Structural Analysis of Cardanol and Its Biological Activities on Human Keratinocyte Cells
<b>Background/Objectives:</b> Cashew nutshell liquid (CNSL) is obtained during the industrial processing of cashew nuts. It contains anacardic acid (2-hydroxy-6-n-pentadecylbenzoic acid) and cardanol (3-n-pentadecylphenol). Therefore, CNSL provides a rich source of phenolic lipids servin...
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2025-01-01
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| author | Shereen Basiouni Nina Abel Wolfgang Eisenreich Helen L. May-Simera Awad A. Shehata |
| author_facet | Shereen Basiouni Nina Abel Wolfgang Eisenreich Helen L. May-Simera Awad A. Shehata |
| author_sort | Shereen Basiouni |
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| description | <b>Background/Objectives:</b> Cashew nutshell liquid (CNSL) is obtained during the industrial processing of cashew nuts. It contains anacardic acid (2-hydroxy-6-n-pentadecylbenzoic acid) and cardanol (3-n-pentadecylphenol). Therefore, CNSL provides a rich source of phenolic lipids serving as natural antioxidants or precursors for industrial uses. Here, we have analyzed in detail a commercial sample of cardanol by nuclear magnetic resonance (NMR) spectroscopy and its biological activities in the human keratinocyte cell line (HaCaT cells). <b>Methods:</b> The cytotoxic effects, genotoxicity, cell proliferation, and healing properties on HaCaT cells were studied using the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) assay, comet assay, proliferation assay, and scratch assay, respectively. Additionally, the modulatory effect of cardanol on the cellular fatty acid profile of HaCaT cells was analyzed by gas chromatography. <b>Results:</b> NMR showed the structure of cardanol as a mixture of the 8′-monoene (42%), the 8′,11′-diene (22%), and the 8′,11′,14′-triene (36%) for the pentadecyl side chain with all double bonds in Z configuration. The cytotoxic effects on HaCaT cells only occurred at high concentrations of cardanol (>10 µg/mL), which caused significant reductions in cell viability. Using the comet assay, a dose-dependent increase in DNA damage was found at concentrations above 10 µg/mL. Scratch assays revealed that cardanol achieved 99% wound closure of HaCaT cells treated with 1 µg/mL cardanol after 48 h. Cardanol at 1 and 0.1 µg/mL significantly enhanced HaCaT cell proliferation and promoted migration, contributing to accelerated wound healing processes. As shown by gas chromatography, 1 µg/mL cardanol increased the total amount of polyunsaturated fatty acids (PUFA), including ω-3, ω-6, and ω-9 fatty acids. <b>Conclusions:</b> Together, these findings suggest that concentrations of <10 µg/mL cardanol are safe and exhibit beneficial biological activities, particularly wound-healing effects on HaCaT cells. Further studies are necessary to explore additional potential applications of cardanol, to refine its formulations for clinical use, and to ensure its safety and action in other target cells and species. |
| format | Article |
| id | doaj-art-3a098e66248c4c2bb37c923bb72bb426 |
| institution | DOAJ |
| issn | 2218-1989 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | MDPI AG |
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| series | Metabolites |
| spelling | doaj-art-3a098e66248c4c2bb37c923bb72bb4262025-08-20T02:44:32ZengMDPI AGMetabolites2218-19892025-01-011528310.3390/metabo15020083Structural Analysis of Cardanol and Its Biological Activities on Human Keratinocyte CellsShereen Basiouni0Nina Abel1Wolfgang Eisenreich2Helen L. May-Simera3Awad A. Shehata4Institute of Molecular Physiology, Johannes Gutenberg University, 55128 Mainz, GermanyStructural Membrane Biochemistry, Bavarian NMR Center, Technical University of Munich (TUM), 85748 Garching, GermanyStructural Membrane Biochemistry, Bavarian NMR Center, Technical University of Munich (TUM), 85748 Garching, GermanyInstitute of Molecular Physiology, Johannes Gutenberg University, 55128 Mainz, GermanyStructural Membrane Biochemistry, Bavarian NMR Center, Technical University of Munich (TUM), 85748 Garching, Germany<b>Background/Objectives:</b> Cashew nutshell liquid (CNSL) is obtained during the industrial processing of cashew nuts. It contains anacardic acid (2-hydroxy-6-n-pentadecylbenzoic acid) and cardanol (3-n-pentadecylphenol). Therefore, CNSL provides a rich source of phenolic lipids serving as natural antioxidants or precursors for industrial uses. Here, we have analyzed in detail a commercial sample of cardanol by nuclear magnetic resonance (NMR) spectroscopy and its biological activities in the human keratinocyte cell line (HaCaT cells). <b>Methods:</b> The cytotoxic effects, genotoxicity, cell proliferation, and healing properties on HaCaT cells were studied using the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) assay, comet assay, proliferation assay, and scratch assay, respectively. Additionally, the modulatory effect of cardanol on the cellular fatty acid profile of HaCaT cells was analyzed by gas chromatography. <b>Results:</b> NMR showed the structure of cardanol as a mixture of the 8′-monoene (42%), the 8′,11′-diene (22%), and the 8′,11′,14′-triene (36%) for the pentadecyl side chain with all double bonds in Z configuration. The cytotoxic effects on HaCaT cells only occurred at high concentrations of cardanol (>10 µg/mL), which caused significant reductions in cell viability. Using the comet assay, a dose-dependent increase in DNA damage was found at concentrations above 10 µg/mL. Scratch assays revealed that cardanol achieved 99% wound closure of HaCaT cells treated with 1 µg/mL cardanol after 48 h. Cardanol at 1 and 0.1 µg/mL significantly enhanced HaCaT cell proliferation and promoted migration, contributing to accelerated wound healing processes. As shown by gas chromatography, 1 µg/mL cardanol increased the total amount of polyunsaturated fatty acids (PUFA), including ω-3, ω-6, and ω-9 fatty acids. <b>Conclusions:</b> Together, these findings suggest that concentrations of <10 µg/mL cardanol are safe and exhibit beneficial biological activities, particularly wound-healing effects on HaCaT cells. Further studies are necessary to explore additional potential applications of cardanol, to refine its formulations for clinical use, and to ensure its safety and action in other target cells and species.https://www.mdpi.com/2218-1989/15/2/83cashewcardanolCNSLcytotoxicitygenotoxicitywound healing |
| spellingShingle | Shereen Basiouni Nina Abel Wolfgang Eisenreich Helen L. May-Simera Awad A. Shehata Structural Analysis of Cardanol and Its Biological Activities on Human Keratinocyte Cells Metabolites cashew cardanol CNSL cytotoxicity genotoxicity wound healing |
| title | Structural Analysis of Cardanol and Its Biological Activities on Human Keratinocyte Cells |
| title_full | Structural Analysis of Cardanol and Its Biological Activities on Human Keratinocyte Cells |
| title_fullStr | Structural Analysis of Cardanol and Its Biological Activities on Human Keratinocyte Cells |
| title_full_unstemmed | Structural Analysis of Cardanol and Its Biological Activities on Human Keratinocyte Cells |
| title_short | Structural Analysis of Cardanol and Its Biological Activities on Human Keratinocyte Cells |
| title_sort | structural analysis of cardanol and its biological activities on human keratinocyte cells |
| topic | cashew cardanol CNSL cytotoxicity genotoxicity wound healing |
| url | https://www.mdpi.com/2218-1989/15/2/83 |
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