In Vitro and In Silico Anti-Acetylcholinesterase Activity from <i>Macaranga tanarius</i> and <i>Syzygium jambos</i>
<i>Macaranga tanarius</i> (MT) and <i>Syzygium jambos</i> (SJ) are pharmacologically reported to have anti-oxidant, anti-inflammatory, and anti-diabetic effects, and can be neuroprotective agents. Our previous work revealed that MT and SJ exhibited 76.32% and 93.81% inhibitio...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-04-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/27/9/2648 |
| _version_ | 1827672089588400128 |
|---|---|
| author | Mira Syahfriena Amir Rawa Nurul Amira Nurul Azman Suriani Mohamad Toshihiko Nogawa Habibah A. Wahab |
| author_facet | Mira Syahfriena Amir Rawa Nurul Amira Nurul Azman Suriani Mohamad Toshihiko Nogawa Habibah A. Wahab |
| author_sort | Mira Syahfriena Amir Rawa |
| collection | DOAJ |
| description | <i>Macaranga tanarius</i> (MT) and <i>Syzygium jambos</i> (SJ) are pharmacologically reported to have anti-oxidant, anti-inflammatory, and anti-diabetic effects, and can be neuroprotective agents. Our previous work revealed that MT and SJ exhibited 76.32% and 93.81% inhibition against acetylcholinesterase (AChE) at 50 μg/mL final concentration in their ethyl acetate and hexane fractions, respectively. This study was aimed to investigate the bioactive constituents of MT and SJ and their molecular mechanism toward AChE inhibition. Bioassay-guided isolation afforded prenylflavonoids <b>1</b>–<b>3</b> from MT and anacardic acid derivatives <b>4</b> and <b>5</b> from SJ that were confirmed by NMR and MS data. Compound <b>5</b> exerted the strongest anti-AChE potential (IC<sub>50</sub>: 0.54 μM), followed by <b>1</b>, <b>4</b>, <b>3</b>, and <b>2</b> (IC<sub>50</sub>: 1.0, 2.4, 6.8, and 33 μM, respectively). In silico molecular docking revealed <b>5</b> formed stronger molecular interactions including three H-bonds than its derivative <b>4</b> based on the saturation of their alkyl chains. The addition of a five carbon-prenyl chain in <b>1</b> increased the number of binding interactions, justifying its greater activity than derivatives <b>2</b> and <b>3</b>. This research reflects the first report of AChE inhibitors from these species, thereby adding pharmacological values to MT and SJ as potential remedies in neuroprotection. |
| first_indexed | 2024-03-10T03:55:48Z |
| format | Article |
| id | doaj.art-ad81c5a2a1ff4ed391f5d1b716ffcc6b |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:55:48Z |
| publishDate | 2022-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-ad81c5a2a1ff4ed391f5d1b716ffcc6b2023-11-23T08:47:33ZengMDPI AGMolecules1420-30492022-04-01279264810.3390/molecules27092648In Vitro and In Silico Anti-Acetylcholinesterase Activity from <i>Macaranga tanarius</i> and <i>Syzygium jambos</i>Mira Syahfriena Amir Rawa0Nurul Amira Nurul Azman1Suriani Mohamad2Toshihiko Nogawa3Habibah A. Wahab4Collaborative Laboratory for Herbal Standardization (CHEST), School of Pharmaceutical Sciences, Universiti Sains Malaysia, George Town 11800, Penang, MalaysiaUSM-RIKEN Interdisciplinary Collaboration for Advanced Sciences (URICAS), Universiti Sains Malaysia, George Town 11800, Penang, MalaysiaUSM-RIKEN Interdisciplinary Collaboration for Advanced Sciences (URICAS), Universiti Sains Malaysia, George Town 11800, Penang, MalaysiaChemical Biology Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako 351-0198, Saitama, JapanCollaborative Laboratory for Herbal Standardization (CHEST), School of Pharmaceutical Sciences, Universiti Sains Malaysia, George Town 11800, Penang, Malaysia<i>Macaranga tanarius</i> (MT) and <i>Syzygium jambos</i> (SJ) are pharmacologically reported to have anti-oxidant, anti-inflammatory, and anti-diabetic effects, and can be neuroprotective agents. Our previous work revealed that MT and SJ exhibited 76.32% and 93.81% inhibition against acetylcholinesterase (AChE) at 50 μg/mL final concentration in their ethyl acetate and hexane fractions, respectively. This study was aimed to investigate the bioactive constituents of MT and SJ and their molecular mechanism toward AChE inhibition. Bioassay-guided isolation afforded prenylflavonoids <b>1</b>–<b>3</b> from MT and anacardic acid derivatives <b>4</b> and <b>5</b> from SJ that were confirmed by NMR and MS data. Compound <b>5</b> exerted the strongest anti-AChE potential (IC<sub>50</sub>: 0.54 μM), followed by <b>1</b>, <b>4</b>, <b>3</b>, and <b>2</b> (IC<sub>50</sub>: 1.0, 2.4, 6.8, and 33 μM, respectively). In silico molecular docking revealed <b>5</b> formed stronger molecular interactions including three H-bonds than its derivative <b>4</b> based on the saturation of their alkyl chains. The addition of a five carbon-prenyl chain in <b>1</b> increased the number of binding interactions, justifying its greater activity than derivatives <b>2</b> and <b>3</b>. This research reflects the first report of AChE inhibitors from these species, thereby adding pharmacological values to MT and SJ as potential remedies in neuroprotection.https://www.mdpi.com/1420-3049/27/9/2648<i>Macaranga tanarius</i><i>Syzygium jambos</i>acetylcholinesterase inhibitorprenylflavonoidanacardic acidisolation |
| spellingShingle | Mira Syahfriena Amir Rawa Nurul Amira Nurul Azman Suriani Mohamad Toshihiko Nogawa Habibah A. Wahab In Vitro and In Silico Anti-Acetylcholinesterase Activity from <i>Macaranga tanarius</i> and <i>Syzygium jambos</i> Molecules <i>Macaranga tanarius</i> <i>Syzygium jambos</i> acetylcholinesterase inhibitor prenylflavonoid anacardic acid isolation |
| title | In Vitro and In Silico Anti-Acetylcholinesterase Activity from <i>Macaranga tanarius</i> and <i>Syzygium jambos</i> |
| title_full | In Vitro and In Silico Anti-Acetylcholinesterase Activity from <i>Macaranga tanarius</i> and <i>Syzygium jambos</i> |
| title_fullStr | In Vitro and In Silico Anti-Acetylcholinesterase Activity from <i>Macaranga tanarius</i> and <i>Syzygium jambos</i> |
| title_full_unstemmed | In Vitro and In Silico Anti-Acetylcholinesterase Activity from <i>Macaranga tanarius</i> and <i>Syzygium jambos</i> |
| title_short | In Vitro and In Silico Anti-Acetylcholinesterase Activity from <i>Macaranga tanarius</i> and <i>Syzygium jambos</i> |
| title_sort | in vitro and in silico anti acetylcholinesterase activity from i macaranga tanarius i and i syzygium jambos i |
| topic | <i>Macaranga tanarius</i> <i>Syzygium jambos</i> acetylcholinesterase inhibitor prenylflavonoid anacardic acid isolation |
| url | https://www.mdpi.com/1420-3049/27/9/2648 |
| work_keys_str_mv | AT mirasyahfrienaamirrawa invitroandinsilicoantiacetylcholinesteraseactivityfromimacarangatanariusiandisyzygiumjambosi AT nurulamiranurulazman invitroandinsilicoantiacetylcholinesteraseactivityfromimacarangatanariusiandisyzygiumjambosi AT surianimohamad invitroandinsilicoantiacetylcholinesteraseactivityfromimacarangatanariusiandisyzygiumjambosi AT toshihikonogawa invitroandinsilicoantiacetylcholinesteraseactivityfromimacarangatanariusiandisyzygiumjambosi AT habibahawahab invitroandinsilicoantiacetylcholinesteraseactivityfromimacarangatanariusiandisyzygiumjambosi |