Method for glycosylation of flavonoid compounds

Patent metadata

Field	Value
Publication number	US-9364492-B2
Application number	US-52306508-A
Country	US
Kind code	B2
Filing date	Jan 18, 2008
Priority date	Jan 19, 2007
Publication date	Jun 14, 2016
Grant date	Jun 14, 2016

Abstract

The present invention provides a method for preparing a glycoside of a flavonoid compound, which comprises the step of treating flavonoid and a glycosyl donor with an enzymatic agent having glycosylation activity and being derived from the genus Trichoderma (preferably Trichoderma viride or Trichoderma reesei ). Such a flavonoid compound includes a catechin compound or a methylated derivative thereof, and the glycosyl donor includes a carbohydrate containing a maltotriose residue (preferably maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose, dextrin, γ-cyclodextrin or soluble starch). Glycosides obtained by the present invention have higher water solubility, improved taste, and increased stability. The present invention also provides novel glycosides of catechin compounds, which are obtained by the method of the present invention.

First claim

The invention claimed is:

1. A compound represented by the following formula:

wherein
at least one of R 1 to R 4 represents an α-linked glucose residue or maltose residue or maltooligosaccharide residue, and each of the others represents OH;
R 5 represents OH or H; and
X represents H or a galloyl group, provided that the following compounds are excluded:
a compound in which R 1 represents glucose, R 2 -R 4 represent OH, and R 5 and X represent H;
a compound in which R 2 represents glucose, R 1 and R 3 -R 4 represent OH, and R 5 and X represent H;
a compound in which R 4 represents glucose, R 1 -R 3 represent OH, and R 5 and represent H;
a compound in which R 2 represents maltose, R 1 and R 3 -R 4 represent OH, and R 5 and X represent H;
a compound in which R 3 represents glucose, R 1 -R 2 and R 4 represent OH, and R 5 and X represent H;
a compound in which R 1 represents maltose, R 2 -R 4 represent OH, and R 5 and X represent H;
a compound in which R 3 represents glucose, R 1 -R 2 and R 4 represent OH, and R 5 and X represent H;
a compound in which R 3 represents glucose, R 1 -R 2 and R 4 -R 5 represent OH, and X represents H;
a compound in which R 2 -R 3 represent glucose, R 1 and R 4 -R 5 represent OH, and X represents H;
a compound in which R 1 and R 3 represent glucose, R 2 and R 4 -R 5 represent OH, and X represents H;
a compound in which R 3 represents glucose, R 1 -R 2 and R 4 -R 5 represent OH, and X represents H;
a compound in which R 4 represents glucose, R 1 -R 3 and R 5 represent OH, and X represents H;
a compound in which R 3 represents glucose, R 1 -R 2 and R 4 represent OH, R 5 represents H, and X represents a galloyl group;
a compound in which R 2 -R 3 represent glucose, R 1 and R 4 -R 5 represent OH, and X represents a galloyl group;
a compound in which R 3 represents glucose, R 1 -R 2 and R 4 -R 5 represent OH, and X represents a galloyl group;
a compound in which R 4 represents glucose, R 1 -R 3 and R 5 represent OH, and X represents a galloyl group;
a compound in which R 4 represents glucose, R 1 -R 3 represent OH, R 5 represents H, and X represents a galloyl group;
a compound in which R 2 represents glucose, R 1 and R 3 -R 5 represent OH, and X represents a galloyl group;
a compound in which R 2 and R 4 represent glucose, R 1 , R 3 , and R 5 represent OH, and X represents a galloyl group;
a compound in which R 2 -R 3 represent glucose, R 1 and R 4 represent OH, and R 5 and X represent H;
a compound in which R 1 and R 3 represent glucose, R 2 and R 4 represent OH, and R 5 and X represent H;
a compound in which R 3 -R 4 represent glucose, R 1 -R 2 represent OH, and R 5 and X represent H;
a compound in which R 1 and R 4 represent glucose, R 2 -R 3 represent OH, and R 5 and X represent H;
a compound in which R 2 and R 4 represent glucose, R 1 , R 3 , and R 5 represent OH, and X represents H; and
a compound in which R 2 and R 4 represent glucose, R 1 and R 3 represent OH, and R 5 and X represent H.

2. The compound according to claim 1 , which is selected from the group consisting of:
5-O-α-D-glucopyranosyl-(−)-epigallocatechin-3-O-gallate;
7-O-(4-O-α-D-glucopyranosyl-α-D-glucopyranosyl)-(−)-epigallocatechin-3-O-gallate;
4′-O-(4-O-α-D-glucopyranosyl-α-D-glucopyranosyl)-(+)-catechin;
3′-O-(4-O-α-D-glucopyranosyl-α-D-glucopyranosyl)-(+)-catechin; and
3′-O-(4-O-α-D-glucopyranosyl-α-D-glucopyranosyl)-(−)-epigallocatechin-3-O-gallate.

3. A food, pharmaceutical or cosmetic composition, which comprises the compound according to claim 1 .

4. A beverage, which comprises the composition according to claim 3 .

5. A compound represented by the following formula:

wherein
at least one of R 1 , R 2 , and R 4 represents an α-linked glucose residue or maltose residue or maltooligosaccharide residue, and each of the others represents OH;
R 3 represents a maltose residue;
R 5 represents OH or H; and
X represents H or a galloyl group.

6. A glycoside of a flavonoid compound selected from the following:
5-O-α-D-glucopyranosyl-(−)-epigallocatechin-3-O-gallate;
3′-O-(4-O-α-D-glucopyranosyl-α-D-glucopyranosyl)-(+)-catechin; and
3′-O-(4-O-α-D-glucopyranosyl-α-D-glucopyranosyl)-(−)-epigallocatechin-3-O-gallate.

7. A food, pharmaceutical or cosmetic composition, which comprises the compound according to claim 2 .

8. A beverage, which comprises the composition according to claim 7 .

Assignees

• Ochiai Misa
• Fukami Harukazu
• Nakao Masahiro
• Noguchi Akio
• Suntory Holdings Ltd

Inventors

• Ochiai Misa
• Fukami Harukazu
• Nakao Masahiro
• Noguchi Akio

Classifications

• A61P7/02

  Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors · CPC title

• A61P39/00

  General protective or antinoxious agents · CPC title

• A61P3/06

  Antihyperlipidemics · CPC title

• A61P37/08

  Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14) · CPC title

• A61P9/12

  Antihypertensives · CPC title