Integrated Process for Production of Galangal Acetate, the "Wasabi-Like" Spicy Compound, and Analysis of Essential Oils of Rhizoma Alpinia officinarum (Hance) Farw

J Food Sci. 2016 Jun;81(6):H1565-75. doi: 10.1111/1750-3841.13326. Epub 2016 May 11.

Abstract

Rhizoma Alpinia officinarum (Hance) Farw, Zingiberaceae (AO), a ginger family herb exhibiting stimulant and a carminative bioactivity, is widely used in European and Asian countries as spicy condiment and medicinal uses. Allyl isothiocyanate (AITC) is the main pungent taste of native Wasabi (Wasabia japonica). The cytotoxicity of AITC has been implicated in thymus, adrenals, and white blood cells. Considering food safety, apparently a safer substitute for wasabi is worthy commercialized. Previously, we found AO crude paste to be rather feasible for use as a "Wasabi-substitute" in fresh meat and cold salads. A process linking cold ethyl acetate (EtAc) extraction with silica gel adsorption and reversed phase high-performance liquid chromatography (RP-HPLC) (mobile phase, 75% methanol) was used to isolate galangal acetate, the Wasabi-like taste constituent. AO contained abundant galangal acetate (3.84 ± 0.07%) compared to A. galangal (0.57 ± 0.16%), and as already confirmed by thin layer chromatography (TLC), gas chromatography (GC)/mass spectrometry (MS)/MS and Nuclear Magnetic Resonance Spectroscopy (NMR), galangal acetate was particularly thermally labile. The steam distilled essential oil (SDEO) of AO (0.14% on wet basis) contained 80 compounds (number of component, %): monoterpene hydrocarbon (21, 13.83%); oxygenated monoterpene (17, 27.08%); sesquiterpene hydrocarbon (20, 31.03%), and oxygenated sesquiterpene (20, 21.85%), respectively. However, no spicy wasabi-like constituent remained in SDEO. Alternatively, n-hexane, EtAc, and methanol extracts of AO all showed potent DPPH- and superoxide anion-scavenging activity. Conclusively, SDEO although contains 80 volatiles, galangal acetate is absent due to thermal instability. Galangal acetate exhibits pleasant "Wasabi-like taste" for which we have successively developed an integrated process for mass production.

Keywords: Alpinia officinarum; antimicrobial; antioxidant; galangal acetate; wasabi substitute.

MeSH terms

  • Acetates / analysis*
  • Alpinia / chemistry*
  • Antioxidants / analysis
  • Asia
  • Food Handling*
  • Gas Chromatography-Mass Spectrometry
  • Hexanes / chemistry
  • Isothiocyanates / analysis
  • Methanol / chemistry
  • Oils, Volatile / analysis*
  • Plant Extracts / analysis
  • Rhizome / chemistry*
  • Tandem Mass Spectrometry
  • Taste

Substances

  • Acetates
  • Antioxidants
  • Hexanes
  • Isothiocyanates
  • Oils, Volatile
  • Plant Extracts
  • n-hexane
  • allyl isothiocyanate
  • Methanol