Diarylalkanes as potent inhibitors of binuclear enzymes
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[0092] Example 4 describes the extraction, separation and purification of the novel diarylpropane: 1-(2-methoxy-4-hydroxyphenyl)-3-(2′-hydroxy-5′-methoxyphenyl)-propane (UP288) (1) from Broussonetia kazinoki Sieb. Et Zucc (Moraceae) (whole plant) using the general method set forth in Examples 1-3. FIG. 4 illustrates the HPLC / UV chromatogram of a HTP fraction that contains the UP288. The structure of the active compound UP288 was elucidated using a combination of spectroscopic methods as set forth in Example 4. FIG. 5 depicts the chemical structure and 13C-NMR spectrum of UP288. FIG. 6 illustrates tyrosinase inhibitory dose response curves and IC50 values for UP288 relative to kojic acid. The figure illustrates that UP288 (1) is as potent a tyrosinase inhibitor as kojic acid, having an IC50=24 μM.
[0093] Surprisingly, two similar diarylalkanes were isolated and identified from a totally different family of plant—Dianella ensifolia (L.) DC. (Liliaceae), as described in Example 5. FIG....
Example
[0094] Example 6 describes the large-scale isolation of UP302a (2), the most potent tyrosinase inhibitor, isolated from Dianella ensifolia (DE) (whole plant). With reference to Example 6, from 4.3 kg of dried biomass, a total of 30 mg of pure UP302a (2) was obtained after multiple column fractionations on silica gel, CG-161, and C-18 resins. The structure and biological function of the isolated compound were confirmed.
[0095] Due to the low natural abundance of diarylalkanes / diarylalkanols, methods to synthesize these biologically active compounds, as an alternative commercial source of this class of compounds was developed. Example 7 describes a general method for the synthesis of diarylalkanes via the reduction of substituted chalcones. For purposes of illustration the reduction of 2,4-dihydroxyphenyl)-3′,4′-dimethoxyphenylchalcone (4) to 1-(2,4-dihydroxyphenyl)-3-(3′,4′-dimethoxyphenyl)-1-propanol (5) using sodium borohydride is described. However, as set forth in Example 7, a nu...
Example
[0096] Using the general reaction described in Example 7, several other substituted diarylpropanones have been converted to diarylpropanes and / or diarylpropanols as demonstrated in Examples 8, 9 and 10. Example 11 demonstrates the synthesis of a diarylpropanol using a flavonoid glycoside isolated from a natural source as the starting material.
[0097] In another embodiment, the present invention includes methods for synthesizing this class of compounds by reaction of two appropriately substituted aromatic compounds. This embodiment is illustrated in Example 12, using the reaction of resorcinol with 3-methoxy-4-hydroxycinnamic acid for purposes of illustration. Feasible chemical reactions for synthesizing these compounds from two substituted aromatic compounds include, but are not limited to Aldol condensation between a substituted benzaldehyde and a substituted acetophenone; Claisen-Schmidt reaction or crossed aldol condensation between an aldehyde and a ketone; Grignard reaction usi...
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