Biofilm inhibition activity of compounds isolated from two Eunicea species collected at the Caribbean Sea

Díaz, Yenny Martínez; Laverde, Gina Vanegas; Gamba, Luis Reina; Mayorga-Wandurraga, Humberto; Arevalo-Ferro, Catalina; Rodríguez, Freddy Ramos; Beltrán, Carmenza Duque; Castellanos, Leonardo

doi:10.1016/j.bjp.2015.08.007

Cited by 31 publications

(23 citation statements)

References 46 publications

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“…Compound 6 was C 19 H 40 O 3 , its optical rotation and NMR data are similar to those of the AKG synthesized (15), and thus, it was named (2S)-3-O-hexadecyl-1,2-propanediol, a natural compound known as chimyl alcohol. Compound 7 had the formula C 21 H 44 O 3 , and its optical rotation and NMR data are in agreement with those of the natural batyl alcohol (12) previously synthesized (15); therefore, it was assigned as (2S)-3-Ooctadecyl-1,2-propanediol.…”

Section: Discussionsupporting

confidence: 74%

“…The LC-MS-ESI of the AKG mixture had ions corresponding with molecular masses of 316 g/mol and 344 g/mol, respectively, and thus, 6 and 7 were identified in a 1:2 ratio as the major AKGs, along with other probable saturated AKGs with lower masses (Figure 2). Recently, only 7 had been purified (12), and unfortunately, we were unable to investigate the effects of all compounds from the two octocorals in the QSI and antibacterial assays because some of them were available in low quantities. Particularly, alkylglycerols (AKGs) are found in low concentrations in marine sponges and corals and at trace levels in mammal, including humans (16).…”

Section: Discussionmentioning

confidence: 99%

“…and showed biofilm inhibition up to 91 % against S. aureus ATCC 25923 (12). 3 only has been isolated from Eunicea sp., and it was effective against biofilm formation by V. harveyi (Phy-2A) and P. aeruginosa (ATCC 27853), with a percentage higher than 25 % (12). In this work, compounds 2 and 3 showed QSI at 20 and 40 µg/well, respectively, but they were less active than KA.…”

Section: Discussionmentioning

confidence: 99%

“…Two cembradiene diterpenoids and other nonpolar compounds were isolated from two octocoral species of the genus Eunicea collected in Santa Marta Bay (Eunicea sp. ), and they afforded only modest activity against a variety of isolated marine bacteria from immersed fouled surfaces (10,12). However, an isolated alkylglycerol (AKG), the 7 (Figure 1), showed remarkable effectiveness against biofilm formation by three of these marine bacteria, namely, Ochrobactrum pseudogringnonense, Alteromonas macleodii and Vibrio harveyi, as well as against a known biofilm-forming bacterium, Staphylococcus aureus ATCC 25923 (12), but other AKGs could not be purified from these Eunicea species due to their low natural abundances.…”

Section: Introductionmentioning

confidence: 99%

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

Barragán

Silva

Moreno

et al. 2018

Vitae

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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.

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Section: Discussionsupporting

confidence: 74%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Barragán

Silva

Moreno

et al. 2018

Vitae

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“…However these methods do not permit to isolate highly purified AG. The column chromatography on silica gel used for isolation of AG from soft coral lipids (Martinez Diaz et al 2015), shark liver oil (Bordier et al 1996) is limiting stage for technological application.…”

Section: Introductionmentioning

confidence: 99%

Technological approach of 1-O-alkyl-sn-glycerols separation from Berryteuthis magister squid liver oil

et al. 2015

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Biological active compounds, 1-O-alkyl-sn-glycerols (AG), were isolated from liver oil of the squid Berryteuthis magister. The main components of the initial lipids were 1-O-alkyl-2,3-diacyl-sn-glycerols (38.50 %) and triacylglycerols (24.26 %). The first step of separation was the alkaline hydrolysis of oil to form a lipid mixture consisting of AG, free fatty acids and cholesterol. AG were separated by double recrystallization from acetone at -20 °C and 1 °C. A simple procedure is proposed for obtaining AG with a purity of 99.22 %, the main component of which is chimyl alcohol (94.39 %). Purity and structure of the obtained products were confirmed by GC and GC-MS technique. Isolated AG may be used in nutrition and cosmetics.

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Antifouling Performance of Cellulose Acetate Films Based on a New Benzoxazine Derivative

et al. 2021

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Fouling is an industrial problem that affects the maritime sector, and it has caused damages to equipment and vessels used in this industry. This research focuses on the synthesis of a novel arylidene‐based benzoxazine compound (HBC) and its use as a modifier for cellulose acetate (CA) matrix to form film samples and the investigation of their antifouling efficacy. The HBC compound was synthesized from a bis(arylidene)cyclopentanone diol compound and characterized appropriately using Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR) spectroscopic methods, respectively. Different weight ratios: 0, 10, 20, 30, and 40 %w/w of HBC to CA were mixed to give the films; CA‐0, CA‐10, CA‐20, CA‐30, and CA‐40, respectively. The fabricated films were characterized by FTIR analysis, and their morphology was examined by scanning electron microscopy (SEM). The thermal stability of the films was also studied using thermal gravimetric analysis (TGA), while the antifouling performance of the films was tested against strains of natural, biofilm‐forming bacteria isolated from artificial nets submerged in the Red Sea. Biofilm inhibitory test and bactericidal assay were conducted on the fabricated film materials using well established standard methods. The results of this investigation indicate that the HBC modified CA films contain relevant bioactive molecules that can inhibit primary colonizers in biofouling formation and will make a good antifouling coating film candidate. The CA‐40 revealed an inhibitory activity of 37 % and a bacterial killing efficacy of 87 %.

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Biofilm inhibition activity of compounds isolated from two Eunicea species collected at the Caribbean Sea

Cited by 31 publications

References 46 publications

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

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

Technological approach of 1-O-alkyl-sn-glycerols separation from Berryteuthis magister squid liver oil

Antifouling Performance of Cellulose Acetate Films Based on a New Benzoxazine Derivative

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