Bromopyrrole Alkaloids of the Sponge Agelas oroides Collected near the Israeli Mediterranean Coastline

Dimitry Kovalerchik, Ravindra Pal Singh, Pnina Schlesinger, Aseel Mahajni, Sigal Shefer, Micha Fridman, Micha Ilan, Shmuel Carmeli*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Chemical investigation of the Mediterranean Sea sponge, Agelas oroides, collected off the Tel Aviv coast, yielded eight new bromopyrrole metabolites, agesamine C (1), dioroidamide A (2), slagenin D (3), (-)-monobromoagelaspongin (4), (-)-11-deoxymonobromoagelaspongin (5), (-)-11-O-methylmonobromoagelaspongin (6), E-dispacamide (7), and pyrrolosine (8), along with 18 known bromopyrrole alkaloids and a known bromotyrosine derivative. The structures of the new metabolites were elucidated by analysis of the spectroscopic and spectrometric data, including 1D and 2D NMR, ECD, and high-resolution mass spectrometry. The sponge extract exhibited antimicrobial activity against pathogenic and environmental bacteria, and quorum sensing inhibitory activity (QSI) against Chromobacterium violaceum. QSI guided separation of the extract established oroidin, benzosceptrin C, and 4,5-dibromopyrrole-2-carboxamide as the active components. The latter compounds were tested for inhibition of growth and biofilm formation in Pseudomonas aeruginosa PAO1. The most active and available compound, oroidin, was assayed for inhibition of growth and biofilm formation in bacteria that were isolated from the sponge and its environment.

Original languageEnglish
Pages (from-to)374-384
Number of pages11
JournalJournal of Natural Products
Volume83
Issue number2
DOIs
StatePublished - 28 Feb 2020

Funding

FundersFunder number
School of Chemistry
Ministry of Science, Technology and Space
Israel Science Foundation2577/18
Ministry of Science and Technology, Israel3-1034

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