benzofurans and benzophenone

A re-cultivation of the thermophilic fungus Aspergillus terreus TM8, and working up of its extract afforded the dichloro-benzophenone derivative, dihydrogeodin (1) in addition to the butyrolactones I (2), V (3) and VI (4). A literature surveying revealed one recent structural assignment trial for dihydrogeodin (1), however, with some inaccuracies. We report herein a full assignment of dihydrogeodin (1) using extensive study of 1D, 2D NMR and ESI HR mass data. For the first time as well, we report the planar structure of 1 using X-ray crystallography. Docking and molecular dynamic simulation of dihydrogeodin (1) on the isomerase cyclophilin A has revealed its significant potential activity as an antiviral and immunosuppressive agent.

Topics: 4-Butyrolactone; Antiviral Agents; Aspergillus; Benzofurans; Benzophenones; Crystallography, X-Ray; Cyclophilin A; Immunosuppressive Agents; Molecular Docking Simulation; Molecular Dynamics Simulation; Molecular Structure

An experimental protocol to achieve the Meerwein-Ponndorf-Verley (MPV) reduction of ketones under mildly basic conditions is reported. The transformation is tolerant of a range of ketone substrates, including

Topics: Benzofurans; Benzophenones; Catalysis; Heterocyclic Compounds; Ketones; Molecular Structure; Oxidation-Reduction; Stereoisomerism

Tattooing has recently become increasingly popular. Using tiny needles, tattooists place the tattoo ink in the dermis along with numerous unknown ingredients. Most tattoos consist of black inks, which are predominantly composed of soot products (carbon black with polycyclic aromatic hydrocarbons).. Black tattoos cause skin problems, including allergic reactions, but the responsible substance frequently remains unknown.. We applied gas chromatograph-mass spectrometry analysis to search for hazardous compounds in 14 different commercially available black tattoo ink samples.. The analysis revealed that all inks contained the softener substance dibutyl phthalate (0.12-691.2 µg/g). Some of the inks contained hexachloro-1,3-butadiene (0.08-4.52 µg/g), metheneamine (0.08-21.64 µg/g), dibenzofuran (0.02-1.62 µg/g), benzophenone (0.26-556.66 µg/g), and 9-fluorenone (0.04-3.04 µg/g).. The sensitizing agent dibutyl phthalate acts directly on keratinocytes and can drive Th2 responses following skin exposure via induction of thymic stromal lymphopoietin gene expression. Hexachloro-1,3-butadiene is genotoxic in vitro and 9-fluorenone is cytotoxic, generating reactive oxygen species under light exposure. The substances found in the inks might be partially responsible for adverse skin reactions to tattoos.

Topics: Benzofurans; Benzophenones; Butadienes; Dibutyl Phthalate; Fluorenes; Gas Chromatography-Mass Spectrometry; Humans; Ink; Methenamine; Tattooing