39886-85-6Relevant articles and documents
Biotransformation of pungent constituents from ginger (Zingiber officinale Roscoe) by Colletotrichum gloeosporioides yields oxidative ortho–ortho coupling products
de ávila, Roberta Marques Dias,Toffano, Leonardo,Fernandes, Jo?o Batista,da Silva, Maria Fátima das Gra?as Fernandes,de Sousa, Lorena Ramos Freitas,Vieira, Paulo Cezar
, (2021/02/22)
This work investigated the biotransformation of ginger constituents (zingerone, [6]-shogaol, [6]-gingerol, and methyl-[6]-gingerol) by the pathogenic fungus Colletotrichum gloeosporioides. Experiments were carried out with and without deuterium-labelled compounds. The product metabolites were analyzed by liquid chromatography coupled to tandem mass spectrometry and liquid chromatography solid phase extraction-nuclear magnetic resonance. Substrates supplied to the fungus were incorporated into metabolic pathways mostly by oxidation reactions, including aromatic carbon–carbon coupling. Zingerone and [6]-gingerol biotransformation products included biphenol dimers. A biodegradation pathway for biphenol formation was proposed based on the presence of the intermediate 4-(2-hydroxyethyl)-2-methoxyphenol, commonly identified from [6]-gingerol and [6]-shogaol biodegradation. This intermediate likely originates from a Baeyer–Villiger reaction followed by hydrolysis. The C–C coupling of molecules could result in phenolic oxidative ortho–ortho coupling, suggesting that biphenol dimers are products of C. gloeosporioides laccase catalysis.
A new method for the demetallation of tricarbonyliron diene complexes by total hydrogenation with Raney nickel. Application to a very short synthesis of (+)-[6]-gingerdiol
Franck-Neumann, Michel,Geoffroy, Philippe,Bissinger, Paul,Adelaide, Sylvie
, p. 6401 - 6404 (2007/10/03)
Demetallation of tricarbonyliron diene complexes is rapidly achieved by treatment with freshly prepared Raney nickel. The ligands which are totally hydrogenated during the decomplexation are easily isolated in high yields, without racemization, if chiral.
