Biotransformation of pungent constituents from ginger (Zingiber officinale Roscoe) by Colletotrichum gloeosporioides yields oxidative ortho-ortho coupling products

Author(s)

Dias de Avila, Roberta Marques ; Toffano, Leonardo ; Fernandes, Joao Batista ; dos Gracas Fernandes da Silva, Maria Fatima ; Freitas de Sousa, Lorena Ramos ; Vieira, Paulo Cezar

• Document type: Journal article
• Source: BIOCATALYSIS AND BIOTRANSFORMATION; v. 40, n. 2, p. 12-pg., 2021-02-03.

Abstract

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. (AU)

• FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Grantee: Arlene Gonçalves Corrêa
• Support Opportunities: Research Grants - Research Centers in Engineering Program