A new method for isolating (E)-azastilbene derivatives with antimicrobial properties from aqueous samples

Authors

  • Mariusz Kluska Siedlce University of Natural Sciences and Humanities
  • Ewa Witkowska- Krajewska Hospital Solec Sp. z o. o.
  • Wiesław Prukała Adam Mickiewicz University in Poznan

Keywords:

surface water, waste water, disinfectants, extraction, (E)-azastilbenes

Abstract

This paper presents the results of a study aimed at developing the extraction process and determining long-term stability of (E)-azastilbene derivatives in order to explore their possible use as preservative, antiseptic and disinfectant substances. The study was performer in three different matrices: distilled, surface and waste water. Test substances included bromide of (E)-N-(o-bromobenzyl)-4’-hydroxystilbazole-4 and chloride of (E)-N-(p-chlorobenzyl)-4’-hydroxystilbazole-4. The extraction process involved the use of three stationary phases: octyl, octadecyl and naphthylpropyl. The highest recovery values (amounting to approx. 95%) were obtained in the naphthylpropyl column for all of the above-mentioned matrices. A decline in the stability of the analysed derivatives after a 28-day period was below 14% in all matrix types.

Downloads

Download data is not yet available.

References

Buszewski, B. & Szultka, M. (2012). Past, present, and future of solid phase extraction: a review. Crit. Rev. Anal. Chem. 42(3): 198–213. DOI: 10.1080/07373937.2011.645413.

Buszewski, B., Nowaczyk, J., Ligor, T., Olszowy, P., Ligor, M. et al. (2009). Preparation and characterization of microporous fibers for sample preparation and LC-MS determination of drugs. J. Sep. Sci. 32: 2448–2454. DOI: 10.1002/jssc.200900094.

Buszewski, B., Olszowy, P., Pikus, S. & Kozak, M. (2014). Electropolymerized nanoporous polymeric SPME coatings: preparation and characterization by small angle X-ray scattering and scanning electron microscopy. Monatsh. Chem. 145: 527–531. DOI: 10.1007/s00706-013-1115-3.

Buszewski, B., Olszowy, P., Szultka, M. & Jezewska, A. (2012). New approaches to extraction techniques in determination of 4,40-methylenebis(2-chloroaniline) in air and water solutions. Talanta 93: 117–121. DOI: 10.1016/j.talanta.2012.01.057.

Buszewski, B., Szultka, M., Olszowy, P., Bocian, S. & Ligor. T. (2011). A novel approach to the rapid determination of amoxicillin in human plasma by solid phase microextraction and liquid chromatography. Analyst 136: 2635–2642. DOI: 10.1039/C1AN00005E.

Buszewski, B., Welerowicz, T., Tęgowska, E. & Krzemiński, T.F. (2009). Determination of ß-blockers antagonists In biological samples by solid-phase extraction with cholesteroli phase and LC/MS. Anal. Bioanal. Chem. 393: 263–272. DOI: 10.1007/s00216-010-3483-4.

Castro, R., Natera, R., Duran, E. & Garcia-Barroso, C. (2008). Application of solid phase extraxtion techniques to analyse volatile compounds in wines and other enological products. Eur. Food Res. Techn. 228(1): 1−18. DOI: 10.1007/s00217-008-0900-4.

Gadzala-Kopciuch, R., Ricanyova, J. & Buszewski, B. (2009). Isolation and detection of steroids from human urine by molecularly imprinted solid-phase extraction and liquid chromatography. J. Chromatogr. B 877: 1177–1184. DOI: 10.1016/j.jchromb.2009.09.048.

Gadzała-Kopciuch, R.M., Kluska, M., Wełniak, M. & Buszewski, B. (2005). Silicon dioxide surfaces with aryl interaction sits for chromatographic applications. Mater. Chem. Physics 89: 228–237. DOI: 10.1016/j.matchemphys.2004.03.022.

Guerrero, E.D., Chinnici, F., Natali, N., Marin, R.N. & Riponi C. (2008). Solid-phase extraction method for determination of volatile compounds in traditional balsamic vinegar. J. Sep. Sci. 31(16-17): 3030−3036. DOI: 10.1002/jssc.200890060.

Kartoglu, U., Ozgüler, N.K., Wolfson, L.J. & Kurzatkowski, W. (2010). Validation of the shake test for detecting freeze damage to adsorbed vaccines. Bull. World Health Organ. 88: 624–631. DOI: 10.2471/BLT.08.056879.

Kataoka, H. (2005). Recent advances in solid-phase microextraction and related techniques for pharmaceutical and biomedical analysis. Curr. Pharm. Anal. 1: 65–84. DOI: 10.2174/1573412052953373.

Kluska, M., Liepinsh, E., Pypowski, K. & Erchak, N. (2008). Separation of azepinio-methyl derivatives of ESsilanates by the use of aryl stationary phases in HPLC. J. Liq. Chromatogr. Rel. Technol. 31: 675–682. DOI: 10.1080/10826070701853826.

Konieczka, P. & Namieśnik, J. (2007). Ocena i kontrola jakości wyników pomiarów analitycznych. WNT, Warszawa. Lord, H. & Pawliszyn, J. (2000). Evolution of solid-phase microextraction technology. J. Chromatogr. A 885: 153–193. DOI: 10.1016/S0021-9673(00)00535-5.

Mehdinia, A. & Aziz-Zanjani, M.O. (2013). Advances for sensitive, rapid and selective extraction in different configurations of solid-phase microextraction. Trends Anal. Chem. 51, 13–22. DOI: 10.1016/j.trac.2013.05.013.

Michel, M. & Buszewski, B. (2009). Porous graphitic carbon sorbents in biomedical and environmental applications. Adsorption 15: 193–202. DOI: 10.1007/s00216-010-3483-4.

Oriel, B.S. & Itani, K.M. (2017). The impact of surgical hand antisepsis technique on surgical site infection. Am. J. Surgery 213: 24–29. DOI: 10.1089/sur.2016.085.

Pandey, A.K., Kumar, P., Singh, P., Tripathi, N.N. & Bajpai, V.K. (2016). Essential oils: sources of antimicrobials and food preservatives. Front Microbiol. 7: 2161−2195. DOI: 10.3389/fmicb.2016.02161.

Pisanello, D. (2014). Chemistry of Foods: EU Legal and Regulatory Approaches, SpringerBriefs in Chemistry of Foods, DOI: 10.1007/978-3-319-03434-8_2.

Prukała, W. & Kedzia, B. (1999). Antimicrobial activity of some N-alkyl and N-nitrobenzyl substituted halides of (E)-4’-hydroxy-3’-methoxystilbazoles-4. Il Farmaco 54: 584–587. DOI: 10.1016/S0014-827X(99)00067-1.

Prukała, W., Prukała, D., Pypowski, K., Chrząścik, I. & Kluska, M. (2008a). Separation of biologically active isomers of (E)-N-meta- and paranitroazastilbenes by the HPLC technique. J. Liq. Chromatogr. Rel. Technol. 31: 578–585. DOI: 10.1080/01630560701815218.

Prukała, W., Prukała, D., Pypowski, K., Chrząścik, I. & Kluska, M. (2008b). Chromatography of biologically active chlorides of (E)-N-o-(m- or p-)chlorobenzyl-y-azastilbenols-2’(3’ or 4’). J. Liq. Chromatogr. Rel. Technol. 31: 2612–2620. DOI: 10.1080/10826070802352850.

Regulation (EU) 1308/2013 establishing common organisation of the markets in agricultural products (Dairy Designations) http://eur-lex.europa.eu/.

Sawa, T., Shimizu, M., Moriyama, K. & Wiener-Kronish, J.P. (2014). Association between Pseudomonas aeruginosa type III secretion, antibiotic resistance, and clinical outcome: a review. Crit. Care 18: 668–673. DOI: 10.1186/s13054-014-0668-9.

Szultka-Mlyńska, M., Olszowy, P. & Buszewski, B. (2016). Nanoporous conducting polymer–based coatings in microextraction techniques for environmental and biomedical applications. Crit. Rev. Anal. Chem. 46(3): 236–247. DOI: 10.1080/10408347.2015.1081051.

Szumski, M., Kłodzińska, E., Jarmalaviciene, R., Maruska, A. & Buszewski B. (2007). Considerations on influence of chargé distribution on determination of bio-molecules and microorganisms and tailoring the monolithic (continuous bed) materials for bioseparations. J. Biochem. Biophys. Methods 70: 107–115. DOI: 10.1016/j.jbbm.2006.09.013.

Wang, S.S., Fitz-Simmons, S.C., O’Leary, L.A., Rock, M.J., Gwinn, M.L. et al. (2001). Early diagnosis of cystic fibrosis in the newborn period and risk of Pseudomonas aeruginosa acquisition in the first 10 years of life: A registry-based longitudinal study. Pediatrics 107(2): 274–279. DOI: 10.1542/peds.107.2.274.

Wyrzykiewicz, E. & Prukała, W. (1995). Synthesis and antimicrobial properties of N-substituted halides of (E)-azastilbenols. Il Farmaco 50: 779–782.

Yahr, T.L. & Greenberg, E.P. (2004). The genetic basis for the commitment to chronic versus acute infection in Pseudomonas aeruginosa. Mol. Cell 19: 497–498. DOI: 10.1016/j.molcel.2004.11.009.

Downloads

Published

2018-03-26

How to Cite

Kluska, M., Witkowska- Krajewska, E., & Prukała, W. (2018). A new method for isolating (E)-azastilbene derivatives with antimicrobial properties from aqueous samples. Oceanological and Hydrobiological Studies, 47(1), 19–26. Retrieved from https://czasopisma.bg.ug.edu.pl/index.php/oandhs/article/view/8629

Issue

Section

Articles