Diversification of Chemical Structures of Methoxylated Flavonoids and Genes Encoding Flavonoid-O-Methyltransferases

Liu, Yuting; Fernie, Alisdair R.; Tohge, Takayuki

doi:10.3390/plants11040564

Cited by 21 publications

(25 citation statements)

References 104 publications

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“…Studies have revealed that plant OMTs methylate a wide range of compounds with a high degree of selectivity (Liu et al, 2022). Zubieta et al (2001) reported the crystal structures of ChOMT and IOMT from M. sativa.…”

Section: Discussionmentioning

confidence: 99%

Methylated chalcones are required for rhizobial nod gene induction in the Medicago truncatula rhizosphere

Wu,

Zhuang,

Chen

et al. 2024

New Phytologist

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Summary Legume nodulation requires the detection of flavonoids in the rhizosphere by rhizobia to activate their production of Nod factor countersignals. Here we investigated the flavonoids involved in nodulation of Medicago truncatula. We biochemically characterized five flavonoid‐O‐methyltransferases (OMTs) and a lux‐based nod gene reporter was used to investigate the response of Sinorhizobium medicae NodD1 to various flavonoids. We found that chalcone‐OMT 1 (ChOMT1) and ChOMT3, but not OMT2, 4, and 5, were able to produce 4,4′‐dihydroxy‐2′‐methoxychalcone (DHMC). The bioreporter responded most strongly to DHMC, while isoflavones important for nodulation of soybean (Glycine max) showed no activity. Mutant analysis revealed that loss of ChOMT1 strongly reduced DHMC levels. Furthermore, chomt1 and omt2 showed strongly reduced bioreporter luminescence in their rhizospheres. In addition, loss of both ChOMT1 and ChOMT3 reduced nodulation, and this phenotype was strengthened by the further loss of OMT2. We conclude that: the loss of ChOMT1 greatly reduces root DHMC levels; ChOMT1 or OMT2 are important for nod gene activation in the rhizosphere; and ChOMT1/3 and OMT2 promote nodulation. Our findings suggest a degree of exclusivity in the flavonoids used for nodulation in M. truncatula compared to soybean, supporting a role for flavonoids in rhizobial host range.

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Section: Discussionmentioning

confidence: 99%

Methylated chalcones are required for rhizobial nod gene induction in the Medicago truncatula rhizosphere

Wu,

Zhuang,

Chen

et al. 2024

New Phytologist

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“…Influenza A viruses (IAV) A/Vladivostok/2/09 (H1N1), A/Almaty/8/98 (H3N2), A/Tern/South Africa/1/61 (H5N3), and A/chicken/FPV/Rostock/1934 (H7N1) were chosen to represent both seasonal human and potentially zoonotic avian influenza A virus subtypes. As previous studies have found higher antiviral activity of the isorhamnetin aglycone over quercetin and kaempferol aglycones, we chose to characterize naturally occurring isorhamnetin glycosides as they contain additional reactogenic groups with potential antiviral effects. − Toxicity and efficiency of individual compounds were evaluated in MDCK and embryonated chicken eggs (Tables and ). All tested isorhamnetin glycosides displayed low toxicity in ovo.…”

Section: Discussionmentioning

confidence: 99%

“…Antiviral activity of the flavonoids against influenza infection was determined on MDCK cells infected with 100 TCID50 of the influenza virus (post-treatment method). Virus-induced cell death was measured using the MTT assay . The effective concentration for 50% cell death (EC 50 ) was calculated.…”

Section: Methodsmentioning

confidence: 99%

Naturally Occurring Isorhamnetin Glycosides as Potential Agents Against Influenza Viruses: Antiviral and Molecular Docking Studies

Bogoyavlenskiy,

Zaitseva,

Alexyuk

et al. 2023

ACS Omega

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Influenza remains one of the most widespread infections, causing an annual illness in adults and children. Therefore, the search for new antiviral drugs is one of the priorities of practical health care. Eight isorhamnetin glycosides were purified from Persicaria species, characterized by nuclear magnetic resonance spectroscopy and mass spectrometry and then evaluated as potential agents against influenza virus. A comprehensive in vitro and in vivo assessment of the compounds revealed that compound 5 displayed the most potent inhibitory activity with an EC 50 value of 1.2–1.3 μM, better than standard drugs (isorhamnetin 28.0–56.0 μM and oseltamivir 1.3–9.1 μM). Molecular docking results also revealed that compound 5 has the lowest binding energy (−10.7 kcal/mol) among the tested compounds and isorhamnetin (−8.1 kcal/mol). The ability of the isorhamnetin glycosides to suppress the reproduction of the influenza virus was studied on a model of a cell culture and chicken embryos. The ability of active compounds to influence the structure of the virion, as well as the activity of hemagglutinin and neuraminidase, has been demonstrated. Compound 1, 5, and 6 demonstrated the most effective inhibition of virus replication for all tested viruses. Molecular dynamics simulation techniques were run for 100 ns for compound 5 with two protein receptors Hem (1RUY) and Neu (3BEQ). These results revealed that the Hem-complex system acquired a relatively more stable conformation and even better descriptors than the other Neu-complex studied systems, suggesting that it can be an effective inhibiting drug toward hemagglutinin than neuraminidase inhibition. Based on the reported results, compound 5 can be a good candidate to be evaluated for effectiveness in preclinical testing.

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“…It was reported that stachydrine is a proline betaine, and choline is also a precursor of glycine betaine [71,81,82]. All the bio-syntheses of stachydrine, choline and multi-methoxy flavonoids were catalyzed by S-adenosyl-methionine (SAM)-dependent methyltransferases with a universal methyl donor SAM [83][84][85]. Differently, the sub-classified N-methyltransferases is responsible for the bio-syntheses of stachydrine and choline, while the sub-classified O-methyltransferases is responsible for those of multi-methoxy flavonoids [85].…”

Section: The Contents Of Stachydrine Choline and Synephrine In These ...mentioning

confidence: 99%

“…All the bio-syntheses of stachydrine, choline and multi-methoxy flavonoids were catalyzed by S-adenosyl-methionine (SAM)-dependent methyltransferases with a universal methyl donor SAM [83][84][85]. Differently, the sub-classified N-methyltransferases is responsible for the bio-syntheses of stachydrine and choline, while the sub-classified O-methyltransferases is responsible for those of multi-methoxy flavonoids [85]. The similar changing trends of stachydrine/choline and multi-methoxy flavonoids in the same tissue of the Citrus genus plants indicated there was a kind of intrinsic mechanism for simultaneously regulating both two sub-classified enzymes with a similar effect, and more probably there are some physiological needs regulating the whole biosynthesis pathway involving SAM-dependent methyltransferases down in the fruits and peels of these citrus genus plants.…”

Section: The Contents Of Stachydrine Choline and Synephrine In These ...mentioning

confidence: 99%

Stachydrine and Synephrine, a Pair of Bioactive Equilibrists in Four Chinese Herbs from <em>Citrus</em> Genus

Sun¹,

Xia²,

Yuan³

et al. 2023

Preprint

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Four Chinese herbs Zhishi, Zhiqiao, Qingpi and Chenpi from Citrus genus were widely used for treating various cardiovascular and gastrointestinal diseases. Although many pharmacological functions of these herb decoctions can be clarified from the bioactivities of identified ingredients, some of them remain confusing. To clarify the reasons of those confusing functions, depending on the extended structure-activity relationships of cholinergic and anti-cholinergic agents, here a simple method for quickly discovering possible choline analogs was established using a specific TLC method, and then stachydrine and choline were first identified from these Citrus herb decoctions based on their NMR and HRMS data. After this, two TLCS methods were first established respectively for the quantitatively analyses of stachydrine and choline, and the contents of both two ingredients and synephrine in 39 samples were determined using the valid TLCS and HPLC methods, respectively. The results showed the contents of stachydrine were 2.4 times to those of synephrine in Zhiqiao while about 1/3 to 2/3 in Zhishi, Qingpi and Chenpi. Simultaneously, the contents of stachydrine, choline and synephrine in these herbs present similar changing trends along with the delay of harvest time. However, the contents of synephrine decrease most rapidly, while those of stachydrine decrease most slowly. Based on these above, comparing with the pharmacological activities and pharmacokinetics reported of stachydrine and synephrine, it indicated that stachydrine and synephrine can be considered as a pair of bioactive equilibrists, especially in the cardio-cerebrovascular protection from these citrus herbs. Simultaneously, it confirmed that stachydrine should play an important role in the pharmacological functions, especially in dual-directionally regulating the uterus and various beneficial effects on cardio-cerebrovascular system, kidney and liver, of these citrus herbs.

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Diversification of Chemical Structures of Methoxylated Flavonoids and Genes Encoding Flavonoid-O-Methyltransferases

Cited by 21 publications

References 104 publications

Methylated chalcones are required for rhizobial nod gene induction in the Medicago truncatula rhizosphere

Methylated chalcones are required for rhizobial nod gene induction in the Medicago truncatula rhizosphere

Naturally Occurring Isorhamnetin Glycosides as Potential Agents Against Influenza Viruses: Antiviral and Molecular Docking Studies

Stachydrine and Synephrine, a Pair of Bioactive Equilibrists in Four Chinese Herbs from <em>Citrus</em> Genus

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