A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light

Gao, Yuqi; Hou, Yi; Zhu, Liming; Chen, Guzhou; Xu, Dongyang; Zhang, Shengyong; He, Yu‐Peng; Xie, Weiqing

doi:10.1039/c9ra07198a

Cited by 19 publications

(14 citation statements)

References 48 publications

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“…The coexistence of cross dimers may be the result of reactive oxygen species (ROS)-mediated metabolism, where a phenolic radical intermediate covalently combines with another phenolic radical intermediate to give cross dimer. The ROS may originate from metabolism, visible light [80], and even air. For heat-stressed plants, ROS may also come from ferroptosis [27,81].…”

Section: Resultsmentioning

confidence: 99%

Simultaneous Study of Anti-Ferroptosis and Antioxidant Mechanisms of Butein and (S)-Butin

Liu

Cai

et al. 2020

Molecules

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To elucidate the mechanism of anti-ferroptosis and examine structural optimization in natural phenolics, cellular and chemical assays were performed with 2′-hydroxy chalcone butein and dihydroflavone (S)-butin. C11-BODIPY staining and flow cytometric assays suggest that butein more effectively inhibits ferroptosis in erastin-treated bone marrow-derived mesenchymal stem cells than (S)-butin. Butein also exhibited higher antioxidant percentages than (S)-butin in five antioxidant assays: linoleic acid emulsion assay, Fe3+-reducing antioxidant power assay, Cu2+-reducing antioxidant power assay, 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide radical (PTIO•)-trapping assay, and α,α-diphenyl-β-picrylhydrazyl radical (DPPH•)-trapping assay. Their reaction products with DPPH• were further analyzed using ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-Q-TOF-MS). Butein and (S)-butin produced a butein 5,5-dimer (m/z 542, 271, 253, 225, 135, and 91) and a (S)-butin 5′,5′-dimer (m/z 542, 389, 269, 253, and 151), respectively. Interestingly, butein forms a cross dimer with (S)-butin (m/z 542, 523, 433, 419, 415, 406, and 375). Therefore, we conclude that butein and (S)-butin exert anti-ferroptotic action via an antioxidant pathway (especially the hydrogen atom transfer pathway). Following this pathway, butein and (S)-butin yield both self-dimers and cross dimers. Butein displays superior antioxidant or anti-ferroptosis action to (S)-butin. This can be attributed the decrease in π-π conjugation in butein due to saturation of its α,β-double bond and loss of its 2′-hydroxy group upon biocatalytical isomerization.

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Section: Resultsmentioning

confidence: 99%

Simultaneous Study of Anti-Ferroptosis and Antioxidant Mechanisms of Butein and (S)-Butin

Liu

Cai

et al. 2020

Molecules

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“…Taking into consideration the anticancer, anti-inflammatory, antioxidant, and antibacterial potential of hybrid flavonoids, Gao et al [110] developed a methodology based on the asymmetric coupling of 2-hydroxychalcone using an appropriate Brønsted acid as the catalyst, an adequate nucleophile, and a visible light as the reaction promotor [110]. Subsequently, this photochemical bio-inspired reaction was applied to obtain enantiomeric forms of hybrid flavonoids with indole, cyclohexa-1,3-dione, or phloroglucinol, highlighting the formation of the 2-hydroxychalcone phloroglucinol hybrid (compound E, Figure 38) as a result of the counter-anion-directed enantioselective addition of 2-hydroxychalcone and phloroglucinol with an enantiomeric excess of 70% [110]. Another example of the implementation of a biomimetic reactional approach is the synthetic methodology developed by Yang et al [111].…”

Section: Other Synthetic Methologiesmentioning

confidence: 99%

Stereoselective Synthesis of Flavonoids: A Brief Overview

2023

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Stereoselective synthesis has been emerging as a resourceful tool because it enables the obtaining of compounds with biological interest and high enantiomeric purity. Flavonoids are natural products with several biological activities. Owing to their biological potential and aiming to achieve enantiomerically pure forms, several methodologies of stereoselective synthesis have been implemented. Those approaches encompass stereoselective chalcone epoxidation, Sharpless asymmetric dihydroxylation, Mitsunobu reaction, and the cycloaddition of 1,4-benzoquinone. Chiral auxiliaries, organo-, organometallic, and biocatalysis, as well as the chiral pool approach were also employed with the goal of obtaining chiral bioactive flavonoids with a high enantiomeric ratio. Additionally, the employment of the Diels–Alder reaction based on the stereodivergent reaction on a racemic mixture strategy or using catalyst complexes to synthesise pure enantiomers of flavonoids was reported. Furthermore, biomimetic pathways displayed another approach as illustrated by the asymmetric coupling of 2-hydroxychalcones driven by visible light. Recently, an asymmetric transfer hydrogen-dynamic kinetic resolution was also applied to synthesise (R,R)-cis-alcohols which, in turn, would be used as building blocks for the stereoselective synthesis of flavonoids.

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“…The reaction was proposed to occur through tandem double-bond isomerization and then the dehydration cyclization process of 2-hydroxychalcone (232), giving rise to the avylium cation, which is transferred to hybrid avonoids (234) by the attack of nucleophiles in situ with a yield of 33-99% (Scheme 50). 121 3.1.6. Catalytic asymmetric synthesis.…”

Section: Synthetic Approachesmentioning

confidence: 99%

Different routes for the construction of biologically active diversely functionalized bicyclo[3.3.1]nonanes: an exploration of new perspectives for anticancer chemotherapeutics

et al. 2023

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A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light

Abstract: An efficient protocol for the synthesis of hybrid flavonoids was achieved via a bio-inspired tandem reaction of 2-hydroxychalcone with various nucleophiles.

Cited by 19 publications

References 48 publications

Simultaneous Study of Anti-Ferroptosis and Antioxidant Mechanisms of Butein and (S)-Butin

Simultaneous Study of Anti-Ferroptosis and Antioxidant Mechanisms of Butein and (S)-Butin

Stereoselective Synthesis of Flavonoids: A Brief Overview

Different routes for the construction of biologically active diversely functionalized bicyclo[3.3.1]nonanes: an exploration of new perspectives for anticancer chemotherapeutics

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