Diarylalkanes as potent inhibitors of binuclear enzymes

Abstract

The present invention implements a strategy that combines an enzyme inhibition assay with a chemical dereplication process to identify active plant extracts and the particular compounds—diarylalkanes and/or diarylalkanols within those extracts that specifically inhibit binuclear enzyme function. Included in the present invention are compositions of matter comprised of one or more of diarylalkanes and/or diarylalkanols, which inhibit the activity of binuclear enzymes, particularly tyrosinase and which prevent melanin overproduction. The present invention also provides a method for inhibiting the activity of a binuclear enzyme, particularly tyrosinase and a method for preventing and treating diseases and conditions related to binuclear enzyme function. The present invention further includes a method for preventing and treating melanin overproduction and diseases and conditions of the skin related thereto. The method for preventing and treating diseases and conditions related to binuclear enzyme function and melanin overproduction is comprised of administering to a host in need thereof an effective amount of a composition comprising one or more diarylalkanes and/or diarylalkanols synthesized and/or isolated from one or more plants together with a pharmaceutically acceptable carrier.

1 . A method for inhibiting the activity of a binuclear enzyme said method comprising administering an effective amount of a composition comprising one or more diarylalkanes.  
   
   
       2 . The method of  claim 1  wherein said diarylalkane is selected from the group of compounds having the following structure:  
     
       
         
         
             
             
         
       
     
     wherein 
 Ar 1  and Ar 2  are independently selected from the group consisting of a substituted 5- or 6-membered aromatic or heteroaromatic ring, wherein each 6-membered aromatic or heteroaromatic ring is independently substituted with 1-5 R′ groups (R′ 1 -R′ 5 ), and each 5-membered aromatic or heteroaromatic ring is substituted with 1-4 R′ groups (R′ 1 -R′ 4 ), except when Ar 1  and Ar 2  are both a 6-membered aromatic ring, i.e. a phenyl group at least one of Ar 1  and Ar 2  are substituted with 1-5 R′ groups (R′ 1 -R′ 5 ), wherein at least 2 of said of R′ 1 -R′ 5  are not H wherein  
 R′ independently selected from the group consisting of —H, —OH, —SH, —OR, —CN, —SR, —NH 2 , —NHR, —NR 2 , X, and a glycoside of a monosaccharide or oligosaccharide comprised of 2-6 monosaccharides, wherein said monosaccharide(s) are independently selected from the group consisting of an aldopentose, methyl-aldopentose, aldohexose, ketohexose and chemical derivatives thereof; wherein R is an alkyl group having between 1-20 carbon atoms and X is a halogen, selected from the group consisting of Cl, Br, F, I;  
 R 6 , and R 7  are independently selected from the group consisting of —H, —OH, —OR, —CN, —NHR, —NH 2  and —X, wherein R is an alkyl group having between 1-20 carbon atoms and wherein X is a halogen, selected from the group consisting of Cl, Br, F and I; and  
 n=1 to 10.  
 
   
   
       3 . The method of  claim 2  wherein n=2-4.  
   
   
       4 . The method of  claim 1  wherein said diarylalkanes are selected from the group of compounds represented by the following general structure:  
     
       
         
         
             
             
         
       
     
     wherein 
 R 1 , R 2 , R 3 , R 4 , R 5  R′ 1 , R′ 2 , R′ 3 , R′ 4 , and R′ 5  are independently selected from the group consisting of —H, —OH, —SH, —OR, —CN, —SR, —NH 2 , —NHR, —NR 2 , X, and a glycoside of a monosaccharide or oligosaccharide comprised of 2-6 monosaccharides, wherein said monosaccharide(s) are independently selected from the group consisting of an aldopentose, methyl-aldopentose, aldohexose, ketohexose and chemical derivatives thereof; wherein R is an alkyl group having between 1-20 carbon atoms and X is a halogen, selected from the group consisting of Cl, Br, F, I, and wherein at least 2 of R 1 -R 5  or at least 2 of R′ 1 -R′ 5  are not H;  
 R 6 , and R 7  are independently selected from the group consisting of —H, —OH, —OR, —CN, —NHR, —NH 2  and —X, wherein R is an alkyl group having between 1-20 carbon atoms and wherein X is a halogen, selected from the group consisting of Cl, Br, F, I; and  
 n=1 to 10.  
 
   
   
       5 . The method of  claim 4  wherein n=2-4.  
   
   
       6 . The method of  claim 1  wherein said diarylalkane is selected from the group consisting of 1-(2-methoxy-4-hydroxyphenyl)-3-(2′-hydroxy-5′-methoxyphenyl)-propane, 1-(3-methyl-2,4-dimethoxyphenyl)-3-(2′,4′-dihydroxyphenyl)-propane, 1-(3-methyl-2,4-dimethoxyphenyl)-3-(2′,5′-dihydroxyphenyl)-propane, 1-(2,4-dihydroxyphenyl)-3-(3′,4′-dihydroxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-3-(3′,4′-dimethoxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-3-(2′-hydroxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-3-(2′-methoxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-3-(4′-methoxyphenyl)-1-propanol, 1-(2,4,6-trihydroxyphenyl)-3-(4′-aminophenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-3-phenyl-1-propanol, 1-(2,4-dihydroxyphenyl)-3-(3′-methoxy-4′-hydroxyphenyl)-1-propanol, 1-(2-hydroxy-4-methoxyphenyl)-3-(3′,4′,5′-trimethoxyphenyl)-1-propanol, 1-(2-hydroxy-4-methoxyphenyl)-3-(2′,4′-dimethoxyphenyl)-1-propanol, 1-(2-hydroxy-5-methoxyphenyl)-3-(3′,4′-dimethoxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-2-(4′-methoxyphenyl)-1-ethanol, 1-(2-hydroxy-4-methoxyphenyl)-3-(2′,3′,4′,5′-tetrahydro-benzo(b)dioxocin-8′-yl)-1-propanol, 3-(5′-chloro-1′-methyl-1′-hydro-imidazol-2′-yl)-1-(2-hydroxy-4-methoxyphenyl)-1-propanol, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(3′-methoxy-4′-hydroxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-2-(3′,4′-dimethoxyphenyl)-1-ethanol, 1,4-bis-(3,4-dihydroxyphenyl)-2,3-dimethyl-buthane, 1-(2-hydroxy-5-methoxyphenyl)-3-(2′,4′-dimethoxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-2-(2′,4′-dichlorophenyl)-1-ethanol, 1-(2,4,6-trihydroxyphenyl)-3-(3′-Hydroxy-4′-methoxyphenyl)-1-propanol, 1,3-bis(2,4-dimethoxyphenyl)-propan-1,3-diol, 1-(2,4,6-trihydroxyphenyl)-3-(3′-Hydroxy-4′-methoxyphenyl)-1-propanol and 1-(2,4,6-trimethoxyphenyl)-3-(3′,4′-dimethoxyphenyl)-1-propanol.  
   
   
       7 . The method of  claim 1  wherein said diarylalkane is obtained by organic synthesis or is isolated from one or more plants.  
   
   
       8 . The method of  claim 7  wherein said diarylalkane is isolated from a plant part selected from the group consisting of stems, stem barks, trunks, trunk barks, twigs, tubers, roots, root barks, young shoots, seeds, rhizomes, flowers and other reproductive organs, leaves and other aerial parts.  
   
   
       9 . The method of  claim 7  wherein said diarylalkane is isolated from a plant family selected from the group consisting of Compositae, Fabaceae, Lauraceae, Leguminosae, Liliaceae, Loranthaceae, Moracea, and Myristicaceae.  
   
   
       10 . The method of  claim 7  wherein said diarylalkane is isolated from a plant genus selected from the group consisting of  Acacia, Broussonetia, Dianella, Helichrysum, Iryanthera, Knema, Lindera, Pterocarpus, Viscum , and  Xanthocercis.    
   
   
       11 . The method of  claim 1  wherein binuclear enzyme is selected from the group consisting of tyrosinase, arginase, urease, cytochrome c oxidase, proton pumping heme-copper oxidase, bifunctional carbon monoxide dehydrogenase/acetyl-coenzyme A synthase, ribonucleotide reductase, metalo-beta-lactamase, H(+)-ATPase and alternative oxidase, and bacterial phosphotriesterase.  
   
   
       12 . The method of  claim 1  wherein said binuclear enzyme is tyrosinase.  
   
   
       13 . A method for preventing and treating diseases and conditions related to binuclear enzymes said method comprising administering to a host in need thereof an effective amount of a composition comprising one or more diarylalkane(s).  
   
   
       14 . The method of  claim 13  wherein said diarylalkane is selected from the group of compounds having the following structure:  
     
       
         
         
             
             
         
       
     
     wherein 
 Ar 1  and Ar 2  are independently selected from the group consisting of a substituted 5- or 6-membered aromatic or heteroaromatic ring, wherein each 6-membered aromatic or heteroaromatic ring is independently substituted with 1-5 R′ groups (R′ 1 -R′ 5 ), and each 5-membered aromatic or heteroaromatic ring is substituted with 1-4 R′ groups (R′ 1 -R′ 4 ), except when Ar 1  and Ar 2  are both a 6-membered aromatic ring, i.e. a phenyl group at least one of Ar 1  and Ar 2  are substituted with 1-5 R′ groups (R′ 1 -R′ 5 ), wherein at least 2 of said of R′ 1 -R′ 5  are not H wherein  
 R′ independently selected from the group consisting of —H, —OH, —SH, —OR, —CN, —SR, —NH 2 , —NHR, —NR 2 , X, and a glycoside of a monosaccharide or oligosaccharide comprised of 2-6 monosaccharides, wherein said monosaccharide(s) are independently selected from the group consisting of an aldopentose, methyl-aldopentose, aldohexose, ketohexose and chemical derivatives thereof; wherein R is an alkyl group having between 1-20 carbon atoms and X is a halogen, selected from the group consisting of Cl, Br, F and I;  
 R 6 , and R 7  are independently selected from the group consisting of —H, —OH, —OR, —CN, —NHR, —NH 2 , and —X, wherein R is an alkyl group having between 1-20 carbon atoms and wherein X is a halogen, selected from the group consisting of Cl, Br, F, I; and  
 n=1 to 10.  
 
   
   
       15 . The method of  claim 14  wherein n=2-4.  
   
   
       16 . The method of  claim 13  wherein said diarylalkanes are selected from the group of compounds represented by the following general structure:  
     
       
         
         
             
             
         
       
     
     wherein 
 R 1 , R 2 , R 3 , R 4 , R 5  R′ 1 , R′ 2 , R′ 3 , R′ 4 , and R′ 5  are independently selected from the group consisting of —H, —OH, —SH, —OR, —CN, —SR, —NH 2 , —NHR, —NR 2 , X, and a glycoside of a monosaccharide or oligosaccharide comprised of 2-6 monosaccharides, wherein said monosaccharide(s) are independently selected from the group consisting of an aldopentose, methyl-aldopentose, aldohexose, ketohexose and chemical derivatives thereof; wherein R is an alkyl group having between 1-20 carbon atoms and X is a halogen, selected from the group consisting of Cl, Br, F, I, and wherein at least 2 of R 1 -R 5  or at least 2 of R′ 1 -R′ 5  are not H;  
 R 6 , and R 7  are independently selected from the group consisting of —H, —OH, —OR, —CN, —NHR, —NH 2 , and —X, wherein R is an alkyl group having between 1-20 carbon atoms and wherein X is a halogen, selected from the group consisting of Cl, Br, F and I; and  
 n=1 to 10.  
 
   
   
       17 . The method of  claim 14  wherein n=2-4.  
   
   
       18 . The method of  claim 13  wherein said diarylalkane is selected from the group consisting of 1-(2-methoxy-4-hydroxyphenyl-)-3-(2′-hydroxy-5′-methoxyphenyl)-propane, 1-(3-methyl-2,4-dimethoxyphenyl)-3-(2′,4′-dihydroxyphenyl)-propane, 1-(3-methyl-2,4-dimethoxyphenyl)-3-(2′,5′-dihydroxyphenyl)-propane, 1-(2,4-dihydroxyphenyl)-3-(3′,4′-dihydroxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-3-(3′,4′-dimethoxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-3-(2′-hydroxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-3-(2′-methoxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-3-(4′-methoxyphenyl)-1-propanol, 1-(2,4,6-trihydroxyphenyl)-3-(4′-aminophenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-3-phenyl-1-propanol, 1-(2,4-dihydroxyphenyl)-3-(3′-methoxy-4′-hydroxyphenyl)-1-propanol, 1-(2-hydroxy-4-methoxyphenyl)-3-(3′,4′,5′-trimethoxyphenyl)-1-propanol, 1-(2-hydroxy-4-methoxyphenyl)-3-(2′,4′-dimethoxyphenyl)-1-propanol, 1-(2-hydroxy-5-methoxyphenyl)-3-(3′,4′-dimethoxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-2-(4′-methoxyphenyl)-1-ethanol, 1-(2-hydroxy-4-methoxyphenyl)-3-(2′,3′,4′,5′-tetrahydro-benzo(b)dioxocin-8′-yl)-1-propanol, 3-(5′-chloro-1′-methyl-1′-hydro-imidazol-2′-yl)-1-(2-hydroxy-4-methoxyphenyl)-1-propanol, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(3′-methoxy-4′-hydroxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-2-(3′,4′-dimethoxyphenyl)-1-ethanol, 1,4-bis-(3,4-dihydroxyphenyl)-2,3-dimethylbutane, 1-(2-hydroxy-5-methoxyphenyl)-3-(2′,4′-dimethoxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-2-(2′,4′-dichlorophenyl)-1-ethanol, 1-(2,4,6-trihydroxyphenyl)-3-(3′-hydroxy-4′-methoxyphenyl)-1-propanol, 1,3-bis(2,4-dimethoxyphenyl)-propan-1,3-diol, 1-(2,4,6-trihydroxyphenyl)-3-(3′-hydroxy-4′-methoxyphenyl)-1-propanol and 1-(2,4,6-trimethoxyphenyl)-3-(3′,4′-dimethoxyphenyl)-1-propanol.  
   
   
       19 . The method of  claim 13  wherein said diarylalkane is obtained by organic synthesis or is isolated from one or more plants.  
   
   
       20 . The method of  claim 19  wherein said diarylalkane is isolated from a plant part selected from the group consisting of stems, stem barks, trunks, trunk barks, twigs, tubers, roots, root barks, young shoots, seeds, rhizomes, flowers and other reproductive organs, leaves and other aerial parts.  
   
   
       21 . The method of  claim 19  wherein said diarylalkane is isolated from a plant family selected from the group consisting of Compositae, Fabaceae, Lauraceae, Leguminosae, Liliaceae, Loranthaceae, Moracea, and Myristicaceae.  
   
   
       22 . The method of  claim 19  wherein said diarylalkane is isolated from a plant genus selected from the group consisting of  Acacia, Broussonetia, Dianella, Helichrysum, Iryanthera, Knema, Lindera, Pterocarpus, Viscum , and  Xanthocercis.    
   
   
       23 . The method of  claim 13  wherein binuclear enzyme is selected from the group consisting of tyrosinase, arginase, urease, cytochrome c oxidase, proton pumping heme-copper oxidase, bifunctional carbon monoxide dehydrogenase/acetyl-coenzyme A synthase, ribonucleotide reductase, metalo-beta-lactamase, H(+)-ATPase and alternative oxidase, and bacterial phosphotriesterase.  
   
   
       24 . The method of  claim 13  wherein the composition is administered in a dosage selected from 0.01 to 200 mg/kg of host body weight.  
   
   
       25 . The method of  claim 13  wherein the composition is administered in a dosage selected from of 0.001% to 100% based on total weight of a therapeutical formulation.  
   
   
       26 . The method of  claim 13  wherein the composition is administered in a pharmaceutical, dermatological or cosmetic formulation comprised of approximately 0.001 weight percent (wt %) to 99.9 wt % of a diarylalkane or a mixture of diarylalkanes in a pharmaceutically, dermatologically or cosmetically acceptable carrier.  
   
   
       27 . The method of  claim 13  wherein the routes of the administration are selected from the group consisting of topical, aerosol, suppository, intradermic, intramusclar and intravenous administration.  
   
   
       28 . The method of  claim 27  wherein the composition is administered using a nonsticking gauze, a bandage, a swab, a cloth wipe, a patch, a mask, a protectant, a cleanser, a dental flossing material, an antiseptic, a solution, a cream, a lotion, an ointment, a gel or an emulsion, a liquid, a toothpaste, a mouse washing solution, a cosmetic paste, a soap, or a powder.  
   
   
       29 . The method of  claim 13  wherein the composition is further comprised of a conventional excipient that is pharmaceutically, dermatologically and cosmetically suitable for topical application and optionally an adjuvant, and/or a carrier, and/or a regular or controlled releasing vehicle.  
   
   
       30 . The method of  claim 13  wherein disease or condition mediated by a binuclear enzyme is selected from the group consisting of microbial infection, fungal infection, malaria infection, viral infection, reduced nitric oxide production, abnormal male and female sexual arousal, inflammatory conditions, oxidative stress, abnormal drug metabolism, cancers and solid tumors.  
   
   
       31 . The method of  claim 13  wherein the disease or condition mediated by a binuclear enzyme is selected from the group consisting of periodontal diseases, oral pre-cancerous conditions, oral cancers, and other oral malignancies, sensitive gums and teeth, sequelae, pulpitis, irritation, pain and inflammation caused by the physical implantation of oral dentures, trauma, injuries, bruxism and other minor wounds in mouth, on the gums or on the tongue, dental plague and calculus, tooth decalcification, proteolysis and caries (decay).  
   
   
       32 . A method for the prevention and treatment of diseases and conditions related to the overproduction or uneven distribution of melanin, said method comprising administering internally or topically to a host in need thereof a therapeutically effective amount of one or more diarylalkanes.  
   
   
       33 . The method of  claim 32  wherein said diseases and conditions related to the overproduction uneven distribution of melanin are selected from the group consisting of skin darkening and damage due to exposure to ultra violet light, sun tan, hyper pigmentation spots caused by skin aging, liver disease, thermal burns and topical wounds, skin pigmentation due to inflammatory conditions caused by fungal, microbial and viral infections, vitilago, carcinoma and melanoma.  
   
   
       34 . A method for delivering a metal ion comprising administering to a host in need thereof a therapeutically effective amount of one or more diarylalkanes, together with the metal ion(s) to be delivered.  
   
   
       35 . The method of  claim 34  wherein said metal ion is selected from the group consisting of copper, iron, zinc, boron, lithium, selenium, calcium, chromium, molybdenum, magnesium and manganese.  
   
   
       36 . The method of  34  wherein said metal ion is delivered into the blood stream, across a membrane, or through the skin.  
   
   
       37 . The method of  claim 34  wherein said membrane is the blood/brain barrier.  
   
   
       38 . The method of  claim 34  wherein said metal is administered to treat a disease or condition selected from the group consisting of anemia and other iron deficiencies, inflammation; obesity and diabetes mellitus, viral infections, insomnia, suppressed immune function, osteoporosis, amenorrhea, dysmenorrheal, epilepsy, hypertension, cholesterolemea, coronary and cerebral vasospasms, diarrhea, Parkinson's disease, Alzheimer's disease, cancers, rheumatoid arthritis, periodontal diseases, oral pre-cancerous conditions, oral cancers, and other oral malignancies, sensitive gums and teeth, sequelae, pulpitis, irritation, pain and inflammation caused by the physical implantation of oral dentures, trauma, injuries, bruxism and other minor wounds in mouth, on the gums or on the tongue, dental plague and calculus, tooth decalcification, proteolysis and caries (decay), male infertility and macular degeneration.  
   
   
       39 . A diarylalkane selected from the group of compounds having the following general formula:  
     
       
         
         
             
             
         
       
     
     wherein 
 Ar 1  and Ar 2  are independently selected from the group consisting of a substituted 5- or 6-membered aromatic or heteroaromatic ring, wherein each 6-membered aromatic or heteroaromatic ring is independently substituted with 1-5 R′ groups (R′ 1 -R′ 5 ), and each 5-membered aromatic or heteroaromatic ring is substituted with 1-4 R′ groups (R′ 1 -R′4), except when Ar 1  and Ar 2  are both a 6-membered aromatic ring, i.e. a phenyl group at least one of Ar 1  and Ar 2  are substituted with 1-5 R′ groups (R′ 1 -R′ 5 ), wherein at least 2 of said of R′ 1 -R′ 5  are not H wherein  
 R′ is independently selected from the group consisting of —H, —OH, —SH, —OR, —CN, —SR, —NH 2 , —NHR, —NR 2 , X, and a glycoside of a monosaccharide or oligosaccharide comprised of 2-6 monosaccharides, wherein said monosaccharide(s) are independently selected from the group consisting of an aldopentose, methyl-aldopentose, aldohexose, ketohexose and chemical derivatives thereof; wherein R is an alkyl group having between 1-20 carbon atoms and X is a halogen, selected from the group consisting of Cl, Br, F and I;  
 R 6 , and R 7  are independently selected from the group consisting of —H, —OH, —OR, —CN, —NHR, —NH 2  and —X, wherein R is an alkyl group having between 1-20 carbon atoms and wherein X is a halogen, selected from the group consisting of Cl, Br, F and I; and  
 n=1 to 10.  
 
   
   
       40 . The diarylalkane of  claim 39  wherein n=2-4.  
   
   
       41 . A diarylalkane of selected from the group of compounds having the following general structure:  
     
       
         
         
             
             
         
       
     
     wherein 
 R 1 , R 2 , R 3 , R 4 , R 5  R′ 1 , R′ 2 , R′ 3 , R′ 4 , and R′ 5  are independently selected from the group consisting of —H, —OH, —SH, —OR, —CN, —SR, —NH 2 , —NHR, —NR 2 , X, and a glycoside of a monosaccharide or oligosaccharide comprised of 2-6 monosaccharides, wherein said monosaccharide(s) are independently selected from the group consisting of an aldopentose, methyl-aldopentose, aldohexose, ketohexose and chemical derivatives thereof; wherein R is an alkyl group having between 1-20 carbon atoms and X is a halogen, selected from the group consisting of Cl, Br, F, I, and wherein at least 2 of R 1 -R 5  or at least 2 of R′ 1 -R 15  are not H;  
 R 6 , and R 7  are independently selected from the group consisting of —H, —OH, —OR, —CN, —NHR, —NH 2  and —X, wherein R is an alkyl group having between 1-20 carbon atoms and wherein X is a halogen, selected from the group consisting of Cl, Br, F and I; and  
 n=1 to 10.  
 
   
   
       42 . The diarylalkane of  claim 41  wherein n=2-4.  
   
   
       43 . The diarylalkane of  claim 41  wherein at least one of R 6  and/or R 7  is an OH group.  
   
   
       44 . A diarylalkane selected from the group consisting of 1-(2-methoxy-4-hydroxyphenyl)-3-(2′-hydroxy-5′-methoxyphenyl)-propane, 1-(3-methyl-2,4-dimethoxyphenyl)-3-(2′,4′-dihydroxyphenyl)-propane, 1-(3-methyl-2,4-dimethoxyphenyl)-3-(2′,5′-dihydroxyphenyl)-propane, 1-(2,4-dihydroxyphenyl)-3-(3′,4′-dihydroxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-3-(3′,4′-dimethoxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-3-(2′-hydroxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-3-(2′-methoxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-3-(4′-methoxyphenyl)-1-propanol, 1-(2,4,6-trihydroxyphenyl)-3-(4′-aminophenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-3-phenyl-1-propanol, 1-(2,4-dihydroxyphenyl)-3-(3′-methoxy-4′-hydroxyphenyl)-1-propanol, 1-(2-hydroxy-4-methoxyphenyl)-3-(3′,4′,5′-trimethoxyphenyl)-1-propanol, 1-(2-hydroxy-4-methoxyphenyl)-3-(2′,4′-dimethoxyphenyl)-1-propanol, 1-(2-hydroxy-5-methoxyphenyl)-3-(3′,4′-dimethoxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-2-(4′-methoxyphenyl)-1-ethanol, 1-(2-hydroxy-4-methoxyphenyl)-3-(2′,3′,4′,5′-tetrahydro-benzo(b)dioxocin-8′-yl)-1-propanol, 3-(5′-chloro-1′-methyl-1′-hydro-imidazol-2′-yl)-1-(2-hydroxy-4-methoxyphenyl)-1-propanol, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(3′-methoxy-4′-hydroxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-2-(3′,4′-dimethoxyphenyl)-1-ethanol, 1,4-bis-(3,4-dihydroxyphenyl)-2,3-dimethylbutane, 1-(2-hydroxy-5-methoxyphenyl)-3-(2′,4′-dimethoxyphenyl)-1-propanol, 1-(2,4-dihydroxyphenyl)-2-(2′,4′-dichlorophenyl)-1-ethanol, 1-(2,4,6-trihydroxyphenyl)-3-(3′-hydroxy-4′-methoxyphenyl)-1-propanol, 1,3-bis(2,4-dimethoxyphenyl)-propan-1,3-diol, 1-(2,4,6-trihydroxyphenyl)-3-(3′-hydroxy-4′-methoxyphenyl)-1-propanol and 1-(2,4,6-trimethoxyphenyl)-3-(3′,4′-dimethoxyphenyl)-1-propanol.  
   
   
       45 . A method for synthesizing a diarylalkane comprising reducing a compound having the following general structure:  
     
       
         
         
             
             
         
       
     
     wherein 
 R 1 , R 2 , R 3 , R 4 , R 5  R′ 1 , R′ 2 , R′ 3 , R′ 4 , and R′ 5  are independently selected from the group consisting of —H, —OH, —SH, —OR, —CN, —SR, —NH 2 , —NHR, —NR 2 , X, and a glycoside of a monosaccharide or oligosaccharide comprised of 2-6 monosaccharides, wherein said monosaccharide(s) are independently selected from the group consisting of an aldopentose, methyl-aldopentose, aldohexose, ketohexose and chemical derivatives thereof; wherein R is an alkyl group having between 1-20 carbon atoms and X is a halogen, selected from the group consisting of Cl, Br, F, I, and wherein at least 2 of R 1 -R 5  or at least 2 of R′ 1 -R′ 5  are not H;  
 R 6  and R 7  are independently selected from the group consisting of —H, —OH, —OR, —CN, —NHR, —NH 2 , —X, wherein one or more R 6  and R 7  together form a ═O—, wherein R is an alkyl group having between 1-20 carbon atoms and wherein X is a halogen, selected from the group consisting of Cl, Br, F and I; and  
 n=1 to 10.  
 
   
   
       46 . The method of  claim 41  wherein said diarylalkane is obtained by organic synthesis or is isolated from one or more plants.  
   
   
       47 . The method of  claim 41  wherein said diarylalkane is reduced from a substituted diarylalkanone with a reducing agent selected from the group consisting of a borohydride, H, in the presence of a catalyst, NaH and LiAlH 4 .