Literature Information

Title	Enzymatic Sulfation of Phenolic Hydroxy Groups of Various Plant Metabolites by an Arylsulfotransferase
Author	Michael A. van der Horst Aloysius F. Hartog Rabab El Morabet Arthur Marais Menzo Kircz Ron Wever
DOI	10.1002/ejoc.201402875
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.

Experimental results

• Enzyme

Uniprot ID: B8FRJ0

Protein: Arylsulfotransferase

Organism: Desulfitobacterium hafniense (strain DCB-2 / DSM 10664)

Length: 628 AA

Taxonomic identifier: 272564 [NCBI]

• Pfam

Source	Domain	Start	End	E-value (Domain)	Coverage
Pfam-A	Arylsulfotran_N	38	117	3.1e-20	0.978
Pfam-A	Arylsulfotrans	127	485	4.9e-106	0.976

Program: hmmscan

Version: 3.1b2 (February 2015)

Method: hmmscan --domtblout hmmscan.tbl --noali -E 1e-5 pfam query.fa

Date: Mon Jul 20 14:32:16 2020

Description:

Arylsulfotran_N

Pfam

This family consists of several bacterial Arylsulfotransferase proteins. Arylsulfotransferase (ASST) transfers a sulfate group from phenolic sulfate esters to a phenolic acceptor substrate¹. This domain has an Ig-like fold.

InterPro

This entry represents the N-terminal Ig-like domain found in arylsulfotransferases. Arylsulphotransferase (ASST) transfers a sulphate group from phenolic sulphate esters to a phenolic acceptor substrate¹.

Arylsulfotrans

Pfam

This family consists of several bacterial Arylsulfotransferase proteins. Arylsulfotransferase (ASST) transfers a sulfate group from phenolic sulfate esters to a phenolic acceptor substrate¹.

InterPro

This entry represents a group of arylsulphotransferase (ASST) mostly from bacteria. It transfers a sulphate group from phenolic sulphate esters to a phenolic acceptor substrate¹.

Information is taken from Pfam and InterPro web site.

• Reaction

phloretin + 4-Nitrophenyl sulfate ⇒ monosulfate

phloretin + 4-Nitrophenyl sulfate ⇒ 4,4’-phloretin disulfate

References