3--4--7-trihydroxyisoflavone and 1-1-diphenyl-2-picrylhydrazyl

7,3',4'-Trihydroxyisoflavone (734THIF) is a secondary metabolite of daidzein and has been recently found to possess antioxidant, melanin inhibition, and skin cancer chemopreventive activities. However, the poor water solubility of 734THIF impedes its absorption and skin penetration and, therefore, limits its pharmacological effects when applied topically to the skin. We seek to use the nanoprecipitation method to prepare optimal eudragit E100 (EE)-polyvinyl alcohol (PVA)-loaded 734THIF nanoparticles (734N) to improve its physicochemical properties and thereby increase its water solubility, skin penetration, and biological activities. EE-PVA-loaded 734THIF nanoparticles (734N) were prepared, and their morphology and particle size were evaluated using a particle size analyzer and by electron microscopy. The drug loading and encapsulation efficiencies and in vitro solubility were determined using high-performance liquid chromatography. Hydrogen-bond formation was evaluated by (1)H-nuclear magnetic resonance and Fourier transform infrared spectroscopy, and crystalline-to-amorphous transformation was determined by differential scanning calorimetry and X-ray diffractometry. In vitro skin penetration was analyzed using fresh pig skin mounted on Franz diffusion cells, and cytotoxicity against human keratinocyte HaCaT cells was evaluated using the MTT assay. Antioxidant activity was determined by 2,2-diphenyl-1-picrylhydrazyl-free radical scavenging ability. EE-PVA-loaded 734THIF nanoparticles showed good drug loading and encapsulation efficiencies and were characterized by improved physicochemical properties, including reduction in particle size, amorphous transformation, and intermolecular hydrogen-bond formation. This is associated with increased water solubility and enhanced in vitro skin penetration, with no cytotoxicity toward HaCaT cells. In addition, 734THIF nanoparticles retained their antioxidant activity. In conclusion, 734THIF nanoparticles are characterized by improved physicochemical properties, increased water solubility, and enhanced skin penetration, and these may have potential use in the future as a topical delivery formulation for the treatment of skin diseases.

Topics: Acrylates; Administration, Topical; Animals; Antioxidants; Biphenyl Compounds; Calorimetry, Differential Scanning; Cell Survival; Chromatography, High Pressure Liquid; Freeze Drying; Humans; Isoflavones; Nanoparticles; Particle Size; Picrates; Polymers; Polyvinyl Alcohol; Proton Magnetic Resonance Spectroscopy; Skin; Skin Absorption; Solubility; Spectroscopy, Fourier Transform Infrared; Sus scrofa; Water; X-Ray Diffraction

The present study describes the biotransformation of a commercially available crude extract of soy isoflavones, which contained significant amounts of the soy isoflavone glycosides daidzin and genistin, by recombinant

Topics: Antioxidants; Bacillus megaterium; Biotransformation; Biphenyl Compounds; Escherichia coli; Glycine max; Glycosides; Isoflavones; Monophenol Monooxygenase; Picrates

In order to explore the anti-inflammatory principles of the mycelia of Cordyceps sinensis, the crude extract and partially purified fractions were examined for their inhibition of superoxide anion generation and elastase release. Further chemical investigation of the bioactive fractions has resulted in the identification of 50 compounds, including five constituents, cordysinins A-E (1-5), reported from a natural source for the first time. In addition, compounds were examined for their anti-inflammatory activity. 1-(5-Hydroxymethyl-2-furyl)-β-carboline displayed the most significant inhibition of superoxide anion generation and elastase release with IC50 values of 0.45±0.15 and 1.68±0.32 μM, respectively.

Topics: Anti-Inflammatory Agents; Biphenyl Compounds; Carbolines; Cordyceps; Humans; Inhibitory Concentration 50; Molecular Structure; Mycelium; Pancreatic Elastase; Picrates; Stereoisomerism; Superoxides; Taiwan