Identification and cloning of an NADPH-dependent hydroxycinnamoyl-CoA double bond reductase involved in dihydrochalcone formation in Malus×domestica Borkh.

Ibdah, Mwafaq; Berim, Anna; Martens, Stefan; Valderrama, A.L. Herrera; Palmieri, L.; Lewinsohn, Efraim; Gang, David R.

doi:10.1016/j.phytochem.2014.07.027

Cited by 32 publications

(37 citation statements)

References 37 publications

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“…The accumulation of dihydroferulic acid hexosides 5 and 12 can possibly be explained by the activity of an alkenal DBR. The activities of an Arabidopsis DBR reducing the C7-C8 double bond of p-coumaraldehyde and coniferaldehyde, and an apple (Malus 3 domestica) DBR reducing the double bond in p-coumaroyl-CoA and feruloyl-CoA, have been shown by enzymatic assays (Youn et al, 2006b;Ibdah et al, 2014). Vanillic acid hexoside 13 also accumulated in the CAD1-deficient poplars (Table V).…”

Section: Discussionmentioning

confidence: 86%

“…Thus, for this mechanism to operate, a prior double bond reduction of sinapic acid to dihydrosinapic acid (or from sinapaldehyde to dihydrosinapaldehyde followed by its oxidation to dihydrosinapic acid) is necessary, after which dihydrosinapic acid is hydroxylated to syringyl lactic acid. As stated above, DBR enzymes from Arabidopsis and apple reducing the C7-C8 double bond of phenylpropanoids have been described (Youn et al, 2006b;Ibdah et al, 2014).…”

Section: Discussionmentioning

confidence: 98%

“…06, 208.04, 179.07, 164.05, and 149.02 were reminiscent of a sinapic acid-derived moiety (Widhalm and Dudareva, 2015). DBR has been found to reduce the C7-C8 double bond of p-coumaraldehyde and coniferaldehyde in Arabidopsis (Youn et al, 2006b), but it also might reduce the corresponding hydroxycinnamoyl-CoAs (Ibdah et al, 2014). The functions of a heterotrimeric C4H/C3H protein complex in the hydroxylation of p-coumaryl shikimate toward caffeoyl shikimate and a similar heterodimeric C4H/C3H protein complex that is able to convert p-coumaric acid directly into caffeic acid in poplar have been described by Chen et al (2011).…”

Section: Profiling Of Methanol-soluble Phenolicsmentioning

confidence: 99%

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Different Routes for Conifer- and Sinapaldehyde and Higher Saccharification upon Deficiency in the Dehydrogenase CAD1

Déjardin²,

et al. 2017

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In the search for renewable energy sources, genetic engineering is a promising strategy to improve plant cell wall composition for biofuel and bioproducts generation. Lignin is a major factor determining saccharification efficiency and, therefore, is a prime target to engineer. Here, lignin content and composition were modified in poplar (Populus tremula 3 Populus alba) by specifically down-regulating CINNAMYL ALCOHOL DEHYDROGENASE1 (CAD1) by a hairpin-RNA-mediated silencing approach, which resulted in only 5% residual CAD1 transcript abundance. These transgenic lines showed no biomass penalty despite a 10% reduction in Klason lignin content and severe shifts in lignin composition. Nuclear magnetic resonance spectroscopy and thioacidolysis revealed a strong increase (up to 20-fold) in sinapaldehyde incorporation into lignin, whereas coniferaldehyde was not increased markedly. Accordingly, ultra-high-performance liquid chromatography-mass spectrometry-based phenolic profiling revealed a more than 24,000-fold accumulation of a newly identified compound made from 8-8 coupling of two sinapaldehyde radicals. However, no additional cinnamaldehyde coupling products could be detected in the CAD1-deficient poplars. Instead, the transgenic lines accumulated a range of hydroxycinnamate-derived metabolites, of which the most prominent accumulation (over 8,500-fold) was observed for a compound that was identified by purification and nuclear magnetic resonance as syringyl lactic acid hexoside. Our data suggest that, upon down-regulation of CAD1, coniferaldehyde is converted into ferulic acid and derivatives, whereas sinapaldehyde is either oxidatively coupled into S9(8-8)S9 and lignin or converted to sinapic acid and derivatives. The most prominent sink of the increased flux to hydroxycinnamates is syringyl lactic acid hexoside. Furthermore, low-extent saccharification assays, under different pretreatment conditions, showed strongly increased glucose (up to +81%) and xylose (up to +153%) release, suggesting that down-regulating CAD1 is a promising strategy for improving lignocellulosic biomass for the sugar platform industry.

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Section: Discussionmentioning

confidence: 86%

Section: Discussionmentioning

confidence: 98%

Section: Profiling Of Methanol-soluble Phenolicsmentioning

confidence: 99%

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Different Routes for Conifer- and Sinapaldehyde and Higher Saccharification upon Deficiency in the Dehydrogenase CAD1

Déjardin²,

et al. 2017

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“…The role of dihydrochalcone glycosides in plants and their biosynthesis are, however, not yet well understood. Research to date focussed mainly on phloridzin, a major dihydrochalcone glucoside in apple leaves (Gosch et al, 2009;Ibdah et al, 2014). Its role in disease resistance is controversial (Gosch et al, 2009).…”

Section: Resultsmentioning

confidence: 99%

Production of dihydrochalcone-rich green rooibos (Aspalathus linearis) extract taking into account seasonal and batch-to-batch variation in phenolic composition of plant material

Beer

Miller

2017

South African Journal of Botany

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a b s t r a c t a r t i c l e i n f o Available online xxxx Edited by: J. van StadenRandomly selected rooibos plants from three plantations were harvested (a few branches per plant) at intervals from early summer to late spring. The aspalathin and nothofagin content of the plant material was highest at the first harvest date (3.76% and 0.54%, respectively) in summer whereafter their content decreased gradually to the lowest levels in winter and increased to 3.31% and 0.36%, respectively in mid-spring. Commercial green rooibos production batches (n = 47), produced over a period of 49 days (end of January until mid-March) from plant material harvested from one plantation were analysed to provide further insight into expected batch-to-batch variation in aspalathin, nothofagin, orientin and iso-orientin content. The aspalathin content of green rooibos varied between 2.50% and 4.49%, even though the plant material was harvested from the same plantation. The other compounds were present in the plant material in much lower quantities (b0.5%). The iso-orientin and orientin contents of the green rooibos samples did not vary substantially. The variation observed in the plant material was subsequently also observed in the freeze-dried hot water extracts prepared from the commercial green rooibos production batches, with the theoretical dried extract yield varying between 15.07% and 22.89%. The aspalathin content and total polyphenol content of the dried extract varied between 8.11% and 12.33% and between 29.7 and 43.5 g gallic acid equivalents/100 g, respectively. The mean content values for the other compounds were less than 1.2%. Combined these major dihydrochalcones and flavones comprised between 10.22% and 14.88% of the freeze-dried extract. Aspalathin contributed between 13.1% and 22.8% of the total antioxidant capacity (2873-4286 μmol Trolox equivalents/g) of the dried extract as determined by the DPPH radical scavenging assay.

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“…The enumerated considerations and examples make evident that to predict a candidate gene/enzyme involved in the proposed reaction sequence is almost impossible. Although other reductases, like the hydroxycinnamoyl-CoA double bond reductases implicated in dihydrochalcone formation, might appear more legitimate candidates to tackle the alkene moiety within vomilenine (Youn et al 2006;Ibdah et al 2014), the newly acquired function of VR2, seemingly deriving from the CAD enzyme family, comprises the NADPH-dependent reduction of the aforementioned alkene component with very high specificity. Proximity of the hydroxyl group at position 21 of the parent scaffold seems, therefore, mandatory, since neither the structurally related vinorine (no OH-group at C-21) nor raucaffricine (vomilenine-21-D-glucopyranoside) were processed as VR2 substrates.…”

Section: Discussionmentioning

confidence: 99%

A novel cinnamyl alcohol dehydrogenase (CAD)-like reductase contributes to the structural diversity of monoterpenoid indole alkaloids in Rauvolfia

Geissler

Burghard

Volk

et al. 2015

Planta

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Based on findings described herein, we contend that the reduction of vomilenine en route to antiarrhythmic ajmaline in planta might proceed via an alternative, novel sequence of biosynthetic steps. In the genus Rauvolfia, monoterpenoid indole alkaloids (MIAs) are formed via complex biosynthetic sequences. Despite the wealth of information about the biochemistry and molecular genetics underlying these processes, many reaction steps involving oxygenases and oxidoreductases are still elusive. Here, we describe molecular cloning and characterization of three cinnamyl alcohol dehydrogenase (CAD)-like reductases from Rauvolfia serpentina cell culture and R. tetraphylla roots. Functional analysis of the recombinant proteins, with a set of MIAs as potential substrates, led to identification of one of the enzymes as a CAD, putatively involved in lignin formation. The two remaining reductases comprise isoenzymes derived from orthologous genes of the investigated alternative Rauvolfia species. Their catalytic activity consists of specific conversion of vomilenine to 19,20-dihydrovomilenine, thus proving their exclusive involvement in MIA biosynthesis. The obtained data suggest the existence of a previously unknown bypass in the biosynthetic route to ajmaline further expanding structural diversity within the MIA family of specialized plant metabolites.

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Identification and cloning of an NADPH-dependent hydroxycinnamoyl-CoA double bond reductase involved in dihydrochalcone formation in Malus×domestica Borkh.

Cited by 32 publications

References 37 publications

Different Routes for Conifer- and Sinapaldehyde and Higher Saccharification upon Deficiency in the Dehydrogenase CAD1

Different Routes for Conifer- and Sinapaldehyde and Higher Saccharification upon Deficiency in the Dehydrogenase CAD1

Production of dihydrochalcone-rich green rooibos (Aspalathus linearis) extract taking into account seasonal and batch-to-batch variation in phenolic composition of plant material

A novel cinnamyl alcohol dehydrogenase (CAD)-like reductase contributes to the structural diversity of monoterpenoid indole alkaloids in Rauvolfia

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