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Qualitative and Quantitative Analysis of Sucrose Esters by Ultra-Performance Convergence Chromatography Combined with Mass Spectrometry

Mengfei Xie, Xue Xue, Ping Lan, Yong Wang

Abstract


Acquity Ultra Performance Convergence Chromatography (UPC2) coupled with Single Quadrupole (SQ) Detector 2 mass spectrometry was applied to the specific quantitative trace analysis of sucrose esters. This analysis method was successfully applied to analyze sucrose esters containing various fatty acyl chains. UPC2-MS is significantly faster than HPLC-ELSD and RPLC (running time is only 2 min), which improves the performance significantly, and further screening of the peak time and mass number makes the results more precise. The use of less toxic, economical supercritical CO2 as the solvent is in line with the concept of green chemistry.

Keywords


Ultra-performance convergence chromatography; Sucrose ester analysis; Supercritical CO2 solvent.

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References


Flores MV, Halling PJ. Full model for reversible kinetics of lipase-catalyzed sugar-ester synthesis in 2-methyl 2-butanol. Biotechnol Bioeng. 2002 Jun 30;78(7):795-801. doi: 10.1002/bit.10260. PMID: 12001171.

Teng Y, Stewart SG, Hai YW, Li X, Banwell MG, Lan P. Sucrose fatty acid esters: synthesis, emulsifying capacities, biological activities and structure-property profiles. Crit Rev Food Sci Nutr. 2020 Aug 4:1-21. doi: 10.1080/10408398.2020.1798346. Epub ahead of print. PMID: 32746632.

Chen J, Li Y, Chen X, Mai Y, Gao M, Zhang J, Wang X. Efficient Solvent?Free Synthesis of Sucrose Esters via Sand?Milling Pretreatment on Solid–Liquid Mixtures. Journal of Surfactants and Detergents. 2019, 22, 1515-1520. doi: 10.1002/jsde.12314.

Gutiérrez MF, Rivera JL, Suaza A, Orjuela A. Kinetics of the transesterification of methyl palmitate and sucrose using surfactants. Chemical Engineering Journal. 2018, 347, 877-888.

Yang, Z.; Huang, Z.-L. Enzymatic synthesis of sugar fatty acid esters in ionic liquids. Catal. Sci. Technol., 2012,2, 1767-1775. doi: 10.1039/C2CY20109G.

Csóka G, Marton S, Zelko R, Otomo N, Antal I. Application of sucrose fatty acid esters in transdermal therapeutic systems. Eur J Pharm Biopharm. 2007 Feb;65(2):233-7. doi: 10.1016/j.ejpb.2006.07.009.

Valdés K, Morilla MJ, Romero E, Chávez J. Physicochemical characterization and cytotoxic studies of nonionic surfactant vesicles using sucrose esters as oral delivery systems. Colloids Surf B Biointerfaces. 2014 May 1;117:1-6. doi: 10.1016/j.colsurfb.2014.01.029.

Bnyan R, Khan I, Ehtezazi T, Saleem I, Gordon S, O'Neill F, Roberts M. Surfactant Effects on Lipid-Based Vesicles Properties. J Pharm Sci. 2018 May;107(5):1237-1246. doi: 10.1016/j.xphs.2018.01.005.

Orjuela, A.; Gutierrez, M. F.; Suaza, A.; Rivera, J. L. Production of sucroesters using solvent-free reactive systems containing emulsifiers. Ingeniería e Investigación. 2018, 38, 16-23.doi: 10.15446/ing.investig.v38n1.61432.

Ye Ran, Pyo Sang-Hyun, Hayes DouglasG. Lipase-Catalyzed Synthesis of Saccharide-Fatty Acid Esters Using Suspensions of Saccharide Crystals in Solvent-Free Media Journal of the American Oil Chemists' Society. 2010 Mar;87(3):281-293. doi: 10.1007/s11746-009-1504-2.

Trabelsi I, Essid K, Frikha MH. Synthesis of Sucrose Fatty Acid Esters by Using Mixed Carboxylic-fatty Anhydrides. J Oleo Sci. 2020;69(7):693-701. doi: 10.5650/jos.ess19239.

Liang MY, Banwell MG, Wang Y, Lan P. Effect of Variations in the Fatty Acid Residue of Lactose Monoesters on Their Emulsifying Properties and Biological Activities. J Agric Food Chem. 2018 Nov 28;66(47):12594-12603. doi: 10.1021/acs.jafc.8b05794.

Liang MY, Chen Y, Banwell MG, Wang Y, Lan P. Enzymatic Preparation of a Homologous Series of Long-Chain 6- O-Acylglucose Esters and Their Evaluation as Emulsifiers. J Agric Food Chem. 2018 Apr 18;66(15):3949-3956. doi: 10.1021/acs.jafc.8b00913.

Chidara, VK, Stadem S, Webster DC & Du. Survey of several catalytic systems for the epoxidation of a biobased ester sucrose soyate. Catalysis Communications. 2018. 111, 31–35. doi:10.1016/j.catcom.2018.03.027.

Gutiérrez MF, Suaza A, Rivera JL, Orjuela A. Solid–Liquid Equilibria and Characterization of the Reaction Mixture To Produce Sucrose Palmitate in Solvent-Free Media. J Chem Eng. 2019.64; 5:2052–2061.

Kondamudi N, McDougal OM. Microwave?Assisted Synthesis and Characterization of Stearic Acid Sucrose Ester: A Bio?Based Surfactant. Journal of Surfactants and Detergents. 2019, 22, 721-729. doi:10.1002/jsde.12280.

Inprakhon P, Wongthongdee N, Amornsakchai T, et al. Lipase-catalyzed synthesis of sucrose monoester: Increased productivity by combining enzyme pretreatment and non-aqueous biphasic medium. Journal of Biotechnology. 2017 Oct;259:182-190. doi: 10.1016/j.jbiotec.2017.07.021.

Wang X, Zou W, Sun X, Zhang Y, Wei L, Jin Q, Wang X. Chemoenzymatic synthesis of 1,3-dioleoyl-2-palmitoylglycerol. Biotechnol Lett. 2015 Mar;37(3):691-6. doi: 10.1007/s10529-014-1714-z.

Arrendale RF, Severson RF, Sisson VA, et al. Characterization of the sucrose ester fraction from Nicotiana glutinosa. Journal of Agricultural and Food Chemistry. 1990 Jan;38(1):75-85. DOI: 10.1021/jf00091a015.

Hali?ski ?P, Stepnowski P. GC-MS and MALDI-TOF MS profiling of sucrose esters from Nicotiana tabacum and N. rustica. Z Naturforsch C J Biosci. 2013 May-Jun;68(5-6):210-22. doi: 10.1515/znc-2013-5-607.

Simonovska B, Srbinoska M, Vovk I. Analysis of sucrose esters--insecticides from the surface of tobacco plant leaves. J Chromatogr A. 2006 Sep 15;1127(1-2):273-7. doi: 10.1016/j.chroma.2006.05.103.

Wang, Q.; Zhang, S.; Zhang, P.; Zhu, J.; Yang, J. Separation and Quantitation of Sucrose Esters Using HPLC with Evaporative Light Scattering Detection. Journal of Liquid Chromatography & Related Technologies. 2007; 29: 2399-2412. doi:10.1080/10826070600864874.

Miao XW, Chang ZD, Li WJ, Zhao RR, Dong B, Liang LF. Analysis of Sucrose Esters by HPLC Using Charged Aerosol Detector. Advanced Materials Research. 2012, 554-556: 1962-1966. doi:10.4028/www.scientific.net/AMR.554-556.1962.

Chortyk OT, Kays SJ, Teng Q. Characterization of Insecticidal Sugar Esters of Petunia. J. Agric. Food Chem. 1997, 45;1: 270–275.doi: 10.1021/jf960322f.

Li W, Fitzloff JF. Determination of 24(R)-pseudoginsenoside F(11) in North American ginseng using high performance liquid chromatography with evaporative light scattering detection. J Pharm Biomed Anal. 2001 May;25(2):257-65. doi: 10.1016/s0731-7085(00)00494-5.

Avery BA, Venkatesh KK, Avery MA. Rapid determination of artemisinin and related analogues using high-performance liquid chromatography and an evaporative light scattering detector. J Chromatogr B Biomed Sci Appl. 1999 Jun 25;730(1):71-80. doi: 10.1016/s0378-4347(99)00185-1.

Górecki T, Lynen F, Szucs R, Sandra P. Universal response in liquid chromatography using charged aerosol detection. Anal Chem. 2006 May 1;78(9):3186-92. doi: 10.1021/ac060078j.

Kou D, Manius G, Zhan S, Chokshi HP. Size exclusion chromatography with Corona charged aerosol detector for the analysis of polyethylene glycol polymer. J Chromatogr A. 2009 Jul 10;1216(28):5424-8. doi: 10.1016/j.chroma.2009.05.043.

Wang Y, Liu M, Zhu Y, Cheng K, Da Wu, Liu B, Li F. Identifying the tobacco related free radicals by UPCC-QTOF-MS with radical trapping method in mainstream cigarette smoke. Talanta. 2016 Nov 1;160:106-112. doi: 10.1016/j.talanta.2016.07.002.

Lv C, Chen L, Fu P, Yang N, Liu Q, Xu Y, Sun Q, Li R, Zhan C, Zhang W, Liu R. Simultaneous quantification of 11 active constituents in Shexiang Baoxin Pill by ultraperformance convergence chromatography combined with tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 May 1;1052:135-141. doi: 10.1016/j.jchromb.2017.03.033.

Lv C, He B, Sui Z, Li Q, Bi K. Identification and determination of the major constituents in Kai-Xin-San by UPLC-Q/TOF MS and UFLC-MS/MS method. J Mass Spectrom. 2016 Jul;51(7):479-90. doi: 10.1002/jms.3773.

Tang Jf, Li Wx, Tan Xj, Li P, Xiao Xh, Wang Jb, Zhu Mj, Li Xl, Meng F. A novel and improved UHPLC-QTOF/MS method for the rapid analysis of the chemical constituents of Danhong injection. Anal Methods. 2016;8:2904-2914. doi: 10.1039/C5AY03173G

Deng H, Wang Y, Bian Z, Liu S, Fan Z, Li Z, Yang F, Tang G. Enantioseparation of nornicotine in tobacco by ultraperformance convergence chromatography with tandem mass spectrometry. J Sep Sci. 2017, 40, 4645-4652.doi: 10.1002/jssc.201700759.

Potier P, Bouchu A, Descotes G, Queneau Y. Lipase-Catalysed Selective Synthesis of Sucrose Mixed Diesters. Synthesis. 2001;3: 0458-0462.

Mitsubishi Chemicals, Sucrose fatty acid esters “RyotoTM Sugar Ester”, (2019) https://www.m-chemical.co.jp/en/products/departments/group/mfc/product/1201443_7739.html.


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