Preparation and Taste of Certain Glycosides of Flavanones and of Dihydrochalcones

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概要

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• The 7-O-[2-O-(α-L-Rhamnopyranosyl)-β-L-quinovoside] of naringenin and of hesPeretin, and their dihydrochalcone (DHC) derivatives were synthesized by the method of Koenigs-Knorr (Ag_2CO_3 and quinoline). The reaction of TMS ethers of naringenin and of hesperetin with each of the α-acetofluoro derivatives of D-glucose, L-rhamnose, 2-O-(α-L-rhamnopyranosyl)-L-rhamnose, and 2-O-(α-L-rhamnopy-ranosyl)-D-glucose (neohesperidose), using boron trifluoride etherate as an activator, yielded coupling prod-ucts which, after deprotection, gave naringenin 4'-O-β-D-glucoside, naringenin 4'-O-α-L-rhamnoside, narin-genin 4'-0-[2-0-(α-L-rhamnopyranosyl)-2-L-rhamnoside], hesperetin 3'-0-[2-0-(α-L-rhamnopyranosyl)-2-L-rhamnoside], and naringenin 4'-0-β-neohesperidoside, respectively. Catalytic hydrogenation of these flavanones gave the corresponding DHC derivatives. Hesperetin DHC 4'-O-[2-O-(α-L-rhamnopy-ranosyl-β-L-quinovoside] was 30O times sweeter than sucrose, while the other compounds were bitter or tasteless.

• 社団法人日本農芸化学会の論文
• 1994-08-23

著者

• Nakajima Ryuta

  Department of Applied Biological Chemistry, Faculty of Agriculture, Shizuoka University

• Nakajima R

  Department Of Food Science School Of Food And Nutritional Sciences University Of Shizuoka

• Nakajima Ryuta

  Department Of Applied Biological Chemistry Faculty Of Agriculture Shizuoka University

• Esaki S

  Univ. Shizuoka Shizuoka Jpn

• Esaki Sachiko

  Department of Food Science, School of Food and Nutritional Sciences, University of Shizuoka

• Nishiyama Kiyotoshi

  Department of Food Science, School of Food and Nutritional Sciences, University of Shizuoka

• Sugiyama Naoko

  Department of Food Science, School of Food and Nutritional Sciences, University of Shizuoka

• Takao Yoshihiro

  Department of Food Science, School of Food and Nutritional Sciences, University of Shizuoka

• Kamiya Shintaro

  Department of Food Science, School of Food and Nutritional Sciences, University of Shizuoka

• Sugiyama N

  Tokyo Univ. Fisheries Tokyo Jpn

• Nishiyama K

  Department Of Biochemistry And Applied Biosciences Faculty Of Agriculture University Of Miyazaki

• Kamiya S

  Department Of Food Science School Of Food And Nutritional Sciences University Of Shizuoka

• Takao Yoshihiro

  Department Of Food Science School Of Food And Nutritional Sciences University Of Shizuoka

• Nishiyama Kiyotoshi

  Department of Biochemistry and Applied Biosciences, Faculty of Agriculture, University of Miyazaki

• KAMIYA SHINTARO

  Department of Agricultural Chemistry, Faculty of Agriculture, Shizuoka University

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