Synthesis of new coumarin[1,3]oxazine derivatives of 7‐hydroxy‐6‐isobornyl‐4‐methylcoumarin and their antioxidant activity

Попова, С. А.; Шевченко, О. Г.; Chukicheva, I. Yu.

doi:10.1111/cbdd.13955

Cited by 10 publications

(6 citation statements)

References 75 publications

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“…The metabolomic analysis also found some compounds in yellow mushrooms, such as vanillic acid, 6-hydroxy-4-methylcoumarin, skimmine, curdione, α-ionone, phytocassane D, and eudesmic acid, that were not detected in white mushrooms ( Table S2 ). These compounds have high medicinal values, including antibacterial, antitumor, anti-inflammatory, and antioxidant properties and enhance the health benefits of yellow mushrooms [ 30 , 31 , 32 , 33 , 34 ].…”

Section: Discussionmentioning

confidence: 99%

Chemical Constituents and Molecular Mechanism of the Yellow Phenotype of Yellow Mushroom (Floccularia luteovirens)

Gan

Bao

Liu

et al. 2022

JoF

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(1) Background: Yellow mushroom (Floccularia luteovirens) is a natural resource that is highly nutritional, has a high economic value, and is found in Northwest China. Despite its value, the chemical and molecular mechanisms of yellow phenotype formation are still unclear. (2) Methods: This study uses the combined analysis of transcriptome and metabolome to explain the molecular mechanism of the formation of yellow mushroom. Subcellular localization and transgene overexpression techniques were used to verify the function of the candidate gene. (3) Results: 112 compounds had a higher expression in yellow mushroom; riboflavin was the ninth most-expressed compound. HPLC showed that a key target peak at 23.128 min under visible light at 444 nm was Vb2. All proteins exhibited the closest relationship with Agaricus bisporus var. bisporus H97. One riboflavin transporter, CL911.Contig3_All (FlMCH5), was highly expressed in yellow mushrooms with a different value (log2 fold change) of −12.98, whereas it was not detected in white mushrooms. FlMCH5 was homologous to the riboflavin transporter MCH5 or MFS transporter in other strains, and the FlMCH5-GFP fusion protein was mainly located in the cell membrane. Overexpression of FlMCH5 in tobacco increased the content of riboflavin in three transgenic plants to 26 μg/g, 26.52 μg/g, and 36.94 μg/g, respectively. (4) Conclusions: In this study, it is clear that riboflavin is the main coloring compound of yellow mushrooms, and FlMCH5 is the key transport regulatory gene that produces the yellow phenotype.

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Section: Discussionmentioning

confidence: 99%

Chemical Constituents and Molecular Mechanism of the Yellow Phenotype of Yellow Mushroom (Floccularia luteovirens)

Gan

Bao

Liu

et al. 2022

JoF

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“…Popova and colleagues synthesized novel [1,3]oxazine derivatives of 7-hydroxy-6isobornyl-4-methylcoumarin [45]. Total antioxidant activity was measured in vitro in terms of the inhibition of Fenton-reaction-induced lipid peroxidation in mouse brain homogenates (1 h incubation at 37 centigrade), followed by TBA reaction.…”

Section: Coumarins Substituted At Positions 7 And/ormentioning

confidence: 99%

Antioxidant Activity of Coumarins and Their Metal Complexes

Todorov

Saso²,

Kostova

2023

Pharmaceuticals

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Ubiquitously present in plant life, coumarins, as a class of phenolic compounds, have multiple applications—in everyday life, in organic synthesis, in medicine and many others. Coumarins are well known for their broad spectrum of physiological effects. The specific structure of the coumarin scaffold involves a conjugated system with excellent charge and electron transport properties. The antioxidant activity of natural coumarins has been a subject of intense study for at least two decades. Significant research into the antioxidant behavior of natural/semi-synthetic coumarins and their complexes has been carried out and published in scientific literature. The authors of this review have noted that, during the past five years, research efforts seem to have been focused on the synthesis and examination of synthetic coumarin derivatives with the aim to produce potential drugs with enhanced, modified or entirely novel effects. As many pathologies are associated with oxidative stress, coumarin-based compounds could be excellent candidates for novel medicinal molecules. The present review aims to inform the reader on some prominent results from investigations into the antioxidant properties of novel coumarin compounds over the past five years.

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“…These findings highlight the potential of 4-hydroxycoumarin as valuable compound with significant therapeutic applications. [74,75] In this context, Gu and his research group were successful in carrying out the reaction of salicylaldehyde 1, 1,3-cyclohexanedione 7 and 4-hydroxy-2Hchromen-2-one 35 to afford coumarin substituted fused chromenes 36 (Scheme 15). [54] Similarly, Das et al developed a highly product-selective three-component reaction of salicylaldehydes 1, active methylene compounds 7, 11, 2 and coumarin 35 to construct coumarin-substituted chromenes 37, 38, 39 (Scheme 16).…”

Section: H-chromene-coumarin Hybridsmentioning

confidence: 99%

A Brief Review on the Synthesis of 4H‐Chromene‐Embedded Heterocycles

Sharon,

Padmaja,

Reddy

2024

ChemistrySelect

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Chromenes are an essential class of oxygen‐containing heterocyclic compounds with intriguing biological activity. It is an important moiety for the discovery of new drug candidates. Chromenes are naturally abundant as alkaloids, tocopherols, flavones, and anthocyanins. The incorporation of 4H‐chromene, along with various bioactive heterocycles such as indole, pyrazole, kojic acid, pyran‐2‐one, quinoline, pyridine, pyrimidine, coumarin, sesamol, furan, uracil, benzoimidazole, benzotriazole, thiazole, isoxazole and barbituric acid moieties, into a molecular scaffold has the potential to combine the properties of both components. The synergistic effect of combining different heterocyclic moieties within a 4H‐chromene nucleus results in the formation of valuable compounds with significant biological importance. This review summarizes the different synthetic techniques used for preparing 4H‐chromene‐embedded heterocycles. The common mechanisms of key reactions and the significance of the method are discussed.

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Synthesis of new coumarin[1,3]oxazine derivatives of 7‐hydroxy‐6‐isobornyl‐4‐methylcoumarin and their antioxidant activity

Cited by 10 publications

References 75 publications

Chemical Constituents and Molecular Mechanism of the Yellow Phenotype of Yellow Mushroom (Floccularia luteovirens)

Chemical Constituents and Molecular Mechanism of the Yellow Phenotype of Yellow Mushroom (Floccularia luteovirens)

Antioxidant Activity of Coumarins and Their Metal Complexes

A Brief Review on the Synthesis of 4H‐Chromene‐Embedded Heterocycles

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