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Enzymatic Sulfation of Phenolic Hydroxy Groups of Various Plant Metabolites by an Arylsulfotransferase
Author(s) -
van der Horst Michael A.,
Hartog Aloysius F.,
El Morabet Rabab,
Marais Arthur,
Kircz Menzo,
Wever Ron
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402875
Subject(s) - sulfation , chemistry , phloretin , sulfate , sulfotransferase , enzyme , catalysis , organic chemistry , stereochemistry , biochemistry
Abstract The bacterial arylsulfate sulfotransferase (AST) from Desulfitobacterium hafniense was used as a catalytic tool to derivatize poorly soluble aromatic compounds (polyphenols). As examples, we sulfated the natural occurring compounds p ‐coumaric acid, 6‐hydroxyflavone, resveratrol, phloretin, and quercetin, using p ‐nitrophenylsulfate as the sulfate donor. The water‐soluble sulfate esters were purified and characterized. Depending on the nature of the compound, one or more sulfate groups could be introduced in a stepwise order. The sulfation of resveratrol resulted in two different monosulfates (4′‐ and 3‐sulfates), the 3,4′‐disulfate, and the 3,5,4′‐trisulfate. Sulfation of phloretin resulted in a monosulfate (4′‐sulfate) and a disulfate (4,4′‐disulfate). Although quercetin has five hydroxy groups that could be sulfated, surprisingly this enzyme system primarily catalyses the sulfation only at the 4′ position. This simple enzymatic one‐step sulfation method is easy to use, and it allows a convenient and simple production of sulfated compounds with improved solubility.