were performed to determine antifungal activity (MIC and MFC), to verify potential modes of action on the fungal cell membrane and wall, and to assess cytotoxicity in human keratinocytes. The tested compound exhibited predicted affinity for all fungal targets, with the highest predicted affinity observed for thymidylate synthase (−102.589 kJ/mol). MIC and CFM values ranged from 264.52 μM (62.5 μg/mL) to 4232.44 μM (1000 μg/mL). The antifungal effect likely occurs due to the action of the compound on the plasma membrane. Therefore, (E)-benzylidene-chroman-4-one showed fungicidal-like activity against Candida spp., possibly targeting the plasma membrane.

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Efeito antifúngico de α-pineno isolado e em associação com antifúngicos frente às cepas de Candida albicans

Cited by 4 publications

References 0 publications

α-Pinene: Docking Study, Cytotoxicity, Mechanism of Action, and Anti-Biofilm Effect against Candida albicans

α-Pinene: Docking Study, Cytotoxicity, Mechanism of Action, and Anti-Biofilm Effect against Candida albicans

Exploring the chemical composition, in vitro and in silico study of the anticandidal properties of annonaceae species essential oils from the Amazon

In Silico and In Vitro Evaluation of the Antifungal Activity of a New Chromone Derivative against Candida spp.

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