Exploring the Antibacterial and Antibiofilm Efficacy of Psammogeton biternatum Edgew and Identification of a Novel Quinoline Alkaloid using X-ray Crystallography

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dc.authoridAhmad, Dr. Rizwan/0000-0001-6490-8219
dc.authoridRiaz, Muhammad/0000-0001-9327-1368
dc.authoridAlqathama, Aljawharah/0000-0003-0855-2013
dc.contributor.authorMasood, Faiza
dc.contributor.authorKhan, Wajiha
dc.contributor.authorKhan, Imran
dc.contributor.authorKhan, Uzma
dc.contributor.authorMajid, Abdul
dc.contributor.authorKhan, Sebghat Ullah
dc.contributor.authorSahin, Onur
dc.date.accessioned2025-03-23T19:35:49Z
dc.date.available2025-03-23T19:35:49Z
dc.date.issued2024
dc.departmentSinop Üniversitesi
dc.description.abstractThe prevalence of resistance to harmful human pathogens is steadily rising, emphasizing the urgent need to identify novel antimicrobial compounds. For this purpose, plants stand out as a significant source of bioactives worthy of exploration. Among these, alkaloids, a vast and structurally diverse category of plant secondary metabolites, have emerged as a foundation for crucial antibacterial medications such as metronidazole and the quinolones. In the current work, the crude methanol leaf extract of Psammogeton biternatum Edgew collected from District Bannu, Pakistan, was subjected to TLC (indirect) bioautography and X-ray crystallography for the isolation of potential antibacterial agents. From the crude extract, a novel quinoline alkaloid called quinoline dione ((3R,3aS,5aR)-3,5a,9-trimethyl-3a,4,5,5a-tetrahydro-2H-isoxazolo[2,3-a] quinoline-2,8(3H)-dione (C14H17NO3)) was isolated. The crystal information (M = 247.296 g/mol) is as follows: orthorhombic, P2(1)2(1)2(v), a = 7.7339(14) & Aring;, b = 10.7254(19) & Aring;, c = 15.730(2) & Aring;, V = 1304.8(4) & Aring;3, Z = 4, T = 296 K, mu(Mo K alpha) = 0.088 mm-1, rho calc = 1.259 g/cm(3), 13928 reflections measured (5.86 degrees <= 2 Theta <= 51.98 degrees), 2478 unique (R- int = 0.1613, R sigma = 0.1335). The final R (1) was 0.1098 (I >= 2u(I)), and wR (2) was 0.2183. The antibacterial activity for both crude extract of leaves and quinoline dione was determined by a well diffusion method. The quinoline dione alkaloid demonstrated excellent inhibition zones against methicillin-resistant Staphylococcus aureus (18 mm), Bacillus subtills (17 mm), Escherichia coli (20 mm), and Pseudomonas aeruginosa (23 mm) compared to the crude extract. The antibiofilm potential was recorded against Pseudomonas aeruginosa by the 96-well microtiter plate method. A dose-dependent biofilm inhibition response was recorded, which increased with the increase in concentration. Moreover, quinoline dione showed a greater antibiofilm effect as compared to the crude extract, which may be linked to the presence of a particular active functional group positioned on the compound isolated in its pure form. Through in silico studies, i.e., molecular docking, quinoline dione shows strong binding energies with the LasR transcriptional regulator (6MVN) at -9.3 and LasR transcriptional activator (3IX4) at -9.2 kcal/mol, as well as moderate affinities with other targets such as AHL synthase LasI (PDB ID 1RO5) and OprM channel (PDB ID 3D5K), indicating its potential as a quorum sensing inhibitor. Thus, the antibacterial and antibiofilm potential of quinoline dione was confirmed.
dc.description.sponsorshipUniversity Higher Education Fund under the Research Support Program for Central Laboratories at King Khalid University [CL/PRI/A/2]
dc.description.sponsorshipThe authors extend their appreciation to University Higher Education Fund for funding this research work under the Research Support Program for Central Laboratories at King Khalid University through project number CL/PRI/A/2.
dc.identifier.doi10.1021/acsomega.4c05459
dc.identifier.endpage43569
dc.identifier.issn2470-1343
dc.identifier.issue43
dc.identifier.pmid39494018
dc.identifier.scopus2-s2.0-85206558450
dc.identifier.scopusqualityQ1
dc.identifier.startpage43557
dc.identifier.urihttps://doi.org/10.1021/acsomega.4c05459
dc.identifier.urihttps://hdl.handle.net/11486/5943
dc.identifier.volume9
dc.identifier.wosWOS:001338118500001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherAmer Chemical Soc
dc.relation.ispartofAcs Omega
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_WOS_20250323
dc.subjectBacterial Biofilm
dc.subjectNatural-Products
dc.subjectDocking
dc.titleExploring the Antibacterial and Antibiofilm Efficacy of Psammogeton biternatum Edgew and Identification of a Novel Quinoline Alkaloid using X-ray Crystallography
dc.typeArticle

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