Efficient Synthesis of Flavanone Glucuronides

被引：15

作者：

Boumendjel, Ahcene ^{[2
]}

Blanc, Madeleine ^{[2
]}

Williamson, Gary ^{[1
]}

Barron, Denis ^{[1
]}

机构：

[1] Nestle Res Ctr, CH-1000 Lausanne 26, Switzerland

[2] Grenoble Univ, Dept Pharmacochim Mol, UMR 5063, ICMG FR 2607, F-38041 Grenoble 9, France

来源：

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 2009年 / 57卷 / 16期

关键词：

Tarragon; Artemisia dracunculus; flavanone glucuronides; human metabolites; synthesis; enzymatic deprotection; BIOLOGICAL-ACTIVITY; ORANGE JUICE; FLAVONOIDS; PLASMA; IDENTIFICATION; NARINGENIN; HESPERETIN; INGESTION; HUMANS; BIOAVAILABILITY;

D O I：

10.1021/jf9011467

中图分类号：

S [农业科学];

学科分类号：

09 ;

摘要：

The first efficient synthesis of flavanone glucuronides as potential human metabolites is described. The synthetic strategy is based on acetyl protection, followed by a combination of chemical and enzymatic deprotection steps. As an example, the method is applied to a synthesis of 7,4'-di-O-methyleriodictyol 3'-O-beta-D-glucuronide. The aglycone is a flavanone naturally present in tarragon spice (Artemisia dracunculus) as well as in various Chinese, Brazilian, and Malaysian medicinal plants.

引用

页码：7264 / 7267

页数：4

共 35 条

[1]

Abe Ken-Ichi, 1993, Shoyakugaku Zasshi, V47, P43

[2] A facile synthesis of isoflavone 7-O-glucuronides [J].

Al-Maharik, Nawaf ;

Botting, Nigel P. .

TETRAHEDRON LETTERS, 2006, 47 (49) :8703-8706

[3]

Backheet E.Y., 2003, Bull. Pharm. Sci. Assiut Univ, V26, P55, DOI [10.21608/bfsa.2003.65468, DOI 10.21608/BFSA.2003.65468, 10.21608/BFSA.2003.65468]

[4] CHEMICAL-CONSTITUENTS OF THE AERIAL PARTS OF ARTEMISIA-DRACUNCULUS [J].

BALZA, F ;

JAMIESON, L ;

TOWERS, GHN .

JOURNAL OF NATURAL PRODUCTS, 1985, 48 (02) :339-340

[5]

Barron D, 2002, METHODS IN POLYPHENOL ANALYSIS, P187

[6]

Barron D, 2008, REC ADV POLYPHEN RES, V1, P317

[7] Update on uses and properties of Citrus flavonolds:: New findings in anticancer, cardiovascular, and anti-inflammatory activity [J].

Benavente-Garcia, O. ;

Castillo, J. .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2008, 56 (15) :6185-6205

[8] Absorption, metabolism and excretion of flavanones from single portions of orange fruit and juice and effects of anthropometric variables and contraceptive pill use on flavanone excretion [J].

Brett, Gary M. ;

Hollands, Wendy ;

Needs, Paul W. ;

Teucher, Birgit ;

Dainty, Jack R. ;

Davis, Barry D. ;

Brodbelt, Jennifer S. ;

Kroon, Paul A. .

BRITISH JOURNAL OF NUTRITION, 2009, 101 (05) :664-675

[9] Identification of isomeric flavonoid glucuronides in urine and plasma by metal complexation and LC-ESI-MS/MS [J].

Davis, Barry D. ;

Needs, Paul W. ;

Kroon, Paul A. ;

Brodbelt, Jennifer S. .

JOURNAL OF MASS SPECTROMETRY, 2006, 41 (07) :911-920

[10] The major phenolic compounds in the leaves of Cyclopia species (honeybush tea) [J].

De Nysschen, AM ;

Van Wyk, BE ;

Van Heerden, FR ;

Schutte, AL .

BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 1996, 24 (03) :243-246

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