Furofuranoid-Type Lignans and Related Phenolics from <i>Anisacanthus virgularis</i> (Salisb.) Nees with Promising Anticholinesterase and Anti-Ageing Properties: A Study Supported by Molecular Modelling
Lignan phytomolecules demonstrate promising anti-Alzheimer activity by alleviating dementia and preserving nerve cells. The purpose of this work is to characterize the lignans of <i>Anisacanthus virgularis</i> and explore their potential anti-acetylcholinesterase and anti-ageing effects....
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MDPI AG
2024-01-01
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| author | Mohamed A. A. Orabi Reda A. Abdelhamid Hanan Elimam Yaseen A. M. M. Elshaier Ahmed A. Ali Nayef Aldabaan Abdulaziz Hassan Alhasaniah Mohamed S. Refaey |
| author_facet | Mohamed A. A. Orabi Reda A. Abdelhamid Hanan Elimam Yaseen A. M. M. Elshaier Ahmed A. Ali Nayef Aldabaan Abdulaziz Hassan Alhasaniah Mohamed S. Refaey |
| author_sort | Mohamed A. A. Orabi |
| collection | DOAJ |
| description | Lignan phytomolecules demonstrate promising anti-Alzheimer activity by alleviating dementia and preserving nerve cells. The purpose of this work is to characterize the lignans of <i>Anisacanthus virgularis</i> and explore their potential anti-acetylcholinesterase and anti-ageing effects. Phytochemical investigation of <i>A. virgularis</i> aerial parts afforded a new furofuranoid-type lignan (<b>1</b>), four known structural analogues, namely pinoresinol (<b>2</b>), epipinoresinol (<b>3</b>), phillyrin (<b>4</b>), and pinoresinol 4-<i>O</i>-<i>β</i>-<span style="font-variant: small-caps;">d</span>-glucoside (<b>5</b>), in addition to <i>p</i>-methoxy-<i>trans</i>-methyl cinnamate (<b>6</b>) and 1H-indole-3-carboxaldehyde (<b>7</b>). The structures were established from thorough spectroscopic analyses and comparisons with the literature. Assessment of the anticholinesterase activity of the lignans <b>1</b>–<b>5</b> displayed noticeable enzyme inhibition of <b>1</b> (IC<sub>50</sub> = 85.03 ± 4.26 nM) and <b>5</b> (64.47 ± 2.75 nM) but lower activity of compounds <b>2</b>–<b>4</b> as compared to the reference drug donepezil. These findings were further emphasized by molecular docking of <b>1</b> and <b>5</b> with acetylcholinesterase (AChE). Rapid overlay chemical similarity (ROCS) and structure–activity relationships (SAR) analysis highlighted and rationalized the anti-AD capability of these compounds. Telomerase activation testing of the same isolates revealed 1.64-, 1.66-, and 1.72-fold activations in cells treated with compounds <b>1</b>, <b>5</b>, and <b>4</b>, respectively, compared to untreated cells. Our findings may pave the way for further investigations into the development of anti-Alzheimer and/or anti-ageing drugs from furofuranoid-type lignans. |
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| spelling | doaj.art-c79df7a2f7e94555bb3486f72bbd80a92024-01-29T14:10:33ZengMDPI AGPlants2223-77472024-01-0113215010.3390/plants13020150Furofuranoid-Type Lignans and Related Phenolics from <i>Anisacanthus virgularis</i> (Salisb.) Nees with Promising Anticholinesterase and Anti-Ageing Properties: A Study Supported by Molecular ModellingMohamed A. A. Orabi0Reda A. Abdelhamid1Hanan Elimam2Yaseen A. M. M. Elshaier3Ahmed A. Ali4Nayef Aldabaan5Abdulaziz Hassan Alhasaniah6Mohamed S. Refaey7Department of Pharmacognosy, College of Pharmacy, Najran University, Najran 66454, Saudi ArabiaDepartment of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Assiut-Branch, Assiut 71524, EgyptDepartment of Biochemistry, Faculty of Pharmacy, University of Sadat City, Sadat City 32958, EgyptDepartment of Organic and Medicinal Chemistry, Faculty of Pharmacy, University of Sadat City, Sadat City 32958, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut 71526, EgyptDepartment of Pharmacology, College of Pharmacy, Najran University, Najran 66454, Saudi ArabiaDepartment of Clinical Laboratory Sciences, College of Applied Medical Sciences, Najran University, Najran 66454, Saudi ArabiaDepartment of Pharmacognosy, Faculty of Pharmacy, University of Sadat City, Sadat City 32958, EgyptLignan phytomolecules demonstrate promising anti-Alzheimer activity by alleviating dementia and preserving nerve cells. The purpose of this work is to characterize the lignans of <i>Anisacanthus virgularis</i> and explore their potential anti-acetylcholinesterase and anti-ageing effects. Phytochemical investigation of <i>A. virgularis</i> aerial parts afforded a new furofuranoid-type lignan (<b>1</b>), four known structural analogues, namely pinoresinol (<b>2</b>), epipinoresinol (<b>3</b>), phillyrin (<b>4</b>), and pinoresinol 4-<i>O</i>-<i>β</i>-<span style="font-variant: small-caps;">d</span>-glucoside (<b>5</b>), in addition to <i>p</i>-methoxy-<i>trans</i>-methyl cinnamate (<b>6</b>) and 1H-indole-3-carboxaldehyde (<b>7</b>). The structures were established from thorough spectroscopic analyses and comparisons with the literature. Assessment of the anticholinesterase activity of the lignans <b>1</b>–<b>5</b> displayed noticeable enzyme inhibition of <b>1</b> (IC<sub>50</sub> = 85.03 ± 4.26 nM) and <b>5</b> (64.47 ± 2.75 nM) but lower activity of compounds <b>2</b>–<b>4</b> as compared to the reference drug donepezil. These findings were further emphasized by molecular docking of <b>1</b> and <b>5</b> with acetylcholinesterase (AChE). Rapid overlay chemical similarity (ROCS) and structure–activity relationships (SAR) analysis highlighted and rationalized the anti-AD capability of these compounds. Telomerase activation testing of the same isolates revealed 1.64-, 1.66-, and 1.72-fold activations in cells treated with compounds <b>1</b>, <b>5</b>, and <b>4</b>, respectively, compared to untreated cells. Our findings may pave the way for further investigations into the development of anti-Alzheimer and/or anti-ageing drugs from furofuranoid-type lignans.https://www.mdpi.com/2223-7747/13/2/150<i>Anisacanthus virgularis</i>furofuranoid lignansanticholinesterasetelomeraseAlzheimer’s diseasemolecular docking |
| spellingShingle | Mohamed A. A. Orabi Reda A. Abdelhamid Hanan Elimam Yaseen A. M. M. Elshaier Ahmed A. Ali Nayef Aldabaan Abdulaziz Hassan Alhasaniah Mohamed S. Refaey Furofuranoid-Type Lignans and Related Phenolics from <i>Anisacanthus virgularis</i> (Salisb.) Nees with Promising Anticholinesterase and Anti-Ageing Properties: A Study Supported by Molecular Modelling Plants <i>Anisacanthus virgularis</i> furofuranoid lignans anticholinesterase telomerase Alzheimer’s disease molecular docking |
| title | Furofuranoid-Type Lignans and Related Phenolics from <i>Anisacanthus virgularis</i> (Salisb.) Nees with Promising Anticholinesterase and Anti-Ageing Properties: A Study Supported by Molecular Modelling |
| title_full | Furofuranoid-Type Lignans and Related Phenolics from <i>Anisacanthus virgularis</i> (Salisb.) Nees with Promising Anticholinesterase and Anti-Ageing Properties: A Study Supported by Molecular Modelling |
| title_fullStr | Furofuranoid-Type Lignans and Related Phenolics from <i>Anisacanthus virgularis</i> (Salisb.) Nees with Promising Anticholinesterase and Anti-Ageing Properties: A Study Supported by Molecular Modelling |
| title_full_unstemmed | Furofuranoid-Type Lignans and Related Phenolics from <i>Anisacanthus virgularis</i> (Salisb.) Nees with Promising Anticholinesterase and Anti-Ageing Properties: A Study Supported by Molecular Modelling |
| title_short | Furofuranoid-Type Lignans and Related Phenolics from <i>Anisacanthus virgularis</i> (Salisb.) Nees with Promising Anticholinesterase and Anti-Ageing Properties: A Study Supported by Molecular Modelling |
| title_sort | furofuranoid type lignans and related phenolics from i anisacanthus virgularis i salisb nees with promising anticholinesterase and anti ageing properties a study supported by molecular modelling |
| topic | <i>Anisacanthus virgularis</i> furofuranoid lignans anticholinesterase telomerase Alzheimer’s disease molecular docking |
| url | https://www.mdpi.com/2223-7747/13/2/150 |
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