57960-04-0Relevant academic research and scientific papers
Free-radical-scavenging, antityrosinase, and cellular melanogenesis inhibitory activities of synthetic isoflavones
Lu, Tzy-Ming,Ko, Horng-Huey,Ng, Lean-Teik,Hsieh, Yen-Pin
, p. 963 - 979 (2015/06/25)
In this study, we examined the potential of synthetic isoflavones for application in cosmeceuticals. Twenty-five isoflavones were synthesized and their capacities of free-radical-scavenging and mushroom tyrosinase inhibition, as well as their impact on cell viability of B16F10 murine melanoma cells and HaCaT human keratinocytes were evaluated. Isoflavones that showed significant mushroom tyrosinase inhibitory activities were further studied on reduction of cellular melanin formation and antityrosinase activities in B16F10 melanocytes in vitro. Among the isoflavones tested, 6-hydroxydaidzein (2) was the strongest scavenger of both ABTS.+ and DPPH. radicals with SC50 values of 11.3±0.3 and 9.4±0.1 μM, respectively. Texasin (20) exhibited the most potent inhibition of mushroom tyrosinase (IC50 14.9±4.5 μM), whereas retusin (17) showed the most efficient inhibition both of cellular melanin formation and antityrosinase activity in B16F10 melanocytes, respectively. In summary, both retusin (17) and texasin (20) exhibited potent free-radical-scavenging capacities as well as efficient inhibition of cellular melanogenesis, suggesting that they are valuable hit compounds with potential for advanced cosmeceutical development.
Inhibitors for expression of IgE receptor on human mast cell from Puerariae Flos
Tamura, Satoru,Yoshihira, Kunichika,Tokumaru, Mariko,Zisheng, Xu,Murakami, Nobutoshi
scheme or table, p. 3872 - 3875 (2010/08/19)
Bioassay-guided separation of the extract of the medicinal plant, Puerariae Flos, disclosed the two isoflavones tectorigenin (1) and genistein (2) as the inhibitors for expression of IgE receptor (FcRI), the key molecule triggering the allergic reactions, on human mast cells. As a result of analysis of structure-activity relationship of the naturally occurring and synthesized isoflavones, 7-O-methyl glycitein (11) was disclosed as the more potent inhibitor than tectorigenin (1). These isoflavone ingredients suppressed expression of FcRI more potently than the active flavonoids found previously. In addition, tectorigenin (1) was clarified to particularly reduce generation of γ-chain subunit to suppress expression of FcRI among the three subunits.
Synthesis of various kinds of isoflavones, isoflavanes, and biphenyl- ketones and their 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activities
Goto, Hideyuki,Terao, Yoshiyasu,Akai, Shuji
experimental part, p. 346 - 360 (2009/12/27)
Forty-eight kinds of isoflavones (8), thirty-one isoflavanes (9), and forty-seven biphenyl-ketones (10, 10') were synthesized from eleven kinds of substituted phenols (11) and six phenylacetic acids (12). Among them, seventy-five compounds are new. The radical scavenging activities of these compounds were evaluated using 1,1- diphenyl-2-picrylhydrazyl (DPPH) at pH 6.0. We found that thirty-nine out of forty-three compounds having a catechol moiety on either the A- or the B-ring exhibited a high activity (ED50=12-54 μM) similar to that of catechin. In these cases, the remaining part of their structure seemed to have little effect on their activity. Many 6- or 8-hydroxyisoflavanes (9E-I) and their biphenyl-ketone derivatives (10E-H) also showed a high activity (ED50=50=26-32 μM). This study suggests that natural isoflavones have the possibilities of exhibiting antioxidant activities through the hydroxylation at the C6-, C8-, or C3'-position or the formation of the isoflavanes (9) and/or the biphenyl-ketone derivatives (10') by metabolism or biotransformation.
