Marine sponges, a well-documented prolific source of natural products, harbor highly diverse microbial communities. Their extracts were previously shown to contain quorum sensing (QS) signal molecules of the N-acyl homoserine lactone (AHL) type, known to orchestrate bacterial gene regulation. Some bacteria and eukaryotic organisms are known to produce molecules that can interfere with QS signaling, thus affecting microbial genetic regulation and function. In the present study, we established the production of both QS signal molecules as well as QS inhibitory (QSI) molecules in the sponge species Sarcotragus spinosulus. A total of eighteen saturated acyl chain AHLs were identified along with six unsaturated acyl chain AHLs. Bioassay-guided purification led to the isolation of two brominated metabolites with QSI activity. The structures of these compounds were elucidated by comparative spectral analysis of 1HNMR and HR-MS data and were identified as 3-bromo-4-methoxyphenethylamine (1) and 5,6-dibromo-N,N-dimethyltryptamine (2). The QSI activity of compounds 1 and 2 was evaluated using reporter gene assays for long- and short-chain AHL signals (Escherichia coli pSB1075 and E. coli pSB401, respectively). QSI activity was further confirmed by measuring dose-dependent inhibition of proteolytic activity and pyocyanin production in Pseudomonas aeruginosa PAO1. The obtained results show the coexistence of QS and QSI in S. spinosulus, a complex signal network that may mediate the orchestrated function of the microbiome within the sponge holobiont.
- Klíčová slova
- 3-bromo-4-methoxyphenethylamine, 5,6-dibromo-N,N-dimethyltryptamine, N-acyl homoserine lactone, Sarcotragus spinosulus, quorum sensing, quorum sensing inhibition, sponge,
- MeSH
- Escherichia coli účinky léků fyziologie MeSH
- faktory virulence MeSH
- fylogeneze MeSH
- luminiscenční měření MeSH
- Porifera genetika metabolismus mikrobiologie MeSH
- proteasy chemie farmakologie MeSH
- pyokyanin chemie farmakologie MeSH
- quorum sensing účinky léků MeSH
- zvířata MeSH
- Check Tag
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- faktory virulence MeSH
- proteasy MeSH
- pyokyanin MeSH
Corylus avellana L. (Betulaceae) leaves, consumed as infusion, are used in traditional medicine, for the treatment of hemorrhoids, varicose veins, phlebitis, and edema due to their astringent, vasoprotective, and antiedema properties. In previous works we reported from the leaves of Corylus avellana cv. "Tonda di Giffoni" diarylheptanoid derivatives, a class of plant secondary metabolites with a wide variety of bioactivities. With the aim to give an interesting and economically feasible opportunity to C. avellana leaves as source of functional ingredients for pharmaceutical and cosmetic formulations, "green" extracts were prepared by employing "eco-friendly" extraction protocols as maceration, infusion and SLDE-Naviglio extraction. Metabolite profiles of the extracts were obtained by 1H NMR experiments and data were processed by multivariate statistical analysis to highlight differences in the extracts and to evidence the extracts with the highest concentrations of bioactive metabolites. Based on the NMR data, a total of 31 compounds were identified. The metabolite variation among the extracts was evaluated using Principle Component Analysis (PCA) and Partial Least Squares-Discriminant Analysis (PLS-DA). Furthermore, the total phenolic content of the extracts was measured by Folin-Ciocalteu colorimetric assay and the antioxidant activity of extracts was assayed by the spectrophotometric tests DPPH• and ABTS and by an in vitro test based on the evaluation of cellular reactive oxygen species production stimulated by pyocyanin.
- Klíčová slova
- Corylus avellana leaves, Multivariate Data Analysis, NMR metabolomics, antioxidant activity, “Nocciola di Giffoni”, “green” extracts,
- MeSH
- fenoly analýza farmakologie MeSH
- lidé MeSH
- líska chemie metabolismus MeSH
- listy rostlin chemie MeSH
- metabolomika metody MeSH
- nukleární magnetická rezonance biomolekulární metody MeSH
- protonová magnetická rezonanční spektroskopie metody MeSH
- pyokyanin farmakologie MeSH
- reaktivní formy kyslíku metabolismus MeSH
- rostlinné extrakty analýza chemie farmakologie MeSH
- scavengery volných radikálů analýza farmakologie MeSH
- technologie zelené chemie metody MeSH
- THP-1 buňky MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- fenoly MeSH
- pyokyanin MeSH
- reaktivní formy kyslíku MeSH
- rostlinné extrakty MeSH
- scavengery volných radikálů MeSH