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

Li Yun Lin, Kun Hung Shen, Xiang Yü Yeh, Bou Yü Huang, Hui Er Wang, Kuan Chou Chen, Robert Y. Peng

Research output: Contribution to journalArticle

1 Citation (Scopus)

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.

Original languageEnglish
Pages (from-to)H1565-H1575
JournalJournal of Food Science
Volume81
Issue number6
DOIs
Publication statusPublished - 2016

Fingerprint

Alpinia officinarum
Alpinia
Eutrema japonica
Volatile Oils
essential oils
Acetates
acetates
Steam
Monoterpenes
Sesquiterpenes
Hydrocarbons
steam
allyl isothiocyanate
Wasabia
Methanol
Condiments
Zingiberaceae
monoterpenoids
sesquiterpenoids
Ginger

Keywords

  • Alpinia officinarum
  • antimicrobial
  • antioxidant
  • galangal acetate
  • wasabi substitute

ASJC Scopus subject areas

  • Food Science

Cite this

Integrated Process for Production of Galangal Acetate, the “Wasabi-Like” Spicy Compound, and Analysis of Essential Oils of Rhizoma Alpinia officinarum (Hance) Farw. / Lin, Li Yun; Shen, Kun Hung; Yeh, Xiang Yü; Huang, Bou Yü; Wang, Hui Er; Chen, Kuan Chou; Peng, Robert Y.

In: Journal of Food Science, Vol. 81, No. 6, 2016, p. H1565-H1575.

Research output: Contribution to journalArticle

Lin, Li Yun ; Shen, Kun Hung ; Yeh, Xiang Yü ; Huang, Bou Yü ; Wang, Hui Er ; Chen, Kuan Chou ; Peng, Robert Y. / Integrated Process for Production of Galangal Acetate, the “Wasabi-Like” Spicy Compound, and Analysis of Essential Oils of Rhizoma Alpinia officinarum (Hance) Farw. In: Journal of Food Science. 2016 ; Vol. 81, No. 6. pp. H1565-H1575.
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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.",
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AU - Shen, Kun Hung

AU - Yeh, Xiang Yü

AU - Huang, Bou Yü

AU - Wang, Hui Er

AU - Chen, Kuan Chou

AU - Peng, Robert Y.

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N2 - 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.

AB - 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.

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KW - wasabi substitute

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