Purification and structure determination of glucosides of capsaicin and dihydrocapsaicin from various Capsicum fruits.
Two new glucosides, capsaicin-beta-D-glucopyranoside (1) and dihydrocapsaicin-beta-D-glucopyranoside (2), were discovered in the fruit of the Capsicum annuum cultivar 'High Heat'. They were sequentially purified by acetone extraction, n-hexane extraction, and acetonitrile extraction, followed by medium-pressure liquid chromatography and high-performance liquid chromatography performed on an octadecylsilane column. Their chemical structures were elucidated by proton nuclear magnetic resonance, carbon nuclear magnetic resonance, and hydrolysis with alpha- and beta-glucosidases. The glucosides were also detected in various pungent cultivars of C. annuum, Capsicum frutescens, and Capsicum chinense by liquid chromatography-mass spectrometry. However, they were not detected in nonpungent cultivars of C. annuum. Furthermore, a positive correlation was observed between the quantity of the capsaicinoids, capsaicin, and dihydrocapsaicin and their glucosides.
Higashiguchi
Fumiharu
F
Central Research Laboratory, Ezaki Glico Company, Ltd., Nishiyodogawa-Ku, Osaka, Japan. higashiguchi-fumiharu@glico.co.jp
Nakamura
Hiroyasu
H
Hayashi
Hideo
H
Kometani
Takashi
T
D002211:Capsaicin / Q000031:analogs & derivatives / Q000737:chemistry* / Q000302:isolation & purification*; D002212:Capsicum / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D005638:Fruit / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry* / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D000520:alpha-Glucosidases / Q000378:metabolism; D001617:beta-Glucosidase / Q000378:metabolism
D005960:Glucosides; D000520:alpha-Glucosidases; D001617:beta-Glucosidase; D002211:Capsaicin; C012906:dihydrocapsaicin