Skip to main content
SpringerLink
Log in

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

  • Chapter
  • First Online:
Green Chromatographic Techniques

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.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
eBook
USD 16.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  • Ali M, Thomson M, Afzal M (2000a) Garlic and onions: their effect oneicosanoid metabolism and its clinical relevance. Prostaglandins Leukot Essent Fat Acids 62:55–73

    Article  CAS  Google Scholar 

  • 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 62:253–259

    Article  CAS  Google Scholar 

  • Amagase H (2006) Clarifying the real bioactive constituents of garlic. J Nutr 136:716S–725S

    CAS  Google Scholar 

  • Ankri S, Mirelman D (1999) Antimicrobial properties of allicin from garlic. Microbes Infect 2:125–129

    Article  Google Scholar 

  • Ariga T, Seki T (2006) Antithrombotic and anticancer effects of garlic-derived sulfur compounds: a review. Biofactors 26:93–103

    Article  CAS  Google Scholar 

  • Block E (1985) The chemistry of garlic and onions. Sci Am 252:114–119

    Article  CAS  Google Scholar 

  • Block E (2010) Garlic and other alliums: the lore and the science. The Royal Society of Chemistry, Cambridge

    Google Scholar 

  • 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 878:763–768

    Article  CAS  Google Scholar 

  • Brodnitz MH, Pascale JV, Derslice LV (1971) Flavor components of garlic extract. J Agr Food Chem 19:273–275

    Article  CAS  Google Scholar 

  • Brown PR, Grushka E (eds) (2001) Advances in Chromatography 41. Marcel Dekker, New York

    Google Scholar 

  • 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 55:1280–1288

    Article  CAS  Google Scholar 

  • Cremlyn RJW (1996) An introduction to organosulfur chemistry. Wiley, New York

    Google Scholar 

  • Crews P, Rodriguez J, Jaspars M (2009) Organic structure analysis. Oxford University Press, New York

    Google Scholar 

  • Cruz-Villalon G (2001) Synthesis of allicin and purification by solid-phase extraction. Anal Biochem 290:376–378

    Article  CAS  Google Scholar 

  • 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

    CAS  Google Scholar 

  • 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 11:268

    Article  CAS  Google Scholar 

  • 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 43:2332–2338

    Article  CAS  Google Scholar 

  • 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 56:4229–4235

    Article  CAS  Google Scholar 

  • 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 72:325–34

    Article  CAS  Google Scholar 

  • Guardia M, Garrigues S (eds) (2012) Handbook of green analytical chemistry. Wiley, Chichester

    Chapter  Google Scholar 

  • 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

    Google Scholar 

  • 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 54:1535–1540

    Article  CAS  Google Scholar 

  • 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 64:85–91

    Article  CAS  Google Scholar 

  • 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

    Google Scholar 

  • 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

    Google Scholar 

  • Lanzotti V (2006) The analysis of onion and garlic. J Chromatogr A 1112:3–22

    Google Scholar 

  • Lawson LD, Hughes BG (1992) Characterization of the formation of allicin and other thiosulfinates from garlic. Planta Med 58:345–350

    Article  CAS  Google Scholar 

  • 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 49:2592–2599

    Article  CAS  Google Scholar 

  • 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 436:187–189

    Article  CAS  Google Scholar 

  • 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 15:929–934

    Article  CAS  Google Scholar 

  • Miron T, Bercovici T, Rabinkov A, Wilchek M, Mirelman D (2004) [3H] Allicin: preparation and applications. Anal Biochem 331:364–369

    Article  CAS  Google Scholar 

  • Oommen S, Anto RJ, Srinivas G, Karunagaran D (2004) Allicin (from garlic) induces caspase-mediated apoptosis in cancer cells. Eur J Pharmacol 485:97–103

    Article  CAS  Google Scholar 

  • 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 53:832–836

    Article  CAS  Google Scholar 

  • 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

    Google Scholar 

  • 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

    CAS  Google Scholar 

  • Song K, Milner JA (2001) The influence of heating on the anticancer properties of garlic. J Nutr 131:1054S–1057S

    CAS  Google Scholar 

  • Yu T, Wu C (1989) Stability of allicin in garlic juice. J Food Sci 54:977–981

    Article  CAS  Google Scholar 

  • 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 37:730–734

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors gratefully acknowledge the support of the Research Resources Center at the University of Illinois, Chicago.

Author information

Authors and Affiliations

  1. Illinois Mathematics and Science Academy, 1500 Sullivan Rd, 60506-1000, Aurora, IL, USA

    Jenny Lee

  2. Protein Research Laboratory, Research Resources Center, University of Illinois at Chicago, 835 S. Wolcott Avenue, 60612, Chicago, IL, USA

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

Authors
  1. Jenny Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shalini Gupta MS
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jin-Sheng Huang Ph.D.
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Lasanthi P. Jayathilaka Ph.D.
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Bao-Shiang Lee Ph.D.
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Bao-Shiang Lee Ph.D. .

Editor information

Editors and Affiliations

  1. Department of Applied Chemistry, Aligarh Muslim University, Faculty of Engineering & Technology, Aligarh, India

    Dr. Inamuddin

  2. Department of Applied Chemistry, Aligarh Muslim University, Faculty of Engineering & Technology, Aligarh, India

    Ali Mohammad

Rights and permissions

Reprints and permissions

Copyright information

© 2014 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Lee, J., Gupta, S., Huang, JS., Jayathilaka, L., Lee, BS. (2014). Preparation and Purification of Garlic-Derived Organosulfur Compound Allicin by Green Methodologies. In: Inamuddin, D., Mohammad, A. (eds) Green Chromatographic Techniques. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-7735-4_6

Download citation

Publish with us

Policies and ethics

Search

Navigation