Synthesis of Four Natural Prenylflavonoids and Their Estrogen‐like Activities

Abstract

Four prenylflavonoids, bavachin 1, isobavachin 2, 7,4'-dihydroxy-8-prenylflavone 3, and 8-prenylapigenin 4 were synthesized and recognized for possessing estrogen-like activity in MCF-7/BOS cells, as evaluated by an estrogen-screening assay. All compounds significantly stimulated the proliferation of MCF-7/BOS cells in a dose-dependent manner. Isobavachin 2 showed the most potent activity, while bavachin 1 was the weakest. The estrogenic potency of these compounds is ranked as follows: 2 > 4 > 3 > 1.

Design, Synthesis, and Biological Evaluation of Prenylated Chalcones as Vasorelaxant Agents

“…Acetophenones 5a -d were prepared according to the reported methods [14,15]. Condensation of 5a -d with corresponding benzaldehydes in aqueous alcoholic alkali solution afforded chalcones 6a -f. Demethoxymethylation of 6a -f was carried out in catalytic amounts of 3 N HCl in MeOH / THF (1 : 1, v/v) at reflux temperature, leading to the products 4a -f. The structures of the synthesized compounds were elucidated by 1 H-NMR and ESI-MS.…”

“…Reagents and solvents were purchased from known commercial suppliers and were used without further purification. Compounds 5a -d and 4f were prepared according to the approaches in previous references [14,15].…”

GuA6DT, a Regiospecific Prenyltransferase from Glycyrrhiza uralensis, Catalyzes the 6‐Prenylation of Flavones

“…[1] In fact, many prenylated flavonoids have been identified as pharmacologically active compounds with diverse properties, including antioxidation, antitumor, antibacterial, antiviral, and estrogenic activities. [2][3][4][5][6] As revealed through structure-activity relationship studies, substitutions with prenyl chains of varying length and type on the flavonoid skeleton can enhance their bioactivity and bioavailability, compared with the nonprenylated parent molecules. This enhancement is likely a result of the presence of the lipophilic prenyl side chain, which increases the membrane permeability and enhances the binding affinity of these compounds to the target proteins.…”

Inhibitory Effects of Bakuchiol, Bavachin, and Isobavachalcone Isolated fromPiper longumon Melanin Production in B16 Mouse Melanoma Cells

“…The compounds were identified by comparison of their spectral data (UV, ½ D , MS, and NMR) with data previously reported. [11][12][13][14][15][16] Next, compounds 1-3 were examined with regard to their ability to suppress melanin biosynthesis in B16 cells. The addition of the isolated compounds to the cells prior to stimulation with 100 nM -MSH markedly decreased the production of melanin, in a dose-dependent manner (Fig.…”