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