# US 2008/0187622 A1 · Method for manufacturing alpha-glycosylisoquercitrin, intermediate product and by-product thereof

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- Number: US 2008/0187622 A1
- Document ID: US20080187622A1
- Status: Published application
- Kind: A1
- Application number: 10/740,607
- Filed: 2003-12-22
- Published: 2008-08-07
- Earliest claimed: 2003-09-29
- Assignees: San-Ei Gen F.F.I., Inc.
- Inventors: Masamitsu Moriwaki; Kazuhiro Emura; Hisashi Tanaka
- Web page: https://patentgrep.com/patent/US20080187622A1

## CPC

- C12P 19/60: having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin {(C12P19/605)}
- A23L 5/41: Retaining or modifying natural colour by use of additives, e.g. optical brighteners (A23L5/42 takes precedence)
- A23L 33/105: Plant extracts, their artificial duplicates or their derivatives
- A61K 31/352: condensed with carbocyclic rings, e.g. methantheline {(cannabinoids A61K31/658)}
- A61K 31/7048: having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin {, digitoxin or digoxin}
- A61P 3/02: Nutrients, e.g. vitamins, minerals
- A61P 7/10: Antioedematous agents; Diuretics
- A61P 9/14: Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 39/06: Free radical scavengers or antioxidants
- C12P 17/06: containing a six-membered hetero ring, e.g. fluorescein
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides a method for producing isoquercitrin, α-glycosylisoquercitrin, and rhamnose, the method comprising a step of naringin-degrading enzyme treatment during the isoquercitrin production from rutin in the presence of an edible component, such as gelatin, wheat gluten, chitosan, lecithin, a glycerol fatty acid ester, xanthan gum, carrageenan, sodium chondroitin sulfate, casein, enzymatically decomposed gelatin, sodium alginate, konjac extract, gellan gum, guar gum, soybean protein, agar, pectin, yeast extract, egg-white peptide, cluster dextrin, gum arabic, arginine, sodium metaphosphate, karaya gum, locust bean gum, sodium pyrophosphate, glucosamine, chitin, sodium glutamate, dextrin, trehalose, or a grain-based food ingredients. According to the present invention, isoquercitrin and α-glycosylisoquercitrin, which are of use as antioxidants, anti-fading agents, flavor change inhibitors, etc., can be produced in enhanced yields.

## Claims

### Claim 1

A method for producing isoquercitrin comprising the steps of:
treating rutin with an enzyme having a naringin-degrading activity in the presence of at least one edible component selected from the group consisting of gelatin, wheat gluten, chitosan, lecithin, a glycerol fatty acid ester, xanthan gum, carrageenan, sodium chondroitin sulfate, casein, enzymatically decomposed gelatin, sodium alginate, konjac extract, gellan gum, guar gum, soybean protein, agar, pectin, yeast extract, egg-white peptide, cluster dextrin, gum arabic, arginine, sodium metaphosphate, karaya gum, locust bean gum, sodium pyrophosphate, glucosamine, chitin, sodium glutamate, dextrin, and trehalose; and
obtaining an isoquercitrin fraction from the matter treated above.

### Claim 2 (depends on 1)

The method for producing isoquercitrin according to claim 1, wherein the glycerol fatty acid ester is at least one member selected from the group consisting of hexaglycerol distearate, tetraglycerol monooleate, tetraglycerol monostearate, decaglycerol monooleate, and decaglycerol stearate.

### Claim 3

A method for producing isoquercitrin comprising the steps of:
treating rutin with an enzyme having a naringin-degrading activity in the presence of at least one edible component selected from kudzu starch, potato starch, and grain-based food ingredients; and
obtaining an isoquercitrin fraction from the matter treated above.

### Claim 4 (depends on 3)

The method for producing isoquercitrin according to claim 3, wherein the grain-based food ingredients are food ingredients made from grain selected from the group consisting of rice, barley, wheat, rye, triticale, oat, corn, barnyard millet, foxtail millet, sorghum, millet, Job's-tears, legumes, and buckwheat.

### Claim 5 (depends on 3)

The method for producing isoquercitrin according to claim 3, wherein the grain-based food ingredients are food ingredients made from wheat selected from the group consisting of wheat protein, wheat flour, wheat bran, and wheat germ.

### Claim 6 (depends on 1, 2, 3, 4, 5)

A method for producing α-glycosylisoquercitrin as represented by Formula (1) below:
wherein “Glc” refers to a glucose residue, and n represents an integer of 1 or more,
the method comprising treating isoquercitrin obtained according to the process recited in any of claims 1 to 5 with a glycosyltransferase.

### Claim 7 (depends on 6)

The method for producing α-glycosylisoquercitrin according to claim 6, wherein n in Formula (1) is an integer of 1 to 7.

### Claim 8

A method for producing rhamnose comprising the steps of:
treating rutin with an enzyme having a naringin-degrading activity in the presence of at least one edible component selected from the group consisting of gelatin, wheat gluten, chitosan, lecithin, a glycerol fatty acid ester, xanthan gum, carrageenan, sodium chondroitin sulfate, casein, enzymatically decomposed gelatin, sodium alginate, konjac extract, gellan gum, guar gum, soybean protein, agar, pectin, yeast extract, egg-white peptide, cluster dextrin, gum arabic, arginine, sodium metaphosphate, karaya gum, locust bean gum, sodium pyrophosphate, glucosamine, chitin, sodium glutamate, dextrin, and trehalose; and
obtaining a rhamnose fraction from the matter treated above.

### Claim 9 (depends on 8)

The method for producing rhamnose according to claim 8, wherein the glycerol fatty acid ester is at least one member selected from the group consisting of hexaglycerol distearate, tetraglycerol monooleate, tetraglycerol monostearate, decaglycerol monooleate, and decaglycerol stearate.

### Claim 10

A method for producing rhamnose comprising the steps of:
treating rutin with an enzyme having a naringin-degrading activity in the presence of at least one edible component selected from kudzu starch, potato starch, and food ingredients made from grains; and
obtaining a rhamnose fraction from the matter treated above.

### Claim 11 (depends on 10)

The method for producing rhamnose according to claim 10, wherein the food ingredients are food ingredients made from grains selected from the group consisting of rice, barley, wheat, rye, triticale, oat, corn, barnyard millet, foxtail millet, sorghum, millet, Job's-tears, legumes, and buckwheat.

### Claim 12 (depends on 10)

The method for producing rhamnose according to claim 10, wherein the food ingredients are food ingredients made from wheat selected from the group consisting of wheat protein, wheat flour, wheat bran, and wheat germ.

### Claim 13 (depends on 1, 2, 3, 4, 5)

An isoquercitrin formulation comprising as an active ingredient isoquercitrin obtained according to a process recited in any of claims 1 to 5.

### Claim 14 (depends on 6, 7)

An α-glycosylisoquercitrin formulation comprising as an active ingredient α-glycosylisoquercitrin obtained according to a process recited in claim 6 or 7.