The Inhibitory Activity of Anthraquinones against Pathogenic Protozoa, Bacteria, and Fungi and the Relationship to Structure

Plant-derived anthraquinones were evaluated in cell assays for their inhibitory activities against the parasitic protozoa <i>Trichomonas vaginalis</i> human strain G3 that causes the sexually transmitted disease trichomoniasis in women, <i>Tritrichomonas foetus</i> bovine str...

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Main Authors: Mendel Friedman, Alexander Xu, Rani Lee, Daniel N. Nguyen, Tina A. Phan, Sabrina M. Hamada, Rima Panchel, Christina C. Tam, Jong H. Kim, Luisa W. Cheng, Kirkwood M. Land
Format: Article
Language:English
Published: MDPI AG 2020-07-01
Series:Molecules
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Online Access:https://www.mdpi.com/1420-3049/25/13/3101
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author Mendel Friedman
Alexander Xu
Rani Lee
Daniel N. Nguyen
Tina A. Phan
Sabrina M. Hamada
Rima Panchel
Christina C. Tam
Jong H. Kim
Luisa W. Cheng
Kirkwood M. Land
author_facet Mendel Friedman
Alexander Xu
Rani Lee
Daniel N. Nguyen
Tina A. Phan
Sabrina M. Hamada
Rima Panchel
Christina C. Tam
Jong H. Kim
Luisa W. Cheng
Kirkwood M. Land
author_sort Mendel Friedman
collection DOAJ
description Plant-derived anthraquinones were evaluated in cell assays for their inhibitory activities against the parasitic protozoa <i>Trichomonas vaginalis</i> human strain G3 that causes the sexually transmitted disease trichomoniasis in women, <i>Tritrichomonas foetus</i> bovine strain D1 that causes sexually transmitted diseases in farm animals (bulls, cows, and pigs), <i>Tritrichomonas foetus</i>-like strain C1 that causes diarrhea in domestic animals (cats and dogs), and bacteria and fungi. The anthraquinones assessed for their inhibitory activity were anthraquinone, aloe-emodin (1,8-dihydroxy-3-hydroxymethylanthraquinone), anthrarufin (1,5-dihydroxyanthraquinone), chrysazin (1,8-dihydroxyanthraquinone), emodin (1,3,8-trihydroxy-6-methylanthraquinone), purpurin (1,2,4-trihydroxyanthraquinone), and rhein (1,8-dihydroxy-3-carboxyanthraquinone). Their activities were determined in terms of IC<sub>50</sub> values, defined as the concentration that inhibits 50% of the cells under the test conditions and calculated from linear dose response plots for the parasitic protozoa, and zone of inhibition for bacteria and fungi, respectively. The results show that the different substituents on the anthraquinone ring seem to influence the relative potency. Analysis of the structure–activity relationships in protozoa indicates that the aloe-emodin and chrysazin with the highest biological activities merit further study for their potential to help treat the diseases in women and domestic and farm animals. Emodin also exhibited antifungal activity against <i>Candida albicans</i>. The suggested mechanism of action and the additional reported beneficial biological properties of anthraquinones suggest that they have the potential to ameliorate a broad spectrum of human diseases.
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spelling doaj.art-5d3d2353e1124f50901f5cdf900a591e2023-11-20T06:06:27ZengMDPI AGMolecules1420-30492020-07-012513310110.3390/molecules25133101The Inhibitory Activity of Anthraquinones against Pathogenic Protozoa, Bacteria, and Fungi and the Relationship to StructureMendel Friedman0Alexander Xu1Rani Lee2Daniel N. Nguyen3Tina A. Phan4Sabrina M. Hamada5Rima Panchel6Christina C. Tam7Jong H. Kim8Luisa W. Cheng9Kirkwood M. Land10Healthy Processed Foods Research Unit, Agricultural Research Service, United States Department of Agriculture, Albany, CA 94710, USADepartment of Biological Sciences, University of the Pacific, Stockton, CA 95211, USADepartment of Biological Sciences, University of the Pacific, Stockton, CA 95211, USADepartment of Biological Sciences, University of the Pacific, Stockton, CA 95211, USADepartment of Biological Sciences, University of the Pacific, Stockton, CA 95211, USADepartment of Biological Sciences, University of the Pacific, Stockton, CA 95211, USADepartment of Biological Sciences, University of the Pacific, Stockton, CA 95211, USAFoodborne Toxins Detection and Prevention Research Unit, Agricultural Research Service, United States Department of Agriculture, Albany, CA 94710, USAFoodborne Toxins Detection and Prevention Research Unit, Agricultural Research Service, United States Department of Agriculture, Albany, CA 94710, USAFoodborne Toxins Detection and Prevention Research Unit, Agricultural Research Service, United States Department of Agriculture, Albany, CA 94710, USADepartment of Biological Sciences, University of the Pacific, Stockton, CA 95211, USAPlant-derived anthraquinones were evaluated in cell assays for their inhibitory activities against the parasitic protozoa <i>Trichomonas vaginalis</i> human strain G3 that causes the sexually transmitted disease trichomoniasis in women, <i>Tritrichomonas foetus</i> bovine strain D1 that causes sexually transmitted diseases in farm animals (bulls, cows, and pigs), <i>Tritrichomonas foetus</i>-like strain C1 that causes diarrhea in domestic animals (cats and dogs), and bacteria and fungi. The anthraquinones assessed for their inhibitory activity were anthraquinone, aloe-emodin (1,8-dihydroxy-3-hydroxymethylanthraquinone), anthrarufin (1,5-dihydroxyanthraquinone), chrysazin (1,8-dihydroxyanthraquinone), emodin (1,3,8-trihydroxy-6-methylanthraquinone), purpurin (1,2,4-trihydroxyanthraquinone), and rhein (1,8-dihydroxy-3-carboxyanthraquinone). Their activities were determined in terms of IC<sub>50</sub> values, defined as the concentration that inhibits 50% of the cells under the test conditions and calculated from linear dose response plots for the parasitic protozoa, and zone of inhibition for bacteria and fungi, respectively. The results show that the different substituents on the anthraquinone ring seem to influence the relative potency. Analysis of the structure–activity relationships in protozoa indicates that the aloe-emodin and chrysazin with the highest biological activities merit further study for their potential to help treat the diseases in women and domestic and farm animals. Emodin also exhibited antifungal activity against <i>Candida albicans</i>. The suggested mechanism of action and the additional reported beneficial biological properties of anthraquinones suggest that they have the potential to ameliorate a broad spectrum of human diseases.https://www.mdpi.com/1420-3049/25/13/3101<i>Trichomonas vaginalis</i><i>Tritrichomonas foetus</i>cell assaystrichomoniasistrichomonosisanthraquinones
spellingShingle Mendel Friedman
Alexander Xu
Rani Lee
Daniel N. Nguyen
Tina A. Phan
Sabrina M. Hamada
Rima Panchel
Christina C. Tam
Jong H. Kim
Luisa W. Cheng
Kirkwood M. Land
The Inhibitory Activity of Anthraquinones against Pathogenic Protozoa, Bacteria, and Fungi and the Relationship to Structure
Molecules
<i>Trichomonas vaginalis</i>
<i>Tritrichomonas foetus</i>
cell assays
trichomoniasis
trichomonosis
anthraquinones
title The Inhibitory Activity of Anthraquinones against Pathogenic Protozoa, Bacteria, and Fungi and the Relationship to Structure
title_full The Inhibitory Activity of Anthraquinones against Pathogenic Protozoa, Bacteria, and Fungi and the Relationship to Structure
title_fullStr The Inhibitory Activity of Anthraquinones against Pathogenic Protozoa, Bacteria, and Fungi and the Relationship to Structure
title_full_unstemmed The Inhibitory Activity of Anthraquinones against Pathogenic Protozoa, Bacteria, and Fungi and the Relationship to Structure
title_short The Inhibitory Activity of Anthraquinones against Pathogenic Protozoa, Bacteria, and Fungi and the Relationship to Structure
title_sort inhibitory activity of anthraquinones against pathogenic protozoa bacteria and fungi and the relationship to structure
topic <i>Trichomonas vaginalis</i>
<i>Tritrichomonas foetus</i>
cell assays
trichomoniasis
trichomonosis
anthraquinones
url https://www.mdpi.com/1420-3049/25/13/3101
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