A UDP-Glucose:Monoterpenol Glucosyltransferase Adds to the Chemical Diversity of the Grapevine Metabolome

Bönisch, Friedericke; Frotscher, Johanna; Stanitzek, Sarah; Rühl, Ernst; Wüst, Matthias; Bitz, Oliver; Schwab, Wilfried

doi:10.1104/pp.113.232470

Cited by 100 publications

(100 citation statements)

References 98 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Members of the family‐1 UGTs show high variability in their substrate preferences. Many UGTs show relatively broad substrate specificity (Hefner, Arend, Warzecha, Siems, & Stöckigt, ; Bönisch et al, ; Song, Gu, et al, ), whereas other UGTs are quite specific (Jugdé, Nguy, Moller, Cooney, & Atkinson, ). It is therefore not surprising that CsUGT85A53‐1, CsUGT85A53‐2, and CsUGT85A53‐3 displayed broad substrate tolerance in vitro.…”

Section: Discussionmentioning

confidence: 99%

“…Besides, glycosylation facilitates sorting of secondary metabolites, intercellular transport, storage, and accumulation in plant cells (J. Wang & Hou, ). In many flowers and fruit, aroma and flavour compounds accumulate as nonvolatile glycosides (Bönisch et al, , ; Song, Hong, et al, ). Glycosylation reactions are mediated by UDP‐glycosyltransferases (UGTs) that catalyse the transfer of an activated nucleotide sugar (such as UDP‐glucose) to acceptor aglycons to form O ‐, S ‐, and N ‐glycosides as well as sugar esters.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Glucosylation of (Z)‐3‐hexenol informs intraspecies interactions in plants: A case study in Camellia sinensis

Jing

Zhang

Gao

et al. 2018

Plant Cell & Environment

Self Cite

121

View full text Add to dashboard Cite

Plants emit a variety of volatiles in response to herbivore attack, and (Z)‐3‐hexenol and its glycosides have been shown to function as defence compounds. Although the ability to incorporate and convert (Z)‐3‐hexenol to glycosides is widely conserved in plants, the enzymes responsible for the glycosylation of (Z)‐3‐hexenol remained unknown until today. In this study, uridine‐diphosphate‐dependent glycosyltransferase (UGT) candidate genes were selected by correlation analysis and their response to airborne (Z)‐3‐hexenol, which has been shown to be taken up by the tea plant. The allelic proteins UGT85A53‐1 and UGT85A53‐2 showed the highest activity towards (Z)‐3‐hexenol and are distinct from UGT85A53‐3, which displayed a similar catalytic efficiency for (Z)‐3‐hexenol and nerol. A single amino acid exchange E59D enhanced the activity towards (Z)‐3‐hexenol, whereas a L445M mutation reduced the catalytic activity towards all substrates tested. Transient overexpression of CsUGT85A53‐1 in tobacco significantly increased the level of (Z)‐3‐hexenyl glucoside. The functional characterization of CsUGT85A53 as a (Z)‐3‐hexenol UGT not only provides the foundation for the biotechnological production of (Z)‐3‐hexenyl glucoside but also delivers insights for the development of novel insect pest control strategies in tea plant and might be generally applicable to other plants.

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Glucosylation of (Z)‐3‐hexenol informs intraspecies interactions in plants: A case study in Camellia sinensis

Jing

Zhang

Gao

et al. 2018

Plant Cell & Environment

Self Cite

121

View full text Add to dashboard Cite

show abstract

“…K M values of 213 mM to 899 mM were determined for UGT71K3 enzymes when HDMF and EHMF were used as acceptor substrates (Table I) Beekwilder et al, 2004); 10 mM to 5600 mM for strawberry alcohol acyl-CoA transferase (additional AAT from F. 3 ananassa; Aharoni et al, 2000); 9 mM to 464 mM for different monoterpenol glucosyltransferases from grape (Bönisch et al, 2014a(Bönisch et al, , 2014b; 356 mM for a cinnamate glucosyltransferase from strawberry (Lunkenbein et al, 2006); and 14 mM to 291 mM for three glucosyltransferase from Stevia rebaudiana (Richman et al, 2005). The methyltransferase that transforms HDMF to its methoxy derivative has a K m of 440 mM (Wein et al, 2002;Zorrilla-Fontanesi et al, 2012).…”

Section: Glucosylation Of Volatile Metabolites In Strawberrymentioning

confidence: 99%

“…Knowledge of the underlying catalytic and regulatory mechanisms and their physiological roles would be of great biotechnological importance for the synthesis of bioactive secondary metabolites in vitro and for the metabolic engineering of crops with important agronomic traits through efficient breeding strategies Kristensen et al, 2005;Weis et al, 2008). Although the ubiquitous GT family has been intensively studied for many years (Gachon et al, 2005) and enzymes involved in the glucosylation of plant products such as anthocyanidins, flavonoids, terpenes, alcohols (Cheng et al, 1994;Almeida et al, 2007;Griesser et al, 2008aGriesser et al, , 2008bBönisch et al, 2014aBönisch et al, , 2014bOhgami et al, 2015), and plant hormones have been functionally characterized, little is actually known about the glucosylation of strawberry aroma chemicals.…”

mentioning

confidence: 99%

Glucosylation of 4-Hydroxy-2,5-Dimethyl-3(2H)-Furanone, the Key Strawberry Flavor Compound in Strawberry Fruit

et al. 2016

Self Cite

View full text Add to dashboard Cite

ORCID IDs: 0000-0002-7852-1194 (C.S.); 0000-0002-9753-3967 (W.S.).Strawberries emit hundreds of different volatiles, but only a dozen, including the key compound HDMF [4-hydroxy-2,5-dimethyl-3(2H)-furanone] contribute to the flavor of the fruit. However, during ripening, a considerable amount of HDMF is metabolized to the flavorless HDMF b-D-glucoside. Here, we functionally characterize nine ripening-related UGTs (UDPglucosyltransferases) in Fragaria that function in the glucosylation of volatile metabolites by comprehensive biochemical analyses. Some UGTs showed a rather broad substrate tolerance and glucosylated a range of aroma compounds in vitro, whereas others had a more limited substrate spectrum. The allelic UGT71K3a and b proteins and to a lesser extent UGT73B24, UGT71W2, and UGT73B23 catalyzed the glucosylation of HDMF and its structural homolog 2(or 5)-ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone. Site-directed mutagenesis to introduce single K458R, D445E, D343E, and V383A mutations and a double G433A/I434V mutation led to enhanced HDMF glucosylation activity compared to the wild-type enzymes. In contrast, a single mutation in the center of the plant secondary product glycosyltransferase box (A389V) reduced the enzymatic activity. Down-regulation of UGT71K3 transcript expression in strawberry receptacles led to a significant reduction in the level of HDMF-glucoside and a smaller decline in HDMF-glucoside-malonate compared with the level in control fruits. These results provide the foundation for improvement of strawberry flavor and the biotechnological production of HDMF-glucoside.

show abstract

“…Most of these genes have been investigated in previous works but they were not considered as candidates for monoterpene glucosylation in view of their decreasing expression during berry development (Khater et al, 2011; Bönisch et al, 2014a,b). However, they might be involved in the production of glucosylated monoterpenes with a similar trend, like the high oxidation state monoterpenoids sharing the same biclusters (Table 2 and Supplementary Table S9), which were not quantified in those papers.…”

Section: Resultsmentioning

confidence: 99%

Drawing Links from Transcriptome to Metabolites: The Evolution of Aroma in the Ripening Berry of Moscato Bianco (Vitis vinifera L.)

et al. 2017

View full text Add to dashboard Cite

Monoterpenes confer typical floral notes to “Muscat” grapevine varieties and, to a lesser extent, to other aromatic non-Muscat varieties. Previous studies have led to the identification and functional characterization of some enzymes and genes in this pathway. However, the underlying genetic map is still far from being complete. For example, the specific steps of monoterpene metabolism and its regulation are largely unknown. With the aim of identifying new candidates for the missing links, we applied an integrative functional genomics approach based on the targeted metabolic and genome-wide transcript profiling of Moscato Bianco ripening berries. In particular, gas chromatography-mass spectrometry analysis of free and bound terpenoid compounds was combined with microarray analysis in the skins of berries collected at five developmental stages from pre-veraison to over-ripening. Differentially expressed metabolites and probes were identified in the pairwise comparison between time points by using the early stage as a reference. Metabolic and transcriptomic data were integrated through pairwise correlation and clustering approaches to discover genes linked with particular metabolites or groups of metabolites. These candidate transcripts were further checked for co-localization with quantitative trait loci (QTLs) affecting aromatic compounds. Our findings provide insights into the biological networks of grapevine secondary metabolism, both at the catalytic and regulatory levels. Examples include a nudix hydrolase as component of a terpene synthase-independent pathway for monoterpene biosynthesis, genes potentially involved in monoterpene metabolism (cytochrome P450 hydroxylases, epoxide hydrolases, glucosyltransferases), transport (vesicle-associated proteins, ABCG transporters, glutathione S-transferases, amino acid permeases), and transcriptional control (transcription factors of the ERF, MYB and NAC families, intermediates in light- and circadian cycle-mediated regulation with supporting evidence from the literature and additional regulatory genes with a previously unreported association to monoterpene accumulation).

show abstract

A UDP-Glucose:Monoterpenol Glucosyltransferase Adds to the Chemical Diversity of the Grapevine Metabolome

Cited by 100 publications

References 98 publications

Glucosylation of (Z)‐3‐hexenol informs intraspecies interactions in plants: A case study in Camellia sinensis

Glucosylation of (Z)‐3‐hexenol informs intraspecies interactions in plants: A case study in Camellia sinensis

Glucosylation of 4-Hydroxy-2,5-Dimethyl-3(2H)-Furanone, the Key Strawberry Flavor Compound in Strawberry Fruit

Drawing Links from Transcriptome to Metabolites: The Evolution of Aroma in the Ripening Berry of Moscato Bianco (Vitis vinifera L.)

Contact Info

Product

Resources

About