US2018214387A1PendingUtilityA1
Aqueous solution comprising a polyphenol
Est. expiryJul 20, 2035(~8.9 yrs left)· nominal 20-yr term from priority
Inventors:Guido Grentzmann
A61K 47/36A61K 9/08A61P 13/12A61K 47/26A61M 1/287A61K 31/05
44
PatentIndex Score
0
Cited by
0
References
0
Claims
Abstract
Aqueous solution, comprising, in dissolved state,—at least one stilbenoid—at least one saccharide, and method for increasing the solubility of a stilbenoid in water
Claims
exact text as granted — not AI-modified1 .- 19 . (canceled)
20 . A method for increasing the solubility of a stilbenoid in water, comprising:
dissolving at least one reducing alpha-glucan in a total concentration of ≥0.75% by weight (7.5 g/L) in the water, dissolving the stilbenoid in the water, wherein the concentration of the stilbenoid is ≥1.5 mg/L, wherein the resveratrol derivative is selected from following compounds 1-12, 15, 16, 17, 18:
wherein in compound 2 and compound 3
R1=R2=R4=OH, R3=R5=R6=H; or
R1=R2=R4=OCH3, R3=R5=R6=H; or
R1=R2=R4=OCH3, R3=R5=H; R6=OH; or
R1=R2=R3=R5=OCH3, R4=R6=H; or
R1=R2=R3=R5=OCH3, R4=H, R6=OH; or
R1=R2=R3=R4=OCH3, R5=R6=H; or
R1=R2=R3=R4=OCH3, R5=H, R6=OH.
wherein in compound 4 R is one of the following moieties;
wherein in compound 5
R1 is hydrogen or a group of formula
R2 is hydrogen or forms together with the oxygen to which it is bound an acyl group (—OCO—R3), wherein R3 is a C1-C22 alkyl group or a C2-C22 alkenyl group, wherein, if R2 is hydrogen R1 forms a group of above-shown formula,
wherein in compound 6, R is one of the following moieties:
wherein in compound 8
R1=OCH3, R2=OH, R3=O-Glucose; or
R1=OCH3, R2=H, R3=O-Glucose; or
R1=OCH3, R2=OH, R3=OH; or
R1=OCH3, R2=H, R3=OH; or
R1=OH, R2=OH, R3=O-Glucose; or
R1=OH, R2=OH, R3=OH;
wherein in compound 12
R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 are independently chosen from hydrogen, hydroxyl, hydrocarbyl, substituted hydrocarbyl, hydrocarbyloxy, substituted hydrocarbyloxy, and sulfoxy; provided that at least one of the R groups is a hydroxyl or substituted hydroxyl group; and provided that if compound 12 is monomeric, then compound 12 is other than resveratrol,
wherein in compound 15
R1, R2 and R3, independently from one another, represent H or (C1-C3)alkyl; R4 and R5 are identical or different and represent hydrogen, linear or branched (C1-C5)alkyl,
a prenyl group —CH2-CH═C(CH3)2, a geranyl group —CH2-CH═C(CH3)(CH2)2CH═C(CH3)2
or R4 and R1, and independently R5 and R2, together with the atoms they are linked to, form one of the following groups:
with the provisos that R4 and R5 are not both hydrogen and that when R1=R2=R3=H, R4 and R5 are not a prenyl group and hydrogen, respectively,
wherein in compound 18 X, Y, and Z are either hydrogen or a protective group, provided that at least one of X, Y, and Z is the protective group;
and
wherein the stilbenoid is selected from the group consisting of resveratrol, a resveratrol derivative, piceatannol, pterostilbene and dihydro-resveratrol.
21 . The method according to claim 20 , wherein the reducing alpha-glucan is a disaccharide, an oligosaccharide or a polysaccharide, wherein an oligo- or polysaccharide comprises up to 2500 monosaccharide units, or a mixture of different mono-, di-, oligo- and/or poly-saccharides.
22 . The method according to claim 20 , wherein the reducing alpha-glucan is selected from maltose, maltotriose, isomaltotriose and maltoteraose, nigerose, Isomaltose, melibiose, maltodextrin, icodextrin, an oligomer or a polymer that can be obtained by limited hydrolysis of a linear or branched glucan, such as starch, amylose, amylopectin, glycogen, dextran, pullulan, or a mixture of two or more thereof.
23 . The method according to claim 20 , wherein the reducing alpha-glucan is icodextrin.
24 . The method according to claim 20 , wherein the at least one reducing alpha-glucan is present in a total concentration of ≥2.4% by weight.
25 . The method according to claim 20 , wherein the at least one reducing alpha-glucan is present in a total concentration of 2.0-15% by weight.
26 . The method according to claim 20 , wherein the at least one reducing alpha-glucan has a molecular weight of 90 D to 1.5 kD.
27 . The method according to claim 20 , wherein the at least one reducing alpha-glucan has a molecular weight of 1.5 kD to 50 kD.
28 . The method according to claim 20 , having an acidic pH between 1 and 6.
29 . An aqueous solution, comprising, in dissolved state, at least one stilbenoid and at least one saccharide,
for use in peritoneal dialysis, in parenteral nutrition, in treatment of peritoneal disease or disorders, and in peritoneal treatment before, during or after surgery.
30 . An aqueous solution, according to claim 29 , wherein the stilbenoid is resveratrol, dihydro resveratrol, piceatannol, pterostilbene, piceid, or a resveratrol derivative which is selected from following compounds 1-12, 15, 16, 17, 18:
wherein in compound 2 and compound 3
R1=R2=R4=OH, R3=R5=R6=H; or
R1=R2=R4=OCH3, R3=R5=R6=H; or
R1=R2=R4=OCH3, R3=R5=H; R6=OH; or
R1=R2=R3=R5=OCH3, R4=R6=H; or
R1=R2=R3=R5=OCH3, R4=H, R6=OH; or
R1=R2=R3=R4=OCH3, R5=R6=H; or
R1=R2=R3=R4=OCH3, R5=H, R6=OH.
wherein in compound 4 R is one of the following moieties:
wherein in compound 5
R1 is hydrogen or a group of formula
R2 is hydrogen or forms together with the oxygen to which it is bound an acyl group (—OCO—R3), wherein R3 is a C1-C22 alkyl group or a C2-C22 alkenyl group, wherein, if R2 is hydrogen R1 forms a group of above-shown formula,
wherein in compound 6, R is one of the following moieties:
wherein in compound 8
R1=OCH3, R2=OH, R3=O-Glucose; or
R1=OCH3, R2=H, R3=O-Glucose; or
R1=OCH3, R2=OH, R3=OH; or
R1=OCH3, R2=H, R3=OH; or
R1=OH, R2=OH, R3=O-Glucose; or
R1=OH, R2=OH, R3=OH;
wherein in compound 12
R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 are independently chosen from hydrogen, hydroxyl, hydrocarbyl, substituted hydrocarbyl, hydrocarbyloxy, substituted hydrocarbyloxy, and sulfoxy; provided that at least one of the R groups is a hydroxyl or substituted hydroxyl group; and provided that if compound 12 is monomeric, then compound 12 is other than resveratrol,
wherein in compound 15
R1, R2 and R3, independently from one another, represent H or (C1-C3)alkyl; R4 and R5 are identical or different and represent hydrogen, linear or branched (C1-C5)alkyl,
a prenyl group —CH2-CH═C(CH3)2, a geranyl group —CH2-CH═C(CH3)(CH2)2CH═C(CH3)2
or R4 and R1, and independently R5 and R2, together with the atoms they are linked to, form one of the following groups:
with the provisos that R4 and R5 are not both hydrogen and that when R1=R2=R3=H, R4 and R5 are not a prenyl group and hydrogen, respectively,
wherein in compound 18 X, Y, and Z are either hydrogen or a protective group, provided that at least one of X, Y, and Z is the protective group.
31 . An aqueous solution, according to claim 29 , wherein the saccharide is a monosaccharide, a disaccharide, an oligosaccharide or a polysaccharide, wherein an oligo- or polysaccharide comprises up to 2500 monosaccharide units, or a mixture of different mono-, di-, oligo- and/or poly-saccharides.
32 . An aqueous solution, according to claim 29 , wherein the saccharide is a glucan, preferably a reducing alpha-glucan.
33 . An aqueous solution, according to claim 32 , wherein the glucan is selected from sucrose, maltose, maltotriose, isomaltotriose and maltoteraose, nigerose, isomaltose, gentiobiose, melibiose, maltodextrin, icodextrin, an oligomer or a polymer that can be obtained by limited hydrolysis of a linear or branched glucan, such as starch, amylose, amylopectin, glycogen, dextran, pullulan, or a mixture of two or more thereof.
34 . An aqueous solution, according to claim 29 , wherein the saccharide is selected from glucose, fructose, sucrose, maltose, a homo-oligomer thereof, a hetero-oligomer thereof, or a mixture of two or more thereof.
35 . An aqueous solution, according to claim 29 , wherein the at least one stilbenoid is present in a concentration of 0.1 mg/L to 100 mg/L.
36 . An aqueous solution, according to claim 29 , wherein the at least one stilbenoid is present in a concentration of 0.02 μM to 315 μM.
37 . An aqueous solution, according to claim 29 , wherein the at least one stilbenoid is present in a concentration of ≥1.5 mg/L.
38 . An aqueous solution, according to claim 29 , wherein the stilbenoid has a structure of the formula 100,
wherein R 4 is
wherein R 1 , R 2 , R 3 , R 11 , R 12 , R 13 , R 14 , and R 15 are —H, —OH, —O—R Alk , —CHO, —CR Alk O, —COOH, —COO—R Alk , —CO—NH—C n H 2n —COOH, —CO—NH—C n H 2n —COO − ,
—CN, —Cl, —Br, —I, —NO 2 ,
—C n H 2n CN, —C n H 2n —Cl, —C n H 2n —Br, —C n H 2n —I, —C n H 2n —NO 2 ,
—O—PO 3 2− , —O—PO 3 H − , —O—PO 3 H 2 , —NH2, —NHR Alk , —NR Alk1 R Alk2 , —N + H3, —N + H2R Alk , —N + HR Alk1 R Alk2 , —N + R Alk1 R Alk2 R Alk3 ,
—CN, —B(OH) 2 , —OCHO, —O—CR Alk O, —OCF 3 , —O—CN, —OCH 2 CN,
or one of the following moieties:
and/or where R Alk , R Alk1 and Ralk2 may be CH 3 , C 2 H 5 , C 3 H 7 or C 4 H 9 ,
and/or where C n H 2n may be CH 2 , O 2 H 4 , O 3 H 6 , C 4 H 8 ,
and/or where R11, R12, R13, R14 or R15 may be a mono or oligo saccharide,
and/or where X − maybe a free soluble cation,
with the proviso that at least one of R 1 , R 2 , R 3 , R 11 , R 12 , R 13 , R 14 , and R 15 , preferably at least two thereof, is a hydroxyl group.
39 . An aqueous solution, comprising, in dissolved state
at least one reducing alpha-glucan in a total concentration of ≥0.75% by weight (7.5 g/L), a stilbenoid which is selected from resveratrol, a resveratrol derivative, piceatannol, pterostilbene or dihydro-resveratrol, in a concentration of ≥1.5 mg/L
40 . A food comprising a food additive, the food additive comprising, in dissolved state:
at least one reducing alpha-glucan in a total concentration of ≥20.75% by weight (7.5 g/L), a stilbenoid which is selected from resveratrol, a resveratrol derivative, piceatannol, pterostilbene, piceid or dihydro-resveratrol, in a concentration of ≥1.5 mg/L wherein the resveratrol derivative is selected from following compounds 1-12, 15, 16, 17, 18:
wherein in compound 2 and compound 3
R1=R2=R4=OH, R3=R5=R6=H; or
R1=R2=R4=OCH3, R3=R5=R6=H; or
R1=R2=R4=0CH3, R3=R5=H; R6=OH; or
R1=R2=R3=R5=OCH3, R4=R6=H; or
R1=R2=R3=R5=OCH3, R4=H, R6=OH; or
R1=R2=R3=R4=OCH3, R5=R6=H; or
R1=R2=R3=R4=OCH3, R5=H, R6=OH.
wherein in compound 4 R is one of the following moieties:
wherein in compound 5
R1 is hydrogen or a group of formula
R2 is hydrogen or forms together with the oxygen to which it is bound an acyl group (—OCO—R3), wherein R3 is a C1-C22 alkyl group or a C2-C22 alkenyl group,
wherein, if R2 is hydrogen R1 forms a group of above-shown formula,
wherein in compound 6, R is one of the following moieties:
wherein in compound 8
R1=OCH3, R2=OH, R3=O-Glucose; or
R1=OCH3, R2=H, R3=O-Glucose; or
R1=OCH3, R2=OH, R3=OH; or
R1=OCH3, R2=H, R3=OH; or
R1=OH, R2=OH, R3=O-Glucose; or
R1=OH, R2=OH, R3=OH;
wherein in compound 12
R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 are independently chosen from hydrogen, hydroxyl, hydrocarbyl, substituted hydrocarbyl, hydrocarbyloxy, substituted hydrocarbyloxy, and sulfoxy; provided that at least one of the R groups is a hydroxyl or substituted hydroxyl group; and provided that if compound 12 is monomeric, then compound 12 is other than resveratrol,
wherein in compound 15
R1, R2 and R3, independently from one another, represent H or (C1-C3)alkyl; R4 and R5 are identical or different and represent hydrogen, linear or branched (C1-C5)alkyl,
a prenyl group —CH2-CH═C(CH3)2, a geranyl group —CH2-CH═C(CH3)(CH2)2CH═C(CH3)2
or R4 and R1, and independently R5 and R2, together with the atoms they are linked to, form one of the following groups:
with the provisos that R4 and R5 are not both hydrogen and that when R1=R2=R3=H, R4 and R5 are not a prenyl group and hydrogen, respectively,
wherein in compound 18 X, Y, and Z are either hydrogen or a protective group, provided that at least one of X, Y, and Z is the protective group.
41 . The food of claim 40 , wherein the use is for increasing the content of resveratrol, a resveratrol derivative, piceatannol, pterostilbene or dihydro-resveratrol in the food.
42 . A water based food comprising:
water; and a reducing alpha-glucan for solubilization and stabilization of resveratrol, a resveratrol derivative, piceatannol, pterostilbene or dihydro-resveratrol in the water based food, wherein the resveratrol derivative is selected from following compounds 1-12, 15, 16, 17, 18:
wherein in compound 2 and compound 3
R1=R2=R4=OH, R3=R5=R6=H; or
R1=R2=R4=OCH3, R3=R5=R6=H; or
R1=R2=R4=OCH3, R3=R5=H; R6=OH; or
R1=R2=R3=R5=OCH3, R4=R6=H; or
R1=R2=R3=R5=OCH3, R4=H, R6=OH; or
R1=R2=R3=R4=OCH3, R5=R6=H; or
R1=R2=R3=R4=OCH3, R5=H, R6=OH.
wherein in compound 4 R is one of the following moieties;
wherein in compound 5
R1 is hydrogen or a group of formula
R2 is hydrogen or forms together with the oxygen to which it is bound an acyl group (—OCO—R3), wherein R3 is a C1-C22 alkyl group or a C2-C22 alkenyl group, wherein, if R2 is hydrogen R1 forms a group of above-shown formula,
wherein in compound 6, R is one of the following moieties:
wherein in compound 8
R1=OCH3, R2=OH, R3=O-Glucose; or
R1=OCH3, R2=H, R3=O-Glucose; or
R1=OCH3, R2=OH, R3=OH; or
R1=OCH3, R2=H, R3=OH; or
R1=OH, R2=OH, R3=O-Glucose; or
R1=OH, R2=OH, R3=OH;
wherein in compound 12
R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 are independently chosen from hydrogen, hydroxyl, hydrocarbyl, substituted hydrocarbyl, hydrocarbyloxy, substituted hydrocarbyloxy, and sulfoxy; provided that at least one of the R groups is a hydroxyl or substituted hydroxyl group; and provided that if compound 12 is monomeric, then compound 12 is other than resveratrol,
wherein in compound 15
R1, R2 and R3, independently from one another, represent H or (C1-C3)alkyl; R4 and R5 are identical or different and represent hydrogen, linear or branched (C1-C5)alkyl,
a prenyl group —CH2-CH═C(CH3)2, a geranyl group —CH2-CH═C(CH3)(CH2)2CH═C(CH3)2
or R4 and R1, and independently R5 and R2, together with the atoms they are linked to, form one of the following groups:
with the provisos that R4 and R5 are not both hydrogen and that when R1=R2=R3=H, R4 and R5 are not a prenyl group and hydrogen, respectively,
wherein in compound 18 X, Y, and Z are either hydrogen or a protective group, provided that at least one of X, Y, and Z is the protective group.
43 . The water-based food of claim 42 , wherein the reducing alpha-glucan is selected from the group consisting of maltose, maltotriose, isomaltotriose, maltoteraose, maltodextrin, icodextrin, an oligomer or a polymer that can be obtained by limited hydrolysis of a linear or branched glucan, such as starch, amylose, amylopectin, glycogen, dextran, pullulan, or a mixture of two or more thereof.Join the waitlist — get patent alerts
Track US2018214387A1 — get alerts on status changes and closely related new filings.
We store only your email — no account needed. See our privacy policy.