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

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.

1′-Acetoxychavicol Acetate from Alpinia galanga Represses Proliferation and Invasion, and Induces Apoptosis via HER2-signaling in Endocrine-Resistant Breast Cancer Cells

“…The 1 H NMR and 13 H spectra from our study was similar to the study of Azuma et al and Murakami et al [25,26]. Similarly, the mass spectrum showed the molecular ion peak m/z of ACA to equal 234.0889, which correlated with the work of Lin et al [27].…”

Evaluation of Diarylheptanoid–Terpene Adduct Enantiomers from Alpinia officinarum for Neuroprotective Activities

“…The co-isolated diarylheptanoids 7 and 8 could be employed as dienophiles to couple with dienes (α-farnesene or β-myrcene, which have been identified previously from the essential oil of A . officinarum ) via a nonstereoselective Diels–Alder cycloaddition to form racemates (+)- 1 /(−)- 1 –(+)- 5 /(−)- 5 . Interestingly, when β-myrcene functions as a diene, the two possible regioisomeric products, 1 (“ meta ” product) and 2 (“ para ” product), were both obtained.…”

“…The rhizomes of Alpinia officinarum Hance (Zingiberaceae), commonly known as lesser galangal, is a well-known traditional Chinese medicine and has been widely used for the remedy of gastrointestinal diseases such as stomachache, dyspepsia, and gastrofrigid vomiting. , Due to its pungent, spicy taste and aromatic odor, the rhizomes of A. officinarum have also been used as a popular culinary spice exhibiting aromatic smell and providing peppery flavor in stir-fry, curry, and other meat dishes in Southeast Asia . Previous phytochemical studies on A. officinarum had resulted in the isolation of diarylheptanoids, , flavonoids, , and terpenes and in the purification of an essential oil . Recently, both a monoterpene-based (officinaruminane B) and a sesquiterpene-based (alpinisin A) diarylheptanoid–terpene adduct with novel carbon skeletons were reported from the rhizomes of A. officinarum .…”

Alpinia galanga or Lengkuas (Zingiberaceae): A Possible Treatment for COVID-19

“…In addition, there are various components in the lengkuas rhizome, such as flavonoids, phenolic acids, and terpenoids 9,10 , while there are main active compounds found in the lengkuas rhizome, namely kaempferol, galangin, and etc 8,11,12,13,14,15 . Therefore, this study aimed to demonstrate lengkuas for the future prospects against SARS-CoV-2.…”