Ellagic acid/ellagitannins are plant polyphenolic antioxidants that are synthesized from gallic acid and have been associated with a reduced risk of cancer and cardiovascular diseases. Here, we report the identification and characterization of five glycosyltransferases (GTs) from two genera of the Rosaceae family (Fragaria and Rubus; F.×ananassa FaGT2*, FaGT2, FaGT5, F. vesca FvGT2, and R. idaeus RiGT2) that catalyze the formation of 1-O-galloyl-β-D-glucopyranose (β-glucogallin) the precursor of ellagitannin biosynthesis. The enzymes showed substrate promiscuity as they formed glucose esters of a variety of (hydroxyl)benzoic and (hydroxyl)cinnamic acids. Determination of kinetic values and site-directed mutagenesis revealed amino acids that affected substrate preference and catalytic activity. Green immature strawberry fruits were identified as the main source of gallic acid, β-glucogallin, and ellagic acid in accordance with the highest GT2 gene expression levels. Injection of isotopically labeled gallic acid into green fruits of stable transgenic antisense FaGT2 strawberry plants clearly confirmed the in planta function. Our results indicate that GT2 enzymes might contribute to the production of ellagic acid/ellagitannins in strawberry and raspberry, and are useful to develop strawberry fruit with additional health benefits and for the biotechnological production of bioactive polyphenol

Schulenburg, K.; Feller, A.C.; Hoffmann, T.; Schecker, J.H.; Martens, S.; Schwab, W. (2016). Formation of β-glucogallin, the precursor of ellagic acid in strawberry and raspberry. JOURNAL OF EXPERIMENTAL BOTANY, 67 (8): 2299-2308. doi: 10.1093/jxb/erw036 handle: http://hdl.handle.net/10449/30838

Formation of β-glucogallin, the precursor of ellagic acid in strawberry and raspberry

Feller, Antje Christin;Martens, Stefan;
2016-01-01

Abstract

Ellagic acid/ellagitannins are plant polyphenolic antioxidants that are synthesized from gallic acid and have been associated with a reduced risk of cancer and cardiovascular diseases. Here, we report the identification and characterization of five glycosyltransferases (GTs) from two genera of the Rosaceae family (Fragaria and Rubus; F.×ananassa FaGT2*, FaGT2, FaGT5, F. vesca FvGT2, and R. idaeus RiGT2) that catalyze the formation of 1-O-galloyl-β-D-glucopyranose (β-glucogallin) the precursor of ellagitannin biosynthesis. The enzymes showed substrate promiscuity as they formed glucose esters of a variety of (hydroxyl)benzoic and (hydroxyl)cinnamic acids. Determination of kinetic values and site-directed mutagenesis revealed amino acids that affected substrate preference and catalytic activity. Green immature strawberry fruits were identified as the main source of gallic acid, β-glucogallin, and ellagic acid in accordance with the highest GT2 gene expression levels. Injection of isotopically labeled gallic acid into green fruits of stable transgenic antisense FaGT2 strawberry plants clearly confirmed the in planta function. Our results indicate that GT2 enzymes might contribute to the production of ellagic acid/ellagitannins in strawberry and raspberry, and are useful to develop strawberry fruit with additional health benefits and for the biotechnological production of bioactive polyphenol
Ellagic acid
Ellagitannin
Fragaria
β-glucogallin
Glucose ester
Glycosyltransferase
Rubus
Settore BIO/11 - BIOLOGIA MOLECOLARE
2016
Schulenburg, K.; Feller, A.C.; Hoffmann, T.; Schecker, J.H.; Martens, S.; Schwab, W. (2016). Formation of β-glucogallin, the precursor of ellagic acid in strawberry and raspberry. JOURNAL OF EXPERIMENTAL BOTANY, 67 (8): 2299-2308. doi: 10.1093/jxb/erw036 handle: http://hdl.handle.net/10449/30838
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