Validation of the Antioxidant and Enzyme Inhibitory Potential of Selected Triterpenes Using In Vitro and In Silico Studies, and the Evaluation of Their ADMET Properties
The antioxidant and enzyme inhibitory potential of fifteen cycloartane-type triterpenes’ potentials were investigated using different assays. In the phosphomolybdenum method, cycloalpioside D (<b>6</b>) (4.05 mmol TEs/g) showed the highest activity. In 1,1-diphenyl-2-picrylhydrazyl (DPPH...
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oai:doaj.org-article:db56720169794d9da42b232f005f8f0d2021-11-11T18:21:56ZValidation of the Antioxidant and Enzyme Inhibitory Potential of Selected Triterpenes Using In Vitro and In Silico Studies, and the Evaluation of Their ADMET Properties10.3390/molecules262163311420-3049https://doaj.org/article/db56720169794d9da42b232f005f8f0d2021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6331https://doaj.org/toc/1420-3049The antioxidant and enzyme inhibitory potential of fifteen cycloartane-type triterpenes’ potentials were investigated using different assays. In the phosphomolybdenum method, cycloalpioside D (<b>6</b>) (4.05 mmol TEs/g) showed the highest activity. In 1,1-diphenyl-2-picrylhydrazyl (DPPH*) radical and 2,2′-azino-bis(3-ethylbenzothiazoline)-6-sulfonic acid (ABTS) cation radical scavenging assays, cycloorbicoside A-7-monoacetate (<b>2</b>) (5.03 mg TE/g) and cycloorbicoside B (<b>10</b>) (10.60 mg TE/g) displayed the highest activities, respectively. Oleanolic acid (<b>14</b>) (51.45 mg TE/g) and 3-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-xylopyranoside-(23<i>R</i>,24<i>S</i>)-16β,23;16α,24-diepoxycycloart-25(26)-en-3β,7β-diol 7-monoacetate (<b>4</b>) (13.25 mg TE/g) revealed the highest reducing power in cupric ion-reducing activity (CUPRAC) and ferric-reducing antioxidant power (FRAP) assays, respectively. In metal-chelating activity on ferrous ions, compound <b>2</b> displayed the highest activity estimated by 41.00 mg EDTAE/g (EDTA equivalents/g). The tested triterpenes showed promising AChE and BChE inhibitory potential with 3-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-xylopyranoside-(23<i>R</i>,24<i>S</i>)-16β,23;16α,24-diepoxycycloart-25(26)-en-3β,7β-diol 2′,3′,4′,7-tetraacetate (<b>3</b>), exhibiting the highest inhibitory activity as estimated from 5.64 and 5.19 mg GALAE/g (galantamine equivalent/g), respectively. Compound <b>2</b> displayed the most potent tyrosinase inhibitory activity (113.24 mg KAE/g (mg kojic acid equivalent/g)). Regarding α-amylase and α-glucosidase inhibition, 3-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-xylopyranoside-(23<i>R</i>,24<i>S</i>)-16β,23;16α,24-diepoxycycloart-25(26)-en-3β,7β-diol (<b>5</b>) (0.55 mmol ACAE/g) and compound <b>3</b> (25.18 mmol ACAE/g) exerted the highest activities, respectively. In silico studies focused on compounds <b>2</b>, <b>6</b>, and <b>7</b> as inhibitors of tyrosinase revealed that compound <b>2</b> displayed a good ranking score (−7.069 kcal/mole) and also that the ΔG free-binding energy was the highest among the three selected compounds. From the ADMET/TOPKAT prediction, it can be concluded that compounds <b>4</b> and <b>5</b> displayed the best pharmacokinetic and pharmacodynamic behavior, with considerable activity in most of the examined assays.Nilufar Z. MamadalievaFadia S. YoussefHidayat HussainGokhan ZenginAdriano MollicaNawal M. Al MusayeibMohamed L. AshourBernhard WestermannLudger A. WessjohannMDPI AGarticleantioxidantsenzyme inhibitionin vitro assaystriterpenesvirtual screeninginflammationOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6331, p 6331 (2021) |
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| collection |
DOAJ |
| language |
EN |
| topic |
antioxidants enzyme inhibition in vitro assays triterpenes virtual screening inflammation Organic chemistry QD241-441 |
| spellingShingle |
antioxidants enzyme inhibition in vitro assays triterpenes virtual screening inflammation Organic chemistry QD241-441 Nilufar Z. Mamadalieva Fadia S. Youssef Hidayat Hussain Gokhan Zengin Adriano Mollica Nawal M. Al Musayeib Mohamed L. Ashour Bernhard Westermann Ludger A. Wessjohann Validation of the Antioxidant and Enzyme Inhibitory Potential of Selected Triterpenes Using In Vitro and In Silico Studies, and the Evaluation of Their ADMET Properties |
| description |
The antioxidant and enzyme inhibitory potential of fifteen cycloartane-type triterpenes’ potentials were investigated using different assays. In the phosphomolybdenum method, cycloalpioside D (<b>6</b>) (4.05 mmol TEs/g) showed the highest activity. In 1,1-diphenyl-2-picrylhydrazyl (DPPH*) radical and 2,2′-azino-bis(3-ethylbenzothiazoline)-6-sulfonic acid (ABTS) cation radical scavenging assays, cycloorbicoside A-7-monoacetate (<b>2</b>) (5.03 mg TE/g) and cycloorbicoside B (<b>10</b>) (10.60 mg TE/g) displayed the highest activities, respectively. Oleanolic acid (<b>14</b>) (51.45 mg TE/g) and 3-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-xylopyranoside-(23<i>R</i>,24<i>S</i>)-16β,23;16α,24-diepoxycycloart-25(26)-en-3β,7β-diol 7-monoacetate (<b>4</b>) (13.25 mg TE/g) revealed the highest reducing power in cupric ion-reducing activity (CUPRAC) and ferric-reducing antioxidant power (FRAP) assays, respectively. In metal-chelating activity on ferrous ions, compound <b>2</b> displayed the highest activity estimated by 41.00 mg EDTAE/g (EDTA equivalents/g). The tested triterpenes showed promising AChE and BChE inhibitory potential with 3-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-xylopyranoside-(23<i>R</i>,24<i>S</i>)-16β,23;16α,24-diepoxycycloart-25(26)-en-3β,7β-diol 2′,3′,4′,7-tetraacetate (<b>3</b>), exhibiting the highest inhibitory activity as estimated from 5.64 and 5.19 mg GALAE/g (galantamine equivalent/g), respectively. Compound <b>2</b> displayed the most potent tyrosinase inhibitory activity (113.24 mg KAE/g (mg kojic acid equivalent/g)). Regarding α-amylase and α-glucosidase inhibition, 3-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-xylopyranoside-(23<i>R</i>,24<i>S</i>)-16β,23;16α,24-diepoxycycloart-25(26)-en-3β,7β-diol (<b>5</b>) (0.55 mmol ACAE/g) and compound <b>3</b> (25.18 mmol ACAE/g) exerted the highest activities, respectively. In silico studies focused on compounds <b>2</b>, <b>6</b>, and <b>7</b> as inhibitors of tyrosinase revealed that compound <b>2</b> displayed a good ranking score (−7.069 kcal/mole) and also that the ΔG free-binding energy was the highest among the three selected compounds. From the ADMET/TOPKAT prediction, it can be concluded that compounds <b>4</b> and <b>5</b> displayed the best pharmacokinetic and pharmacodynamic behavior, with considerable activity in most of the examined assays. |
| format |
article |
| author |
Nilufar Z. Mamadalieva Fadia S. Youssef Hidayat Hussain Gokhan Zengin Adriano Mollica Nawal M. Al Musayeib Mohamed L. Ashour Bernhard Westermann Ludger A. Wessjohann |
| author_facet |
Nilufar Z. Mamadalieva Fadia S. Youssef Hidayat Hussain Gokhan Zengin Adriano Mollica Nawal M. Al Musayeib Mohamed L. Ashour Bernhard Westermann Ludger A. Wessjohann |
| author_sort |
Nilufar Z. Mamadalieva |
| title |
Validation of the Antioxidant and Enzyme Inhibitory Potential of Selected Triterpenes Using In Vitro and In Silico Studies, and the Evaluation of Their ADMET Properties |
| title_short |
Validation of the Antioxidant and Enzyme Inhibitory Potential of Selected Triterpenes Using In Vitro and In Silico Studies, and the Evaluation of Their ADMET Properties |
| title_full |
Validation of the Antioxidant and Enzyme Inhibitory Potential of Selected Triterpenes Using In Vitro and In Silico Studies, and the Evaluation of Their ADMET Properties |
| title_fullStr |
Validation of the Antioxidant and Enzyme Inhibitory Potential of Selected Triterpenes Using In Vitro and In Silico Studies, and the Evaluation of Their ADMET Properties |
| title_full_unstemmed |
Validation of the Antioxidant and Enzyme Inhibitory Potential of Selected Triterpenes Using In Vitro and In Silico Studies, and the Evaluation of Their ADMET Properties |
| title_sort |
validation of the antioxidant and enzyme inhibitory potential of selected triterpenes using in vitro and in silico studies, and the evaluation of their admet properties |
| publisher |
MDPI AG |
| publishDate |
2021 |
| url |
https://doaj.org/article/db56720169794d9da42b232f005f8f0d |
| work_keys_str_mv |
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