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Article

Magnificines A and B, Antimicrobial Marine Alkaloids Featuring a Tetrahydrooxazolo[3,2-a]azepine-2,5(3H,6H)-dione Backbone from the Red Sea Sponge Negombata magnifica

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Department of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia
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Department of Medical Parasitology, Faculty of Medicine, Princess Al-Jawhara Center of Excellence in Research of Hereditary Disorders, King Abdulaziz University, Jeddah 21589, Saudi Arabia
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UMR 8038 CiTCoM, Faculté de Pharmacie de Paris, Université Paris Descartes, Avenue de l’observatoire, 75006 Paris, France
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Molecules of Communication and Adaptation of Microorganisms (UMR 7245), National Museum of Natural History, CNRS, 75231 Paris, France
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Natural Products Unit, King Fahd Medical Research Center, King Abdulaziz University, Jeddah 21589, Saudi Arabia
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Department of Medical Laboratory Sciences, Faculty of Applied Medical Sciences, King Abdulaziz University, Jeddah 21589, Saudi Arabia
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Suez Canal University Hospital, Suez Canal University, Ismailia 41522, Egypt
*
Authors to whom correspondence should be addressed.
Academic Editor: Vassilios Roussis
Mar. Drugs 2021, 19(4), 214; https://doi.org/10.3390/md19040214
Received: 24 March 2021 / Revised: 8 April 2021 / Accepted: 9 April 2021 / Published: 12 April 2021
Investigation of the Red Sea sponge Negombata magnifica gave two novel alkaloids, magnificines A and B (1 and 2) and a new β-ionone derivative, (±)-negombaionone (3), together with the known latrunculin B (4) and 16-epi-latrunculin B (5). The analysis of the NMR and HRESIMS spectra supported the planar structures and the relative configurations of the compounds. The absolute configurations of magnificines A and B were determined by the analysis of the predicted and experimental ECD spectra. Magnificines A and B possess a previously unreported tetrahydrooxazolo[3,2-a]azepine-2,5(3H,6H)-dione backbone and represent the first natural compounds in this class. (±)-Negombaionone is the first β-ionone of a sponge origin. Compounds 1-3 displayed selective activity against Escherichia coli in a disk diffusion assay with inhibition zones up to 22 mm at a concentration of 50 µg/disc and with MIC values down to 8.0 µM. Latrunculin B and 16-epi-latrunculin B inhibited the growth of HeLa cells with IC50 values down to 1.4 µM. View Full-Text
Keywords: Red Sea sponge; Negombata magnifica; marine alkaloids; β-ionone; magnificines A and B; (±)-negombaionone; latrunculin B and 16-epi-latrunculin B; antimicrobial activity; E. coli; cell line growth inhibition; HeLa cells Red Sea sponge; Negombata magnifica; marine alkaloids; β-ionone; magnificines A and B; (±)-negombaionone; latrunculin B and 16-epi-latrunculin B; antimicrobial activity; E. coli; cell line growth inhibition; HeLa cells
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MDPI and ACS Style

Youssef, D.T.A.; Asfour, H.Z.; Genta-Jouve, G.; Shaala, L.A. Magnificines A and B, Antimicrobial Marine Alkaloids Featuring a Tetrahydrooxazolo[3,2-a]azepine-2,5(3H,6H)-dione Backbone from the Red Sea Sponge Negombata magnifica. Mar. Drugs 2021, 19, 214. https://doi.org/10.3390/md19040214

AMA Style

Youssef DTA, Asfour HZ, Genta-Jouve G, Shaala LA. Magnificines A and B, Antimicrobial Marine Alkaloids Featuring a Tetrahydrooxazolo[3,2-a]azepine-2,5(3H,6H)-dione Backbone from the Red Sea Sponge Negombata magnifica. Marine Drugs. 2021; 19(4):214. https://doi.org/10.3390/md19040214

Chicago/Turabian Style

Youssef, Diaa T.A., Hani Z. Asfour, Grégory Genta-Jouve, and Lamiaa A. Shaala 2021. "Magnificines A and B, Antimicrobial Marine Alkaloids Featuring a Tetrahydrooxazolo[3,2-a]azepine-2,5(3H,6H)-dione Backbone from the Red Sea Sponge Negombata magnifica" Marine Drugs 19, no. 4: 214. https://doi.org/10.3390/md19040214

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