Inhibition of quorum sensing by compounds from two Eunicea species and synthetic saturated alkylglycerols

Background: the emergence of bacterial resistance has led to a search for new natural products as alternatives starting points to prevent and control diseases caused by microorganisms. Among the potential candidates were bioactive compounds from octocorals of the genus Eunicea due to their chemical...

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Autores principales:	Clara BARRAGÁN A., Edelberto SILVA G., Bárbara MORENO M., Humberto MAYORGA W.
Formato:	article
Lenguaje:	EN
Publicado:	Universidad de Antioquia 2018
Materias:	Natural products alkylglycerols synthesis quorum sensing inhibition antibacterial Food processing and manufacture TP368-456 Pharmaceutical industry HD9665-9675
Acceso en línea:	https://doaj.org/article/98925969d95b4c87870ef49e3d0773a0
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spelling	oai:doaj.org-article:98925969d95b4c87870ef49e3d0773a02021-11-19T04:08:47ZInhibition of quorum sensing by compounds from two Eunicea species and synthetic saturated alkylglycerols0121-40042145-2660https://doaj.org/article/98925969d95b4c87870ef49e3d0773a02018-08-01T00:00:00Zhttps://revistas.udea.edu.co/index.php/vitae/article/view/330856https://doaj.org/toc/0121-4004https://doaj.org/toc/2145-2660 Background: the emergence of bacterial resistance has led to a search for new natural products as alternatives starting points to prevent and control diseases caused by microorganisms. Among the potential candidates were bioactive compounds from octocorals of the genus Eunicea due to their chemical structures and their wide range of biological activities. Objective: the purpose of this study was to evaluate the quorum sensing inhibition (QSI) and antibacterial activity of compounds previously isolated from two Eunicea species and synthesized alkylglycerols (AKG). Methods: the QSI of three nonpolar compounds and a mixture of AKGs from Eunicea were evaluated by a microtiter plate assay using Chromobacterium violaceum (ATCC 31532). Four naturally occurring, saturated, and enantiomerically pure AKGs, all of which were derived from the chiral precursor (R)-solketal, were synthesized from alkyl chains of 12, 14, 16 and 18 carbons, and their structures were spectroscopically verified by NMR, ESI-MS and optical rotation data. Their QSI by the disc diffusion assay and minimum inhibitory concentrations (MIC) against 14 clinical bacterial isolates in microtiter plates were determined. Results: cembradiene 1, the AKG mixture and AKG (2S)-3-O-dodecyl-1,2-propanediol 4 inhibit QS at the same concentration as kojic acid (10 µg/well or 20 µg/disc, respectively). In this study, the bioactive compounds 1, stearyl oleate 2, acylglycerol 3 and AKGs 4 and (2S)-3-O-tetradecyl-1,2-propanediol 5 showed in vitro IQS activity for the first time. Additionally, 4 and 5 displayed in vitro antibacterial activity against Listeria innocua and Staphylococcus aureus (MIC = 32 µg/mL for both 4 and 5), Enterococcus faecalis (128 µg/mL and 64 µg/mL respectively), Micrococcus luteus (128 µg/mL for both) and Brevibacillus brevis (Bacillus brevis) (512 µg/mL and 64 µg/mL respectively). Conclusion: results suggest that natural compounds 1, 2, 3, 4 and 5 showed QSI, also 4 and 5 have antibacterial activity and they are an interesting alternative to continue researching their effect against pathogenic microorganisms. Clara BARRAGÁN A.Edelberto SILVA G.Bárbara MORENO M.Humberto MAYORGA W.Universidad de AntioquiaarticleNatural productsalkylglycerolssynthesisquorum sensing inhibitionantibacterialFood processing and manufactureTP368-456Pharmaceutical industryHD9665-9675ENVitae, Vol 25, Iss 2 (2018)
institution	DOAJ
collection	DOAJ
language	EN
topic	Natural products alkylglycerols synthesis quorum sensing inhibition antibacterial Food processing and manufacture TP368-456 Pharmaceutical industry HD9665-9675
spellingShingle	Natural products alkylglycerols synthesis quorum sensing inhibition antibacterial Food processing and manufacture TP368-456 Pharmaceutical industry HD9665-9675 Clara BARRAGÁN A. Edelberto SILVA G. Bárbara MORENO M. Humberto MAYORGA W. Inhibition of quorum sensing by compounds from two Eunicea species and synthetic saturated alkylglycerols
description	Background: the emergence of bacterial resistance has led to a search for new natural products as alternatives starting points to prevent and control diseases caused by microorganisms. Among the potential candidates were bioactive compounds from octocorals of the genus Eunicea due to their chemical structures and their wide range of biological activities. Objective: the purpose of this study was to evaluate the quorum sensing inhibition (QSI) and antibacterial activity of compounds previously isolated from two Eunicea species and synthesized alkylglycerols (AKG). Methods: the QSI of three nonpolar compounds and a mixture of AKGs from Eunicea were evaluated by a microtiter plate assay using Chromobacterium violaceum (ATCC 31532). Four naturally occurring, saturated, and enantiomerically pure AKGs, all of which were derived from the chiral precursor (R)-solketal, were synthesized from alkyl chains of 12, 14, 16 and 18 carbons, and their structures were spectroscopically verified by NMR, ESI-MS and optical rotation data. Their QSI by the disc diffusion assay and minimum inhibitory concentrations (MIC) against 14 clinical bacterial isolates in microtiter plates were determined. Results: cembradiene 1, the AKG mixture and AKG (2S)-3-O-dodecyl-1,2-propanediol 4 inhibit QS at the same concentration as kojic acid (10 µg/well or 20 µg/disc, respectively). In this study, the bioactive compounds 1, stearyl oleate 2, acylglycerol 3 and AKGs 4 and (2S)-3-O-tetradecyl-1,2-propanediol 5 showed in vitro IQS activity for the first time. Additionally, 4 and 5 displayed in vitro antibacterial activity against Listeria innocua and Staphylococcus aureus (MIC = 32 µg/mL for both 4 and 5), Enterococcus faecalis (128 µg/mL and 64 µg/mL respectively), Micrococcus luteus (128 µg/mL for both) and Brevibacillus brevis (Bacillus brevis) (512 µg/mL and 64 µg/mL respectively). Conclusion: results suggest that natural compounds 1, 2, 3, 4 and 5 showed QSI, also 4 and 5 have antibacterial activity and they are an interesting alternative to continue researching their effect against pathogenic microorganisms.
format	article
author	Clara BARRAGÁN A. Edelberto SILVA G. Bárbara MORENO M. Humberto MAYORGA W.
author_facet	Clara BARRAGÁN A. Edelberto SILVA G. Bárbara MORENO M. Humberto MAYORGA W.
author_sort	Clara BARRAGÁN A.
title	Inhibition of quorum sensing by compounds from two Eunicea species and synthetic saturated alkylglycerols
title_short	Inhibition of quorum sensing by compounds from two Eunicea species and synthetic saturated alkylglycerols
title_full	Inhibition of quorum sensing by compounds from two Eunicea species and synthetic saturated alkylglycerols
title_fullStr	Inhibition of quorum sensing by compounds from two Eunicea species and synthetic saturated alkylglycerols
title_full_unstemmed	Inhibition of quorum sensing by compounds from two Eunicea species and synthetic saturated alkylglycerols
title_sort	inhibition of quorum sensing by compounds from two eunicea species and synthetic saturated alkylglycerols
publisher	Universidad de Antioquia
publishDate	2018
url	https://doaj.org/article/98925969d95b4c87870ef49e3d0773a0
work_keys_str_mv	AT clarabarragana inhibitionofquorumsensingbycompoundsfromtwoeuniceaspeciesandsyntheticsaturatedalkylglycerols AT edelbertosilvag inhibitionofquorumsensingbycompoundsfromtwoeuniceaspeciesandsyntheticsaturatedalkylglycerols AT barbaramorenom inhibitionofquorumsensingbycompoundsfromtwoeuniceaspeciesandsyntheticsaturatedalkylglycerols AT humbertomayorgaw inhibitionofquorumsensingbycompoundsfromtwoeuniceaspeciesandsyntheticsaturatedalkylglycerols
_version_	1718420509344923648

Inhibition of quorum sensing by compounds from two Eunicea species and synthetic saturated alkylglycerols

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