Lichen butyrolactone derivatives disrupt oral bacterial membrane
We have previously demonstrated that out of the butyrolactones series synthesized based on the natural lichen metabolite lichesterinic acid, compound (B-13) was the most effective against oral bacteria. However, its antibacterial mechanism is still unknown. In this study, we have investigated its ba...
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| Veröffentlicht in: | Fitoterapia 2019-09, Vol.137, p.104274, Article 104274 |
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| creator | Sweidan, Alaa Smida, Imen Chollet-Krugler, Marylène Sauvager, Aurélie Vallet, Julien Gouault, Nicolas Oliviero, Nolwenn Tamanai-Shacoori, Zohreh Burel, Agnès van de Weghe, Pierre Chokr, Ali Tomasi, Sophie Bousarghin, Latifa |
| description | We have previously demonstrated that out of the butyrolactones series synthesized based on the natural lichen metabolite lichesterinic acid, compound (B-13) was the most effective against oral bacteria. However, its antibacterial mechanism is still unknown. In this study, we have investigated its bacterial localization by synthesizing a fluorescently labeled B-13 with NBD while maintaining its antibacterial activity. We showed that this compound binds to Streptococcus gordonii cell surface, as demonstrated by HPLC analysis. By adhering to cell surface, B-13 induced cell wall disruption leading to the release of bacterial constituents and consequently, the death of S. gordonii, a Gram-positive bacterium. A Gram-negative counterpart, Porphyromanas gingivalis, showed also cracked and ruptured cells in the presence of B-13. Besides, we also demonstrated that the analog of B-13, B-12, has also induced disruption of P. gingivalis and S. gordonii. This study revealed that butyrolactones can be considered as potent antibacterial compounds against oral pathogens causing medical complications.
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| doi_str_mv | 10.1016/j.fitote.2019.104274 |
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[Display omitted]</description><subject>Antibacterial activity</subject><subject>Antibacterial materials</subject><subject>Bacteria</subject><subject>Butyrolactone</subject><subject>Cell surface</subject><subject>Cell wall</subject><subject>Cell walls</subject><subject>Chemical Sciences</subject><subject>Complications</subject><subject>Disruption</subject><subject>High-performance liquid chromatography</subject><subject>Lichen</subject><subject>Life Sciences</subject><subject>Liquid chromatography</subject><subject>Localization</subject><subject>Lymphocytes B</subject><subject>Medicinal Chemistry</subject><subject>Pharmaceutical sciences</subject><subject>Pharmacology</subject><subject>Porphyromanas gingivalis</subject><subject>Streptococcus gordonii</subject><subject>Synthesis</subject><issn>0367-326X</issn><issn>1873-6971</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kE1r3DAQhkVoSbZJ_kEohp568Hb0YUu6hITQNoWFXlrITcjSmGjZtbaSvJB_Xy1Oc-xphtEz74iHkBsKawq0_7Jdj6HEgmsGVNeRYFKckRVVkre9lvQdWQHvZctZ_3RBPuS8BaAdF_ScXHDKheBarMjdJrhnnJphLi8p7qwrccLGYwpHW8IRc-NDTvOhNDHZXTNUoL7Vbo_7IdkJr8j70e4yXr_WS_L729dfD4_t5uf3Hw_3m9YJCaXFsfODGz1TggvZMa4BtLRqBMUY66y3wlPXq1EDt1x3apB6FD2XQ281Vv6SfF5yn-3OHFLY2_Riog3m8X5jTjNgTIEScKSV_bSwhxT_zJiL2cY5TfV7hjENSlGQvFJioVyKOScc32IpmJNiszWLYnNSbBbFde3ja_g87NG_Lf1zWoHbBcCq4xgwmewCTg59SOiK8TH8_8JfxaCNKQ</recordid><startdate>20190901</startdate><enddate>20190901</enddate><creator>Sweidan, Alaa</creator><creator>Smida, Imen</creator><creator>Chollet-Krugler, Marylène</creator><creator>Sauvager, Aurélie</creator><creator>Vallet, Julien</creator><creator>Gouault, Nicolas</creator><creator>Oliviero, Nolwenn</creator><creator>Tamanai-Shacoori, Zohreh</creator><creator>Burel, Agnès</creator><creator>van de Weghe, Pierre</creator><creator>Chokr, Ali</creator><creator>Tomasi, Sophie</creator><creator>Bousarghin, Latifa</creator><general>Elsevier B.V</general><general>Elsevier Science Ltd</general><general>Elsevier</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7U7</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>M7N</scope><scope>P64</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0001-9827-527X</orcidid><orcidid>https://orcid.org/0000-0001-9595-7873</orcidid></search><sort><creationdate>20190901</creationdate><title>Lichen butyrolactone derivatives disrupt oral bacterial membrane</title><author>Sweidan, Alaa ; 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However, its antibacterial mechanism is still unknown. In this study, we have investigated its bacterial localization by synthesizing a fluorescently labeled B-13 with NBD while maintaining its antibacterial activity. We showed that this compound binds to Streptococcus gordonii cell surface, as demonstrated by HPLC analysis. By adhering to cell surface, B-13 induced cell wall disruption leading to the release of bacterial constituents and consequently, the death of S. gordonii, a Gram-positive bacterium. A Gram-negative counterpart, Porphyromanas gingivalis, showed also cracked and ruptured cells in the presence of B-13. Besides, we also demonstrated that the analog of B-13, B-12, has also induced disruption of P. gingivalis and S. gordonii. This study revealed that butyrolactones can be considered as potent antibacterial compounds against oral pathogens causing medical complications.
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| subjects | Antibacterial activity Antibacterial materials Bacteria Butyrolactone Cell surface Cell wall Cell walls Chemical Sciences Complications Disruption High-performance liquid chromatography Lichen Life Sciences Liquid chromatography Localization Lymphocytes B Medicinal Chemistry Pharmaceutical sciences Pharmacology Porphyromanas gingivalis Streptococcus gordonii Synthesis |
| title | Lichen butyrolactone derivatives disrupt oral bacterial membrane |
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