- Novel synthetic method of nordihydroguaiaretic acid (NDGA)
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Nordihydroguaiaretic acid has wide physiological activity and pharmacological activity. The invention discloses a novel synthetic method of nordihydroguaiaretic acid, wherein the method comprises thefollowing steps: carrying out reductive coupling reaction on veratone serving as a raw material under the action of a catalyst to obtain pinacol; reducing pinacol by trialkylsilane or triarylsilane under the catalysis of protonic acid or Lewis acid to generate 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane; and finally, under the action of haloid acid or Lewis acid, breaking ether bonds, and synthesizing nordihydroguaiaretic acid. The structure of the compound is characterized by 1H-NMR. Raw materials and reagents used in the method are easy to obtain, the reaction route is short, the reaction conditions are mild, the yield is high, the cost is low, and a simple and convenient path is opened up for industrial synthesis of nordihydroguaiaretic acid.
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- Phenolic compound production by Larrea divaricata Cav. plant cell cultures and effect of precursor feeding
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This paper summarizes progress made in using Larrea divaricata Cav. cell cultures for the production of the cytotoxic lignan nordihydroguaiaretic acid (NDGA) and the phenylpropanoids p-coumaric acid, ferulic acid and sinapyl alcohol. In order to improve the biomass formation and production of these phenolic compounds, four precursors (l-phenylalanine, cinnamic acid, ferulic acid, and sinapic acid) were fed to L. divaricata cell cultures. Feeding l-phenylalanine (0.5, 1 and 3 mM) resulted in an increase of NDGA of up to 301.35 ± 1.19, 285.23 ± 28.44 and 190.53 ± 19.50 μg/g DW. The addition of 0.5 μM cinnamic acid enhanced the cell culture growth, but not the NDGA production. When cinnamic acid (1 and 1.5 μM), ferulic acid (0.1, 0.5 and 1 mM) and sinapic acid (0.1, 0.5 and 1 mM) were added, the media became too toxic for the cells, and the production of NDGA and the phenylpropanoids was suppressed. The content of p-coumaric acid in the medium supplemented with 3 mM l-phenylalanine increased from 47.43 ± 9.01 to 1157.28 ± 47.79 μg/g DW, whereas the sinapyl alcohol content was not affected by any of the precursors tested, presenting similar values to the control medium.
- Palacio, Lorena,Cantero, Juan José,Cusidó, Rosa,Goleniowski, Marta
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experimental part
p. 418 - 422
(2011/09/20)
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- Diarylalkanes as potent inhibitors of binuclear enzymes
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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.
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Page/Page column 17
(2008/06/13)
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