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2014 | OriginalPaper | Chapter

6. Preparation and Purification of Garlic-Derived Organosulfur Compound Allicin by Green Methodologies

Authors : Jenny Lee, Shalini Gupta, MS, Jin-Sheng Huang, Ph.D., Lasanthi P. Jayathilaka, Ph.D., Bao-Shiang Lee, Ph.D.

Published in: Green Chromatographic Techniques

Publisher: Springer Netherlands

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Abstract

Effective green chemistry, green reversed-phase high-performance liquid chromatography (RP-HPLC), and green thin layer chromatography (TLC) methods used for preparing and purifying allicin, a garlic-derived organosulfur compound, are described here. A greener version of the acidic oxidation reaction of diallyl disulfide (DADS) is used to produce allicin with high yield. Green RP-HPLC eliminates the liquid/liquid extraction step from either the DADS acidic oxidation reaction mixture or from garlic extract, allowing the single-step purification of allicin. The proposed method involved the use of eco-friendly ethanol as the alternative eluent for acetonitrile. The pure allicin HPLC fraction prepared this way is quite stable and can be used directly for chemical and biological applications. In addition, by changing silica gel TLC plate to RP-C18 TLC plate, 50 % aqueous ethanol, instead of a solvent blend of hexane : isopropanol (92:8) can be used to identify the allicin on TLC plate. Here, the traditional usage of toxic organic solvents has been avoided and a more efficient chemical reaction scheme is employed, which permits the classification of the present method as green. These green methodologies are used successfully to prepare pure allicin, investigate the thermal, pH, and vacuum drying decomposition of the allicin, and analyze various preparations of garlic extract.

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Literature
go back to reference Ali M, Thomson M, Afzal M (2000a) Garlic and onions: their effect oneicosanoid metabolism and its clinical relevance. Prostaglandins Leukot Essent Fat Acids 62:55–73CrossRef Ali M, Thomson M, Afzal M (2000a) Garlic and onions: their effect oneicosanoid metabolism and its clinical relevance. Prostaglandins Leukot Essent Fat Acids 62:55–73CrossRef
go back to reference Ali M, Al-Qattan KK, Al-Enezi F, Khanafer RM, Mustafa T (2000b) Effect of allicin from garlic powder on serum lipids and blood pressure in rats fed with a high cholesterol diet. Prostaglandins Leukot Essent Fat Acids 62:253–259CrossRef Ali M, Al-Qattan KK, Al-Enezi F, Khanafer RM, Mustafa T (2000b) Effect of allicin from garlic powder on serum lipids and blood pressure in rats fed with a high cholesterol diet. Prostaglandins Leukot Essent Fat Acids 62:253–259CrossRef
go back to reference Amagase H (2006) Clarifying the real bioactive constituents of garlic. J Nutr 136:716S–725S Amagase H (2006) Clarifying the real bioactive constituents of garlic. J Nutr 136:716S–725S
go back to reference Ankri S, Mirelman D (1999) Antimicrobial properties of allicin from garlic. Microbes Infect 2:125–129CrossRef Ankri S, Mirelman D (1999) Antimicrobial properties of allicin from garlic. Microbes Infect 2:125–129CrossRef
go back to reference Ariga T, Seki T (2006) Antithrombotic and anticancer effects of garlic-derived sulfur compounds: a review. Biofactors 26:93–103CrossRef Ariga T, Seki T (2006) Antithrombotic and anticancer effects of garlic-derived sulfur compounds: a review. Biofactors 26:93–103CrossRef
go back to reference Block E (2010) Garlic and other alliums: the lore and the science. The Royal Society of Chemistry, Cambridge Block E (2010) Garlic and other alliums: the lore and the science. The Royal Society of Chemistry, Cambridge
go back to reference Brettschneider F, Jankowski V, Günthner T, Salem S, Nierhaus M, Schulz A, ZW, Jankowski J (2010) Replacement of acetonitrile by ethanol as solvent in reversed phase chromatography of biomolecules. J Chromatogr B 878:763–768CrossRef Brettschneider F, Jankowski V, Günthner T, Salem S, Nierhaus M, Schulz A, ZW, Jankowski J (2010) Replacement of acetonitrile by ethanol as solvent in reversed phase chromatography of biomolecules. J Chromatogr B 878:763–768CrossRef
go back to reference Brodnitz MH, Pascale JV, Derslice LV (1971) Flavor components of garlic extract. J Agr Food Chem 19:273–275CrossRef Brodnitz MH, Pascale JV, Derslice LV (1971) Flavor components of garlic extract. J Agr Food Chem 19:273–275CrossRef
go back to reference Brown PR, Grushka E (eds) (2001) Advances in Chromatography 41. Marcel Dekker, New York Brown PR, Grushka E (eds) (2001) Advances in Chromatography 41. Marcel Dekker, New York
go back to reference Cavagnaro PF, Camargo A, Galmarini CR, Simon PW (2007) Effect of cooking on garlic (Allium sativum L.) antiplatelet activity and thiosulfinates content. J Agric Food Chem 55:1280–1288CrossRef Cavagnaro PF, Camargo A, Galmarini CR, Simon PW (2007) Effect of cooking on garlic (Allium sativum L.) antiplatelet activity and thiosulfinates content. J Agric Food Chem 55:1280–1288CrossRef
go back to reference Cremlyn RJW (1996) An introduction to organosulfur chemistry. Wiley, New York Cremlyn RJW (1996) An introduction to organosulfur chemistry. Wiley, New York
go back to reference Crews P, Rodriguez J, Jaspars M (2009) Organic structure analysis. Oxford University Press, New York Crews P, Rodriguez J, Jaspars M (2009) Organic structure analysis. Oxford University Press, New York
go back to reference Cruz-Villalon G (2001) Synthesis of allicin and purification by solid-phase extraction. Anal Biochem 290:376–378CrossRef Cruz-Villalon G (2001) Synthesis of allicin and purification by solid-phase extraction. Anal Biochem 290:376–378CrossRef
go back to reference Cutler RR, Wilson P (2004) Antibacterial activity of a new, stable, aqueous extract of allicin againstmethicillan-resistant Staphylococcus aureus. Br J Biomed Sci 61:71–74 Cutler RR, Wilson P (2004) Antibacterial activity of a new, stable, aqueous extract of allicin againstmethicillan-resistant Staphylococcus aureus. Br J Biomed Sci 61:71–74
go back to reference Feng Y, Zhu X, Wang Q, Jiang Y, Shang H, Cui L, Cao Y (2012) Allicin enhances host pro-inflammatory immune responses and protects against acute murine malaria infection. Malar J 11:268CrossRef Feng Y, Zhu X, Wang Q, Jiang Y, Shang H, Cui L, Cao Y (2012) Allicin enhances host pro-inflammatory immune responses and protects against acute murine malaria infection. Malar J 11:268CrossRef
go back to reference Freeman F, Kodera Y (1995) Garlic chemistry: stability of s-(2-propenyl)-2-propene-1-sulfinothioate (allicin) in blood, solvents, and simulated physiological fluids. J Agric Food Chem 43:2332–2338CrossRef Freeman F, Kodera Y (1995) Garlic chemistry: stability of s-(2-propenyl)-2-propene-1-sulfinothioate (allicin) in blood, solvents, and simulated physiological fluids. J Agric Food Chem 43:2332–2338CrossRef
go back to reference Fujisawa H, Suma K, Origuchi K, Kumagai H, Seki T, Ariga T (2008) Biological and chemical stability of garlic-derived allicin. J Agric Food Chem 56:4229–4235CrossRef Fujisawa H, Suma K, Origuchi K, Kumagai H, Seki T, Ariga T (2008) Biological and chemical stability of garlic-derived allicin. J Agric Food Chem 56:4229–4235CrossRef
go back to reference Gonen A, Harats D, Rabinkov A, Miron T, Mirelman D, Wilchek M, Weiner L, Ulman E, Levkovitz H, Ben-Shushan D, Shaish A (2005) Theantiatherogenic effect of allicin: possible mode of action. Pathobiology 72:325–34CrossRef Gonen A, Harats D, Rabinkov A, Miron T, Mirelman D, Wilchek M, Weiner L, Ulman E, Levkovitz H, Ben-Shushan D, Shaish A (2005) Theantiatherogenic effect of allicin: possible mode of action. Pathobiology 72:325–34CrossRef
go back to reference Guardia M, Garrigues S (eds) (2012) Handbook of green analytical chemistry. Wiley, ChichesterCrossRef Guardia M, Garrigues S (eds) (2012) Handbook of green analytical chemistry. Wiley, ChichesterCrossRef
go back to reference Hahn G (1996) History, folk medicine, and legendary uses of garlic. In: Koch HP, Lawson LD (eds) Garlic: the science and therapeuticapplication of allium sativum L and related species (2nd ed.). Williams and Wilkins, Baltimore Hahn G (1996) History, folk medicine, and legendary uses of garlic. In: Koch HP, Lawson LD (eds) Garlic: the science and therapeuticapplication of allium sativum L and related species (2nd ed.). Williams and Wilkins, Baltimore
go back to reference Ichikawa M, Ide N, Yoshida J, Yamaguchi H, Ono K (2006) Determination of seven organosulfur compounds in garlic by high-performance liquid chromatography. J Agric Food Chem 54:1535–1540CrossRef Ichikawa M, Ide N, Yoshida J, Yamaguchi H, Ono K (2006) Determination of seven organosulfur compounds in garlic by high-performance liquid chromatography. J Agric Food Chem 54:1535–1540CrossRef
go back to reference Ilic DP, Nikolic VD, Nikolic LB, Stankovic MZ, Stanojevic LP (2010) Thermal degradation, antioxidant and antimicrobial activity of the synthesized allicin and allicin incorporated in gel. Hemijska Industrija 64:85–91CrossRef Ilic DP, Nikolic VD, Nikolic LB, Stankovic MZ, Stanojevic LP (2010) Thermal degradation, antioxidant and antimicrobial activity of the synthesized allicin and allicin incorporated in gel. Hemijska Industrija 64:85–91CrossRef
go back to reference Islam MS, Kusumoto Y, Al-Mamun MA (2011) Cytotoxicity and cancer (HeLa) cell killing efficacy of aqueous garlic (Allium sativum) extract. J Sci Res 3:375–382 Islam MS, Kusumoto Y, Al-Mamun MA (2011) Cytotoxicity and cancer (HeLa) cell killing efficacy of aqueous garlic (Allium sativum) extract. J Sci Res 3:375–382
go back to reference Kim HJ, Han MH, Kim GY, Choi YW, Choi YH (2012) Hexane extracts of garlic cloves induce apoptosis through the generation of reactive oxygen species in Hep3B human hepatocarcinoma cells. Oncol Reports 28:1757–1763 Kim HJ, Han MH, Kim GY, Choi YW, Choi YH (2012) Hexane extracts of garlic cloves induce apoptosis through the generation of reactive oxygen species in Hep3B human hepatocarcinoma cells. Oncol Reports 28:1757–1763
go back to reference Lanzotti V (2006) The analysis of onion and garlic. J Chromatogr A 1112:3–22 Lanzotti V (2006) The analysis of onion and garlic. J Chromatogr A 1112:3–22
go back to reference Lawson LD, Hughes BG (1992) Characterization of the formation of allicin and other thiosulfinates from garlic. Planta Med 58:345–350CrossRef Lawson LD, Hughes BG (1992) Characterization of the formation of allicin and other thiosulfinates from garlic. Planta Med 58:345–350CrossRef
go back to reference Lawson LD, Wang ZJ (2001) Low allicin release from garlic supplements: a major problem due to the sensitivities of alliinase activity. J Agric Food Chem 49:2592–2599CrossRef Lawson LD, Wang ZJ (2001) Low allicin release from garlic supplements: a major problem due to the sensitivities of alliinase activity. J Agric Food Chem 49:2592–2599CrossRef
go back to reference Lee J, Gupta S, Huang J, Jayathilaka LP, Lee B (2013) HPLC-MTT assay: anti-cancer activity of aqueous garlic extract is from allicin. Anal Biochem 436:187–189CrossRef Lee J, Gupta S, Huang J, Jayathilaka LP, Lee B (2013) HPLC-MTT assay: anti-cancer activity of aqueous garlic extract is from allicin. Anal Biochem 436:187–189CrossRef
go back to reference Macpherson LJ, Geierstanger BH, Viswanath V, Bandell M, Eid SR, Hwang SW, Patapoutian A (2005) The pungency of garlic: activation of TRPA1 and TRPV1 in response to allicin. Curr Biol 15:929–934CrossRef Macpherson LJ, Geierstanger BH, Viswanath V, Bandell M, Eid SR, Hwang SW, Patapoutian A (2005) The pungency of garlic: activation of TRPA1 and TRPV1 in response to allicin. Curr Biol 15:929–934CrossRef
go back to reference Miron T, Bercovici T, Rabinkov A, Wilchek M, Mirelman D (2004) [3H] Allicin: preparation and applications. Anal Biochem 331:364–369CrossRef Miron T, Bercovici T, Rabinkov A, Wilchek M, Mirelman D (2004) [3H] Allicin: preparation and applications. Anal Biochem 331:364–369CrossRef
go back to reference Oommen S, Anto RJ, Srinivas G, Karunagaran D (2004) Allicin (from garlic) induces caspase-mediated apoptosis in cancer cells. Eur J Pharmacol 485:97–103CrossRef Oommen S, Anto RJ, Srinivas G, Karunagaran D (2004) Allicin (from garlic) induces caspase-mediated apoptosis in cancer cells. Eur J Pharmacol 485:97–103CrossRef
go back to reference Shadkchan Y, Shemesh E, Mirelman D, Miron T, Rabinkov A, Wilchek M, Osherov N (2004) Efficacy of allicin, the reactive molecule of garlic, in inhibiting Aspergillus spp. in vitro, and in a murine model of disseminated aspergillosis. J Antimicrob Chemother 53:832–836CrossRef Shadkchan Y, Shemesh E, Mirelman D, Miron T, Rabinkov A, Wilchek M, Osherov N (2004) Efficacy of allicin, the reactive molecule of garlic, in inhibiting Aspergillus spp. in vitro, and in a murine model of disseminated aspergillosis. J Antimicrob Chemother 53:832–836CrossRef
go back to reference Shashikanth KN, Basappa SC, Murthy V (1985) Allicin concentration in the gut of rats and its influence on the microflora. J Food Sci Technol 22:110–112 Shashikanth KN, Basappa SC, Murthy V (1985) Allicin concentration in the gut of rats and its influence on the microflora. J Food Sci Technol 22:110–112
go back to reference Song K, Milner JA (1999) Heating garlic inhibits its ability to suppress 7, 12-dimethylbenz(a)anthracene-induced DNA adduct formation in rat mammary tissue. J Nutr 129:657–661 Song K, Milner JA (1999) Heating garlic inhibits its ability to suppress 7, 12-dimethylbenz(a)anthracene-induced DNA adduct formation in rat mammary tissue. J Nutr 129:657–661
go back to reference Song K, Milner JA (2001) The influence of heating on the anticancer properties of garlic. J Nutr 131:1054S–1057S Song K, Milner JA (2001) The influence of heating on the anticancer properties of garlic. J Nutr 131:1054S–1057S
go back to reference Yu T, Wu C (1989) Stability of allicin in garlic juice. J Food Sci 54:977–981CrossRef Yu T, Wu C (1989) Stability of allicin in garlic juice. J Food Sci 54:977–981CrossRef
go back to reference Yu T, Wu C, Chen S (1989) Effects of pH adjustment and heat treatment on the stability and the formation of volatile compounds of garlic. J Agric Food Chem 37:730–734CrossRef Yu T, Wu C, Chen S (1989) Effects of pH adjustment and heat treatment on the stability and the formation of volatile compounds of garlic. J Agric Food Chem 37:730–734CrossRef
Metadata
Title
Preparation and Purification of Garlic-Derived Organosulfur Compound Allicin by Green Methodologies
Authors
Jenny Lee
Shalini Gupta, MS
Jin-Sheng Huang, Ph.D.
Lasanthi P. Jayathilaka, Ph.D.
Bao-Shiang Lee, Ph.D.
Copyright Year
2014
Publisher
Springer Netherlands
DOI
https://doi.org/10.1007/978-94-007-7735-4_6

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