Peroxisome proliferator activated receptor ligand and process for producing the same

• US 7,888,388 B2
• Filed: 09/18/2008
• Issued: 02/15/2011
• Est. Priority Date: 10/11/2001
• Status: Active Grant

• Current Assignee: Kaneka Corporation
• Original Assignee: Kaneka Corporation
• Inventors: Kitahara, Mikio, Mimaki, Yoshihiro, Kitamura, Shiro, Sashida, Yutaka, Kuroda, Minpei, Mae, Tatsumasa, Tsukagawa, Misuzu, Nakagawa, Kaku, Ueda, Yasuyoshi
• Primary Examiner(s): Andres; Janet L.
• Assistant Examiner(s): Covington; Raymond
• Application Number:
  US12/233,069
• Publication Number:
  US 20090036519A1
• Time in Patent Office: 880 Days
• Field of Search: 514/456, 514/457
• US Class Current: 514/456
• CPC Class Codes: A23K 20/111 Aromatic compounds
• CPC Class Codes: A23K 20/121 containing oxygen or sulfur as hetero atom
• CPC Class Codes: A23K 50/00 Feeding-stuffs specially adapted for particular animals
• CPC Class Codes: A23K 50/40 for carnivorous animals, e.g. cats or dogs
• CPC Class Codes: A23L 33/10 using additives addition of substantially indigestible substances A23L33/21
• CPC Class Codes: A23L 33/105 Plant extracts, their artificial duplicates or their derivatives
• CPC Class Codes: A61K 2300/00 Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
• CPC Class Codes: A61K 31/12 Ketones
• CPC Class Codes: A61K 31/353 3,4-Dihydrobenzopyrans, e.g. chroman, catechin
• CPC Class Codes: A61K 31/37 Coumarins, e.g. psoralen
• CPC Class Codes: A61K 36/484 Glycyrrhiza (licorice)
• 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 3/04 Anorexiants; Antiobesity agents
• CPC Class Codes: A61P 3/06 Antihyperlipidemics
• CPC Class Codes: A61P 3/10 for hyperglycaemia, e.g. antidiabetics
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 37/02 Immunomodulators
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• 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
• CPC Class Codes: A61P 9/12 Antihypertensives
• CPC Class Codes: C07D 311/06 : with oxygen or sulfur atoms directly attached in position 2

Abstract

The present invention easily and efficiently provides a peroxisome proliferator-activated receptor ligand, and a composition for amelioration of insulin resistance or for prevention and/or amelioration of the insulin resistance syndrome containing the same, as an active ingredient.

The present invention relates to a peroxisome proliferator-activated receptor ligand which comprises a prenylflavonoid, a chalcone derivative exclusive of prenylflavonoids, a flavonol derivative exclusive of prenylflavonoids, and a salt, a glycoside and/or an esterified substance thereof acceptable as a pharmaceutical preparation or a food or a beverage; a composition containing the above ligand; a plant-derived extract containing the above ligand; and a process for producing the above extract.

Claims

1. A method for inhibiting or ameliorating an insulin resistance syndrome

which comprises administering a composition comprising, as an active ingredient, at least one prenylflavonoid selected from the group consisting of a 3-arylcoumarin compound, an isoflav-3-ene compound, an isoflavan compound, an isoflavanone compound, an isoflavone compound, a flavonol compound, a flavanone compound, a chalcone compound and a dibenzoylmethane compound to a subject,

wherein the prenylflavonoid has a peroxisome proliferator-activated receptor γ

ligand activity.

2. The method according to claim 1,

wherein the prenylflavonoid comprises a 3-arylcoumarin compound represented by the general formula (1):

3. The method according to claim 2,

wherein the 3-arylcoumarin compound represented by the general formula (1) is glycycoumarin or glycyrin.

4. The method according to claim 1,

wherein the prenylflavonoid comprises an isoflav-3-ene compound represented by the general formula (2):

5. The method according to claim 4,

wherein the isoflav-3-ene compound represented by the general formula (2) is dehydroglyasperin D, dehydroglyasperin C or glabrene.

6. The method according to claim 1,

wherein the prenylflavonoid comprises an isoflavan compound represented by the general formula (3):

7. The method according to claim 6,

wherein the isoflavan compound represented by the general formula (3) is glyasperin D, glabridin, hispaglabridin B, 4′

-O-methylglabridin or 3′

-hydroxy-4′

-O-methylglabridin.

8. The method according to claim 1,

wherein the prenylflavonoid comprises an isoflavanone compound represented by the general formula (4):

9. The method according to claim 8,

wherein the isoflavanone compound represented by the general formula (4) is glyasperin B or glycyrrhisoflavanone.

10. The method according to claim 1,

wherein the prenylflavonoid comprises an isoflavone compound represented by the general formula (5):

11. The method according to claim 1,

wherein the isoflavone compound represented by the general formula (5) is glyurallin B, lupiwighteone, semilicoisoflavone B or glycyrrhisoflavone.

12. The method according to claim 1,

wherein the prenylflavonoid comprises a flavonol compound represented by the general formula (6):

13. The method according to claim 12,

wherein the flavonol compound represented by the general formula (6) is isolicoflavonol, licoflavonol or topazolin.

14. The method according to claim 1,

wherein the prenylflavonoid comprises a flavanone compound represented by the general formula (7):

15. The method according to claim 14,

wherein the flavanone compound represented by the general formula (7) is glabrol.

16. The method according to claim 1,

wherein the prenylflavonoid comprises a chalcone compound represented by the general formula (8):

17. The method according to claim 16,

wherein the chalcone compound represented by the general formula (8) is licochalcone C.

18. The method according to claim 1,

wherein the prenylflavonoid comprises a dibenzoylmethane compound represented by the general formula (9):

19. The method according to claim 18,

wherein the dibenzoylmethane compound represented by the general formula (9) is glycyrdione A or glycyrdione C.

21. The method according to claim 1,

wherein the insulin resistance syndrome is at least one symptom or disease selected from the group consisting of hyperinsulinemia, diabetes mellitus, dyslipidemia, obesity, hypertension and arteriosclerosis.

22. The method according to claim 21,

wherein the symptom or disease is diabetes mellitus.

23. The method according to claim 1,

wherein the composition comprises at least one member selected from the group consisting of glycycoumarin, glycyrin, glyurallin B, dehydroglyasperin D, isolicoflavonol, dehydroglyasperin C, glyasperin B, glycyrrhisoflavanone, lupiwighteone, glyasperin D, semilicoisoflavone B, licoflavonol, topazolin, glycyrrhisoflavone, glabridin, glabrene, hispaglabridin B, 4′

-O-methylglabridin, 3′

-hydroxy-4′

-O-methylglabridin, glabrol, licochalcone C, glycyrdione A and glycyrdione C.

24. The method according to claim 1,

wherein the composition comprises at least one member selected from the group consisting of glabrene, glabridin, glabrol, 3′

-hydroxy-4′

-O-methylglabridin, 4′

-O-methylglabridin and hispaglabridin B.

20. A method for inhibiting or ameliorating inflammations or cancers

which comprises administering a composition comprising, as an active ingredient, at least one prenylflavonoid selected from the group consisting of a 3-arylcoumarin compound, an isoflav-3-ene compound, an isoflavan compound, an isoflavanone compound, an isoflavone compound, a flavonol compound, a flavanone compound, a chalcone compound and a dibenzoylmethane compound to a subject,

wherein the prenylflavonoid has a peroxisome proliferator-activated receptor γ

ligand activity.