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OwnerBernadette Geers, Ralf Otto +4inventors
InventorsBernadette Geers, Ralf Otto, Albrecht Weiss, Dirk Petersohn, Klaus Rudolf Schroeder, Kordula Schlotmann
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The invention relates to flavone and isoflavone glycoside derivatives of general formula (I): [A1-C(═O)O]m—[X—O-Z]-[O—C(═O)-A2]n (I), wherein [X—O-Z] represents a flavone or isoflavone glycoside structure, wherein X represents a flavone or isoflavone parent substance of formula (IIa) or (IIb), said (iso)flavone parent substance being mono- or multisubstituted and/or mono- or multireduced (hydrogenated), wherein Z (sugar) represents a mono-, di- or polysaccharide which is acetally bonded to the radical X and is ester-substituted with A2 n-times, [A1-C(═O)] representing an acyl radical on the flavone or isoflavone parent substance, wherein A1 and A2, independently of each other, represent a polyunsaturated C15-C25-alkenyl radical with at least 4 isolated and/or at least 2 conjugated double bonds or an arylaliphatic radical with 1-4 methylene groups between the ester group and the aromatic ring, wherein [C(═O)A2] represents an acyl radical on the sugar Z, wherein n is a whole number (1, 2, 3, . . . ) but not 0, wherein m is a whole number including 0 (0, 1, 2, 3, . . . ) and wherein R1, R2 and R3 represent hydroxyl groups or hydrogen atoms.
Flavone and isoflavone glycoside derivatives corresponding to general formula (I):
The derivatives claimed in any of the preceding claims, characterized in that the (iso)flavone glycoside parent substance X—O-Z is naringin corresponding to formula (III):
The derivatives claimed in any of the preceding claims, characterized in that X—O-Z is naringin corresponding to formula (III);
A process for the production of the derivatives of formula (I) claimed in any of the preceding claims, characterized in that an acetal X—O-Z from sugar and (iso)flavone parent substance, this (iso)flavone parent substance being present in the form of the pure substance or as a mixture of plant extracts of various origins, is esterified or transesterified with a polyunsaturated fatty acid containing at least four isolated double bonds or at least two conjugated double bonds, with an arylaliphatic carboxylic acid, with an ester of these carboxylic acids or with an activated fatty acid derivative in the presence of one or more enzymes as catalysts.
Dependencies are inferred from the claim text.