Extract, consumable product and method for enriching bioactive metabolite in an extract

Abstract

This disclosure relates to methods and compositions with enhanced levels of one or more tyramine containing hydroxycinnamic acid amides. Also disclosed herein are methods for producing a consumable product with enhanced levels of a tyramine containing hydroxycinnamic acid amide. Some embodiments relate to a composition enriched with a tyramine containing hydroxycinnamic acid.

What is claimed is: 
     
         1 . A method for producing a consumable product with enhanced levels of a tyramine containing hydroxycinnamic acid amide, comprising:
 (a) subjecting a plant for producing a compound of Formula Ito an enzymatic material,   
       
         
           
           
               
               
           
         
       
       wherein
 R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9  are each independently selected from hydrogen, deuterium, hydroxyl, halogen, cyano, nitro, optionally substituted amino, optionally substituted C-amido, optionally substituted N-amido, optionally substituted ester, optionally substituted —(O)C 1-6 alkyl, optionally substituted —(O)C 1-6 alkenyl, optionally substituted —(O)C 1-6 alkynl, optionally substituted, —(O)C 4-12 cycloalkyl, optionally substituted —(O)C 1-6 alkylC 4-12 cycloalkyl, optionally substituted —(O)C 4-12 heterocyclyl, optionally substituted —(O)C 1-6 alkylC 4-12 heterocyclyl, optionally substituted —(O)C 4-12 aryl, optionally substituted —(O)C 1-6 alkylC 5-12 aryl, optionally substituted —(O)C 1-12 heteroaryl, and optionally substituted —(O)C 1-6 alkylC 1-12 heteroaryl; the dashed bond is present or absent; 
 X is CH 2  or O; 
 Z is CHR a , NR a , or O; and 
 R a  is selected from hydrogen, deuterium, hydroxyl, halogen, cyano, nitro, optionally substituted amino, optionally substituted C-amido, optionally substituted N-amido, optionally substituted ester, optionally substituted —(O)C 1-6 alkyl, optionally substituted —(O)C 1-6 alkenyl, optionally substituted —(O)C 1-6 alkynl, optionally substituted, —(O)C 4-12 cycloalkyl, optionally substituted —(O)C 1-6 alkylC 4-12 cycloalkyl, optionally substituted —(O)C 4-12 heterocyclyl, optionally substituted —(O)C 1-6 alkylC 4-12 heterocyclyl, optionally substituted —(O)C 4-12 aryl, optionally substituted —(O)C 1-6 alkylC 5-12 aryl, optionally substituted —(O)C 1-12 heteroaryl, and optionally substituted —(O)C 1-6 alkylC 1-12 heteroaryl, 
 the dashed bond is present or absent; and 
 (b) incorporating the plant or extract into a consumable product. 
 
     
     
         2 . The method of  claim 1 , further comprising recovering an extract from the plant. 
     
     
         3 . The method of  claim 1 , further comprising contacting the plant with a precursor of a tyramine containing hydroxycinnamic acid amide. 
     
     
         4 . The method of  claim 1 , wherein the plant is selected from at least one of  Tribulus terrestris, Annona montana, Annona muricata, Annona cherimola, Annona atemoya, Solanum tuberosum, Cannabis sativa, Lycium barbarum, Allium sativum, Solanum lycopersicum, Capsicum annuum, Capsicum frutescens, Solanum tuberosum, Annona  spp.  Lycium barbarum, Ipomoea batatas, Zea Mays, Piper nigrum, Dysphania ambrosioides, Hibiscus sabdariffa, Piper auritum, Solanum lycopersicum , or  Allium fistulosum.    
     
     
         5 . The method of  claim 1 , wherein the enzymatic material is obtained from a different source than the plant. 
     
     
         6 . The method of  claim 1 , wherein the enzymatic material is obtained from a microbe. 
     
     
         7 . The method of  claim 1 , wherein the enzymatic material is obtained from the same source as the plant. 
     
     
         8 . The method of  claim 1 , wherein the enzymatic material comprises one or more endogenous enzymes capable of converting the one or more precursors to the tyramine containing hydroxycinnamic acid amide. 
     
     
         9 . The method of  claim 1 , wherein the enzymatic material comprises a phenylalanine ammonia lyase, 4-courmarate-CoA ligase. cinnamate-4-hydroxylase, coumarate-3-hydroxylase, coumaroyl-CoA 3-hydroxylase, caffeoyl-CoA O-methyltransferase, ferulate-5-hydroxylase, caffeic acid/5-hydroxyferulic acid O-methyltransferase, tyrosine ammonia lyase, or a combination thereof. 
     
     
         10 . The method of  claim 2 , wherein recovering the extract from the plant comprises an ethanol extract. 
     
     
         11 . The method of  claim 1 , further comprising applying an abiotic stress to the plant. 
     
     
         12 . The method of  claim 10 , wherein the abiotic stress is selected from at least one of hyperosmotic stress, salt, temperature stresses, aberrant nutrient conditions, mechanical shock flooding, wounding, anaerobic stress, oxidative stress, ozone, high light, heavy metals, toxic chemicals, ultrasound, ultraviolet light, elicitor chitosan treatment, modified lecithin treatment, or abscisic acid treatment. 
     
     
         13 . The method of  claim 1 , further comprising applying a biotic stress to the plant. 
     
     
         14 . The method of  claim 12 , wherein the biotic stress is false germination. 
     
     
         15 . A method for producing a consumable product with enhanced levels of a tyramine containing hydroxycinnamic acid amide, comprising:
 (a) subjecting a plant for producing a compound of Formula II to an enzymatic material,   
       
         
           
           
               
               
           
         
         wherein 
         R 1 , R 2 , and R 3  are each independently present or absent, and when present are each independently a hydroxy group, halo group, substituted or unsubstituted lower alkyl group, or substituted or unsubstituted lower alkoxy group, 
         the dashed bond is present or absent; and 
         (b) incorporating the plant or extract into a consumable product. 
       
     
     
         16 . The method of  claim 15 , wherein the enzymatic material is obtained from a different source than the plant. 
     
     
         17 . The method of  claim 15 , wherein the enzymatic material is obtained from a microbe. 
     
     
         18 . The method of  claim 15 , wherein the enzymatic material is obtained from the same source as the plant. 
     
     
         19 . The method of  claim 15 , wherein the enzymatic material comprises one or more endogenous enzymes capable of converting the one or more precursors to the tyramine containing hydroxycinnamic acid amide. 
     
     
         20 . The method of  claim 15 , wherein the enzymatic material comprises a phenylalanine ammonia lyase, 4-courmarate-CoA, ligase, cinnamate-4-hydroxylase, coumarate-3-hydroxylase. coumaroyl-CoA 3-hydroxylase, caffeoyl-CoA O-methyltransferase, ferulate-5-hydroxylase, caffeic acid/5-hydroxyferulic acid O-methyltransferase, tyrosine ammonia lyase, or a combination thereof.