Abstract
The aim of this study was to isolate, characterize the antibiofilm agent from Viburnum foetens and to investigate it’s in vitro effects on cariogenic properties of Streptococcus mutans, a major caries causing microorganism. The compound was purified by silica gel chromatography and analyzed with IR, MS, 1H, and 13C NMR spectroscopy. Virulence attributes of S. mutans were assessed at different concentrations of the purified compound. Confocal microscopy was employed to investigate the effect on biofilm architecture. The purified compound was found to be n-octacosanoic acid and exhibited MIC of 80 μg/ml against S. mutans. At a concentration of 10 and 20 μg/ml, adherence to saliva-coated glass surface and ability to form biofilm were reduced to 50%. The n-octacosanoic acid profoundly changed the biofilm architecture and distorted the cell aggregating ability of S. mutans in a unique manner. The active compound, n-octacosanoic acid, demonstrated for the first time, potential antiplaque activity by inhibiting the adherence of S. mutans. The compound strongly inhibited biofilm formation of S. mutans and resulted in a reduction of water-insoluble glucans. These findings suggest that n-octacosanoic acid may have potential to prevent caries by limiting the overgrowth and biofilm formation of S. mutans.
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References
Baytop T (1996) Therapy with medicinal plants in Turkey. Nobel Medical Publishers, Istanbul
Brune RA (1998) Oral streptococci products of their environment. J Dent Res 77:45–52
Ciardi JE, Rosenthal AB, Bowden WH (1981) Rapid quantitative determination of the effect of antiplaque agents and antisera on the growth, acid production and adherence of Streptococcus mutans. J Dent Res 60:756–762
Cwala Z, Igbinosa EO, Okoh AI (2011) Assessments of antibiotics production potentials in four actinomycetes isolated from aquatic environments of the Eastern Cape Province of South Africa. Afr J Pharm Pharmacol 5:118–124
Dubois M, Gilles A, Hamilton JK, Rebers PA, Smith F (1956) Colorimetric method for determination of sugars and related substance. Anal Chem 28:350–356
Fukushima K, Motoda R, Ikeda T (1981) Effects of exogenous insoluble glucan primer on insoluble glucan synthesis by Streptococcus mutans. J Dent Res 60:1707–1712
Hussain Z, Waheed A, Qureshi RA, Burdi DK et al (2004) The effect of medicinal plants of Islamabad and Murree region of Pakistan on insulin secretion from INS-1 cells. Phytother Res 18:73–77
Islam B, Khan SN, Haque I, Alam M et al (2008) Novel anti-adherence activity of mulberry leaves: inhibition of Streptococcus mutans biofilm by 1-deoxynojirimycin isolated from Morus alba. J Antimicrob Chemother 62:751–757
Iwai K, Kim MY, Onodera A, Matsue H (2004) Physiological effects and active ingredients of Viburnum dilatatum Thunb fruits on oxidative stress. Biofactors 21:273–275
Khan R, Islam B, Akram M, Shakil S et al (2009) Antimicrobial activity of five herbal extracts against multi drug resistant (MDR) strains of bacteria and fungus of clinical origin. Molecules 14:586–597
Koo H, Pearson SK, Scott-Anne K, Abranches J et al (2000) Effect of apigenin and tt-farnesol on glucosyltransferases activity, biofilm viability and caries development in rats. Oral Microbiol Immunol 17:337–343
Lankin VZ, Sadovnikova IP (1971) Simple quantitative method of direct transesterification of higher fatty acid in biological samples. Vopr Med Khim 17:331–335
Loeche WJ (1986) The identification of bacteria associated with periodontal disease and dental caries by enzymatic methods. Oral Microbiol Immunol 1:65–72
Marsh PD (2003) Are dental diseases examples of ecological catastrophes? Microbiology 149:279–294
Marsh PD (2004) Dental plaque as a microbial biofilm. Caries Res 38:204–211
Martin MA, Pfaller MA, Massanari RM, Wenzel RP (1989) Use of cellular hydrophobicity, slime production, and species identification markers for the clinical significance of coagulase-negative staphylococcal isolates. Am J Infect Control 17:130–135
Matsumura M, Izumi T, Matsumoto M et al (2003) The role of glucan-binding proteins in the cariogenicity of Streptococcus mutans. Microbiol Immunol 47:213–215
McBride BC, Song M, Krasse B, Olsson J (1984) Biochemical and immunological differences between hydrophobic and hydrophilic strain of Streptococcus mutans. Infect Immun 44:68–75
Menendez R, Marrero D, Mas R, Fernandez I et al (2005) In vitro and in vivo study of octacosanol metabolism. Arch Med Res 36:113–119
Molzer B, Kainz-Korschinsky M, Sundt-Heller R, Berheimer H (1989) Phytanic acid and very long chain fatty acids in genetic peroxisomal disorders. J Clin Chem Clin Biochem 27:309–314
Murray PA, Prakobphol A, Lee T, Hoover CI, Fisher SJ (1992) Adherence of oral streptococci to salivary glycoproteins. Infect Immun 60:31–38
Rosenberg M, Judes H, Weiss E (1983) Cell surface hydrophobicity of dental plaque microorganisms in situ. Infect Immun 42:831–834
Sagdic O, Aksoy A, Ozkan G (2006) Evaluation of the antibacterial and antioxidant potentials of cranberry (gilaburu, Viburnum opulus L.) fruit extract. Acta Aliment 35:487–492
Schilling KM, Bowen WH (1992) Glucans synthesized in situ in experimental salivary pellicle function as specific binding sites for Streptococcus mutans. Infect Immun 60:284–295
Steinberg D, Feldman M, Ofek I, Weiss EI (2004) Effect of a high molecular weight component of cranberry on constituents of dental biofilm. J Antimicrob Chemother 54:86–89
Svanberg M, Westergren G, Olsson J (1984) Oral implantation in humans of Streptococcus mutans strains with different degrees of hydrophobicity. Infect Immun 43:817–821
Tao ZM, Li YY, Ji P, Wang YB, Qin GB (2007) Chemical constituents from aerial part of Curcuma wenyujin. Zhongguo Zhong Yao Za Zhi 32:2604–2646
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This study was supported by internal funds of Biotechnology Unit, AMU and DST grant, 100/IFD/5160/2007-2008 to AUK.
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Rosina Khan and Zakia Khanam contributed equally in this study.
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Khan, R., Khanam, Z. & Khan, A.U. Isolation and characterization of n-octacosanoic acid from Viburnum foetens: a novel antibiofilm agent against Streptococcus Mutans . Med Chem Res 21, 1411–1417 (2012). https://doi.org/10.1007/s00044-011-9658-5
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DOI: https://doi.org/10.1007/s00044-011-9658-5