Bioactive compounds and methods of uses thereof

• US 20060052438A1
• Filed: 04/29/2005
• Published: 03/09/2006
• Est. Priority Date: 04/30/2004
• Status: Active Grant

• Current Assignee: Rutgers University, Regents of The University of Minnesota (University of Minnesota), WellGen, Inc.
• Original Assignee: Regents of The University of Minnesota (University of Minnesota)
• Inventors: Bai, Naisheng, Dong, Zigang, Bode, Ann M., Dushenkov, Slavik, Ho, Chi-Tang
• Granted Patent: US 7,351,739 B2
• Time in Patent Office: Days
• US Class Current: 514/453
• CPC Class Codes: A61K 36/53 Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
• 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 11/06 Antiasthmatics
• CPC Class Codes: A61P 13/08 of the prostate
• CPC Class Codes: A61P 13/12 of the kidneys
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: A61P 17/06 Antipsoriatics
• CPC Class Codes: A61P 19/00 Drugs for skeletal disorders
• CPC Class Codes: A61P 19/02 for joint disorders, e.g. arthritis, arthrosis
• CPC Class Codes: A61P 19/06 Antigout agents, e.g. antihyperuricemic or uricosuric agents
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 27/02 Ophthalmic agents
• 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 31/00 Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: A61P 31/06 for tuberculosis
• CPC Class Codes: A61P 31/08 for leprosy
• CPC Class Codes: A61P 31/10 Antimycotics
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: A61P 31/14 : for RNA viruses
• CPC Class Codes: A61P 31/16 : for influenza or rhinoviruses
• CPC Class Codes: A61P 31/18 : for HIV
• CPC Class Codes: A61P 31/20 : for DNA viruses
• CPC Class Codes: A61P 31/22 : for herpes viruses
• CPC Class Codes: A61P 33/02 : Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
• CPC Class Codes: A61P 33/04 : Amoebicides
• CPC Class Codes: A61P 33/06 : Antimalarials
• CPC Class Codes: A61P 33/10 : Anthelmintics
• CPC Class Codes: A61P 33/12 : Schistosomicides
• CPC Class Codes: A61P 33/14 : Ectoparasiticides, e.g. scabicides
• CPC Class Codes: A61P 35/00 : Antineoplastic agents
• CPC Class Codes: A61P 35/02 : specific for leukemia
• CPC Class Codes: A61P 35/04 : specific for metastasis
• 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 9/00 : Drugs for disorders of the cardiovascular system
• CPC Class Codes: A61P 9/08 : Vasodilators for multiple indications
• 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: C07D 493/20 : Spiro-condensed systems

Abstract

In one aspect, the present invention provides compounds having formula I or IV as shown below: as further defined herein. In additional aspects, the present invention provides compositions and kits comprising the compounds of the invention and methods for their use, for example, for the prevention or treatment of a cancer.

Claims

1. A compound having the formula (I):

2. The compound of claim 1, wherein R¹, R², R³ and R⁴ are each independently selected from the group consisting of hydrogen, methyl, ethyl, acetyl, and propionyl.

3. The compound of claim 2, wherein R¹⁴ and R¹⁵ are methyl.

4. The compound of claim 1, wherein R⁵-R¹³ are each independently selected from the group consisting of hydrogen, methyl, and ethyl.

5. The compound of claim 1, wherein at least four of R⁵-R¹³ are hydrogen.

6. The compound of claim 1, having the formula (II):

7. The compound of claim 6, wherein the compound is rubescensin J.

17. The composition comprising a compound of claim 1, wherein said composition is prepared by a method comprising adsorbing an extract of Rabdosia rubescens to a synthetic resin comprising polyamide moieties or styrene-divinylbenzene moieties, and eluting the synthetic resin with methanol or ethanol to obtain the composition.

19. A pharmaceutical composition comprising the compound of claim 1, 7, 9, 10, 16, 17 or 18 and a pharmaceutically acceptable carrier, diluent, vehicle or excipient.

20. A nutraceutical composition comprising the compound of claim 1, 7, 9, 10, 16, 17 or 18 and a carrier, vehicle or excipient.

21. The nutraceutical composition of claim 19, which is a dietary supplement, food additive, food composition, medical food, or food for special dietary use.

22. A cosmetic composition comprising the compound of claim 1, 7, 9, 10, 16, 17 or 18 and a carrier, vehicle or excipient.

23. A method of preventing or treating a cancer, an inflammatory disorder, an infectious disease, or a symptom thereof in a subject in need thereof comprising administering to the subject an effective amount of a composition comprising the compound of claim 1, 7, 9, 10, 16, 17 or 18.

24. A method of ameliorating or lessening the discomfort associated with a cancer, an inflammatory disorder, an infectious disease, or a symptom thereof in a subject in need thereof comprising administering to the subject an effective amount of a composition comprising the compound of claim 1, 7, 9, 10, 16, 17 or 18.

8. A compound having the formula (III):

9. The compound of claim 8, wherein the compound is rubescensin O-1.

10. A compound having the formula (IV):

11. The compound of claim 10, wherein R¹-R⁴ are each independently hydrogen, methyl, ethyl, acetyl, propionyl, a monosaccharide or a disaccharide.

12. The compound of claim 10, wherein R¹-R⁴ are hydrogen.

13. The compound of claim 10, wherein R¹-R³ are hydrogen and R⁴ is a monosaccharide or a disaccharide.

14. The compound of claim 10, having the formula (V):

15. The compound of claim 14, wherein R¹, R² and R³ are hydrogen, (C₁-C₆)alkyl or (C₁-C₁₂)acyl.

16. The compound of claim 14, wherein the compound is rubescendepside.

18. The composition comprising a compound of claim 10, wherein said composition is prepared by a method comprising adsorbing an extract of Rabdosia rubescens to a synthetic resin comprising polyamide moieties or styrene-divinylbenzene moieties, and eluting the synthetic resin with methanol or ethanol to obtain the composition.