The B-ring hydroxylation pattern of anthocyanins can be determined through activity of the flavonoid 3′-hydroxylase on leucoanthocyanidins

Schwinn, Kathy E.; Miosic, Silvija; Davies, Kevin; Thill, Jana; Gotame, Tek Prasad; Stich, Karl; Halbwirth, Heidi

doi:10.1007/s00425-014-2166-3

Cited by 27 publications

(22 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…WAT11 cells transformed with pYES-DEST52- CsF3 ′ H vector catalyzed the hydroxylation at B-ring 3′-position of naringenin, dihydrokaempferol and kaempferol to eriodictyol, dihydroquercetin and quercetin, respectively, which indicates a broad substrate specificity of CsF3′H. In a recent report [ 36 ] leucopelargonidin was demonstrated to be also a substrate for F3′H. Due to the limited availability of the substrate, this compound was not covered in the present study.…”

Section: Resultsmentioning

confidence: 97%

Cloning and Characterization of a Flavonoid 3′-Hydroxylase Gene from Tea Plant (Camellia sinensis)

Zhou

et al. 2016

IJMS

View full text Add to dashboard Cite

Tea leaves contain abundant flavan-3-ols, which include dihydroxylated and trihydroxylated catechins. Flavonoid 3′-hydroxylase (F3′H: EC 1.14.13.21) is one of the enzymes in the establishment of the hydroxylation pattern. A gene encoding F3′H, designated as CsF3′H, was isolated from Camellia sinensis with a homology-based cloning technique and deposited in the GenBank (GenBank ID: KT180309). Bioinformatic analysis revealed that CsF3′H was highly homologous with the characterized F3′Hs from other plant species. Four conserved cytochrome P450-featured motifs and three F3′H-specific conserved motifs were discovered in the protein sequence of CsF3′H. Enzymatic analysis of the heterologously expressed CsF3′H in yeast demonstrated that tea F3′H catalyzed the 3′-hydroxylation of naringenin, dihydrokaempferol and kaempferol. Apparent Km values for these substrates were 17.08, 143.64 and 68.06 μM, and their apparent Vmax values were 0.98, 0.19 and 0.44 pM·min−1, respectively. Transcription level of CsF3′H in the new shoots, during tea seed germination was measured, along with that of other key genes for flavonoid biosynthesis using real-time PCR technique. The changes in 3′,4′-flavan-3-ols, 3′,4′,5′-flavan-3-ols and flavan-3-ols, were consistent with the expression level of CsF3′H and other related genes in the leaves. In the study of nitrogen supply for the tea plant growth, our results showed the expression level of CsF3′H and all other tested genes increased in response to nitrogen depletion after 12 days of treatment, in agreement with a corresponding increase in 3′,4′-catechins, 3′,4′,5′-catechins and flavan 3-ols content in the leaves. All these results suggest the importance of CsF3′H in the biosynthesis of 3′,4′-catechins, 3′,4′,5′-catechins and flavan 3-ols in tea leaves.

show abstract

Section: Resultsmentioning

confidence: 97%

Cloning and Characterization of a Flavonoid 3′-Hydroxylase Gene from Tea Plant (Camellia sinensis)

Zhou

et al. 2016

IJMS

View full text Add to dashboard Cite

show abstract

“…The resulting pigments are stored in the vacuoles (Matern et al 1986). The hydroxylation pattern of the B-ring can be established at different intermediate levels (Schwinn et al 2014). The synthesis of Cy-derivatives includes a hydroxylation step at the 3 0 -position by F3 0 H, whereas the formation of Dp-based pigments ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Multiple evolution of flavonoid 3′,5′-hydroxylase

Seitz¹,

Ameres²,

Schlangen

et al. 2015

Planta

Self Cite

View full text Add to dashboard Cite

Multiple F3'5'H evolution from F3'H has occurred in dicotyledonous plants. Efficient pollinator attraction is probably the driving force behind, as this allowed for the synthesis of delphinidin-based blue anthocyanins. The cytochrome P450-dependent monooxygenases flavonoid 3'-hydroxylase (F3'H) and flavonoid 3',5'-hydroxylase (F3'5'H) hydroxylate the B-ring of flavonoids at the 3'- and 3'- and 5'-position, respectively. Their divergence took place early in plant evolution. While F3'H is ubiquitously present in higher plants, the distribution of F3'5'H is scattered. Here, we report that F3'5'H has repeatedly evolved from F3'H precursors at least four times in dicotyledonous plants: In the Asteraceae, we identified F3'5'Hs specific for the subfamilies Cichorioideae and Asteroideae, and additionally an F3'5'H that seems to be specific for the genus Echinops of the subfamily Carduoideae; moreover, characterisation of a sequence from Billardiera heterophylla (formerly Sollya heterophylla) (Pittosporaceae) showed that the independent evolution of an F3'5'H has occurred at least once also in another family. The evolution of F3'5'H from an F3'H precursor represents a gain of enzymatic function, probably triggered by an amino acid change at one position of substrate recognition site 6. The gain of F3'5'H activity allows for the synthesis of delphinidin-based anthocyanins which usually provide the basis for lilac to blue flower colours. Therefore, the need for an efficient pollinator attraction is probably the driving force behind the multiple F3'5'H evolution.

show abstract

“…Comparison of the expression of c73764_g1_i1 and c74095_g3_i1 based on transcriptome data showed that the expression of c73764_g1_i1 in the red culm was higher than that in the leaf. F3′H (EC 1.14.13.21) transforms dihydroflavonol into dihydroquercetin by adding a hydroxyl to the 3' position of ring B (Schwinn et al, 2014). The transcriptome data indicated the existence of five F3′H-encoding genes.…”

Section: Transcriptome-based Analysis Of Differentially Expressed Genesmentioning

confidence: 99%

Transcriptome analysis identified genes involved in anthocyanin biosynthesis in Rainbow bamboo (Indosasa hispida MeClure cv. ‘Rainbow’)

et al. 2018

View full text Add to dashboard Cite

Rainbow bamboo (Indosasa hispida) is an ornamental plant, which contains unique red to purple anthocyanin in its culm. However, the biosynthesis and function of anthocyanin in bamboo remains unclear. In this study, RNA-seq was used to investigate the transcriptome of the species and compare the gene expression profiles of red and white culms. The expression levels of genes involved in the anthocyanin biosynthesis pathway were detected using quantitative reverse transcription-polymerase chain reaction (qRT-PCR). In total, 5.92 billion reads were obtained from the culm of Rainbow bamboo, which were assembled into 60,716 unigenes. qRT-PCR showed that the expression levels of anthocyanin biosynthesis-related genes in the red and white culms were higher than that in green leaves and that their levels in the red culm without sheath were higher than that in the white culm with sheath. Transcriptome analysis and qRT-PCR showed that the differences in the expression of genes encoding chalcone isomerase (CHI), dihydroflavonol reductase (DFR), flavonoid 3'-hydroxylase (F3'H), and anthocyanidin 3-O-glycosyltransferase (A3GT) between the culm and leaf were significant. This implies that CHI, DFR, F3'H, and A3GT play important roles in anthocyanin synthesis and accumulation in the culm of Rainbow bamboo.

show abstract

The B-ring hydroxylation pattern of anthocyanins can be determined through activity of the flavonoid 3′-hydroxylase on leucoanthocyanidins

Cited by 27 publications

References 36 publications

Cloning and Characterization of a Flavonoid 3′-Hydroxylase Gene from Tea Plant (Camellia sinensis)

Cloning and Characterization of a Flavonoid 3′-Hydroxylase Gene from Tea Plant (Camellia sinensis)

Multiple evolution of flavonoid 3′,5′-hydroxylase

Transcriptome analysis identified genes involved in anthocyanin biosynthesis in Rainbow bamboo (Indosasa hispida MeClure cv. ‘Rainbow’)

Contact Info

Product

Resources

About