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http://dx.doi.org/10.4014/jmb.1910.10043

Antifungal Effect of Triglycerol Monolaurate Synthesized by Lipozyme 435-Mediated Esterification  

Zhang, Song (School of Food Science and Engineering, South China University of Technology)
Xiong, Jian (School of Food Science and Engineering, South China University of Technology)
Lou, Wenyong (School of Food Science and Engineering, South China University of Technology)
Ning, Zhengxiang (School of Food Science and Engineering, South China University of Technology)
Zhang, Denghui (Innovation Center of Bioactive Molecule Development and Application, South China Institute of Collaborative Innovation)
Yang, Jiguo (School of Food Science and Engineering, South China University of Technology)
Publication Information
Journal of Microbiology and Biotechnology / v.30, no.4, 2020 , pp. 561-570 More about this Journal
Abstract
This study was designed to synthesize triglycerol monolaurate (TGML) with Lipozyme 435 as the catalyst, and explore its effects on the growth of Aspergillus parasiticus (A. parasiticus) and Aspergillus flavus (A. flavus) and the secretion of aflatoxin b1. The highest content of TGML (49.76%) was obtained at a molar ratio of triglycerol to lauric acid of 1.08, a reaction temperature of 84.93℃, a reaction time of 6 h and an enzyme dosage of 1.32%. After purification by molecular distillation combined with the washes with ethyl acetate and water, the purity of TGML reached 98.3%. Through characterization by electrospray-ionization mass spectrometry, infrared spectrum and nuclear magnetic resonance, the structure of TGML was identified as a linear triglycerol combined with lauroyl at the end. Finally, the inhibitory effects of TGML on the growths of A. parasiticus and A. flavus and the secretion of aflatoxin b1 were evaluated by measuring the colony diameter, the inhibition rate of mycelial growth and the content of mycotoxin in the media. The results indicated that TGML had a stronger inhibitory effects on colony growth and mycelial development of both toxic molds compared to sodium benzoate and potassium sorbate, and the secretions of toxins from A. parasiticus and A. flavus were completely suppressed when adding TGML at 10 and 5 mM, respectively. Based on the above results, TGML may be used as a substitute for traditional antifungal agents in the food industry.
Keywords
Triglycerol monolaurate; enzymatic synthesis; purification; antifungal activity; toxin inhibition;
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1 Ma X, Yan RA, Yu SQ, Lu YY, Li Z, Lu HH. 2012. Enzymatic acylation of isoorientin and isovitexin from bamboo-leaf extracts with fatty acids and antiradical activity of the acylated derivatives. J. Agric. Food Chem. 60: 10844-10849.   DOI
2 Saladino F, Bordin K, Manyes L, Luciano FB, Manes J, Fernandez-Franzon M, et al. 2016. Reduction of the aflatoxins B-1, B-2, G(1) and G(2) in Italian piadina by isothiocyanates. Lwt-Food Sci. Technol. 70: 302-308.   DOI
3 Saladino F, Manyes L, Luciano FB, Manes J, Fernandez-Franzon M, Meca G. 2016. Bioactive compounds from mustard flours for the control of patulin production in wheat tortillas. Lwt-Food Sci. Technol. 66: 101-107.   DOI
4 Holmes RA, Boston RS, Payne GA. 2008. Diverse inhibitors of aflatoxin biosynthesis. Appl. Microbiol. Biotechnol. 78: 559-572.   DOI
5 Hohler D. 1998. Ochratoxin A in food and feed: occurrence, legislation and mode of action. Z. Ernahrungswiss 37: 2-12.   DOI
6 Suarez-Quiroz ML, Campos AA, Alfaro GV, Gonzalez-Rios O, Villeneuve P, Figueroa-Espinoza MC. 2013. Anti-Aspergillus activity of green coffee 5-O-caffeoyl quinic acid and its alkyl esters. Microb. Pathogenesis. 61-62: 51-56.   DOI
7 Williams JH, Phillips TD, Jolly PE, Stiles JK, Jolly CM, Aggarwal D. 2004. Human aflatoxicosis in developing countries: a review of toxicology, exposure, potential health consequences, and interventions. Am. J. Clin. Nutr. 80: 1106-1122.   DOI
8 Oliveira PM, Zannini E, Arendt EK. 2014. Cereal fungal infection, mycotoxins, and lactic acid bacteria mediated bioprotection: From crop farming to cereal products. Food Microbiol. 37: 78-95.   DOI
9 Cabral LD, Pinto VF, Patriarca A. 2013. Application of plant derived compounds to control fungal spoilage and mycotoxin production in foods. Int. J. Food Microbiol. 166: 1-14.   DOI
10 Orfanakis A, Hatzakis E, Kanaki K, Pergantis SA, Rizos A, Dais P. 2013. Characterization of polyglycerol polyricinoleate formulations using NMR spectroscopy, mass spectrometry and dynamic light scattering. J. Am. Oil Chem. Soc. 90: 39-51.   DOI
11 Wan FL, Teng YL, Zou L, Yang X, Chen Q, Li AJ, et al. 2016. Effect of addition of purified diglycerol linoleic acid esters on the crystallization behavior of diacylglycerol oils. J. Am. Oil Chem. Soc. 93: 1605-1614.   DOI
12 Shao S, Cai J, Du X, Wang CG, Lin JG, Dai J. 2016. Biotransformation and detoxification of aflatoxin B-1 by extracellular extract of Cladosporium uredinicola. Food Sci. Biotechnol. 25: 1789-1794.   DOI
13 Siahmoshteh F, Hamidi-Esfahani Z, Spadaro D, Shams-Ghahfarokhi M, Razzaghi-Abyaneh M. 2018. Unraveling the mode of antifungal action of Bacillus subtilis and Bacillus amyloliquefaciens as potential biocontrol agents against aflatoxigenic Aspergillus parasiticus. Food Control. 89: 300-307.   DOI
14 Mueller EA, Schlievert PM. 2015. Non-Aqueous glycerol monolaurate gel exhibits antibacterial and anti-biofilm activity against gram-positive and gram-negative pathogens. PLoS One 10(3): e0120280.   DOI
15 Zhang H, Taxipalati M, Yu LY, Que F, Feng FQ. 2013. Structure activity relationship of a U-type antimicrobial microemulsion system. PLoS One. 8: e76245.   DOI
16 Nazareth TM, Bordin K, Manyes L, Meca G, Manes J, Luciano FB. 2016. Gaseous allyl isothiocyanate to inhibit the production of aflatoxins, beauvericin and enniatins by Aspergillus parasiticus and Fusarium poae in wheat flour. Food Control. 62: 317-321.   DOI
17 Ortega-Requena S, Bodalo-Santoyo A, Bastida-Rodriguez J, Maximo-Martin MF, Montiel-Morte MC, Gomez-Gomez M. 2014. Optimized enzymatic synthesis of the food additive polyglycerol polyricinoleate (PGPR) using Novozym (R) 435 in a solvent free system. Biochem. Eng. J. 84: 91-97.   DOI
18 Obonyo M, Zhang L, Thamphiwatana S, Pornpattananangkul D, Fu V, Zhang LF. 2012. Antibacterial activities of liposomal linolenic acids against antibiotic-resistant helicobacter pylori. Mol. Pharmaceut. 9: 2677-2685.   DOI
19 Umerska A, Cassisa V, Matougui N, Joly-Guillou ML, Eveillard M, Saulnier P. 2016. Antibacterial action of lipid nanocapsules containing fatty acids or monoglycerides as co-surfactants. Eur. J. Pharm. Biopharm. 108: 100-110.   DOI
20 Kato T, Nakamura T, Yamashita M, Kawaguchi M, Kato T, Itoh T. 2003. Surfactant properties of purified polyglycerol monolaurates. J. Surfactants Deterg. 6: 331-337.   DOI
21 Wan FL, Teng YL, Wang Y, Li AJ, Zhang N. 2015. Optimization of oligoglycerol fatty acid esters preparation catalyzed by Lipozyme 435. Grasas Aceites. 66(3): e088.   DOI
22 Conley AJ, Kabara JJ. 1973. Antimicrobial action of esters of polyhydric alcohols. Antimicrob. Agents. Chemother. 4: 501-506.   DOI
23 Holstborg J, Pedersen BV, Krog N, Olesen SK. 1999. Physical properties of diglycerol esters in relation to rheology and stability of protein-stabilised emulsions. Colloid Surface B. 12: 383-390.   DOI
24 Peng B, Xiong CY, Huang Y, Hu JN, Zhu XM, Deng ZY. 2018. Enzymatic synthesis of polyglycerol fatty acid esters and their application as emulsion stabilizers. J. Agric. Food Chem. 66: 8104-8113.   DOI
25 REN Chun-fang, ZHOU Li-guo, Dian-qing Y. 2007. The improvement of method determining hydroxyl value in polyglycerol. J. Qilu. Univ. Technol. (Natural Science Edition) 21: 54-55.
26 Martins M, Klusczcovski AM, Scussel VM. 2014. In vitro activity of the Brazil nut (Bertholletia excelsa HBK) oil in aflatoxigenic strains of Aspergillus parasiticus. Eur. Food Res. Technol. 239: 687-693.   DOI
27 Luo CY, Zeng ZL, Gong DM, Zhao CY, Liang QF, Zeng C. 2014. Evaluation of monolaurin from camphor tree seeds for controlling food spoilage fungi. Food Control. 46: 488-494.   DOI
28 Moss MO. 2008. Fungi, quality and safety issues in fresh fruits and vegetables. J. Appl Microbiol. 104: 1239-1243.   DOI
29 Mishra PK, Singh P, Prakash B, Kedia A, Dubey NK, Chanotiya CS. 2013. Assessing essential oil components as plant-based preservatives against fungi that deteriorate herbal raw materials. Int. Biodeterior. Biodegradation 80: 16-21.   DOI
30 Ma MM, Wen XF, Xie YT, Guo Z, Zhao RB, Yu P, et al. 2018. Antifungal activity and mechanism of monocaprin against food spoilage fungi. Food Control. 84: 561-568.   DOI
31 Altieri C, Bevilacqua A, Cardillo D, Sinigaglia M. 2009. Antifungal activity of fatty acids and their monoglycerides against Fusarium spp. in a laboratory medium. Int. J. Food Sci. Tech. 44: 242-245.   DOI
32 Zhang S, Xiong J, Lou W, Ning Z, Zhang D, Yang J. 2019. Antimicrobial activity and action mechanism of triglycerol monolaurate on common foodborne pathogens. Food Control. 98: 113-119.   DOI
33 Tan CP, Nakajima M. 2005. Effect of polyglycerol esters of fatty acids on physicochemical properties and stability of beta-carotene nanodispersions prepared by emulsification/evaporation method. J. Sci. Food Agr. 85: 121-126.   DOI
34 Shimazaki A, Sakamoto JJ, Furuta M, Tsuchido T. 2016. Antifungal activity of diglycerin ester of fatty acids against yeasts and its comparison with those of sucrose monopalmitate and sodium benzoate. Biocontrol. Sci. 21: 123-130.   DOI
35 Ikegawa C, Ogita A, Doi T, Kumazawa F, Fujita KI, Tanaka T. 2017. Involvement of irreversible vacuolar membrane fragmentation in the lethality of food emulsifier diglycerol monolaurate against budding teast. J. Agric. Food Chem. 65: 5650-5656.   DOI
36 Kumar TN, Sastry YSR, Lakshminarayana G. 1989. Preparation and surfactant properties of diglycerol esters of fatty acids. J. Am. Oil Chem. Soc. 66: 153-157.   DOI
37 Eom TK, Kong CS, Byun HG, Jung WK, Kim SK. 2010. Lipase catalytic synthesis of diacylglycerol from tuna oil and its anti-obesity effect in C57BL/6J mice. Process Biochem. 45: 738-743.   DOI
38 Wang WY, Liu CY, Zhang GJ, Yang F, Wang XY, Chen FL, et al. 2019. Green synthesis of decaglycerol laurates by lipase-catalyzed transesterification of methyl laurate with decaglycerol. J. Chem. Article ID 6342475
39 Denecke P, Borner G, Allmen V. 1981. Method of preparing polyglycerol polyricinoleic fatty acid esters. UK Patent. 2: 232.