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A Collection of Bioactive Nitrogen-Containing Molecules from the Marine Sponge Acanthostrongylophora ingens

1
TheBlueChemistryLab, Department of Pharmacy, University of Naples Federico II, 80138 Napoli, Italy
2
Laboratoire Molécules de Communication et Adaptation des Micro-organismes, UMR 7245 CNRS, Muséum National d’Histoire Naturelle, 57 rue Cuvier (C.P. 54), 75005 Paris, France
3
ManRos Therapeutics, Perharidy Peninsula, 29680 Roscoff, France
4
Naturalis Biodiversity Center, P.O. Box 9517, 2300 RA Leiden, The Netherlands
*
Authors to whom correspondence should be addressed.
Mar. Drugs 2019, 17(8), 472; https://doi.org/10.3390/md17080472
Received: 10 July 2019 / Revised: 12 August 2019 / Accepted: 13 August 2019 / Published: 15 August 2019
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Abstract

Thirteen nitrogen-containing molecules (1a/1b and 212) were isolated from the Indonesian sponge Acanthostrongylophora ingens, highlighting the richness of this organism as a source of alkaloids. Their structures were elucidated using one- and two-dimensional NMR spectroscopy and HR-ESI-MS, while the stereochemistry of the diketopiperazines was established using Marfey’s method. All compounds were screened in our standard bioactivity assays, including antibacterial, antikinases, and amyloid β-42 assays. The most interesting bioactivity result was obtained with the known acanthocyclamine A (3), which revealed for the first time a specific Escherichia coli antimicrobial activity and an inhibitory effect on amyloid β-42 production induced by aftin-5 and no cytotoxicity at the dose of 26 µM. These results highlight the potentiality of a bipiperidine scaffold as a promising skeleton for preventing or reducing the production of amyloid β-42, a key player in the initiation of Alzheimer’s disease. View Full-Text
Keywords: Acanthostrongylophora ingens; marine sponge; halicyclamine derivative; diketopiperazine; alkaloid; bipiperidine scaffold; kinase inhibitor; antimicrobial activity; inhibitor of amyloid β-42 Acanthostrongylophora ingens; marine sponge; halicyclamine derivative; diketopiperazine; alkaloid; bipiperidine scaffold; kinase inhibitor; antimicrobial activity; inhibitor of amyloid β-42
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Esposito, G.; Mai, L.H.; Longeon, A.; Mangoni, A.; Durieu, E.; Meijer, L.; Van Soest, R.; Costantino, V.; Bourguet-Kondracki, M.-L. A Collection of Bioactive Nitrogen-Containing Molecules from the Marine Sponge Acanthostrongylophora ingens. Mar. Drugs 2019, 17, 472.

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