Effect of curcuminoids and curcumin derivate products on thioredoxin-glutathione reductase from Taenia crassiceps cysticerci. Evidence suggesting a curcumin oxidation product as a suitable inhibitor.
Curcuma is a traditional ingredient of some Eastern cuisines, and the spice is heralded for its antitumoral and antiparasitic properties. In this report, we examine the effect of the curcuminoides which include curcumin, demethoxycurcumin (DMC) and bis-demethoxycurcumin (BDMC), as well as curcumin d...
| Main Authors: | , , , , , , , |
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| Format: | Article |
| Language: | English |
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Public Library of Science (PLoS)
2019-01-01
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| Series: | PLoS ONE |
| Online Access: | https://doi.org/10.1371/journal.pone.0220098 |
| _version_ | 1819114723847700480 |
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| author | Alberto Guevara-Flores José de Jesús Martínez-González Álvaro Miguel Herrera-Juárez Juan Luis Rendón Martín González-Andrade Patricia Victoria Torres Durán Raúl Guillermo Enríquez-Habib Irene Patricia Del Arenal Mena |
| author_facet | Alberto Guevara-Flores José de Jesús Martínez-González Álvaro Miguel Herrera-Juárez Juan Luis Rendón Martín González-Andrade Patricia Victoria Torres Durán Raúl Guillermo Enríquez-Habib Irene Patricia Del Arenal Mena |
| author_sort | Alberto Guevara-Flores |
| collection | DOAJ |
| description | Curcuma is a traditional ingredient of some Eastern cuisines, and the spice is heralded for its antitumoral and antiparasitic properties. In this report, we examine the effect of the curcuminoides which include curcumin, demethoxycurcumin (DMC) and bis-demethoxycurcumin (BDMC), as well as curcumin degradation products on thioredoxin glutathione reductase from Taenia crassiceps cysticerci Results revealed that both DMC and BDMC were inhibitors of TGR activity in the micromolar concentration range. By contrast, the inhibitory ability of curcumin was a time-dependent process. Kinetic and spectroscopical evidence suggests that an intermediary compound of curcumin oxidation, probably spiroepoxide, is responsible. Preincubation of curcumin in the presence of NADPH, but not glutathione disulfide (GSSG), resulted in the loss of its inhibitory ability, suggesting a reductive stabilizing effect. Similarly, preincubation of curcumin with sulfhydryl compounds fully protected the enzyme from inhibition. Degradation products were tested for their inhibitory potential, and 4-vinylguaiacol was the best inhibitor (IC50 = 12.9 μM), followed by feruloylmethane (IC50 = 122 μM), vanillin (IC50 = 127 μM), and ferulic aldehyde (IC50 = 180 μM). The acid derivatives ferulic acid (IC50 = 465 μM) and vanillic acid (IC50 = 657 μM) were poor inhibitors. On the other hand, results from docking analysis revealed a common binding site on the enzyme for all the compounds, albeit interacting with different amino acid residues. Dissociation constants obtained from the docking were in accord with the inhibitory efficiency of the curcumin degradation products. |
| first_indexed | 2024-12-22T04:49:50Z |
| format | Article |
| id | doaj.art-07179238da7b4ce096d6a000e4128c2f |
| institution | Directory Open Access Journal |
| issn | 1932-6203 |
| language | English |
| last_indexed | 2024-12-22T04:49:50Z |
| publishDate | 2019-01-01 |
| publisher | Public Library of Science (PLoS) |
| record_format | Article |
| series | PLoS ONE |
| spelling | doaj.art-07179238da7b4ce096d6a000e4128c2f2022-12-21T18:38:31ZengPublic Library of Science (PLoS)PLoS ONE1932-62032019-01-01147e022009810.1371/journal.pone.0220098Effect of curcuminoids and curcumin derivate products on thioredoxin-glutathione reductase from Taenia crassiceps cysticerci. Evidence suggesting a curcumin oxidation product as a suitable inhibitor.Alberto Guevara-FloresJosé de Jesús Martínez-GonzálezÁlvaro Miguel Herrera-JuárezJuan Luis RendónMartín González-AndradePatricia Victoria Torres DuránRaúl Guillermo Enríquez-HabibIrene Patricia Del Arenal MenaCurcuma is a traditional ingredient of some Eastern cuisines, and the spice is heralded for its antitumoral and antiparasitic properties. In this report, we examine the effect of the curcuminoides which include curcumin, demethoxycurcumin (DMC) and bis-demethoxycurcumin (BDMC), as well as curcumin degradation products on thioredoxin glutathione reductase from Taenia crassiceps cysticerci Results revealed that both DMC and BDMC were inhibitors of TGR activity in the micromolar concentration range. By contrast, the inhibitory ability of curcumin was a time-dependent process. Kinetic and spectroscopical evidence suggests that an intermediary compound of curcumin oxidation, probably spiroepoxide, is responsible. Preincubation of curcumin in the presence of NADPH, but not glutathione disulfide (GSSG), resulted in the loss of its inhibitory ability, suggesting a reductive stabilizing effect. Similarly, preincubation of curcumin with sulfhydryl compounds fully protected the enzyme from inhibition. Degradation products were tested for their inhibitory potential, and 4-vinylguaiacol was the best inhibitor (IC50 = 12.9 μM), followed by feruloylmethane (IC50 = 122 μM), vanillin (IC50 = 127 μM), and ferulic aldehyde (IC50 = 180 μM). The acid derivatives ferulic acid (IC50 = 465 μM) and vanillic acid (IC50 = 657 μM) were poor inhibitors. On the other hand, results from docking analysis revealed a common binding site on the enzyme for all the compounds, albeit interacting with different amino acid residues. Dissociation constants obtained from the docking were in accord with the inhibitory efficiency of the curcumin degradation products.https://doi.org/10.1371/journal.pone.0220098 |
| spellingShingle | Alberto Guevara-Flores José de Jesús Martínez-González Álvaro Miguel Herrera-Juárez Juan Luis Rendón Martín González-Andrade Patricia Victoria Torres Durán Raúl Guillermo Enríquez-Habib Irene Patricia Del Arenal Mena Effect of curcuminoids and curcumin derivate products on thioredoxin-glutathione reductase from Taenia crassiceps cysticerci. Evidence suggesting a curcumin oxidation product as a suitable inhibitor. PLoS ONE |
| title | Effect of curcuminoids and curcumin derivate products on thioredoxin-glutathione reductase from Taenia crassiceps cysticerci. Evidence suggesting a curcumin oxidation product as a suitable inhibitor. |
| title_full | Effect of curcuminoids and curcumin derivate products on thioredoxin-glutathione reductase from Taenia crassiceps cysticerci. Evidence suggesting a curcumin oxidation product as a suitable inhibitor. |
| title_fullStr | Effect of curcuminoids and curcumin derivate products on thioredoxin-glutathione reductase from Taenia crassiceps cysticerci. Evidence suggesting a curcumin oxidation product as a suitable inhibitor. |
| title_full_unstemmed | Effect of curcuminoids and curcumin derivate products on thioredoxin-glutathione reductase from Taenia crassiceps cysticerci. Evidence suggesting a curcumin oxidation product as a suitable inhibitor. |
| title_short | Effect of curcuminoids and curcumin derivate products on thioredoxin-glutathione reductase from Taenia crassiceps cysticerci. Evidence suggesting a curcumin oxidation product as a suitable inhibitor. |
| title_sort | effect of curcuminoids and curcumin derivate products on thioredoxin glutathione reductase from taenia crassiceps cysticerci evidence suggesting a curcumin oxidation product as a suitable inhibitor |
| url | https://doi.org/10.1371/journal.pone.0220098 |
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