Compositions and products containing s-equol, and methods for their making

Abstract

A composition for use in making commercial food and skin products comprising 5-equol or mixtures, including both a non-racemic mixture and a racemic mixture, of S-equol and R-equol. The composition can be used to make articles of commerce such as food supplements, pharmaceuticals, and medicaments. The compositions are useful in a method of delivering S-equol to a mammal to prevent or treat a disease or associated condition, including hormone-dependent diseases or conditions such as cardiovascular disease, lipid disorder, osteopenia, osteoporosis, liver disease, and acute ovarian estrogen deficiency. The S-equol enantiomer can be produced in a biological synthesis from the metabolism of an isoflavone by an organism.

What is claimed is: 
     
         1 . A method of preventing or treating benign prostatic hyperplasia in a mammal, comprising administering to the mammal the S-enantiomer of equol (S-equol). 
     
     
         2 . The method of  claim 1 , wherein the method comprises administering a pharmaceutical composition consisting essentially of S-equol and a pharmaceutically acceptable adjuvant, carrier, or excipient. 
     
     
         3 . The method of  claim 2 , wherein the S-Equol has an enantiomeric purity of 90% minimum enantiomeric excess (EE). 
     
     
         4 . The method of  claim 3 , wherein the S-Equol has an enantiomeric purity of 96% minimum enantiomeric excess (EE). 
     
     
         5 . The method of  claim 4 , wherein the S-Equol has an enantiomeric purity of 98% minimum enantiomeric excess (EE). 
     
     
         6 . The method of  claim 1 , wherein the method comprises administering the S-equol in a pharmaceutical composition comprising enantiomerically pure S-equol as an active agent and a pharmaceutically acceptable adjuvant, carrier, or excipient. 
     
     
         7 . The method of  claim 6 , wherein the S-equol has an enantiomeric purity of 90% minimum enantiomeric excess (EE). 
     
     
         8 . The method of  claim 7 , wherein the S-equol has an enantiomeric purity of 96% minimum enantiomeric excess (EE). 
     
     
         9 . The method of  claim 8 , wherein the S-equol has an enantiomeric purity of 98% minimum enantiomeric excess (EE). 
     
     
         10 . The method of  claim 1 , wherein the S-equol is administered in an amount sufficient to produce a transient level of S-equol in the blood plasma of the mammal of at least 5 ng/mL. 
     
     
         11 . The method of  claim 1 , wherein the S-equol is conjugated at the C-4′ or C-7 position to form a conjugate selected from the group consisting of glucuronide, sulfate, acetate, propionate, glucoside, acetyl-glucoside, malonyl-glucoside, and mixtures thereof. 
     
     
         12 . The method of  claim 2 , wherein the composition is administered to the mammal orally. 
     
     
         13 . The method of  claim 1 , wherein the S-equol is administered in an amount sufficient to reduce the level of lipids in the blood or serum. 
     
     
         14 . The method of  claim 1 , wherein the S-equol is administered in a food or food additive. 
     
     
         15 . The method of  claim 14 , wherein the S-Equol has an enantiomeric purity of 90% minimum enantiomeric excess (EE). 
     
     
         16 . The method of  claim 13 , wherein the S-Equol has an enantiomeric purity of 96% minimum enantiomeric excess (EE). 
     
     
         17 . The method of  claim 16 , wherein the S-Equol has an enantiomeric purity of 98% minimum enantiomeric excess (EE). 
     
     
         18 . The method of  claim 1 , wherein the S-equol is administered by oral, rectal, optical, buccal, parenteral, topical, or transdermal administration. 
     
     
         19 . The method of  claim 12 , wherein the composition is administered to the mammal in a dose amount of at least about 1 mg S-equol. 
     
     
         20 . The method of  claim 1 , wherein the method comprises administering the S-equol in a pharmaceutical composition comprising a therapeutically effective amount of S-equol and a pharmaceutically acceptable adjuvant, carrier, or excipient, wherein said composition is substantially free of R-equol. 
     
     
         21 . The method of  claim 6 , wherein the composition is administered to the mammal orally. 
     
     
         22 . The method of  claim 21 , wherein the composition is administered to the mammal in a dose amount of at least about 1 mg S-equol. 
     
     
         23 . The method of  claim 1 , wherein the S-equol is present in a composition comprising S-equol and R-equol at a ratio of S-equol to R-equol of greater than 50:50. 
     
     
         24 . The method of  claim 12 , wherein the composition is formulated as a unit dose. 
     
     
         25 . The method of  claim 24 , wherein the unit dose is selected from the group consisting of a tablet, a capsule, a lozenge, and a cachet. 
     
     
         26 . The method of  claim 21 , wherein the composition is formulated as a unit dose. 
     
     
         27 . The method of  claim 26 , wherein the unit dose is selected from the group consisting of a tablet, a capsule, a lozenge, and a cachet.