Molecular Basis for Chemical Evolution of Flavones to Flavonols and Anthocyanins in Land Plants

Li, Dandan; Ni, Rong; Wang, Pingping; Zhang, Xiaoshuang; Wang, Piao-Yi; Zhu, Tingting; Sun, Chun‐Jing; Liu, Chang‐Jun; Lou, Hongxiang; Cheng, Ai‐Xia

doi:10.1104/pp.20.01185

Cited by 51 publications

(66 citation statements)

References 40 publications

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“…Bryophytes contain only flavonoids synthesized early in the phenylpropanoid pathway, that is naringenin chalcone and naringenin, dihydrokaempferol and kaempferol, and dihydroquercetin and quercetin [ 48 , 49 , 50 ]. A gene for narigenin chalcone synthesis is annotated in the KEGG (Kyoto Encyclopedia of Genes and Genomes, Kyoto, Japan) database for P. patens ( Figure S5 ).…”

Section: Resultsmentioning

confidence: 99%

“…The occurrence of quercetin derivatives has been reported in a thin layer chromatography analysis after UV treatment [ 37 ]. Recent work identified P. patens enzymes capable of converting naringenin to apigenin and a dihydrokaempferol derivative [ 49 ]. This indicates that enzymes capable of synthesizing flavonols are present, which might in vitro not reflect the complete in planta spectrum and that the color patterns we found could indeed correspond to the flavonols is mentioned in the results.…”

Section: Discussionmentioning

confidence: 99%

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Physcomitrium patens Mutants in Auxin Conjugating GH3 Proteins Show Salt Stress Tolerance but Auxin Homeostasis Is Not Involved in Regulation of Oxidative Stress Factors

Koochak

Ludwig‐Müller

2021

Plants

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Salt stress is among the most challenging abiotic stress situations that a plant can experience. High salt levels do not only occur in areas with obvious salty water, but also during drought periods where salt accumulates in the soil. The moss Physcomitrium patens became a model for studying abiotic stress in non-vascular plants. Here, we show that high salt concentrations can be tolerated in vitro, and that auxin homeostasis is connected to the performance of P. patens under these stress conditions. The auxin levels can be regulated by conjugating IAA to amino acids by two members of the family of GH3 protein auxin amino acid-synthetases that are present in P. patens. Double GH3 gene knock-out mutants were more tolerant to high salt concentrations. Furthermore, free IAA levels were differentially altered during the time points investigated. Since, among the mutant lines, an increase in IAA on at least one NaCl concentration tested was observed, we treated wild type (WT) plants concomitantly with NaCl and IAA. This experiment showed that the salt tolerance to 100 mM NaCl together with 1 and 10 µM IAA was enhanced during the earlier time points. This is an additional indication that the high IAA levels in the double GH3-KO lines could be responsible for survival in high salt conditions. While the high salt concentrations induced several selected stress metabolites including phenols, flavonoids, and enzymes such as peroxidase and superoxide dismutase, the GH3-KO genotype did not generally participate in this upregulation. While we showed that the GH3 double KO mutants were more tolerant of high (250 mM) NaCl concentrations, the altered auxin homeostasis was not directly involved in the upregulation of stress metabolites.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Physcomitrium patens Mutants in Auxin Conjugating GH3 Proteins Show Salt Stress Tolerance but Auxin Homeostasis Is Not Involved in Regulation of Oxidative Stress Factors

Koochak

Ludwig‐Müller

2021

Plants

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“…Apparently, the early acquisition of flavone biosynthesis by liverworts was an important stress adaptation during land plant evolution [ 50 ], given the crucial role of bryophytes as one of the first lineages of embryophytes colonizing land [ 24 , 53 ]. In this sense, the chemical evolution of flavones to other phenolic compounds (such as flavonols and anthocyanins) facilitated plant adaptation to the terrestrial ecosystem [ 54 ].…”

Section: Discussionmentioning

confidence: 99%

Developmental Stage Determines the Accumulation Pattern of UV-Absorbing Compounds in the Model Liverwort Marchantia polymorpha subsp. ruderalis under Controlled Conditions

Soriano

Del-Castillo-Alonso

Monforte

et al. 2021

Plants

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The liverwort Marchantia polymorpha subsp. ruderalis is an emerging model plant, and some data are available on its responses to ultraviolet (UV) radiation. However, it is unknown if the developmental stage of the thalli modulates the effects of UV radiation on the contents of potentially protecting phenolic compounds. To fill this gap, liverwort samples were exposed or non-exposed to UV radiation for 38 days under controlled conditions, using three developmental stages: gemmae (G), one-month thalli (T1), and two-month thalli (T2). Then, the bulk level of methanol-soluble UV-absorbing compounds and the contents of six flavones (apigenin and luteolin derivatives) were measured. The UV responsiveness decreased with thallus age: G and T1 plants were the most UV-responsive and showed a strong increase in all the variables, with G plants more responsive than T1 plants. In UV-exposed T2 plants, only apigenin derivatives increased and more modestly, probably due to a lower acclimation capacity. Nevertheless, the thalli became progressively tougher due to a decreasing water content, representing a possible structural protection against UV. In UV-exposed plants, the temporal patterns of the accumulation of phenolic compounds were compound-specific. Most compounds decreased with thallus age, but di-glucuronide derivatives showed a bell-shaped pattern, with T1 plants showing the highest contents. A Principal Components Analysis (PCA) ordination of the different samples summarized the results found. The patterns described above should be taken into account to select thalli of an adequate developmental stage for experiments investigating the induction of phenolic compounds by UV radiation.

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“…In order to figure out when and how F3H emerged and evolved, Li Dandan et al systematically analyzed the function of FNS Is and F3Hs from liverworts, the bryophyte Physcomitrium patens (P. patens), the lycophyte Selaginella moellendorffii (S. moellendorffii), gymnosperms, and angiosperms [42]. The most primitive land plants liverworts only produce chalcones, flavanones, and flavones, but no flavonols [43,44].…”

Section: Catalytic Mechanisms and Adversity Resistance Of The Four 2-ogd Members 21 F3hsmentioning

confidence: 99%

Roles of the 2-Oxoglutarate-Dependent Dioxygenase Superfamily in the Flavonoid Pathway: A Review of the Functional Diversity of F3H, FNS I, FLS, and LDOX/ANS

Wang

Yang

et al. 2021

Molecules

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The 2-oxoglutarate-dependent dioxygenase (2-OGD) superfamily is one of the largest protein families in plants. The main oxidation reactions they catalyze in plants are hydroxylation, desaturation, demethylation, epimerization, and halogenation. Four members of the 2-OGD superfamily, i.e., flavonone 3β-hydroxylase (F3H), flavones synthase I (FNS I), flavonol synthase (FLS), and anthocyanidin synthase (ANS)/leucoanthocyanidin dioxygenase (LDOX), are present in the flavonoid pathway, catalyzing hydroxylation and desaturation reactions. In this review, we summarize the recent research progress on these proteins, from the discovery of their enzymatic activity, to their functional verification, to the analysis of the response they mediate in plants towards adversity. Substrate diversity analysis indicated that F3H, FNS Ⅰ, ANS/LDOX, and FLS perform their respective dominant functions in the flavonoid pathway, despite the presence of functional redundancy among them. The phylogenetic tree classified two types of FNS Ⅰ, one mainly performing FNS activity, and the other, a new type of FNS present in angiosperms, mainly involved in C-5 hydroxylation of SA. Additionally, a new class of LDOXs is highlighted, which can catalyze the conversion of (+)-catechin to cyanidin, further influencing the starter and extension unit composition of proanthocyanidins (PAs). The systematical description of the functional diversity and evolutionary relationship among these enzymes can facilitate the understanding of their impacts on plant metabolism. On the other hand, it provides molecular genetic evidence of the chemical evolution of flavonoids from lower to higher plants, promoting plant adaptation to harsh environments.

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Molecular Basis for Chemical Evolution of Flavones to Flavonols and Anthocyanins in Land Plants

Cited by 51 publications

References 40 publications

Physcomitrium patens Mutants in Auxin Conjugating GH3 Proteins Show Salt Stress Tolerance but Auxin Homeostasis Is Not Involved in Regulation of Oxidative Stress Factors

Physcomitrium patens Mutants in Auxin Conjugating GH3 Proteins Show Salt Stress Tolerance but Auxin Homeostasis Is Not Involved in Regulation of Oxidative Stress Factors

Developmental Stage Determines the Accumulation Pattern of UV-Absorbing Compounds in the Model Liverwort Marchantia polymorpha subsp. ruderalis under Controlled Conditions

Roles of the 2-Oxoglutarate-Dependent Dioxygenase Superfamily in the Flavonoid Pathway: A Review of the Functional Diversity of F3H, FNS I, FLS, and LDOX/ANS

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