Novel flavonoids o-a-glucosylated on the b cycle, method for the production thereof and uses

A process for producing O-α-glucosylated flavonoid derivatives, comprising at least one step of incubating a glucansucrose with a flavonoid and at least one sucrose, in which:

• (A) said flavonoid is of formula (I) below:
• in which
• the C ring represents a ring chosen from the group consisting of the rings of formula (II), (III), (IV) or (V) below:
• in which:
• one of the R1, R2 or R3 groups represents a B ring of formula (VI) below:
• in which:
• (a) just one of the groups chosen from R8, R9, R10, R11 and R12 represents a hydroxyl group,
• the other groups among R8, R9, R10, R11 and R12, which may be identical or different, being chosen from the group comprising a hydrogen atom;
• a linear or branched, saturated or unsaturated C1-C10 hydrocarbon-based group, optionally interrupted with at least one heteroatom chosen from O, N or S;
• a halogen atom;
• a C5-C9 aryl;
• a C4-C9 heterocycle;
• a (C1-C3)alkoxy group;
• a C2-C3 acyl;
• a C1-C3 alcohol;
• a —COOH;
• —NH2;
• —CONH2;
• —CHO;
• —SH;
• —C(O)O(C2-C3) group;
• a C1-C3 amine;
• a C1-C3 imine;
• a nitrile group;
• a C1-C3 haloalkyl;
• a C1-C3 thioalkyl;
• a —C(W) group;
• and an —O(W) group;
• W representing a chain consisting of from 1 to 6 glycoside(s);
• or
• (b) R8 and just one of the groups chosen from R10, R11 and R12 represent a hydroxyl group,
• R9 and the other groups among R10, R11 and R12, which may be identical or different, being chosen from the group comprising a hydrogen atom;
• a linear or branched, saturated or unsaturated C1-C10 hydrocarbon-based group, optionally interrupted with at least one heteroatom chosen from O, N or S;
• a halogen atom;
• a C5-C9 aryl;
• a C4-C9 heterocycle;
• a (C1-C3)alkoxy group;
• a C2-C3 acyl;
• a C1-C3 alcohol;
• a —COOH;
• —NH2;
• —CONH2;
• —CHO;
• —SH;
• —C(O)O(C2-C3) group;
• a C1-C3 amine;
• a C1-C3 imine;
• a nitrile group;
• a C1-C3 haloalkyl;
• a C1-C3 thioalkyl;
• a —C(W) group;
• and an —O(W) group;
• W representing a chain consisting of from 1 to 6 glycoside(s);
• or
• (c) R9 and just one of the groups chosen from R11 and R12 represent a hydroxyl group,
• the R8 and R10 groups, and the other group among R11 and R12, which may be identical or different, being chosen from the group comprising a hydrogen atom;
• a linear or branched, saturated or unsaturated C1-C10 hydrocarbon-based group, optionally interrupted with at least one heteroatom chosen from O, N or S;
• a halogen atom;
• a C5-C9 aryl;
• a C4-C9 heterocycle;
• a (Cr C3)alkoxy group;
• a C2-C3 acyl;
• a C1-C3 alcohol;
• a —COOH;
• —NH2;
• —CONH2;
• —CHO;
• —SH;
• —C(O)O(C2-C3) group;
• a C1-C3 amine;
• a C1-C3 imine;
• a nitrile group;
• a C1-C3 haloalkyl;
• a C1-C3 thioalkyl;
• a —C(W) group;
• and an —O(W) group;
• W representing a chain consisting of from 1 to 6 glycoside(s);
• or
• (d) R10 and R12 represent a hydroxyl group,
• the R8, R9 and R11 groups, which may be identical or different, being chosen from the group comprising a hydrogen atom;
• a linear or branched, saturated or unsaturated C1-C19 hydrocarbon-based group, optionally interrupted with at least one heteroatom chosen from O, N or S;
• a halogen atom;
• a C5-C9 aryl;
• a C4-C9 heterocycle;
• a (C1-C3)alkoxy group;
• a C2-C3 acyl;
• a C1-C3 alcohol;
• a —COOH;
• —NH2;
• —CONH2;
• —CHO;
• —SH;
• —C(O)O(C2-C3) group;
• a C1-C3 amine;
• a C1-C3 imine;
• a nitrile group;
• a C1-C3 haloalkyl;
• a C1-C3 thioalkyl;
• a —C(W) group;
• and an —O(W) group;
• W representing a chain consisting of from 1 to 6 glycoside(s);
• or
• (e) R8, R10 and R12 represent a hydroxyl group,
• the R9 and R11 groups, which may be identical or different, being chosen from the group comprising a hydrogen atom;
• a linear or branched, saturated or unsaturated C1-C10 hydrocarbon-based group, optionally interrupted with at least one heteroatom chosen from O, N or S;
• a halogen atom;
• a C5-C9 aryl;
• a C4-C9 heterocycle;
• a (C1-C3)alkoxy group;
• a C2-C3 acyl;
• a C1-C3 alcohol;
• a —COOH;
• —NH2;
• —CONH2;
• —CHO;
• —SH;
• —C(O)O(C2-C3) group;
• a C1-C3 amine;
• a C1-C3 imine;
• a nitrile group;
• a C1-C3 haloalkyl;
• a C1-C3 thioalkyl;
• a —C(W) group;
• and an —O(W) group;
• W representing a chain consisting of from 1 to 6 glycoside(s);
• the R1, R2 and R3 groups which do not represent a B ring of formula (VI), which may be identical or different, being chosen from the group comprising a hydrogen atom;
• a linear or branched C1-C6 alkyl;
• an —OH group;
• a C1-C3 amine;
• a —COOH group;
• —C(O)O(C2-C3);
• a —C(W) group;
• and an —O(W) group;
• W representing a chain consisting of from 1 to 6 glycoside(s);
• R1′, R2′ and R3′, which may be identical or different, being chosen from the group comprising a hydrogen atom;
• a linear or branched, saturated or unsaturated C1-C10 hydrocarbon-based group, optionally interrupted with at least one heteroatom chosen from O, N or S;
• a halogen atom;
• a C5-C9 aryl;
• a C4-C9 heterocycle;
• a (C1-C3)alkoxy group;
• a C2-C3 acyl;
• a C1-C3 alcohol;
• a —COOH;
• —NH2;
• —CONH2;
• —CHO;
• —SH;
• —C(O)O(C2-C3) group;
• a C2-C3 amine;
• a C1-C3 amine;
• a C1-C3 imine;
• a nitrile group;
• a C1-C3 haloalkyl;
• a C1-C3 thioalkyl;
• a —C(W) group;
• and an —O(W) group;
• W representing a chain consisting of from 1 to 6 glycoside(s);
• or the R1 and R1′ groups when R1 does not represent a B ring of formula (VI), or R2 and R2′ groups when R2 does not represent a B ring of formula (VI), or R3 and R3′ groups when R3 does not represent a B ring of formula (VI), together form an ═O group;
• R4, R5, R6 and R7, which may be identical or different, being chosen from the group comprising a hydrogen atom;
• a linear or branched, saturated or unsaturated C1-C10 hydrocarbon-based group, optionally interrupted with at least one heteroatom chosen from O, N or S;
• a halogen atom;
• a C5-C9 aryl;
• a C4-C9 heterocycle;
• a (C1-C3)alkoxy group;
• a C2-C3 acyl;
• a C1-C3 alcohol;
• an —OH;
• COOH;
• —NH2;
• —CONH2;
• —CHO;
• —SH;
• —C(O)O(C2-C3) group;
• a C1-C3 amine;
• a C1-C3 imine;
• a nitrile group;
• a C1-C3 haloalkyl;
• a C1-C3 thioalkyl;
• a —C(W) group;
• and an —O(W) group;
• W representing a chain consisting of from 1 to 6 glycoside(s);
• and
• (B) said glucansucrose being chosen from the group comprising:
• a sequence having at least 80% identity with the sequence SEQ ID NO:1, said sequence having an amino acid X1 representing an amino acid chosen from the group consisting of A, C, E, F, G, H, I, K, M, N, P, Q, S, T, V and Y;
• a sequence having at least 80% identity with the sequence SEQ ID NO:2, said sequence having an amino acid X2 representing an amino acid chosen from the group consisting of A, C, D, F, G, H, K, L, M, N, P, S, V and Y;
• a sequence having at least 80% identity with the sequence SEQ ID NO:3, said sequence having an amino acid X3 representing an amino acid chosen from the group consisting of A, C, G, I, K, M, N and W;
• a sequence having at least 80% identity with the sequence SEQ ID NO:4, said sequence having an amino acid X4 representing an amino acid chosen from the group consisting of C, I, N, P, V and W;
• a sequence having at least 80% identity with the sequence SEQ ID NO:5, said sequence having an amino acid X5 representing an amino acid chosen from the group consisting of A, C, D, G, I, K, L, M, R, V and W;
• a sequence having at least 80% identity with the sequence SEQ ID NO:6, said sequence having an amino acid X6 representing an amino acid chosen from the group consisting of C, G, Q, S and T;
• a sequence having at least 80% identity with the sequence SEQ ID NO:7, said sequence having an amino acid X7 representing an amino acid chosen from the group consisting of A and G;
• a sequence having at least 80% identity with SEQ ID NO:8;
• a sequence having at least 80% identity with SEQ ID NO:9, said sequence having an amino acid X9 representing an amino acid chosen from the group consisting of C, I and L;
• a sequence having at least 80% identity with SEQ ID NO:10;
• a sequence having at least 80% identity with SEQ ID NO:11;
• and
• a sequence having at least 80% identity with SEQ ID NO:12, said sequence having amino acids X9, X10, X11, X12 and X13, with:
• (i) X9 representing, independently of X10, X11, X12 and X13, an amino acid chosen from the group consisting of G, S, V, C, F, N, I, L and W;
• X10 representing, independently of X9, X11, X12 and X13, an amino acid chosen from the group consisting of L, I, H, Y and F;
• with the exception of the case where X9 represents W and X10 represents F;
• X11 representing A;
• X12 representing F;
• and
• X13 representing L;
• (ii) X9 representing W;
• X10 representing F;
• X11 representing, independently of X9, X10, X12 and X13, an amino acid chosen from the group consisting of E and A;
• X12 representing, independently of X9, X10, X11 and X13, an amino acid chosen from the group consisting of L and F;
• and
• X13 representing L;
• with the exception of the case where X11 represents A and X12 represents F;
• or
• (iii) X9 representing W;
• X10 representing F;
• X11 representing A;
• X12 representing, independently of X9, X10, X11 and X13, an amino acid chosen from the list consisting of A, R, D, N, C, E, Q, G, H, I, L, K, M, P, S, T, W, Y and V;
• and
• X13 representing, independently of X9, X10, X11 and X12, an amino acid chosen from the list consisting of A, R, D, N, C, E, Q, G, H, I, K, M, F, P, S, T, W, Y and V.