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The-Antimicrobial-Effects-Of-Wood.Pdf International Journal of Food Microbiology 164 (2013) 99–107 Contents lists available at SciVerse ScienceDirect International Journal of Food Microbiology journal homepage: www.elsevier.com/locate/ijfoodmicro The antimicrobial effects of wood-associated polyphenols on food pathogens and spoilage organisms Carme Plumed-Ferrer a,1, Kati Väkeväinen a,1, Heli Komulainen a, Maarit Rautiainen a, Annika Smeds b, Jan-Erik Raitanen b, Patrik Eklund c, Stefan Willför b, Hanna-Leena Alakomi d, Maria Saarela d, Atte von Wright a,⁎ a University of Eastern Finland, Institute of Public Health and Clinical Nutrition, P.O. Box 1627, FI-70211 Kuopio, Finland b Åbo Akademi University, Process Chemistry Centre, Porthansgatan 3, FI-20500 Turku, Finland c Åbo Akademi University, Laboratory of Organic Chemistry, Biskopsgatan 8, FI-20500 Turku, Finland d VTT Technical Research Centre of Finland, P.O. Box 1000, FI-02044, VTT, Finland article info abstract Article history: The antimicrobial effects of the wood-associated polyphenolic compounds pinosylvin, pinosylvin monomethyl Received 20 December 2012 ether, astringin, piceatannol, isorhapontin, isorhapontigenin, cycloXMe, dHIMP, ArX, and ArXOH were assessed Received in revised form 25 March 2013 against both Gram-negative (Salmonella) and Gram-positive bacteria (Listeria monocytogenes, Staphylococcus Accepted 1 April 2013 epidermidis, Staphylococcus aureus) and yeasts (Candida tropicalis, Saccharomyces cerevisiae). Particularly the Available online 9 April 2013 stilbenes pinosylvin, its monomethyl ether and piceatannol demonstrated a clear antimicrobial activity, which in the case of pinosylvin was present also in food matrices like sauerkraut, gravlax and berry jam, but not in Keywords: wood associated phenolic compounds milk. The destabilization of the outer membrane of Gram-negative microorganisms, as well as interactions stilbenes with the cell membrane, as indicated by the NPN uptake and LIVE/DEAD viability staining experiments, can be pinosylvin one of the specific mechanisms behind the antibacterial action. L. monocytogenes was particularly sensitive Salmonella to pinosylvin, and this effect was also seen in L. monocytogenes internalized in intestinal Caco2 cells at Listeria monocytogenes non-cytotoxic pinosylvin concentrations. In general, the antimicrobial effects of pinosylvin were even more Food spoilage prominent than those of a related stilbene, resveratrol, well known for its various bioactivities. According to our results, pinosylvin could have potential as a natural disinfectant or biocide in some targeted applications. © 2013 Elsevier B.V. All rights reserved. 1. Introduction and therapeutic agents (Mattson et al., 2011; Puupponen-Pimia et al., 2005; Rauha et al., 2000). One of the most studied individual substances The antimicrobial properties of several plant-associated substances, is (E)-resveratrol (3,4′,5-trihydroxystilbene) (Fig. 1), a compound such as flavonoids, tannins, and essential oils have received a lot of present in red grapes and berries (Adrian et al., 2000; Lyons et al., attention during recent years as potential preservatives, disinfectants, 2003). It has both antifungal and antibacterial properties (Man-Ying Chan, 2002), and, furthermore, its practical use as an antimicrobial Abbreviations: ArX, 4,4′-dihydroxy-3,3′-dimethoxy-9-nor-6′,7-cycloligna-7,7′- compound has been suggested (Montero et al., 2003). In bioassays diene-9′-oic acid; ArXOH, 4,4′-dihydroxy-3,3′-dimethoxy-9-nor-6′,7-cycloligna-7,7′- with cancer cell lines and in animal studies, resveratrol appears to diene-9′-ol; As, astringin; bw, bodyweight; cycloX/cyX, (8′S,7R)-4,4′-dihydroxy-3, interfere with the major steps of the carcinogenesis (Boissy et al., 3′-dimethoxy-6′,7-cyclo-9-norlign-9′-oic acid and (8′S,7S)-4,4′-dihydroxy-3,3′-dimethoxy- 2005; Boocock et al., 2007; Jang et al., 1997; Tolomeo et al., 2005). 6′,7-cyclo-9-norlign-9′-oic acid; cycloXMe/CyXMe, (8′S,7R)-4,4′-dihydroxy-3, Other recorded activities include positive effects in processes associated 3′-dimethoxy-6′,7-cyclo-9-norlign-9′-oic acid and (8′S,7S)-4,4′-dihydroxy-3, 3′-dimethoxy-6′,7-cyclo-9-norlign-9′-oic acid; cycloXOH/cyXOH, (8′S,7R)-4,4′- with cardiovascular diseases (Paceasciak et al., 1995), hormone-like dihydroxy-3,3′-dimethoxy-6′,7-cyclo-9-norlign-9′-ol and (8′S,7S)-4,4′-dihydroxy-3, activities (Klinge et al., 2005), and the prevention of type II diabetes 3′-dimethoxy-6′,7-cyclo-9-norlign-9′-ol; dHIMP, (-)-(8′S)-4,4′-dihydroxy-3, by SIRT1 activation (Lagouge et al., 2006). ′ ′ ′ ′ ′ 3 -dimethoxy-9-norlign-9 -ol; dHX, (-)-(8 S)-4,4 -dihydroxy-3,3 -dimethoxy-9- We have previously reported antimicrobial and cytotoxic activities of norlign-9′-oic acid; HEPES, n-Heptadecanoic acid methyl ester; IMP, (-)-(7E)- (8′R)-4,4′-dihydroxy-3,3′-dimethoxy-9-norlign-7-en-9′-ol; IRh, isorhapontin; (E)-pinosylvin (3,5-dihydroxystilbene, PS) (Fig. 1), a naturally occurring NOAEL, No Observed Adverse Effect level; NPN, 1-N-phenylnaphthylamine; stilbene related to resveratrol, present particularly in the heartwood PS, pinosylvin; PSMME, pinosylvin monomethyl ether; X, (-)-(7E)-(8′R)- andknotwoodoftreesofthePinus family (Välimaa et al., 2007). PS 4,4′-dihydroxy-3,3′-dimethoxy-9-norlign-7-en-9′-oic acid; XMe, (-)-Methyl was active against both Gram-negative bacteria (Salmonella, Escherichia (7E)-(8′R)-4,4′-dihydroxy-3,3′-dimethoxy-9-norlign-7-en-9′-oat. coli, Pseudomonas fluorescens) and Gram-positives like Bacillus cereus, ⁎ Corresponding author. Tel.: +358 505376030. E-mail address: atte.vonwright@uef.fi (A. von Wright). Listeria monocytogenes and Staphylococcus aureus, but not against 1 These two authors have equally contributed to the publication. Lactobacillus plantarum. In later studies (unpublished results) with 0168-1605/$ – see front matter © 2013 Elsevier B.V. All rights reserved. http://dx.doi.org/10.1016/j.ijfoodmicro.2013.04.001 100 C. Plumed-Ferrer et al. / International Journal of Food Microbiology 164 (2013) 99–107 R' OH R R OR' OH OH R= OH, R'= H: Pinosylvin R= O-Glu, R'= O-Glu: Astringin R= OMe, R'= H: Pinosylvin monomethylether R= OH, R'= H: Piceatannol R=OH,R'=OH:Resveratrol R= O-Glu, R'= Me: Isorhapontin O MeO MeO MeO R OH OMe HO HO HO OMe Me OMe OH OH OH dHIMP CyXMe R= COOH: ArX R= CH2OH: ArXOH Fig. 1. Molecular structures of the studied compounds. different genera of lactic acid bacteria, both homo- and hetero- 2.2.1. PS, PSMME, As, and IRh fermentative lactobacilli and leuconostocs were markedly resistant PS and PSMME were isolated from Scots pine (Pinus sylvestris L.) to pinosylvin, whereas both lactococci and enterococci were sensitive. heartwood, and As and IRh from Norway spruce (Picea abies) bark. The antifungal activity could be demonstrated both against yeasts The wood material was splintered, freeze-dried and ground, and (Candida albicans, Saccharomyces cerevisiae)andfilamentous fungi approximately 500 g was extracted in a Soxhlet apparatus with (Aspergillus fumigatus, Penicillium brevicompactum). hexane overnight to remove lipophilic extractives, and then with In this study, we have further compared the antimicrobial activity acetone (for PS and PSMME) or ethanol (EtOH) (for As and IRh) over- of pinosylvin with some other naturally occurring stilbenes and with night to yield hydrophilic extractives. The acetone and EtOH extracts some semisynthetically prepared norlignans of similar structure were evaporated to dryness using a rotary evaporator, and approxi- and also assessed the effect in certain food matrices (sauerkraut, mately 40 g of the freeze-dried extracts was mixed with silica gel 60 cold smoked fish, and milk). Since L. monocytogenes was found to be (Fluka), and placed in a sample injection module of a Flash 75i appara- particularly susceptible to pinosylvin, the effect of pinosylvin against tus (Biotage UK Ltd., Hertford, England). PS and PSMME were separated the internalized L. monocytogenes was also studied in a Caco2 cell on a silica cartridge, whereas As and IRh were separated on an RP-18 model. cartridge (75 mm × 30 cm). PS and PSMME, were eluted using a step gradient of dichloromethane:EtOH (98.8:1.2 v/v–96:4 v/v); As and IRh using a step gradient of EtOH:distilled water (10:90 v/v–100:00 v/v). 2. Materials and methods Fractions were collected in 500 ml bottles, and fractions containing PS were evaporated to dryness using a vacuum evaporator to yield an oil. 2.1. Chemicals Crystallization from benzene gave PS as a white solid. The purity was 98% (GC) with an (E)-:(Z)-isomer ratio of 100:0. n-Heptadecanoic acid methyl ester (HEPES) and 1-N- Fractions containing both PS and PSMME were evaporated to phenylnaphthylamine (NPN) were purchased from Sigma-Aldrich dryness using a vacuum evaporator. Distilled water was added to (Steinheim, Germany), and EDTA from Riedel-de-Haen (Seelze, the resulting oil, pH was raised to 13 using KOH (10 M), and the Germany). mixture was extracted three times with methyl tert-butyl ether. The organic phases were combined, acidified to pH 5 using HCl (0.5 M) 2.2. The compounds studied and dried under N2-stream. Acetone was then added, and after evaporation of the solvent, an oil was obtained. Crystallization from Resveratrol was obtained from Sigma-Aldrich (Steinheim, Germany). concentrated acetic acid (AcOH) yielded PSMME as a white solid. The The other compounds, i.e., the stilbene aglycones pinosylvin (PS), PS purity was 99% (GC) with an (E)-:(Z)-isomer ratio of 100:0. Fractions monomethyl ether (PSMME), and piceatannol, the stilbene glucosides containing As and IRh were combined into two separate fractions. astringin (As) and isorhapontin (IRh), and the norlignans cycloXMe, These were further purified using a smaller flash chromatograph dHIMP, ArX and ArXOH (see Fig. 1) were prepared in our laboratories. (Biotage UK Ltd., Flash40i). Approximately 2 g of the extract was The purity and identity of the compounds were determined using GC– separated on a Biotage RP-4 flash cartridge (40 mm × 15 cm) using a FID and GC–MS after silylation (Willför et al., 2003).
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