Grasas y Aceites, Vol 70, No 4 (2019)

Synthesis, characterization and evaluation of 1-monoacylglycerols of unsaturated fatty acids as potential bioactive lipids


https://doi.org/10.3989/gya.1052182

J. Johny
Centre for Lipid Science & Technology, India
orcid http://orcid.org/0000-0003-3109-5519

A. Jatla
Applied Biology, CSIR-Indian Institute of Chemical Technology, India
orcid http://orcid.org/0000-0003-4240-5148

V. K. Eruva
Applied Biology, CSIR-Indian Institute of Chemical Technology, India
orcid http://orcid.org/0000-0003-1015-3660

S. Misra
Applied Biology, CSIR-Indian Institute of Chemical Technology, India
orcid http://orcid.org/0000-0002-3080-7476

S. S. Kaki
Centre for Lipid Science & Technology, India
orcid http://orcid.org/0000-0003-2726-1166

Abstract


The synthesis of 1-monoacylglycerols of selected unsaturated fatty acids and their antimicrobial and cytotoxicity activity is reported in the present study. The monoacylglycerols of fatty acids like undecenoic, oleic, linoleic and erucic acids were prepared by chemical esterification with solketal followed by deprotection. Fatty acids like alpha linolenic, gamma linolenic and ricinoleic acids were initially isolated from natural sources and further enriched in their respective methyl ester forms. The monoacylglycerols of ricinoleic and linolenic acid methyl esters were prepared by enzymatic transesterification with solketal using lipase from Candida antarctica followed by deprotection. The synthesized 1-monoacylglycerols were purified and characterized by spectral studies. The antimicrobial activity revealed that the monoacylglycerol of gamma linolenic acid was the most effective antibacterial followed by the monoacylglycerols of undecenoic and alpha linolenic acids. In the cytotoxicity assay against five cell lines, all the monoacylglycerols exhibited moderate activity but the activity was best against MCF7 Human Breast Adenocarcinoma cell lines.

Keywords


1-monoacylglycerols; Antimicrobial activity; Cytotoxicity; Fatty acids; Lipids; Synthesis

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References


Aarti N, Louk ARMP, Potts RO, Guy RH. 1995. Mechanism of oleic acid-induced skin penetration enhancement in vivo in humans. J. Cont. Release 37, 299–306.

Adlercreutz P. 2013. Immobilisation and application of lipases in organic media. Chem. Soc. Rev. 42, 6406–6436.

Altieri C, Bevilacqua A, Cardillo D, Sinigaglia M. 2009. Effectiveness of fatty acids and their monoglycerides against gram-negative pathogens. Int. J. Food Sci. Technol. 44, 359–366.

Berdeaux O, Christie WW, Gunstone FD, Sebedio JL. 1997. Large-scale synthesis of methyl cis-9,trans-11-octadecadienoate from methyl ricinoleate. J. Am. Oil Chem. Soc. 74, 1011–1015.

Bornscheuer UT. 1995. Lipase-Catalyzed Syntheses of Monoglycerols. Enzyme Microb. Technol. 17, 578–586.

Christie, WW. 1982. The preparation of derivatives of lipids. Lipid Analysis, 2nd ed.; Pergamon Press Ltd.: Oxford, United Kingdom, pp 51–61.

Clinical and Laboratory Standards Institute. 2008. Performance Standards for Antimicrobial Susceptibility Tests; Eighteen informational supplement M100-S18.

Desbois AP, Lawlor KC. 2013. Antibacterial activity of long-chain polyunsaturated fatty acids against Propionibacterium acnes and Staphylococcus aureus. Mar. Drugs 11, 4544–4557.

Dolezalova M, Janis R, Svobodova H, Kasparkova V, Humpolıcek P, Krejci J. 2010. Antimicrobial properties of 1-monoacylglycerols prepared from undecanoic (C11:0) and undecenoic (C11:1) acid. Eur. J. Lipid Sci. Technol. 112, 1106–1114.

Flider FJ. 2005. GLA: Uses and new sources. INFORM 16, 279–282.

Hayes DG, Bengtsson YC, Van Alstine JM, Setterwall F. 1998. Urea complexation for the rapid, ecologically responsible fractionation of fatty acids from seed oil. J. Amer. Oil Chem. Soc. 75, 1403–1409.

Kabara JJ, Marshall DL. 2005. Medium-chain fatty acids and esters, in Davidson PM, Sofos JN, Branen AL. (Eds.). Antimicrobials in Food. CRC Press, Boca Raton, USA, pp. 327–360.

Kabara JJ, Swieczkowski DM, Conley AJ, Truant JP. 1972. Fatty acids and derivatives as antimicrobial agents. Antimicrob. Agents Chemother. 2, 23–28.

Kaki SS, Ravinder T, Ashwini B, Rao BVSK, Prasad RBN. 2014. Enzymatic modification of phosphatidylcholine with n-3 PUFA from silkworm oil fatty acids. Grasas Aceites 65, e021.

Kalpana J, Gousia B, Shruti SD, Rohit RK, Sunil M. 2018. Potential of the bioinspired CaCo3 microspheres loaded with tetracycline in inducing differential cytotoxic effects toward noncancerous and cancer cells: a cytogenetic toxicity assessment using CHO cells in vitro. Chem. Res. Toxicol. 31, 629–636.

Linday ME. 1962. Practical Introduction to Microbiology. E and F.N. Spon Ltd., United Kingdom, p. 177.

Littich R. 2017. Antimicrobial lipids: attenuating the use of medically important antimicrobial drugs in food-producing animals: What role Can cGMP lipids play? Drug Dev. Del. 17, 56–61.

Lu W, Kelly Al, Miao S. 2017. Improved bioavailability of encapsulated bioactive nutrients delivered through monoglyceride-structured o/w emulsions. J. Agric. Food Chem. 65, 3048?3055.

Maryam SF, Ming D, Pan A, Sun Q, Stephanie EC, Lyn MS, Walter CW, Hu FB. 2014. Dietary linoleic acid and risk of coronary heart disease: a systematic review and meta-analysis of prospective cohort studies. Circulation 130, 1568–1578.

Nguemeni C, Gouix E, Bourourou M, Heurteaux C, Blondeau N. 2013. Alpha-linolenic acid: A promising nutraceutical for the prevention of stroke. Pharm. Nutrition 1, 1–8.

Osborn HT, Akoh, CC. 2002. Structured lipids – Novel fats with medical, nutraceutical and food applications. Compr. Rev. Food Sci. Food Saf. 3, 110–120.

Pabis´ S, Kula J. 2016. Synthesis and bioactivity of (r)-ricinoleic acid derivatives: A review. Curr. Med. Chem. 23, 4037–4056.

Pawongrat R, Xu X, Kittikun AH. 2008. Physico-enzymatic production of monoacylglycerols enriched with very-long-chain polyunsaturated fatty acids. J. Sci. Food Agric. 88, 256–262.

Pierard GE, Arrese JE, Pierard-Franchimont C, De Doncker P. 1997. Prolonged effects of anti-dandruff shampoos – time to recurrence of Malassezia ovalis colonisation of skin. Int. J. Cosmet. Sci. 19, 111–117.

Janis R, Krejcí J, Klásek A. 2000. Preparation of 1-monoacylglycerols from glycidol and fatty acids catalyzed by the chromium(III)- fatty acid system. Eur. J. Lipid Sci. Technol. 102, 351–354.

Sonntag NOV. 1982. Glycerolysis of fats and methylesters- Status, review and critique. J. Am. Oil Chem. Soc. 59, 795A-802A.

Thormar H, Hilmarsson H. 2007. The role of microbicidal lipids in host defense against pathogens and their potential as therapeutic agents. Chem. Phys. Lipids 150, 1–11.

Yang D, Cwynar VA, Hart DJ, Madanmohan J, Lee J, Lyons J, Caffrey M. 2012. Preparation of 1-monoacylglycerols via the Suzuki-Miyaura reaction: 2, 3-dihydroxypropyl (Z)-tetradec-7-enoate. Org. Synth. 89, 183–201.

Yoon BK, Jackman JA, Valle-González ER, Cho NJ. 2018. Antibacterial free fatty acids and monoglycerides: Biological activities, experimental testing, and therapeutic applications. Int. J. Mol. Sci. 19, 1114.

Zheng CJ, Jung-Sung Y, Tae-Gyu L, Hee-Young C, Young-Ho K, Won-Gon K. 2005. Fatty acid synthesis is a target for antibacterial activity of unsaturated fatty acids. FEBS Lett. 579, 5157–5162.




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