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Open AccessCommunication

Bioactive Brominated Oxindole Alkaloids from the Red Sea Sponge Callyspongia siphonella

1
Department of Pharmacognosy, Faculty of Pharmacy, Cairo University, 11787 Cairo, Egypt
2
Department of Pharmacognosy, Faculty of Pharmacy, Nahda University, 62513 Beni-Suef, Egypt
3
Department of Pharmacognosy, Faculty of Pharmacy, Beni-Suef University, 62514 Beni-Suef, Egypt
4
Marine Biodiscovery Centre, School of Natural and Computing Sciences, University of Aberdeen, Scotland AB24 3UE, UK
5
School of Computing, Engineering and Physical Sciences, University of the West of Scotland, Paisley PA1 2BE, UK
6
Marine Invertebrates, National Institute of Oceanography and Fisheries, Red Sea Branch, 84511 Hurghada, Egypt
7
Division of Molecular Internal Medicine, Department of Internal Medicine II, University Hospital Würzburg, Grombühlstr. 12, 97080 Würzburg, Germany
8
Department of Biochemistry, Faculty of Pharmacy, Mansoura University, 35516 Mansoura, Egypt
9
Department of Pharmacognosy, College of Pharmacy, King Khalid University, Abha 61441, Saudi Arabia
10
Division of Genetic Engineering and Biotechnology, Department of Microbial Biotechnology, National Research Centre, El Buhouth Street, Dokki, 12622 Giza, Egypt
11
Department of Pharmacognosy, Faculty of Pharmacy, Minia University, 61519 Minia, Egypt
*
Authors to whom correspondence should be addressed.
Mar. Drugs 2019, 17(8), 465; https://doi.org/10.3390/md17080465
Received: 9 July 2019 / Revised: 20 July 2019 / Accepted: 23 July 2019 / Published: 9 August 2019
(This article belongs to the Collection Bioactive Compounds from Marine Invertebrates)
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Abstract

In the present study, LC-HRESIMS-assisted dereplication along with bioactivity-guided isolation led to targeting two brominated oxindole alkaloids (compounds 1 and 2) which probably play a key role in the previously reported antibacterial, antibiofilm, and cytotoxicity of Callyspongia siphonella crude extracts. Both metabolites showed potent antibacterial activity against Gram-positive bacteria, Staphylococcus aureus (minimum inhibitory concentration (MIC) = 8 and 4 µg/mL) and Bacillus subtilis (MIC = 16 and 4 µg/mL), respectively. Furthermore, they displayed moderate biofilm inhibitory activity in Pseudomonas aeruginosa (49.32% and 41.76% inhibition, respectively), and moderate in vitro antitrypanosomal activity (13.47 and 10.27 µM, respectively). In addition, they revealed a strong cytotoxic effect toward different human cancer cell lines, supposedly through induction of necrosis. This study sheds light on the possible role of these metabolites (compounds 1 and 2) in keeping fouling organisms away from the sponge outer surface, and the possible applications of these defensive molecules in the development of new anti-infective agents. View Full-Text
Keywords: Callyspongia siphonella; LC-HRESIMS; metabolomic profiling; oxindole alkaloids; tisindoline; antibacterial; antibiofilm; antitrypanosomal; anticancer Callyspongia siphonella; LC-HRESIMS; metabolomic profiling; oxindole alkaloids; tisindoline; antibacterial; antibiofilm; antitrypanosomal; anticancer
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MDPI and ACS Style

El-Hawary, S.S.; Sayed, A.M.; Mohammed, R.; Hassan, H.M.; Rateb, M.E.; Amin, E.; Mohammed, T.A.; El-Mesery, M.; Bin Muhsinah, A.; Alsayari, A.; Wajant, H.; Anany, M.A.; Abdelmohsen, U.R. Bioactive Brominated Oxindole Alkaloids from the Red Sea Sponge Callyspongia siphonella. Mar. Drugs 2019, 17, 465.

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