Anti-MRSA Constituents from <i>Ruta chalepensis</i> (Rutaceae) Grown in Iraq, and <i>In Silico</i> Studies on Two of Most Active Compounds, Chalepensin and 6-Hydroxy-rutin 3′,7-Dimethyl ether
<i>Ruta chalepensis</i> L. (Rutaceae), a perennial herb with wild and cultivated habitats, is well known for its traditional uses as an anti-inflammatory, analgesic, antipyretic agent, and in the treatment of rheumatism, nerve diseases, neuralgia, dropsy, convulsions and mental disorders...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-02-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/26/4/1114 |
| _version_ | 1827588711817150464 |
|---|---|
| author | Shaymaa Al-Majmaie Lutfun Nahar M. Mukhlesur Rahman Sushmita Nath Priyanka Saha Anupam Das Talukdar George P. Sharples Satyajit D. Sarker |
| author_facet | Shaymaa Al-Majmaie Lutfun Nahar M. Mukhlesur Rahman Sushmita Nath Priyanka Saha Anupam Das Talukdar George P. Sharples Satyajit D. Sarker |
| author_sort | Shaymaa Al-Majmaie |
| collection | DOAJ |
| description | <i>Ruta chalepensis</i> L. (Rutaceae), a perennial herb with wild and cultivated habitats, is well known for its traditional uses as an anti-inflammatory, analgesic, antipyretic agent, and in the treatment of rheumatism, nerve diseases, neuralgia, dropsy, convulsions and mental disorders. The antimicrobial activities of the crude extracts from the fruits, leaves, stem and roots of <i>R. chalepensis</i> were initially evaluated against two Gram-positive and two Gram-negative bacterial strains and a strain of the fungus <i>Candida albicans</i>. Phytochemical investigation afforded 19 compounds, including alkaloids, coumarins, flavonoid glycosides, a cinnamic acid derivative and a long-chain alkane. These compounds were tested against a panel of methicillin-resistant <i>Staphylococcus aureus</i> (MRSA) strains, i.e., ATCC 25923, SA-1199B, XU212, MRSA-274819 and EMRSA-15. The MIC values of the active compounds, chalepin (<b>9</b>), chalepensin (<b>10</b>), rutamarin (<b>11</b>), rutin 3′-methyl ether (<b>14</b>), rutin 7,4′-dimethyl ether (<b>15</b>), 6-hydroxy-rutin 3′,7-dimethyl ether (<b>16</b>) and arborinine (<b>18</b>) were in the range of 32–128 µg/mL against the tested MRSA strains. Compounds <b>10</b> and <b>16</b> were the most active compounds from <i>R. chalepensis</i>, and were active against four out of six tested MRSA strains, and <i>in silico</i> studies were performed on these compounds. The anti-MRSA activity of compound <b>16</b> was comparable to that of the positive control norfloxacin (MICs 32 vs 16 μg/mL, respectively) against the MRSA strain XU212, which is a Kuwaiti hospital isolate that possesses the TetK tetracycline efflux pump. This is the first report on the anti-MRSA property of compounds isolated from <i>R. chalepensis</i> and relevant <i>in silico</i> studies on the most active compounds. |
| first_indexed | 2024-03-09T00:42:42Z |
| format | Article |
| id | doaj.art-32a309683fd246bdac89238adb30dc62 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T00:42:42Z |
| publishDate | 2021-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-32a309683fd246bdac89238adb30dc622023-12-11T17:43:43ZengMDPI AGMolecules1420-30492021-02-01264111410.3390/molecules26041114Anti-MRSA Constituents from <i>Ruta chalepensis</i> (Rutaceae) Grown in Iraq, and <i>In Silico</i> Studies on Two of Most Active Compounds, Chalepensin and 6-Hydroxy-rutin 3′,7-Dimethyl etherShaymaa Al-Majmaie0Lutfun Nahar1M. Mukhlesur Rahman2Sushmita Nath3Priyanka Saha4Anupam Das Talukdar5George P. Sharples6Satyajit D. Sarker7Centre for Natural Products Discovery, School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, James Parsons Building, Byrom Street, Liverpool L3 3AF, UKLaboratory of Growth Regulators, Institute of Experimental Botany ASCR & Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech RepublicMedicines Research Group, School of Health, Sport and Bioscience, University of East London, Water Lane, London E15 4LZ, UKCentre for Natural Products Discovery, School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, James Parsons Building, Byrom Street, Liverpool L3 3AF, UKCancer Biology and Inflammatory Disease Division, CSIR-Indian Institute of Chemical Biology, Kolkata, West Bengal 700032, IndiaDepartment of Life Science and Bioinformatics, Assam University, Silchar, Assam 788011, IndiaCentre for Natural Products Discovery, School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, James Parsons Building, Byrom Street, Liverpool L3 3AF, UKCentre for Natural Products Discovery, School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, James Parsons Building, Byrom Street, Liverpool L3 3AF, UK<i>Ruta chalepensis</i> L. (Rutaceae), a perennial herb with wild and cultivated habitats, is well known for its traditional uses as an anti-inflammatory, analgesic, antipyretic agent, and in the treatment of rheumatism, nerve diseases, neuralgia, dropsy, convulsions and mental disorders. The antimicrobial activities of the crude extracts from the fruits, leaves, stem and roots of <i>R. chalepensis</i> were initially evaluated against two Gram-positive and two Gram-negative bacterial strains and a strain of the fungus <i>Candida albicans</i>. Phytochemical investigation afforded 19 compounds, including alkaloids, coumarins, flavonoid glycosides, a cinnamic acid derivative and a long-chain alkane. These compounds were tested against a panel of methicillin-resistant <i>Staphylococcus aureus</i> (MRSA) strains, i.e., ATCC 25923, SA-1199B, XU212, MRSA-274819 and EMRSA-15. The MIC values of the active compounds, chalepin (<b>9</b>), chalepensin (<b>10</b>), rutamarin (<b>11</b>), rutin 3′-methyl ether (<b>14</b>), rutin 7,4′-dimethyl ether (<b>15</b>), 6-hydroxy-rutin 3′,7-dimethyl ether (<b>16</b>) and arborinine (<b>18</b>) were in the range of 32–128 µg/mL against the tested MRSA strains. Compounds <b>10</b> and <b>16</b> were the most active compounds from <i>R. chalepensis</i>, and were active against four out of six tested MRSA strains, and <i>in silico</i> studies were performed on these compounds. The anti-MRSA activity of compound <b>16</b> was comparable to that of the positive control norfloxacin (MICs 32 vs 16 μg/mL, respectively) against the MRSA strain XU212, which is a Kuwaiti hospital isolate that possesses the TetK tetracycline efflux pump. This is the first report on the anti-MRSA property of compounds isolated from <i>R. chalepensis</i> and relevant <i>in silico</i> studies on the most active compounds.https://www.mdpi.com/1420-3049/26/4/1114<i>Ruta chalepensis</i>Rutaceaechalepensinrutinanti-MRSA<i>in silico</i> |
| spellingShingle | Shaymaa Al-Majmaie Lutfun Nahar M. Mukhlesur Rahman Sushmita Nath Priyanka Saha Anupam Das Talukdar George P. Sharples Satyajit D. Sarker Anti-MRSA Constituents from <i>Ruta chalepensis</i> (Rutaceae) Grown in Iraq, and <i>In Silico</i> Studies on Two of Most Active Compounds, Chalepensin and 6-Hydroxy-rutin 3′,7-Dimethyl ether Molecules <i>Ruta chalepensis</i> Rutaceae chalepensin rutin anti-MRSA <i>in silico</i> |
| title | Anti-MRSA Constituents from <i>Ruta chalepensis</i> (Rutaceae) Grown in Iraq, and <i>In Silico</i> Studies on Two of Most Active Compounds, Chalepensin and 6-Hydroxy-rutin 3′,7-Dimethyl ether |
| title_full | Anti-MRSA Constituents from <i>Ruta chalepensis</i> (Rutaceae) Grown in Iraq, and <i>In Silico</i> Studies on Two of Most Active Compounds, Chalepensin and 6-Hydroxy-rutin 3′,7-Dimethyl ether |
| title_fullStr | Anti-MRSA Constituents from <i>Ruta chalepensis</i> (Rutaceae) Grown in Iraq, and <i>In Silico</i> Studies on Two of Most Active Compounds, Chalepensin and 6-Hydroxy-rutin 3′,7-Dimethyl ether |
| title_full_unstemmed | Anti-MRSA Constituents from <i>Ruta chalepensis</i> (Rutaceae) Grown in Iraq, and <i>In Silico</i> Studies on Two of Most Active Compounds, Chalepensin and 6-Hydroxy-rutin 3′,7-Dimethyl ether |
| title_short | Anti-MRSA Constituents from <i>Ruta chalepensis</i> (Rutaceae) Grown in Iraq, and <i>In Silico</i> Studies on Two of Most Active Compounds, Chalepensin and 6-Hydroxy-rutin 3′,7-Dimethyl ether |
| title_sort | anti mrsa constituents from i ruta chalepensis i rutaceae grown in iraq and i in silico i studies on two of most active compounds chalepensin and 6 hydroxy rutin 3 7 dimethyl ether |
| topic | <i>Ruta chalepensis</i> Rutaceae chalepensin rutin anti-MRSA <i>in silico</i> |
| url | https://www.mdpi.com/1420-3049/26/4/1114 |
| work_keys_str_mv | AT shaymaaalmajmaie antimrsaconstituentsfromirutachalepensisirutaceaegrowniniraqandiinsilicoistudiesontwoofmostactivecompoundschalepensinand6hydroxyrutin37dimethylether AT lutfunnahar antimrsaconstituentsfromirutachalepensisirutaceaegrowniniraqandiinsilicoistudiesontwoofmostactivecompoundschalepensinand6hydroxyrutin37dimethylether AT mmukhlesurrahman antimrsaconstituentsfromirutachalepensisirutaceaegrowniniraqandiinsilicoistudiesontwoofmostactivecompoundschalepensinand6hydroxyrutin37dimethylether AT sushmitanath antimrsaconstituentsfromirutachalepensisirutaceaegrowniniraqandiinsilicoistudiesontwoofmostactivecompoundschalepensinand6hydroxyrutin37dimethylether AT priyankasaha antimrsaconstituentsfromirutachalepensisirutaceaegrowniniraqandiinsilicoistudiesontwoofmostactivecompoundschalepensinand6hydroxyrutin37dimethylether AT anupamdastalukdar antimrsaconstituentsfromirutachalepensisirutaceaegrowniniraqandiinsilicoistudiesontwoofmostactivecompoundschalepensinand6hydroxyrutin37dimethylether AT georgepsharples antimrsaconstituentsfromirutachalepensisirutaceaegrowniniraqandiinsilicoistudiesontwoofmostactivecompoundschalepensinand6hydroxyrutin37dimethylether AT satyajitdsarker antimrsaconstituentsfromirutachalepensisirutaceaegrowniniraqandiinsilicoistudiesontwoofmostactivecompoundschalepensinand6hydroxyrutin37dimethylether |