Antifungal toxicity of linear geranylphenol. Influence of oxigenate substituents

The antioxidant effect of 8PP, a prenylflavonoid from Dalea elegans on Candida albicans biofilms, was investigated. We previously reported that sensitive (SCa) and resistant C. albicans (RCa) biofilms were strongly inhibited by this compound, in a dose-depending manner (50 μM-100 μM), with a prooxidant effect leading to accumulation of endogenous oxidative metabolites and increased antioxidant defenses. In this work, the antifungal activity of high concentrations of 8PP (200-1000 μM), the cellular stress imbalance and the architecture of biofilms were evaluated. Biofilms were studied by crystal violet and confocal scanning laser microscopy (CSLM) with COMSTAT analysis. Superoxide anion radical, the activity of the superoxide dismutase and the total antioxidant capacity were measured. Intracellular ROS were detected by a DCFH-DA and visualized by CSLM; reactive nitrogen intermediates by Griess. An antioxidant effect was detected at 1000 μM and levels of oxidant metabolites remained low, with major changes in the SCa. COMSTAT analysis showed that biofilms treated with higher concentrations exhibited different diffusion distances with altered topographic surface architectures, voids, channels and pores that could change the flow inside the matrix of biofilms. We demonstrate for first time, a concentration-dependent antioxidant action of 8PP, which can alter its antifungal activity on biofilms.

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“…2 and 3). The structure-antifungal activity relationships determined that free -OH are important for their activity (Taborga et al, 2017).…”

Section: Discussionmentioning

confidence: 99%

“…Taborga et al (2017) recently reported geranylphenols having in their structures hydroxyl groups and a geranyl chain attached to an aromatic nucleus, like the configuration of B ring in 8PP structure, which exhibited high percentages of inhibitory activity against standardized and clinical isolates of yeasts belonging to Candida and Cryptococcus genera.…”

mentioning

confidence: 99%

The antioxidant activity of a prenyl flavonoid alters its antifungal toxicity on Candida albicans biofilms

Peralta

Ortega

Cabrera

et al. 2018

Food and Chemical Toxicology

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“…Other synthetic geranylphenols, such as 2-geranyl-5methyl resorcinol and 4-geranyl-5-methyl resorcinol ( Figure 1A), showed antimicrobial and antifungal activities [16][17][18][19] . Recently, our research group has developed the synthesis, structural determination and antifungal activity of a series of linear geranylphenols derivatives of 2-geranylhydroquinones, such 2-geranylphloroglucinol ( Figure 1A) [20][21][22][23][24][25][26] .…”

Section: Linearmentioning

confidence: 99%

Cytotoxic Effect of Geranylphenol Derivatives in the Human Breast Cancer Cell Line MDA-MB-231 and Gastric Cancer Cell Line MKN74

Espinoza

Taborga

Araya

et al. 2020

Bangladesh J Med Sci

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Background: Previous studies have demonstrated that geranyl metabolites, found mainly in marine organisms, exhibit interesting antimicrobial and antifungal activities. In addition, linear geranyl derivatives have been synthesized as drugs and reported cytotoxic and anticancer activities. Aims: Considering the biological testing and the structural features of these compounds, we evaluated seven linear geranylphenol derivatives on the human breast cancer cell line MDA-MB-231, and the human gastric cancer cell line MKN74. Results: We found that compounds 2, 5 and 7 were cytotoxic for both cancer cell lines. From them, the most potent was compound 2, with an IC50=7.5 μM for MKN74 cells, and compound 7, with an IC50=14.73 μM for MDA-MB-231 cells. By nuclear staining and inmunocytochemistry, we detected that the three compounds induced cell death, and by Western blot analysis, we observed a remarkable decrease in the expression of cyclin D1 and the retinoblastoma protein, key regulators of the cell cycle. Conclusion: Considering that compounds 2 and 7 were the most potent compounds inducing cell death, and were able to decrease the expression of retinoblastoma protein and cyclin D1, proteins usually altered in different types of cancers, they appear as promising therapeutic agents against cancer. Bangladesh Journal of Medical Science Vol.19(3) 2020 p.486-500

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“…Based on the NOESY spectrum analysis, either cis or trans configurations were designated to the double bond present within the structure of some studied compounds. Secondary metabolite terpene compounds such as geranylphenol, mainly found in marine organisms, have been proved to be able to exert an antifungal effect (Taborga et al, 2017). Recently, the chemical structure of some A full list of recent articles published in food science related journals that used NOESY to elucidate the chemical structure of food compounds is given in Table 1. ROESY spectra were acquired by Masullo et al (2017) with a 400 ms mixture time at 600…”

Section: Structure Elucidationmentioning

confidence: 99%

“…geranylphenol compounds was evaluated byTaborga et al (2017) who involved 1D NOESY correlations in the chemical structure evaluation.Since protobassic acid saponins present in Sapotaceae family plants are reported to have cytotoxicity and antifungal properties, Chen et al(2017)studied their isolation from the kernels of Palaquium formosanum, which are thought to be effective as a prostate anticancer. In this study, different analysis methods were used, including NMR techniques.Together with those NMR techniques, NOESY spectrum interpretation revealed that there was an equilibrium between two conformations of the 3' -deglucosylated 10 compound.…”

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confidence: 99%

A review on nuclear overhauser enhancement (NOE) and rotating-frame overhauser effect (ROE) NMR techniques in food science: Basic principles and applications

Doost

Akbari

Stevens

et al. 2019

Trends in Food Science & Technology

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The characterization of the original chemical structure and induced changes of micro-and macro-molecules using analytical techniques with concise and detailed outcomes is potentially one of the major challenges for food scientists. To this end, the non-invasive nuclear magnetic resonance (NMR) technique can play a significant role through employment of different NMR methods. The Nuclear Overhauser effect (NOE) and rotating-frame Overhauser effect (ROE) techniques are powerful NMR methods that have attracted great interest because they provide precise information about the three dimensional spatial structure of the molecules, as well as about possible chemical reactions and interactions. Scope and approach In this article, we reviewed the basic principles as well as applications of two NMR techniques: Nuclear Overhauser effect spectroscopy (NOESY) and rotating-frame Overhauser effect spectroscopy (ROESY). Hereby, we focused mainly on the applications and importance of these techniques in food science research. Both the structural (configuration and conformation) changes and the complexes formed by interacting compounds could be better studied using these techniques. Key findings and conclusions The inter-and intra-molecular interactions within food-based ingredient mixtures, as well as configurational and conformational analyses can be more efficiently studied with the aid of NOESY and ROESY. These methods as complementary analysis tools can be exploited for the straightforward elucidation of the spatial proximity of either novel, native or modified compounds. In the future, these techniques may be helpful to better understand the interaction between polymers, such as protein-polysaccharide interactions.

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Antifungal toxicity of linear geranylphenol. Influence of oxigenate substituents

Cited by 5 publications

References 45 publications

The antioxidant activity of a prenyl flavonoid alters its antifungal toxicity on Candida albicans biofilms

The antioxidant activity of a prenyl flavonoid alters its antifungal toxicity on Candida albicans biofilms

Cytotoxic Effect of Geranylphenol Derivatives in the Human Breast Cancer Cell Line MDA-MB-231 and Gastric Cancer Cell Line MKN74

A review on nuclear overhauser enhancement (NOE) and rotating-frame overhauser effect (ROE) NMR techniques in food science: Basic principles and applications

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