Potential Anti-Acetylcholinesterase Activity of <i>Cassia timorensis</i> DC.
Seventeen methanol extracts from different plant parts of five different <i>Cassia</i> species, including <i>C. timorensis</i>, <i>C. grandis</i>, <i>C. fistula</i>, <i>C. spectabilis</i>, and <i>C. alata</i> were screened again...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/19/4545 |
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| author | Nurul Amira Nurul Azman Maram B. Alhawarri Mira Syahfriena Amir Rawa Roza Dianita Amirah Mohd Gazzali Toshihiko Nogawa Habibah A. Wahab |
| author_facet | Nurul Amira Nurul Azman Maram B. Alhawarri Mira Syahfriena Amir Rawa Roza Dianita Amirah Mohd Gazzali Toshihiko Nogawa Habibah A. Wahab |
| author_sort | Nurul Amira Nurul Azman |
| collection | DOAJ |
| description | Seventeen methanol extracts from different plant parts of five different <i>Cassia</i> species, including <i>C. timorensis</i>, <i>C. grandis</i>, <i>C. fistula</i>, <i>C. spectabilis</i>, and <i>C. alata</i> were screened against acetylcholinesterase (AChE). <i>C. timorensis</i> extracts were found to exhibit the highest inhibition towards AChE whereby the leaf, stem, and flower methanol extracts showed 94–97% inhibition. As far as we are aware, <i>C. timorensis</i> is one of the least explored <i>Cassia</i> spp. for bioactivity. Further fractionation led to the identification of six compounds, isolated for the first time from <i>C. timorensis</i>: 3-methoxyquercetin (<b>1</b>), benzenepropanoic acid (<b>2</b>), 9,12,15-octadecatrienoic acid (<b>3</b>), β-sitosterol (<b>4</b>), stigmasterol (<b>5</b>), and 1-octadecanol (<b>6</b>). Compound <b>1</b> showed moderate inhibition towards AChE (IC<sub>50</sub>: 83.71 μM), while the other compounds exhibited poor to slightly moderate AChE inhibitory activity. Molecular docking revealed that the methoxy substitution of <b>1</b> formed a hydrogen bond with TYR121 at the peripheral anionic site (PAS) and the hydroxyl group at C5 formed a covalent hydrogen bond with ASP72. Additionally, the OH group at the C3′ position formed an interaction with the protein at the acyl pocket (PHE288). This possibly explains the activity of <b>1</b> in blocking the entry of acetylcholine (ACh, the neurotransmitter), thus impeding the hydrolysis of ACh. |
| first_indexed | 2024-03-10T15:50:32Z |
| format | Article |
| id | doaj.art-40de329a51fd453c825a57f1cd033b51 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T15:50:32Z |
| publishDate | 2020-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-40de329a51fd453c825a57f1cd033b512023-11-20T16:03:08ZengMDPI AGMolecules1420-30492020-10-012519454510.3390/molecules25194545Potential Anti-Acetylcholinesterase Activity of <i>Cassia timorensis</i> DC.Nurul Amira Nurul Azman0Maram B. Alhawarri1Mira Syahfriena Amir Rawa2Roza Dianita3Amirah Mohd Gazzali4Toshihiko Nogawa5Habibah A. Wahab6School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, MalaysiaSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, MalaysiaSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, MalaysiaSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, MalaysiaSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, MalaysiaUSM-RIKEN Centre for Aging Science (URICAS), Universiti Sains Malaysia, 11800 Minden, MalaysiaSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, MalaysiaSeventeen methanol extracts from different plant parts of five different <i>Cassia</i> species, including <i>C. timorensis</i>, <i>C. grandis</i>, <i>C. fistula</i>, <i>C. spectabilis</i>, and <i>C. alata</i> were screened against acetylcholinesterase (AChE). <i>C. timorensis</i> extracts were found to exhibit the highest inhibition towards AChE whereby the leaf, stem, and flower methanol extracts showed 94–97% inhibition. As far as we are aware, <i>C. timorensis</i> is one of the least explored <i>Cassia</i> spp. for bioactivity. Further fractionation led to the identification of six compounds, isolated for the first time from <i>C. timorensis</i>: 3-methoxyquercetin (<b>1</b>), benzenepropanoic acid (<b>2</b>), 9,12,15-octadecatrienoic acid (<b>3</b>), β-sitosterol (<b>4</b>), stigmasterol (<b>5</b>), and 1-octadecanol (<b>6</b>). Compound <b>1</b> showed moderate inhibition towards AChE (IC<sub>50</sub>: 83.71 μM), while the other compounds exhibited poor to slightly moderate AChE inhibitory activity. Molecular docking revealed that the methoxy substitution of <b>1</b> formed a hydrogen bond with TYR121 at the peripheral anionic site (PAS) and the hydroxyl group at C5 formed a covalent hydrogen bond with ASP72. Additionally, the OH group at the C3′ position formed an interaction with the protein at the acyl pocket (PHE288). This possibly explains the activity of <b>1</b> in blocking the entry of acetylcholine (ACh, the neurotransmitter), thus impeding the hydrolysis of ACh.https://www.mdpi.com/1420-3049/25/19/4545<i>Cassia timorensis</i><i>Senna timoriensis</i>benzenepropanoic acid9,12,15-octadecatrienoic acid3-methoxyquercetinacetylcholinesterase |
| spellingShingle | Nurul Amira Nurul Azman Maram B. Alhawarri Mira Syahfriena Amir Rawa Roza Dianita Amirah Mohd Gazzali Toshihiko Nogawa Habibah A. Wahab Potential Anti-Acetylcholinesterase Activity of <i>Cassia timorensis</i> DC. Molecules <i>Cassia timorensis</i> <i>Senna timoriensis</i> benzenepropanoic acid 9,12,15-octadecatrienoic acid 3-methoxyquercetin acetylcholinesterase |
| title | Potential Anti-Acetylcholinesterase Activity of <i>Cassia timorensis</i> DC. |
| title_full | Potential Anti-Acetylcholinesterase Activity of <i>Cassia timorensis</i> DC. |
| title_fullStr | Potential Anti-Acetylcholinesterase Activity of <i>Cassia timorensis</i> DC. |
| title_full_unstemmed | Potential Anti-Acetylcholinesterase Activity of <i>Cassia timorensis</i> DC. |
| title_short | Potential Anti-Acetylcholinesterase Activity of <i>Cassia timorensis</i> DC. |
| title_sort | potential anti acetylcholinesterase activity of i cassia timorensis i dc |
| topic | <i>Cassia timorensis</i> <i>Senna timoriensis</i> benzenepropanoic acid 9,12,15-octadecatrienoic acid 3-methoxyquercetin acetylcholinesterase |
| url | https://www.mdpi.com/1420-3049/25/19/4545 |
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