Flavonoids O-A-glucosylated on the B cycle, method for the production thereof and uses

Patent metadata

Field	Value
Publication number	US-10647739-B2
Application number	US-201515128673-A
Country	US
Kind code	B2
Filing date	Mar 24, 2015
Priority date	Mar 24, 2014
Publication date	May 12, 2020
Grant date	May 12, 2020

Abstract

The invention relates to a method for producing derivatives of O-α-glucosylated flavonoid, comprising at least one step of incubating a glucansucrase with a flavonoid and at least one sucrose, the flavonoid being a flavonoid which is monohydroxylated or hydroxylated in a non-vicinal manner on the B cycle. The invention also relates to novel O-α-glucosylated flavonoid derivatives, and to the use thereof.

First claim

The invention claimed is:

1. A process for producing O-α-glucosylated flavonoid derivatives, comprising at least one step of incubating a glucansucrase with a flavonoid and at least one sucrose, wherein:
(A) said flavonoid comprises formula (I) below:

wherein the C ring represents a ring chosen from the group consisting of the rings of formula (II) and formula (IV) below:

wherein: the R 1 group represents a B ring of formula (VI) below:

wherein:
(a) just one of the groups chosen from R 8 , R 9 , R 10 , R 11 and R 12 represents a hydroxyl group, the other groups among R 8 , R 9 , R 10 , R 11 and R 12 , which may be identical or different, being chosen from the group consisting of a hydrogen atom; a C 1 alkoxy group; a —C(W) group; and an —O(W) group, wherein W represents a chain consisting of 1 to 6 glycoside(s); or
(b) R 8 and just one of the groups chosen from R 10 , R 11 and R 12 represents a hydroxyl group, R 9 and the other groups among R 10 , R 11 and R 12 , which may be identical or different being chosen from the group consisting of a hydrogen atom; a C 1 alkoxy group; a —C(W) group; and an —O(W) group, wherein W represents a chain consisting of 1 to 6 glycoside(s);
the R 2 and R 3 groups, which may be identical or different, being chosen from the group consisting of a hydrogen atom and an —OH group; R 1 ′, R 2 ′ and R 3 ′ is a hydrogen atom or R 3 and R 3 ′ groups together form an ═O group; R 4 , R 5 , R 6 and R 7 , which may be identical or different, being chosen from the group consisting of a hydrogen atom; a C 1 alkoxy group; an —OH; a —C(W) group; and an —O(W) group, wherein W represents a chain consisting of 1 to 6 glycoside(s); and

(B) said glucansucrase comprises an amino acid sequence having at least 95% identity with the amino acid sequence of SEQ ID NO: 11.

2. The process in of claim 1 , wherein R 10 represents a hydroxyl group, the other groups among R 8 , R 9 , R 11 and R 12 , which may be identical or different, being chosen from the group consisting of a hydrogen atom; a C 1 alkoxy group; a —C(W) group; and an —O(W) group, wherein W represents a chain consisting of 1 to 6 glycoside(s).

3. The process of claim 2 , wherein R 10 represents a hydroxyl group and R 8 , R 9 , R 11 and R 12 represent hydrogen atoms.

4. The process of claim 1 , wherein
R 8 and just one of the groups chosen from R 10 , R 11 and R 12 represent a hydroxyl group,
R 9 and the other groups among R 10 , R 11 and R 12 , which may be identical or different, being chosen from the group consisting of a hydrogen atom; a C 1 alkoxy group; a —C(W) group; and an —O(W) group, wherein W represents a chain consisting of 1 to 6 glycoside(s).

5. The process of claim 4 , wherein R 10 represents a hydroxyl group and R 9 , R 11 and R 12 represent hydrogen atoms.

6. The process of claim 1 , wherein R 1 ′ and R 2 ′ represent hydrogen atoms, R 2 represents a hydrogen atom or an —OH group, and R 3 and R 3 ′ together form an ═O group.

7. The process of claim 1 , wherein two of the R 4 , R 5 , R 6 and R 7 groups represent a hydroxyl group, the other two groups are as defined in claim 1 .

8. The process of claim 7 , wherein R 5 and R 7 represent hydrogen atoms.

9. The process of claim 1 , wherein said flavonoid is of formula (VII), (VII) or (IX) below:

10. The process of claim 1 , wherein said glucansucrase comprises an amino acid sequence having at least 98% identity with the amino acid sequence of SEQ ID NO: 11.

11. The process of claim 1 , wherein said glucansucrase comprises an amino acid sequence having at least 99% identity with the amino acid sequence of SEQ ID NO: 11.

12. The process of claim 1 , wherein said glucansucrase comprises the amino acid sequence of SEQ ID NO: 11.

Assignees

• Agronomique Inst Nat Rech
• Institut Nat Des Sciences Appliquees De Toulouse
• Centre Nat Rech Scient
• Institute Nat Des Sciences Appliquees De Toulouse

Inventors

• Morel Sandrine
• Andre Isabelle
• Brison Yoan
• Cambon Emmanuelle
• Malbert Yannick
• Pompon Denis
• Remaud-Simeon Magali
• Urban Philippe

Classifications

• A61P37/08

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

• C07H1/00

  Processes for the preparation of sugar derivatives · CPC title

• C12P19/46

  having an oxygen atom of the saccharide radical bound to a cyclohexyl radical, e.g. kasugamycin · CPC title

• A61K8/602

  Glycosides, e.g. rutin · CPC title

• A61P9/14

  Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers · CPC title