3-O-glycosylation of kaempferol restricts the supply of the benzenoid precursor of ubiquinone (Coenzyme Q) in Arabidopsis thaliana

Soubeyrand, Eric; Latimer, Scott; Bernert, Ann C.; Keene, Shea A.; Johnson, Timothy S.; Shin, Doosan; Block, Anna; Colquhoun, Thomas A.; Schäffner, Anton R.; Kim, Jeongim; Basset, Gilles J.

doi:10.1016/j.phytochem.2021.112738

Cited by 10 publications

(6 citation statements)

References 26 publications

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“…The glycosylation of kaempferol on its C-3 hydroxyl is believed to prevent the oxidative release of the B-ring as 4HB and thus its incorporation into CoQ biosynthesis [69]. Supporting this model, new experiments using a complex Arabidopsis mutant that lacks the majority of kaempferol 3-O-glycosyltransferase activities, leaving the C-3 hydroxyl of kaempferol unprotected, showed that the release of the B-ring of kaempferol as 4HB is increased, boosting CoQ biosynthesis [77]. Additional studies in mammalian cells using 13 C-B-ring-kaempferol demonstrated that the B-ring is indeed the part of the molecule that is incorporated into CoQ [78], suggesting that the mechanism described in plants is likely to be conserved in vertebrates.…”

Section: Natural Productsmentioning

confidence: 96%

Coenzyme Q Biosynthesis: An Update on the Origins of the Benzenoid Ring and Discovery of New Ring Precursors

Fernández-del-Rio

Clarke

2021

Metabolites

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Coenzyme Q (ubiquinone or CoQ) is a conserved polyprenylated lipid essential for mitochondrial respiration. CoQ is composed of a redox-active benzoquinone ring and a long polyisoprenyl tail that serves as a membrane anchor. A classic pathway leading to CoQ biosynthesis employs 4-hydroxybenzoic acid (4HB). Recent studies with stable isotopes in E. coli, yeast, and plant and animal cells have identified CoQ intermediates and new metabolic pathways that produce 4HB. Stable isotope labeling has identified para-aminobenzoic acid as an alternate ring precursor of yeast CoQ biosynthesis, as well as other natural products, such as kaempferol, that provide ring precursors for CoQ biosynthesis in plants and mammals. In this review, we highlight how stable isotopes can be used to delineate the biosynthetic pathways leading to CoQ.

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Section: Natural Productsmentioning

confidence: 96%

Coenzyme Q Biosynthesis: An Update on the Origins of the Benzenoid Ring and Discovery of New Ring Precursors

Fernández-del-Rio

Clarke

2021

Metabolites

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“…Kaempferols are key players in the regulation of many plant processes. For example, 3-O-glycosylation of kaempferol is a restriction point for the supply of the benzenoid precursor of ubiquinone (Soubeyrand et al, 2018(Soubeyrand et al, , 2021, which plays indispensable roles in plant growth and development (Liu & Lu, 2016). Similarly, catabolism of K-3,7-di-R increases during developmental senescence (Unterlander et al, 2022), and it is also accumulated in response to infections by the caterpillar Pieris brassicae (Onkokesung et al, 2014), and limits polar auxin transport and associated growth and organ development processes (Yin et al, 2014;Kuhn et al, 2016).…”

Section: Discussionmentioning

confidence: 99%

Kaempferol‐3‐rhamnoside overaccumulation in flavonoid 3′‐hydroxylase tt7 mutants compromises seed coat outer integument differentiation and seed longevity

et al. 2023

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Seeds slowly accumulate damage during storage, which ultimately results in germination failure. The seed coat protects the embryo from the external environment, and its composition is critical for seed longevity. Flavonols accumulate in the outer integument. The link between flavonol composition and outer integument development has not been explored.Genetic, molecular and ultrastructural assays on loss-of-function mutants of the flavonoid biosynthesis pathway were used to study the effect of altered flavonoid composition on seed coat development and seed longevity.Controlled deterioration assays indicate that loss of function of the flavonoid 3 0 hydroxylase gene TT7 dramatically affects seed longevity and seed coat development. Outer integument differentiation is compromised from 9 d after pollination in tt7 developing seeds, resulting in a defective suberin layer and incomplete degradation of seed coat starch. These distinctive phenotypes are not shared by other mutants showing abnormal flavonoid composition. Genetic analysis indicates that overaccumulation of kaempferol-3-rhamnoside is mainly responsible for the observed phenotypes. Expression profiling suggests that multiple cellular processes are altered in the tt7 mutant.Overaccumulation of kaempferol-3-rhamnoside in the seed coat compromises normal seed coat development. This observation positions TRANSPARENT TESTA 7 and the UGT78D1 glycosyltransferase, catalysing flavonol 3-O-rhamnosylation, as essential players in the modulation of seed longevity.

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“…4-HB serves as the skeleton for the CoQ head group. When 4-HB was fed to Arabidopsis seedlings, CoQ accumulated to as much as 150% of the control level ( Soubeyrand et al., 2021 ). Overexpression of AT4G19010 or 4CL8 , which encode 4-coumarate CoA ligases responsible for 4-HB production in peroxisomes, increased CoQ accumulation to ∼150% of the wild-type level ( Block et al., 2014 ; Soubeyrand et al., 2019 ).…”

Section: Coq 10 Biofortificationmentioning

confidence: 99%

“…Overexpression of AT4G19010 or 4CL8 , which encode 4-coumarate CoA ligases responsible for 4-HB production in peroxisomes, increased CoQ accumulation to ∼150% of the wild-type level ( Block et al., 2014 ; Soubeyrand et al., 2019 ). In knockout mutants of genes encoding kaempferol 3- O -glycosyltransferase that restricts the supply of 4-HB, CoQ content was elevated to 160% of the wild-type level ( Soubeyrand et al., 2021 ). These results indicated that 4-HB supply limits plant CoQ biosynthesis.…”

Section: Coq 10 Biofortificationmentioning

confidence: 99%

How plants synthesize coenzyme Q

Yang

et al. 2022

Plant Communications

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3-O-glycosylation of kaempferol restricts the supply of the benzenoid precursor of ubiquinone (Coenzyme Q) in Arabidopsis thaliana

Cited by 10 publications

References 26 publications

Coenzyme Q Biosynthesis: An Update on the Origins of the Benzenoid Ring and Discovery of New Ring Precursors

Coenzyme Q Biosynthesis: An Update on the Origins of the Benzenoid Ring and Discovery of New Ring Precursors

Kaempferol‐3‐rhamnoside overaccumulation in flavonoid 3′‐hydroxylase tt7 mutants compromises seed coat outer integument differentiation and seed longevity

How plants synthesize coenzyme Q

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