Stereoselective Synthesis of Flavonoids: A Brief Overview

Pereira, Ana Margarida; Cidade, Honorina; Tiritan, Maria Elizabeth

doi:10.3390/molecules28010426

Cited by 17 publications

(13 citation statements)

References 121 publications

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“…Flavonoids are natural products with several structure-dependent biological and pharmacological activities [ 23 , 24 , 25 ]. Thus, the TFC of S. bullata was also determined ( Table 2 ).…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic, Antibacterial, and Antioxidant Activities of the Leaf Extract of Sinningia bullata

Chen

Lin

et al. 2023

Plants

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Sinningia bullata is a tuberous member of the flowering plant family Gesneriaceae. Prior to this work, the antibacterial, antioxidant, and cytotoxic properties of S. bullata were undetermined. Here, we prepared different extracts from the leaf, stem, and tuber of S. bullata and investigated their pharmacological activities. The leaf extract of S. bullata, obtained by 100% acetone (Sb-L-A), had the highest total flavonoid content, antioxidation capacity, and cytotoxic and antibacterial activities. Sb-L-A displayed a broad range of antibacterial activities against Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa. The inhibition zones of Sb-L-A ranged from 8 to 30 mm and were in the following order: S. aureus > E. coli > P. aeruginosa. Incubation of B16F10 melanoma cells with Sb-L-A at a concentration of 80 μg/mL caused deaths at the rate of 96%, reduced migration by 100%, suppressed proliferation and colony formation by 99%, and induced apoptosis, which was observed in 96% of the B16F10 cells. In addition, the cytotoxic activities of Sb-L-A were synergistically enhanced when coacting with the antitumor drug epothilone B. Sb-L-A was also used to determine the cytotoxic effects against 4T1 mammary carcinoma cells. Sb-L-A of 60 μg/mL boosted the distribution of the G2 phase from 1.4% to 24.4% in the B16F10 cells. Accordingly, Sb-L-A might suppress melanoma cell proliferation by inducing G2 cell-cycle arrest. The most abundant compounds in Sb-L-A were identified using gas chromatography–mass spectrometry. The top two contents in this extract were adlupulone and villosin. Overall, the collective data in this study may indicate the pharmacological potentials of Sb-L-A for possible medical applications.

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“…Flavonoids are natural products with several structure-dependent biological and pharmacological activities [ 23 , 24 , 25 ]. Thus, the TFC of S. bullata was also determined ( Table 2 ).…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic, Antibacterial, and Antioxidant Activities of the Leaf Extract of Sinningia bullata

Chen

Lin

et al. 2023

Plants

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“…In the business, these substances are helpful as sweeteners in sweets and mouthwashes as well as for fostering pollination. [64]…”

Section: Epoxidationmentioning

confidence: 99%

“…[63] To enable the production of chalcone epoxide in 1976, quinine benzylchloride and quinidine benzylchloride were utilized as chiral phase-transfer catalysts for the epoxidation of, unsaturated ketones. [64] However, this process produced little enantiomeric excess The discovery of a synthetic method by Juliá et al [65] that included polymeric L-or D-alanine, an organic solvent, and alkaline hydrogen peroxide marked a turning point in this method's development. To attain better enantiomeric purity, this procedure was improved further.…”

Section: Epoxidationmentioning

confidence: 99%

“…To enable the production of chalcone epoxide in 1976, quinine benzylchloride and quinidine benzylchloride were utilized as chiral phase‐transfer catalysts for the epoxidation of, unsaturated ketones [64] . However, this process produced little enantiomeric excess The discovery of a synthetic method by Juliá et al [65] .…”

Section: Epoxidationmentioning

confidence: 99%

“…created a variety of (S)‐ and (R)‐2’‐methoxymethyl‐hydroxydihydrochalcones, some of which had an enantiomeric excess (ee) value between 84 % and 91 %. In the business, these substances are helpful as sweeteners in sweets and mouthwashes as well as for fostering pollination [64] …”

Section: Epoxidationmentioning

confidence: 99%

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Enantioselective Synthesis of Flavonoids and Their Diverse Applications in Nutrition, Health, and Medicine: A Mini Review

Qayyum,

Shahid,

Mansoor

et al. 2024

ChemistrySelect

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Enantioselective synthesis, which yields one enantiomer in higher concentration or purity than the other, has transformed the production of flavonoids. Flavonoids, which are found in large quantities in nature and are known to exhibit a diverse array of physiological activities, are an ideal choice for enantioselective synthesis due to the significance of chirality in their therapeutic effects. Enantioselective synthesis is used in the medicinal, nutraceutical, and agrochemical sectors to produce flavonoids, which are useful in the development of novel therapeutics with improved effectiveness and fewer adverse reactions. The ability to obtain specific enantiomers of flavonoids facilitates the elucidation of biochemical strategies and the relationship between structure and activity, thereby providing avenues for tailored drug design and optimization. This review highlights the critical role that enantioselective synthesis plays in achieving the full potential of flavonoids for a variety of therapeutic and non‐therapeutic applications. It also discusses the challenges and prospects of enantioselective syntheses to create relevant classes of flavonoid monomers, emphasizing their applications in the field. The review focused on the synthetic methods for fabricating native flavonoids and their analogs, highlighting the critical role that enantioselective synthesis of flavonoids plays in maximizing their therapeutic potential for enhancing human health and wellbeing.

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One‐Pot Synthesis of (S)‐Flavanones by a Double‐Face Promiscuous Chemo‐Enzymatic Cascade of Lipases

Ubertini,

Capecchi,

Tomaino

et al. 2024

ChemCatChem

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The one‐pot stereoselective synthesis of (S)‐flavanones from 2′‐hydroxyacetophenone and substituted aromatic aldehydes was obtained by a double‐face promiscuous chemo‐enzymatic cascade of porcine pancreas and Mucor javanicus lipases. The reaction pathway comprises: A) cross‐aldol condensation catalysed by porcine pancreas lipase to yield chalcone intermediates; B) unprecedented intramolecular oxa‐Michael addition of chalcone intermediates to (S)‐flavanones. Mucor javanicus lipase was the most effective enzyme in step B. Imidazole and 2‐methylimidazole were studied as additive in order to improve the efficacy of the overall transformation. The sustainability of the chemo‐enzymatic cascade was increased by immobilization of lipases on cross‐linked hydroxy‐methylated kraft lignin nanoparticles, by use of concanavalin A. Immobilization conferred considerable stability and reusability at the system for 4 runs. Noteworthy, the reaction mixture was significantly enriched in (S)‐flavanones under both homogeneous and heterogeneous conditions. Computational studies encompassing docking and molecular dynamic analyses showed the role played by evolutionary conserved oxyanion holes and catalytic triad of Mucor javanicus lipase in the stereocontrol of the intra‐molecular oxa‐Michael addition.

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Stereoselective Synthesis of Flavonoids: A Brief Overview

Cited by 17 publications

References 121 publications

Cytotoxic, Antibacterial, and Antioxidant Activities of the Leaf Extract of Sinningia bullata

Cytotoxic, Antibacterial, and Antioxidant Activities of the Leaf Extract of Sinningia bullata

Enantioselective Synthesis of Flavonoids and Their Diverse Applications in Nutrition, Health, and Medicine: A Mini Review

One‐Pot Synthesis of (S)‐Flavanones by a Double‐Face Promiscuous Chemo‐Enzymatic Cascade of Lipases

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