Chūō-ku, Japan
Chūō-ku, Japan

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Katsuragi H.,Sunny Health Co. | Shimoda K.,Oita University | Ohiro A.,Okayama University of Science | Hamada H.,Okayama University of Science
Acta Biologica Hungarica | Year: 2010

The efficient production of β-glycosides of capsaicin and 8-nordihydrocapsaicin by cultured cells of Panax ginseng is reported. Capsaicin 4-O-(6-O-β-D-xylopyranosyl)-β-D-glucopyranoside (β-primeveroside, 12%) together with capsaicin 4-O-β-D-glucoside (6%) was isolated from the cell suspension of P. ginseng after one week of incubation with capsaicin. On the other hand, 8-nordihydrocapsaicin was glycosylated to 8-nordihydrocapsaicin 4-O-β-D-glucoside (5%) and 8-nordihydrocapsaicin 4-O-β-primeveroside (9%) by P. ginseng. Pretreatment of the cultured cells with salicylic acid greatly enhanced the glucosylation activity toward capsaicinoids. When 500 μM of salicylic acid was added to the cultures prior to the addition of substrate, capsaicin was converted into capsaicin 4-O-β-D-glucoside (17%) and capsaicin β-primeveroside (21%) and 8-nordihydrocapsaicin was glycosylated to 8-nordihydrocapsaicin 4-O-β-D-glucoside (16%) and 8-nordihydrocapsaicin β-primeveroside (15%). © 2010 Akadémiai Kiadó, Budapest.


Katsuragi H.,Sunny Health Co. | Shimoda K.,Oita University | Kubota N.,Oita University | Nakajima N.,Okayama Prefectural University | And 2 more authors.
Bioscience, Biotechnology and Biochemistry | Year: 2010

Biotransformations of phenylpropanoids such as cinnamic acid, /7-coumaric acid, caffeic acid, and ferulic acid were investigated with plant-cultured cells of Eucalyptus perriniana. The plant-cultured cells of E. perriniana converted cinnamic acid into cinnamic acid ß-D-glucopyranosyl ester, /7-coumaric acid, and 4-0-/3-D-glucopyranosylcoumaric acid. /7-Coumaric acid was converted into 4-0-ß-D-glucopyranosylcoumaric acid, /7-coumaric acid ß-D-glucopyranosyl ester, 4-0-ß-D-glucopyranosylcoumaric acid ß-D-glucopyranosyl ester, a new compound, caffeic acid, and 3-0-ß-d-glucopyranosylcaffeic acid. On the other hand, incubation of caffeic acid with cultured E. perriniana cells gave 3-0-ß-D- glucopyranosylcaffeic acid, 3-O-(6-O-fi-D-glucopyranosyl)-ß-D- glucopyranosylcaffeic acid, a new compound, 3-0-ß-D-glucopyranosylcaffeic acid ß-D-glu-copyranosyl ester, 4-0-ß-D-glucopyranosylcaffeic acid, 4-0-ß-D-glucopyranosylcaffeic acid ß-D-glucopyranosyl ester, ferulic acid, and 4-0-/3-D-glucopyranosylferulic acid. 4-0-/3-D-Glucopyranosylferulic acid, ferulic acid ß-D-glucopyranosyl ester, and 4-0-/3-D-glucopyranosyl- ferulic acid ß-D-glucopyranosyl ester were isolated from E. perriniana cells treated with ferulic acid.


Sato D.,Oita University | Eshita Y.,Oita University | Katsuragi H.,Sunny Health Co. | Hamada H.,Okayama University of Science | And 2 more authors.
Molecules | Year: 2012

Glycosylation of vanilloids such as vanillin and 8-nordihydrocapsaicin by cultured plant cells of Eucalyptus perriniana was studied. Vanillin was converted into vanillin 4-O-γ-D-glucopyranoside, vanillyl alcohol, and 4-O-γ-D-glucopyranosylvanillyl alcohol by E. perriniana cells. Incubation of cultured E. perriniana cells with 8-nordihydrocapsaicin gave 8-nordihydrocapsaicin 4-O-γ-D-glucopyranoside and 8-nordihydrocapsaicin 4-O-γ-D-gentiobioside. © 2012 by the authors.


Katsuragi H.,Sunny Health Co. | Shimoda K.,Oita University | Yamamoto R.,Okayama University of Science | Ohara T.,Okayama University of Science | Hamada H.,Okayama University of Science
Acta Biologica Hungarica | Year: 2011

Capsaicin 4-O-β-xylooligosaccharides were synthesized by a biocatalytic xylosylation using Aspergillus sp. β-xylosidase. Capsaicin was converted into three new capsaicin glycosides, i.e. capsaicin 4-O-β-xyloside, capsaicin 4-O-β-xylobioside, and capsaicin 4-O-β-xylotrioside in 15, 12 and 10% yield, respectively. All products were isolated from the reaction mixtures by preparative HPLC. The structures of the products were determined by NMR spectroscopic method. © 2011 Akadé miai Kiadó, Budapest.


The stereoselective xylosylation of (RS)-1-phenylalkyl β-D-glucosides was investigated using plant xylosyltransferase isolated from cultured Catharanthus roseus cells. Enzymatic xylosylation of (RS)-1-phenylethyl β-D-glucoside afforded (R)-1-phenylethyl β-primeveroside and (S)-1-phenylethyl β-D-glucoside. The (R)-selective xylosylation of (RS)-1-phenylbutyl β-D-glucoside also occurred to give (R)-1-phenylbutyl β-primeveroside and recovered (S)-1-phenylbutyl β-D-glucoside. © 2010 Elsevier Ltd. All rights reserved.


PubMed | Sunny Health Co.
Type: Journal Article | Journal: Acta biologica Hungarica | Year: 2011

Capsaicin 4-O--xylooligosaccharides were synthesized by a biocatalytic xylosylation using Aspergillus sp. -xylosidase. Capsaicin was converted into three new capsaicin glycosides, i.e. capsaicin 4-O--xyloside, capsaicin 4-O--xylobioside, and capsaicin 4-O--xylotrioside in 15, 12 and 10% yield, respectively. All products were isolated from the reaction mixtures by preparative HPLC. The structures of the products were determined by NMR spectroscopic method.

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