Drugs, foods or drinks with the use of algae-derived physiologically active substances

• US 20030105029A1
• Filed: 08/27/2002
• Published: 06/05/2003
• Est. Priority Date: 11/11/1997
• Status: Active Grant

• Current Assignee: Takara Bio Incorporated (Ningbo Junsheng Investment Group Co., Ltd.)
• Original Assignee: Takara Shuzo Company Limited (Ningbo Junsheng Investment Group Co., Ltd.)
• Inventors: Sakai, Takeshi, Sagawa, Hiroaki, Kato, Ikunoshin, Enoki, Tatsuji, Koyama, Nobuto, Nishiyama, Eiji, Ikai, Katsushige, Tominaga, Takanari, Yu, Fu-Gong
• Granted Patent: US 6,911,432 B2
• Time in Patent Office: Days
• US Class Current: 514/23
• CPC Class Codes: A01N 43/04 with one hetero atom
• CPC Class Codes: A23L 3/3472 Compounds of undetermined constitution obtained from animals or plants
• CPC Class Codes: A23L 3/3544 Organic compounds containing hetero rings
• CPC Class Codes: A23L 3/3562 Sugars; Derivatives thereof
• CPC Class Codes: A23L 33/105 Plant extracts, their artificial duplicates or their derivatives
• CPC Class Codes: A61K 31/341 not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
• CPC Class Codes: A61K 31/7048 having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin , digitoxin or digoxin
• CPC Class Codes: A61P 1/00 Drugs for disorders of the alimentary tract or the digestive system
• CPC Class Codes: A61P 1/04 for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
• CPC Class Codes: A61P 1/10 Laxatives
• CPC Class Codes: A61P 11/06 Antiasthmatics
• CPC Class Codes: A61P 13/12 of the kidneys
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 19/02 for joint disorders, e.g. arthritis, arthrosis
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 25/22 Anxiolytics
• CPC Class Codes: A61P 27/02 Ophthalmic agents
• CPC Class Codes: A61P 27/16 Otologicals
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 3/10 for hyperglycaemia, e.g. antidiabetics
• CPC Class Codes: A61P 35/00 : Antineoplastic agents
• CPC Class Codes: A61P 37/00 : Drugs for immunological or allergic disorders
• CPC Class Codes: A61P 37/02 : Immunomodulators
• CPC Class Codes: A61P 37/08 : Antiallergic agents antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14
• CPC Class Codes: A61P 39/06 : Free radical scavengers or antioxidants
• CPC Class Codes: A61P 43/00 : Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 9/00 : Drugs for disorders of the cardiovascular system
• CPC Class Codes: A61P 9/02 : Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
• CPC Class Codes: A61P 9/10 : for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Abstract

Medicinal compositions for treating, ameliorating or preventing diseases with sensitivity to 3,6-anhydrogalactopyranose are represented by formula (I):

These compositions include foods, drinks, cosmetics, etc. containing as the active ingredient at least one such compound, its aldehyde, its hydrate and 2-O-methylated derivatives thereof and soluble sugar compounds containing the above compound. These compounds show an apoptosis-inducing activity, carcinostatic activity and inhibitory activities on the production of active oxygen, lipid peroxide radicals and NO, which makes them useful also as the active ingredient of antioxidants and preservatives.

Claims

1. A pharmaceutical composition which comprises as an active ingredient at least one member selected from the group consisting of:

a compound selected from the group consisting of 3,6-anhydrogalactopyranose represented by formula (I);

an aldehyde and a hydrate thereof, and 2-O-methylated derivatives of the 3,6-anhydrogalactopyranose, the aldehyde and the hydrate; and

a soluble saccharide containing the compound at its reducing end,

said composition being in the form suitable for treating or preventing a disease sensitive to the compound.

2. The pharmaceutical composition according to claim 1, wherein the saccharide is a product produced by acid decomposition under acidic conditions below pH 7 and/or enzymatic digestion of a substance containing at least one compound selected from the group consisting of 3,6-anhydrogalactopyranose represented by formula 1, an aldehyde and a hydrate thereof, and 2-O-methylated derivatives of the 3,6-anhydrogalactopyranose, the aldehyde and the hydrate.

3. The pharmaceutical composition according to claim 2, wherein the substance containing at least one compound selected from the group consisting of 3,6-anhydrogalactopyranose represented by formula (I), an aldehyde and a hydrate thereof, and 2-O-methylated derivatives of the 3,6-anhydrogalactopyranose, the aldehyde and the hydrate is at least one substance selected from the group consisting of agar, agarose and carrageenan.

4. The pharmaceutical composition according to claim 3, wherein the saccharide is at least one saccharide selected from the group consisting of agarobiose, agarotetraose, agarohexaose, agarooctaose, κ

-carabiose, and β

-D-galactopyranosyl-3,6-anhydro-2-O-methyl-L-galactose.

5. The pharmaceutical composition according to claim 1, wherein the saccharide is at least one saccharide selected from the group consisting of agarobiose, agarotetraose, agarohexaose, agarooctaose, κ

-carabiose, and β

-D-galactopyranosyl-3,6-anhydro-2-O-methyl-L-galactose.

6. The pharmaceutical composition according to claim 1, wherein the disease is a disease that requires induction of apotosis for its treatment or prevention, a carcinomatous disease, a disease that requires inhibition of active oxygen production for its treatment or prevention, a disease that requires inhibition of nitric monoxide production for its treatment or prevention or a disease that requires immunoregulation for its treatment or prevention.

7. A food or drink which comprises, which is produced by adding thereto, and/or which is produced by diluting at least one member selected from the group consisting of:

a compound selected from the group consisting of 3,6-anhydrogalactopyranose represented by the formula (I),

an aldehyde and a hydrate thereof, and 2-O-methylated derivatives of the 3,6-anhydrogalactopyranose, the aldehyde and the hydrate; and

a soluble saccharide containing the compound at its reducing end.

8. The food or drink according to claim 7, wherein the saccharide is a product,produced by acid decomposition under acidic conditions below pH 7 and/or enzymatic digestion of a substance containing at least one compound selected from the group consisting of 3,6-anhydrogalactopyranose represented by formula (I), a aldehyde and a hydrate thereof, and 2-O-methylated derivatives of the 3,6-anhydrogalactopyranose, the aldehyde and the hydrate.

9. The food or drink according to claim 8, wherein the substance containing at least one compound selected from the group consisting of 3,6-anhydrogalactopyranose represented by formula (I), an aldehyde and a hydrate thereof, and 2-O-methylated derivatives of the 3,6-anhydrogalactopyranose, the aldehyde and the hydrate is at least one substance selected from the group consisting of agar, agarose and carrageenan.

10. The food or drink according to claim 7, wherein the saccharide is at least one saccharide selected from the group consisting of agarobiose, agarotetraose, agarohexaose, agarooctaose, κ

-carabiose and β

-D-galactopyranosyl-3,6-anhydro-2-O-methyl-L-galactose.

11. An antioxidant which comprises as an active ingredient at least one member selected from the group consisting of:

a compound selected from the group consisting of 3,6-anhydrogalactopyranose represented by formula (I),

an aldehyde and a hydrate thereof, and 2-O-methylated derivatives of the 3,6-anhydrogalactopyranose, the aldehyde and the hydrate; and

a soluble saccharide containing the compound.

12. The antioxidant according to claim 11, wherein the saccharide is a product produced by acid decomposition under acidic conditions below pH 7 and/or enzymatic digestion of a substance containing at least one compound selected from the group consisting of 3,6-anhydrogalactopyranose represented by formula (I), a aldehyde and a hydrate thereof, and 2-O-methylated derivatives of the 3,6-anhydrogalactopyranose, the aldehyde and the hydrate.

13. The antioxidant according to claim 12, wherein the substance containing at least one compound selected from the group consisting of 3,6-anhydrogalactopyranose represented by formula (I), an aldehyde and a hydrate thereof, and 2-O-methylated derivatives of the 3,6-anhydrogalactopyranose, the aldehyde and the hydrate is at least one substance selected from the group consisting of agar, agarose and carrageenan.

14. The antioxidant according to claim 11, wherein the saccharide is at least one saccharide selected from the group consisting of agarobiose, agarotetraose, agarohexaose, agarooctaose, κ

-carabiose and β

-D-galactopyranosyl-3,6-anhydro-2-O-methyl-L-galactose.

15. The antioxidant according to claims 11, wherein the antioxidant is an inhibitor of active oxygen production.

16. A food or drink which comprises the antioxidant according to claims 11.

17. A saccharide for an antioxidant selected from the group consisting of:

a compound selected from the group consisting of 3,6-anhydrogalactopyranose represented by formula (I),

an aldehyde and a hydrate thereof, and 2-O-methylated derivatives of the 3,6-anhydrogalactopyranose, the aldehyde and the hydrate, and

a soluble saccharide containing the compound.

18. The saccharide for an antioxidant according to claim 17 which is at least one compound selected from the group consisting of agarobiose, agarotetraose, agarohexaose, agarooctaose, κ

-carabiose and β

-D-galactopyranosyl-3,6-anhydro-2-O-methyl-L-galactose.

19. The saccharide for an antioxidant according to claim 17 which is capable of inhibition of active oxygen production.

20. A preservative composition for keeping freshness of food and drinks which comprises as an active ingredient at least one member selected from the group consisting of:

a compound selected from the group consisting of 3,6-anhydrogalactopyranose represented by formula (I),

an aldehyde and a hydrate thereof, and 2-O-methylated derivatives of the 3,6-anhydrogalactopyranose, the aldehyde and the hydrate; and

a soluble saccharide containing the compound.

21. The preservative composition for keeping freshness of foods and drinks according to claim 20, wherein the saccharide is a product produced by acid decomposition under acidic conditions below pH 7 and/or enzymatic digestion of a substance containing at least one compound selected from the group consisting of 3,6-anhydrogalactopyranose represented by formula (I), a aldehyde and a hydrate thereof, and 2-O-methylated derivatives of the 3,6-anhydrogalactopyranose, the aldehyde and the hydrate.

22. the preservative composition for keeping freshness of foods and drinks according to claim 21, wherein the substance containing at least one compound selected from the group consisting of 3,6-anhydrogalactopyranose represented by formula (I), an aldehyde and a hydrate thereof, and 2-O-methylated derivatives of the 3,6-anhydrogalactopyranose, the aldehyde and the hydrate is at least one substance selected from the group consisting of agar, agarose and carrageenan.

23. The preservative composition for keeping freshness keeping of foods and drinks according to claim 20, wherein the saccharide is at least one saccharide selected from the group consisting of agarobiose, agarotetraose, agarohexaose, agarooctaose, κ

-carabiose and β

-D-galactopyranosyl-3,6-anhydro-2-O-methyl-L-galactose.

24. A cosmetic composition which comprises as an active ingredient at least one saccharide selected from the group consisting of agarobiose, agarotetraose, agarohexaose, agarooctaose, κ

-carabiose and β

-D-galactopyranosyl-3,6-anhydro-2-O-methyl-L-galactose.

25. An acidic food or drink which comprises, which is produced by adding thereto, and/or which is produced by diluting at least one member selected from the group consisting of:

a compound selected from the group consisting of 3,6-anhydrogalactopyranose represented by formula (I),

an aldehyde and a hydrate thereof, and 2-O-methylated derivatives of the 3,6-anhydrogalactopyranose, the aldehyde and the hydrate; and

a soluble saccharide containing the compound.

26. The acidic food or drink according to claim 25, wherein the saccharide is at least one saccharide selected from the group consisting of agarobiose, agarotetraose, agarohexaose, agarooctaose, κ

-carabiose and β

-D-galactopyranosyl-3,6-anhydro-2-O-methyl-L-galactose.

27. A method for induction of apoptosis, inhibition of cancer, inhibition of active oxygen production, inhibition of lipid peroxide radical production, inhibition of NO production or immunoregulation, comprising

administering to a patient in need thereof an amount sufficient therefor of a compound selected from the group consisting of 3,6-anhydrogalactopyranose of formula (I),

an aldehyde and a hydrate thereof, and 2-O-methylated derivatives of the 3,6-anhydrogalactopyranose, the aldehyde and the hydrate;

and

a soluble saccharide containing the compound.

28. In a method for preserving freshness of foods and drinks comprising adding an antioxidant or a preservative to a food or drink, the improvement

wherein said antioxidant or preservative is a compound selected from the group consisting of 3,6-anhydrogalactopyranose represented by formula (I),

an aldehyde and a hydrate thereof, and 2-O-methylated derivatives of the 3,6-anhydrogalactopyranose, the aldehyde and the hydrate;

and

a soluble saccharide containing the compound.

29. In a method of inhibiting spoilage of a cosmetic composition, comprising adding a spoilage inhibitor to said cosmetic composition, the improvement wherein

said spoilage inhibitor is at least one saccharide selected from the group consisting of agarobiose, agarotetraose, agarohexaose, agarooctaose, κ

-carabiose and β

-D-galactopyranosyl-3,6-anhydro-2-O-methyl-L-galactose in preparation of a cosmetic composition.