DOI QR코드

DOI QR Code

Analysis of Enantiomeric Composition of Chiral Flavor Components from Dried Ginger (Zingiber afficinale Roscoe)

건생강에 함유된 키랄성 향기성분의 이성질체 조성 분석

  • Published : 2006.08.30

Abstract

The volatile compounds of Zingiber officinale Roscoe were extracted by simultaneous steam distillation and extraction (SDE) method and identified with gas chromatigraphy/mass spectrometer (GC/MS) analysis. Enantiomeric compositions of chiral compounds were determined by multidimensional gas chromatography/mass spectrometer (MDGC/MS). A total of 57 compounds were indentified and quantified, including zingiberene, ${\beta}-sesquiphellandrene$, ${\beta}-bisabolene$, $(E,E)-{\alpha}-farnesene$ and ${\alpha}-curcumene$. Among them, zingiberene (38.41%) was founds as the predominantly abundant component. ${\alpha}-Pinene$ and nerolidol in dried ginger were detected by high enantiomeric purity (>96%) for (S)-form, and ${\beta}-pinene$ was detected only (R)-form. The enantiomeric composition of ${\alpha}-terpineol$ revealed 72.0% for (R)-form, and linalool and 4-terpineol showed mixtures of both enantiomers. (S)-Enantiomer was the major enantiomer of limonene having enatiomeric excess of 17.2%. Hence the enantiomeric composition of these compounds can be used as parameter for authenticty control of Zingiber officinale.

References

  1. Aromenverordnung i. d. F. des Verordnung zur Neuordnung lebensmittel-rechtlicher Kennzei-chnung svorschriften vom 22.12. 1981 (BGBI. I. S. 1652, 1676), der 1. Aend V vom 10.5.1983 (BGBI. I. S. 602) und der ZV erd V vom 10.7.1984 (BGBI I.S. 897)
  2. Codex Alimentarius. 1993. Auslaendische Lebensmittecrecht Behr's Verlag, Muenchen
  3. Werkgoff P, Bretschneider W, Guentert M, Hopp R, Surbrug H. 1990. Chiral analysis in flavor and essential oil chemistry. Part B. Direct enantiomer resolution of trans-$\alpha$- ionon and trans-$\alpha$-damascone by inclusion gas chromatography. In Flavor Science and Technology. Bessiere Y, Thomas AF, eds. Wiley, London. p 33-36
  4. Werkgoff P, Bretschneider W, Brennecke S. 1991. Multidimensionale Praeparative kapillar-gaschromtographie in der Aromastoff-Forschung. Gersterl Aktuell, No. 12
  5. Bernreuther A, Christoph N, Schreler P. 1989. Cetermination of the enantiomeric composition of $\gamma$-lactones in complex natural matrices using multidimensional capillary gas chromatogrphy. J Chromatogr 481: 363-367 https://doi.org/10.1016/S0021-9673(01)96780-9
  6. Bernreuther A, Lander V, Huffer M, Schreier P. 1990. Enantioselective analysis of dec-2-en-5-olide (massoilactone) from natural sources by multidimensional capillary gas chromatography. Flavour Fragr J 5: 71-73 https://doi.org/10.1002/ffj.2730050202
  7. Bernreuther A, Bank J, Krammer G, Schreier P. 1991. Multidimensional gas chromatography/mass spectrometry: A powerful tool for the direct chiral evaluation of aroma compounds in plant tissues. I. 5-alkanolides in fruits. Phytochem Anal 2: 43-46 https://doi.org/10.1002/pca.2800020109
  8. Tressl R, Engel KH. 1984. Analysis of Volatiles, Methods and Application. Schreier P, ed. de Gruyter, Berlin, Germany. p 323-343
  9. Tressl R, Engel KH, Albrecht W, Bille-Abdullah H. 1985. Characterization and Measurment of Flavor Compounds. Bills DD, Mussinan CJ, eds. ACS Symposium Series 289, American Chemical Society, Washington, DC. p 43-60
  10. Pabst A, Barron D, Semont E, Schreier P. 1992. 4-Oxo-$\beta$- ionol and linalool glycosides from raspberry fruits. Phytochemistry 31: 4187-4190 https://doi.org/10.1016/0031-9422(92)80440-P
  11. Ravid U, Putievsky E, Katzir I, Lewinsohn E. 1997. Enantiomeric composition of linalol in the essential oils of Ocimum species and in commercial basil oils. Flavor Fragr J 12: 293-296 https://doi.org/10.1002/(SICI)1099-1026(199707)12:4<293::AID-FFJ648>3.0.CO;2-3
  12. Bouwmeester HJ, Davies JAR, Toxopeus H. 1995. Enantiomeric composition of carvone, limonene, and carveols in seeds of dill and annual and biennial Caraway varieties. J Agric Food Chem 43: 3057-3064 https://doi.org/10.1021/jf00060a013
  13. Wang X, Liu YS, Nair UB, Armstrong DW. 1997. Enantiomeric composition of monoterpenes in conifer resins. Tetrahedron Asymmetry 8: 3977-3984 https://doi.org/10.1016/S0957-4166(97)00600-9
  14. Tamogami S, Awano K, Kitahara T. 2001. Analysis of the enantiomeric ratios of chiral components in absolute jasmine. Flavor Fragr J 16: 161-163 https://doi.org/10.1002/ffj.969
  15. Werkhof P, Brennecke S, Bretschneider W, Gufntert M, Hopp R, Surburg H. 1993. Chirospecific analysis in essential oil, fragrance and flavor research. Lebensm Unters Forsch 196: 307-328 https://doi.org/10.1007/BF01197930
  16. Kreis P, Braunsdorf R, Dietrich A, Hener U, Maas B, Mosandl A. 1993. Progress in Flavour Precursor Studies. Schreier P, Winterhalter P, eds. Allured Publishing Corporation, Carol Stream, IL. p 77
  17. Mollenbeck S, Konig T, Schreier P, Schwab W, Rajaonarivony J, Ranarivelo L. 1997. Chemical composition and analyses of enantiomers of essential oils from Madagascar. Flavour and Fragrance J 12: 63-69 https://doi.org/10.1002/(SICI)1099-1026(199703)12:2<63::AID-FFJ614>3.0.CO;2-Z
  18. European Pharmacopoeia Commission. 2004. PA/PH/Exp. 13A/T (00) 40 DEF monograph no 1338
  19. Connell DW. 1969. The pungent principles of ginger and their importance incertain ginger products. Food Technol Austral 21: 570-575
  20. Lee CB. 1979. Illustrated Flora of Korea. Hyangmoon Publish Co, Seoul, Korea
  21. Leung A. 1980. Encyclopendia of common natural ingredients. John Wiley & Sons, NY, USA. p 270-274
  22. Schultz TH, Flath RA, Mon TR, Enggling SB, Teranishi R. 1977. Isolation of volatile components from a model system. J Agric Food Chem 25: 446-449 https://doi.org/10.1021/jf60211a038
  23. Nickerson GB, Likens ST. 1966. Gas chromatography evidence for the occurrence of hop oil components in beer. J Chromatogr 21: 1-5 https://doi.org/10.1016/S0021-9673(01)91252-X
  24. Robert PA. 1995. Identification of essential oil components by gas chromatography/mass spectroscopy. Allured Publishing Corporation, IL, USA
  25. Stehagen E, Abbrahansom S, Mclafferty FW. 1974. The Wiley/NBS registry of mass spectral data. John Wiley and Sons, NY, USA
  26. Davies NW. 1990. Gas chromatographic retention indices of monoterpenes and sesquiterpenes on methyl silicone and carbowax 20M phases. J Chromatogr 503: 1-24 https://doi.org/10.1016/S0021-9673(01)81487-4
  27. Laboratories SR. 1986. The Sadtler standard gas chromatography retention index library. Sadtler, PA, USA
  28. Schurig V. 1996. Terms for the quantitation of a mixture of stereoisomers. Enantiomer 1: 139-143
  29. Singh G, Maurya S, Catalan C, de Lampasona MP. 2005. Studies on essential oils. Part 42: chemical, antifungal, antioxidant and sprout suppressant studies on ginger essential oil and its oleoresin. Flavour Fragr J 20: 1-6 https://doi.org/10.1002/ffj.1373
  30. Chen CC, Ho CT. 1988. Gas chromatographic analysis of volatile components of ginger oil (Zingiber officinale Roscoe) extracted with liquid carbon dioxide. J Agric Food Chem 36: 322-328 https://doi.org/10.1021/jf00080a020
  31. Kim JS, Koh MS, Kim YH, Kim MK, Hong JS. 1991. Volatile flavor components of Korean ginger (Zingiber officinale Roscoe). Korean J Food Sci Technol 23: 141-149
  32. Moon HI, Lee HJ. 1997. Volatile aromatic components of ginger (Zingiber officinale Roscoe) rhizomes and Japanese spice bush (Lindera obtusiloba BL). Korean J Crop Sci 42: 7-13
  33. Millar JG. 1998. Rapid and simple isolation of zingiberene from ginger essential oil. J Nat Prod 61: 1025-1026 https://doi.org/10.1021/np9800699
  34. Kreck M, Scharrer A, Bilke S, Mosandl A. 2002. Enantioselective analysis of monoterpene compounds in essential oils by stir bar sorptive extraction (SBSE)–enantio-MDGC- MS. Flavour Fragr J 17: 32-40 https://doi.org/10.1002/ffj.1033
  35. Schurig V, Nowotny HP. 1988. Separation of enantiomers on diluted permethylated $\rho$-cyclodextrin by high-resolution gas chromatography. J Chromatogr 441: 155-163 https://doi.org/10.1016/S0021-9673(01)84662-8
  36. Fietzek C, Hermle T, Rosenstiel W, Schurig V. 2001. Chiral discrimination of limonene by use of $\beta$-cyclodextrin-coated quartz-crystal-microbalances (QCMs) and data evaluation by artificial neuronal networks Fresenius J Anal Chem 371: 58-63 https://doi.org/10.1007/s002160100899
  37. Ohloff G. 1990. Riechstoffe und Geruchssinn. Springer, Berlin
  38. Bonnlander B, Cappuccio R, Liverani FS, Winterhalter P. 2006. Analysis of enantiomeric linalool ratio in green and roasted coffee. Flavour Fragr J 21: 637-641 https://doi.org/10.1002/ffj.1633
  39. Nishimura O. 2001. Enantiomer separation of the characteristic odorants in Japanese fresh rhizomes of Zingiber officinale Roscoe (ginger) using multidimensional GC system and confirmation of the odour character of each enantiomer by GC-olfactometry. Flavour Fragr J 16: 13-18 https://doi.org/10.1002/1099-1026(200101/02)16:1<13::AID-FFJ939>3.0.CO;2-M

Cited by

  1. Quality Characteristics of Cookies with Ginger Powder vol.31, pp.6, 2015, https://doi.org/10.9724/kfcs.2015.31.6.703
  2. Identification of volatile flavor compounds in Jeju citrus fruits vol.23, pp.7, 2016, https://doi.org/10.11002/kjfp.2016.23.7.977
  3. Effect of Microbial Fermentation on the Sensory Attributes, Gingerol Content and Volatile Components of Ginger vol.15, pp.4, 2010, https://doi.org/10.3746/jfn.2010.15.4.322
  4. Comparison of Active Ingredients between Field Grown and In Vitro Cultured Rhizome of Korean Native Ginger (Zingiber officinale Roscoe) vol.24, pp.4, 2011, https://doi.org/10.7732/kjpr.2011.24.4.404