Skip to main content

Characterization of gingerol analogues in supercritical carbon dioxide (SC CO2) extract of ginger (Zingiber officinale, R.,)

Abstract

Organically grown ginger rhizome (Zingiber officinale Roscoe) SC CO2 extract obtained at 280 bar and 40 °C and its column chromatographic fractions are characterised for its composition. The components in the extract and fractions are identified by HPLC and LC based MS and are used as standard for the estimation of gingerol analogues in the extract. HPLC and mass analysis of the extracts confirmed the various forms of gingerol constituents [4]-, [6]-, [10]-gingerols and [6]-, [8]-, [10]-shogaols in ginger extracts. SC CO2 extract of organic ginger was found to show 6-gingerol around 25.97 % of total extract. The estimation of [6]-gingerol, [6]-shogaols, [4]gingerol, [10]-gingerol and 6-gingediol content of the SC CO2 purified ginger extract was found to be 75.92 ± 1.14, 1.25 ± 0.04, 4.54 ± 0.04, 13.15 ± 0.30 and 0.37 ± 0.00 % respectively. Antioxidant activity was measured by 2, 2-diphenyl-1-pycryl-hydrazyl (DPPH) free radical scavenging and ferric reducing antioxidant power (FRAP) and the assay have shown 652 ± 0.37 mg TE/g and 3.68 ± 0.18 mg TE/100 g respectively, are significantly higher results with SC CO2 organic ginger extract. Paradol analogues are not detected in this study. Small quantities of [4]-, [10]gingediol and [6]-gingediacetate are also found in ginger extract.

This is a preview of subscription content, access via your institution.

Fig. 1
Fig. 2
Fig. 3

References

  • Aggarwal BB, Shishodia S (2006) Molecular targets of dietary agents for prevention and therapy of cancer. Biochem Pharmacol 71:1397–1421

    CAS  Article  Google Scholar 

  • Aldrich SR (1981) Organic farming. Science 213:708–710

    CAS  Article  Google Scholar 

  • Ali BH, Blunden G, Tanira MO, Nemmar A (2008) Some phytochemical, pharmacological and toxicological properties of ginger (Zingiber officinale Roscoe)—a review of recent research. Food Chem Toxicol 46:409–420

    CAS  Article  Google Scholar 

  • Blois MH (1958) Antioxidant determination by the use of stable free radicals. Nature 181:11991200

    Article  Google Scholar 

  • Chen CC, Ho CT (1988) Gas chromatographic analysis of volatile components of ginger oil (Zingiber officinale Roscoe) extracted with a liquid carbon dioxide. J Agric Food Chem 36:322–328

    CAS  Article  Google Scholar 

  • Chen CC, Kuo MC, Ho CT (1986) High performance liquid chromatographic determination of pungent gingerol compounds of ginger (Zingiber officinale). J of Food Science 51:1364–1365

    CAS  Article  Google Scholar 

  • Diaz-Reinoso B, Moure A, Dominguez H, Parajo JC (2006) Supercritical CO2 extraction and purification of compounds with antioxidant activity. J Agric Food chem 54:2441–2469

    CAS  Article  Google Scholar 

  • Ficker C, Smith ML, Akpagana K, Gbeassor M, Zhang J, Durst T, Assabgui R, Arnason JT (2003) Bioassay-guided isolation and identification of antifungal compounds from ginger. Phytother Res 17:897–902

    CAS  Article  Google Scholar 

  • Govindarajan VS (1982a) Ginger, chemistry, technology and quality evaluation: part 1. CRC Crit Rev Food Sci Nutr 17(1):1–96

    CAS  Article  Google Scholar 

  • Govindarajan VS (1982b) Ginger, chemistry, technology and quality evaluation: part 2. CRC Crit Rev Food Sci Nutr 17(3):189–258

    CAS  Article  Google Scholar 

  • Guo C, Yang J, Wei J, Li Y, Xu J, Jiang Y (2003) Antioxidant activities of peel, pulp and seed fractions of common fruits as determined by FRAP assay. Nutr Res 23:1719–1726

    CAS  Article  Google Scholar 

  • Haksar A, Sharma A, Chawla R, Kumar R, Arora R, Singh S, Prasad J, Gupta M, Tripathi RP, Arora MP, Islam F, Sharma RK (2006) Zingiber offiicinale exhibits behavioral radioprotection against radiation-induced CTA in a gender-specific manner. Pharmacol Biochem Behav 84(2):179–188

    CAS  Article  Google Scholar 

  • Hikino H, Kiso Y, Hamada Y (1985) Antihepatotoxic actions of gingerols and diaryheptanoids. J Ethnopharmocol 14(1):31–39

    CAS  Article  Google Scholar 

  • Hiserodt RD, Franzblau SG, Rosen RT (1998) Isolation of 6-,8-and 10-gingerol from ginger rhizome by HPLC and preliminary evaluation of inhibition of Mycobacteruium avium and Mycobacterium tuberculosis. J Agric Food Chem 46:2504–2508

    CAS  Article  Google Scholar 

  • Kawai T, Kinoshita K, Koyama K, Takahashi K (1994) Anti-emetic principles of magnolia obovata bark and Zingiber officinale rhizome. Plantamedica 60(1):17–20

    CAS  Google Scholar 

  • Kikuzaki H, Kawasaki Y, Nakatani N (1994) Structure of antioxidant compounds in ginger. In: Ho CT, Osawa T, Huang MT, Rosen RT (Eds) Food Phytochemicals for cancer prevention II (ACS Symposium series No. 547). American Chemical Society, Washington, pp 237–243

  • Kim SO, Chun KS, Kundu JK, Surh YJ (2004) Inhibitory effects of [6]-gingerol on PMA-induced COX-2 expression and activation of NF-kappa B and p38 MAPK in mouse skin. Biofactors 21:27–31

    Article  Google Scholar 

  • Kim EC, Min JK, Kim TY, Lee SJ, Yang HO, Han S, Kim YM, Kwon YG (2005) [6]-Gingerol, a pungent ingredient of ginger, inhibits angiogenesis invitro and invivo. Biochem Biophys Res Commun 23:300–308

    Article  Google Scholar 

  • Kobayashi M, Shoji N, Ohizumi Y (1987) Gingerol, a novel cardiotonic agent, activates the Ca2+-pumping ATPase in skeletal and cardiac sarcoplasmic reticulum. Biochim Biophys Acta 903:96–102

    CAS  Article  Google Scholar 

  • Masuda Y, Kikuzaki H, Hisamoto M, Nakatani N (2004) Antioxidant properties of gingerol related compounds from ginger. Biofactors 21:293–296

    CAS  Article  Google Scholar 

  • Phan PV, Sohrabi A, Polotsky A, Hungerfold DS, Lindmark L, Frondoza CG (2005) Ginger extract components suppress induction of chemokine expression in luman synoviocytes. J Altern Complement Med 11(1):149–154

    Article  Google Scholar 

  • Puengphian C, Sirichote A (2008) [6]-gingerol content and bioactive properties of ginger (Zingiber Officinale Roscoe) extracts from supercritical CO2 extraction. Asian J Food Ag-Ind 1(1):29–36

    Google Scholar 

  • Roy BC, Goto M, Hirose T (1996) Extraction of ginger oil with supercritical carbon dioxide: experiments and modeling. Ind Eng Chem 35:607–612

    CAS  Article  Google Scholar 

  • Schwertner HA, Rios DC (2007) High-performance liquid chromatographic analysis of 6gingerol, 8-gingerol, 10-gingerol and 6-shogaol in ginger-containing dietary supplements, spices, teas and beverages. J Chromatogr B 856:41–47

    CAS  Article  Google Scholar 

  • Siderere Y, Maquet A, Elke A (2005) Need for research to support consumer confidence in the growing organic food market. Trends Food Sci Technol 16:332–343

    Article  Google Scholar 

  • Suekawa M, Ishige A, Yusas K, Sudo K (1984) Pharmacological studies on ginger1. pharmacological actions of pungent constituents, [6]-gingerol and [6]-shogaol. J Pharmacobio-Dyn 7:836–848

    CAS  Article  Google Scholar 

  • Swain T, Hillis WE (1959) The phenolic constituents Prunu domestica I-the quantitative analysis of phenolic constituents. J Sci Food Agric 10:63–68

    CAS  Article  Google Scholar 

  • Udaya Sankar K (1989) Studies on Physico-chemical characteristics of volatile oil from pepper (Piper Nigraum) extracted by supercritical carbon dioxide. J SciFood Agric 48:483–493

    Article  Google Scholar 

  • Wood AB (1987) Determination of the pungent principles of chillies and ginge by reversed-phase high performance liquid chromatography with use of a single standard substance. Flavour Fragr J 2(1):1–12

    CAS  Article  Google Scholar 

  • Yai H (1991) [6]-gingerol content and bioactive properties of Ginger (Zingiber Officinale Roscoe) extracts from supercritical CO2 extraction. In: Botany 2000 Asia Zinberacai Workshop. Prince of Songkla University, Thailand, pp 15–18

    Google Scholar 

  • Yemitan OK, Izegbu MC (2006) Protective effects of Zingiber offiicinale (Zingiberaceae) against carbon tetrachloride and acetaminophen-induced hepatotoxicity in rats. Phytotherapy Res 20:997–1002

    Article  Google Scholar 

  • Yonei Y, Ohinata H, Yoshida R, Shimizu Y, Yokoyama C (1995) Extraction of ginger flavor with liquid or supercritical carbon dioxide. J Supercrit Fluids 8:156–161

    CAS  Article  Google Scholar 

  • Young HY, Luo YL, Cheng HY, Hsieh WC (2005) Analgesic and anti-inflammatory activities of [6]-gingerol. J Ethnopharmacol 96:207–210

    CAS  Article  Google Scholar 

  • Zhang X, Iwaoka WT, Huang AS, Nakamoto ST, Wong R (1994) Gingerol decreases after processing and storage of ginger. J Food Sci 59(6):1338–1343

    CAS  Article  Google Scholar 

Download references

Acknowledgments

The authors thank the Director, CFTRI, Mysore for providing the facilities and encouragement. M/s South East Agro India is acknowledged for the supply of SC-CO2 extract of organically grown ginger.

Author information

Affiliations

Authors

Corresponding author

Correspondence to Udaya Sankar Kadimi.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Swapna Sonale, R., Kadimi, U.S. Characterization of gingerol analogues in supercritical carbon dioxide (SC CO2) extract of ginger (Zingiber officinale, R.,). J Food Sci Technol 51, 3383–3389 (2014). https://doi.org/10.1007/s13197-012-0851-4

Download citation

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13197-012-0851-4

Keywords

  • Organic ginger
  • SC CO2 ginger extract
  • [6]-Gingerol
  • Shogaols
  • Total phenolic content
  • Antioxidant activity