Ursolic acid morpholine and diethanolamine salts

Abstract

The invention provides diethanolamine and morpholine salts of ursolic acid. Compositions containing the salts, and methods of using the salts are also provided.

1 . An ursolic acid salt selected from ursolic acid diethanolamine salt and ursolic acid morpholine salt. 
     
     
         2 . The ursolic acid salt according to  claim 1 , wherein the salt is ursolic acid diethanolamine salt of formula 
       
         
           
           
               
               
           
         
       
     
     
         3 . The ursolic acid salt according to  claim 1 , wherein the salt is ursolic acid morpholine salt of formula 
       
         
           
           
               
               
           
         
       
     
     
         4 . A composition comprising a salt according to  claim 2 , and a further agent. 
     
     
         5 . The composition according to  claim 4 , comprising 25 to 1,500 mg of the salt. 
     
     
         6 . The composition according to  claim 4 , comprising 50 to 1,000 mg of the salt. 
     
     
         7 . A composition comprising a salt according to  claim 3 , and a further agent. 
     
     
         8 . The composition according to  claim 7 , comprising 25 to 1,500 mg of the salt. 
     
     
         9 . The composition according to  claim 7 , comprising 50 to 1,000 mg of the salt. 
     
     
         10 . The composition according to  claim 4 , wherein the further agent comprises a physiologically acceptable carrier. 
     
     
         11 . The composition according to  claim 7 , wherein the further agent comprises a physiologically acceptable carrier. 
     
     
         12 . The composition according to  claim 4 , wherein the composition is a pharmaceutical composition, nutraceutical composition, food composition, or dietary supplement. 
     
     
         13 . The composition according to  claim 7 , wherein the composition is a pharmaceutical composition, nutraceutical composition, food composition, or dietary supplement. 
     
     
         14 . The composition according to  claim 12 , comprising 25 to 1,500 mg of the salt. 
     
     
         15 . The composition according to  claim 13 , comprising 25 to 1,500 mg of the salt. 
     
     
         16 . A method for:
 (i) increasing skeletal muscle mass;   (ii) treating skeletal muscle atrophy;   (iii) treating sarcopenia;   (iv) treating cachexia;   (v) increasing strength;   (vi) treating weakness;   (vii) increasing exercise capacity;   (viii) treating fatigue;   (ix) promoting muscle growth;   (x) promoting normal muscle function;   (xi) improving muscle function;   (xii) promoting muscle health;   (xiii) promoting healthy aging in muscles;   (xiv) increasing energy expenditure;   (xv) increasing the ratio of skeletal muscle to fat;   (xvi) reducing fat;   (xvii) treating obesity;   (xviii) treating diabetes;   (xix) lowering blood glucose;   (xx) treating pre-diabetes;   (xxi) treating metabolic syndrome;   (xxii) treating insulin resistance;   (xxiii) reducing plasma cholesterol;   (xxiv) treating hypercholesterolemia;   (xxv) reducing plasma triglycerides;   (xxvi) treating hypertriglyceridemia;   (xxvii) promoting healthy metabolism;   (xxviii) promoting metabolic health;   (xxix) treating hypertension;   (xxx) treating atherosclerosis   (xxxi) treating myocardial ischemia;   (xxxii) treating myocardial infarction;   (xxxiii) treating cardiomyopathy;   (xxxiv) treating cardiac arrhythmia;   (xxxv) treating non-alcoholic fatty liver disease (NAFLD);   (xxxvi) treating liver fibrosis;   (xxxvii) treating liver injury;   (xxxviii) treating lung injury;   (xxxix) treating gastric ulcers;   (xl) treating nephropathy;   (xli) promoting bone formation;   (xlii) promoting normal bone structure;   (xliii) promoting bone health;   (xliv) treating osteoporosis;   (xlv) treating cerebral ischemia;   (xlvi) treating cerebral hemorrhage;   (xlvii) treating stroke;   (xlviii) treating traumatic brain injury;   (xlix) treating dementia;   (l) treating Alzheimer's disease;   (li) treating memory loss;   (lii) treating cognitive dysfunction;   (liii) promoting normal cognitive function;   (liv) treating anxiety;   (lv) treating depression;   (lvi) reducing inflammation;   (lvii) treating arthritis;   (lviii) treating skin ulcers;   (lix) treating skin wounds;   (lx) promoting wound healing;   (lxi) treating skin dryness;   (lxii) treating skin roughness;   (lxiii) treating skin scarring;   (lxiv) treating skin wrinkles;   (lxv) reducing unwanted effects of aging;   (lxvi) treating cancer;   (lxvii) reducing tumor growth;   (lxviii) treating tumor metastasis;   (lxix) treating tumor angiogenesis;   (lxx) increasing tumor cell apoptosis;   (lxxi) decreasing protein oxidation;   (lxxii) decreasing lipid oxidation;   (lxxiii) decreasing DNA oxidation;   (lxxiv) decreasing RNA oxidation;   (lxxv) decreasing oxidation of cellular molecules;   (lxxvi) decreasing DNA damage;   (lxxvii) treating bacterial infection;   (lxxviii) reducing bacterial growth;   (lxxix) treating fungal infection;   (lxxx) reducing fungal growth;   (lxxxi) treating viral infection;   (lxxxii) treating protozoal infection;   (lxxxiii) treating nematode infection; or   (lxxxiv) treating a disease state, condition, or disorder mediated by activating transcription factor 4 (ATF4),   
       in a subject, the method comprising administering to the subject an effective amount of a salt according to  claim 1 . 
     
     
         17 . The method according to  claim 16 , wherein the salt is ursolic acid morpholine salt. 
     
     
         18 . The method according to  claim 16 , comprising administering to the subject a composition that comprises 25 to 1,500 mg of the salt. 
     
     
         19 . The method according to  claim 18 , wherein the subject is a human, non-human primate, horse, pig, rabbit, dog, sheep, goat, cow, cat, guinea pig, hamster, ferret, fish, bird, or rodent. 
     
     
         20 . The method according to  claim 16 , wherein the subject has not been diagnosed with diabetes or cancer.