α-Oligoglucosylation of a sugar moiety enhances the bioavailability of quercetin glucosides in humans

Kaeko Murota; Namiko Matsuda; Yasuaki Kashino; Yutaka Fujikura; Toshiyuki Nakamura; Yoji Kato; Ryosuke Shimizu; Syuji Okuyama; Hisashi Tanaka; Takatoshi Koda; Keiko Sekido; Junji Terao

doi:10.1016/j.abb.2010.06.036

α-Oligoglucosylation of a sugar moiety enhances the bioavailability of quercetin glucosides in humans

Kaeko Murota, Namiko Matsuda, Yasuaki Kashino, Yutaka Fujikura, Toshiyuki Nakamura, Yoji Kato, Ryosuke Shimizu, Syuji Okuyama, Hisashi Tanaka, Takatoshi Koda, Keiko Sekido, Junji Terao

Research output: Contribution to journal › Article › peer-review

70 Citations (Scopus)

Abstract

Dietary intake of quercetin is suggested to be potentially beneficial for the prevention of various diseases. We examined the effect of α-oligoglucosylation of the sugar moiety of quercetin monoglucoside on its bioavailability in humans. Enzymatically modified isoquercitrin (EMIQ) was prepared by enzymatic deglycosylation and the subsequent of α-oligoglucosylation of quercetin 3-O-β-rutinode (rutin). The plasma level of quercetin metabolites was instantly increased by oral intake of EMIQ and its absorption efficiency was significantly higher than that of isoquercitrin (quercetin 3-O-β-glucoside; Q3G), and rutin. The profile of plasma quercetin metabolites after EMIQ consumption did not differ from that after Q3G consumption. The apparent log P of EMIQ indicated that EMIQ is more hydrophilic than Q3G but less than quercetin 3,4'-O-β-diglucoside. These data indicated that enzymatic α-oligoglucosylation to the sugar moiety is effective for enhancing the bioavailability of quercetin glucosides in humans.

Original language	English
Pages (from-to)	91-97
Number of pages	7
Journal	Archives of Biochemistry and Biophysics
Volume	501
Issue number	1
DOIs	https://doi.org/10.1016/j.abb.2010.06.036
Publication status	Published - Sep 2010
Externally published	Yes

Keywords

Bioavailability
EMIQ
Human
Quercetin
α-Glucosylation

ASJC Scopus subject areas

Biophysics
Biochemistry
Molecular Biology

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10.1016/j.abb.2010.06.036

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title = "α-Oligoglucosylation of a sugar moiety enhances the bioavailability of quercetin glucosides in humans",

abstract = "Dietary intake of quercetin is suggested to be potentially beneficial for the prevention of various diseases. We examined the effect of α-oligoglucosylation of the sugar moiety of quercetin monoglucoside on its bioavailability in humans. Enzymatically modified isoquercitrin (EMIQ) was prepared by enzymatic deglycosylation and the subsequent of α-oligoglucosylation of quercetin 3-O-β-rutinode (rutin). The plasma level of quercetin metabolites was instantly increased by oral intake of EMIQ and its absorption efficiency was significantly higher than that of isoquercitrin (quercetin 3-O-β-glucoside; Q3G), and rutin. The profile of plasma quercetin metabolites after EMIQ consumption did not differ from that after Q3G consumption. The apparent log P of EMIQ indicated that EMIQ is more hydrophilic than Q3G but less than quercetin 3,4'-O-β-diglucoside. These data indicated that enzymatic α-oligoglucosylation to the sugar moiety is effective for enhancing the bioavailability of quercetin glucosides in humans.",

keywords = "Bioavailability, EMIQ, Human, Quercetin, α-Glucosylation",

author = "Kaeko Murota and Namiko Matsuda and Yasuaki Kashino and Yutaka Fujikura and Toshiyuki Nakamura and Yoji Kato and Ryosuke Shimizu and Syuji Okuyama and Hisashi Tanaka and Takatoshi Koda and Keiko Sekido and Junji Terao",

note = "Funding Information: This work was supported in part by a grant from the Ministry of Agriculture , Forestry and Fisheries of Japan (MAFF) Food Research Project “Integrated Research on Safety and Physiological Function of Food” .",

year = "2010",

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doi = "10.1016/j.abb.2010.06.036",

language = "English",

volume = "501",

pages = "91--97",

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T1 - α-Oligoglucosylation of a sugar moiety enhances the bioavailability of quercetin glucosides in humans

AU - Murota, Kaeko

AU - Matsuda, Namiko

AU - Kashino, Yasuaki

AU - Fujikura, Yutaka

AU - Nakamura, Toshiyuki

AU - Kato, Yoji

AU - Shimizu, Ryosuke

AU - Okuyama, Syuji

AU - Tanaka, Hisashi

AU - Koda, Takatoshi

AU - Sekido, Keiko

AU - Terao, Junji

N1 - Funding Information: This work was supported in part by a grant from the Ministry of Agriculture , Forestry and Fisheries of Japan (MAFF) Food Research Project “Integrated Research on Safety and Physiological Function of Food” .

PY - 2010/9

Y1 - 2010/9

N2 - Dietary intake of quercetin is suggested to be potentially beneficial for the prevention of various diseases. We examined the effect of α-oligoglucosylation of the sugar moiety of quercetin monoglucoside on its bioavailability in humans. Enzymatically modified isoquercitrin (EMIQ) was prepared by enzymatic deglycosylation and the subsequent of α-oligoglucosylation of quercetin 3-O-β-rutinode (rutin). The plasma level of quercetin metabolites was instantly increased by oral intake of EMIQ and its absorption efficiency was significantly higher than that of isoquercitrin (quercetin 3-O-β-glucoside; Q3G), and rutin. The profile of plasma quercetin metabolites after EMIQ consumption did not differ from that after Q3G consumption. The apparent log P of EMIQ indicated that EMIQ is more hydrophilic than Q3G but less than quercetin 3,4'-O-β-diglucoside. These data indicated that enzymatic α-oligoglucosylation to the sugar moiety is effective for enhancing the bioavailability of quercetin glucosides in humans.

AB - Dietary intake of quercetin is suggested to be potentially beneficial for the prevention of various diseases. We examined the effect of α-oligoglucosylation of the sugar moiety of quercetin monoglucoside on its bioavailability in humans. Enzymatically modified isoquercitrin (EMIQ) was prepared by enzymatic deglycosylation and the subsequent of α-oligoglucosylation of quercetin 3-O-β-rutinode (rutin). The plasma level of quercetin metabolites was instantly increased by oral intake of EMIQ and its absorption efficiency was significantly higher than that of isoquercitrin (quercetin 3-O-β-glucoside; Q3G), and rutin. The profile of plasma quercetin metabolites after EMIQ consumption did not differ from that after Q3G consumption. The apparent log P of EMIQ indicated that EMIQ is more hydrophilic than Q3G but less than quercetin 3,4'-O-β-diglucoside. These data indicated that enzymatic α-oligoglucosylation to the sugar moiety is effective for enhancing the bioavailability of quercetin glucosides in humans.

KW - Bioavailability

KW - EMIQ

KW - Human

KW - Quercetin

KW - α-Glucosylation

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α-Oligoglucosylation of a sugar moiety enhances the bioavailability of quercetin glucosides in humans

Abstract

Keywords

ASJC Scopus subject areas

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