An update of aurones: food resource, health benefit, biosynthesis and application

Yang, Jiali; Gao, Zhengjiao; Yu, Zhiqian; Hou, Yu; Tang, Dingtao; Yan, Huiling; Wu, Fuwang; Chang, Sui Kiat; Pan, Yonggui; Jiang, Yueming; Zhang, Zhengke; Yang, Bao

doi:10.1080/10408398.2023.2248244

Cited by 3 publications

(3 citation statements)

References 101 publications

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“…Aurones, due to their scarce presence in nature in contrast with other polyphenolic compounds (indeed, they belong to the class of minor flavonoids), have been often overlooked in the past decades with respect to their possible interest in a medicinal chemistry context. In the last few decades, the interest for this class of compounds has increased due to their outstanding biological properties, especially in the field of antiviral, anticancer, and antimalarial agents [ 6 , 11 , 12 ]. Despite this, considering their unfavorable P3 properties, an acceptable drug-likeness is still far from being achieved [ 5 ].…”

Section: Discussionmentioning

confidence: 99%

“…However, recent studies have highlighted the intriguing and unique functional properties of aurones. They have demonstrated the ability to selectively modulate biological pathways and specific targets involved in various physiological and pathological processes, including cancer, inflammation, oxidative stress, neurological disorders, and microbial infections [ 6 , 11 , 12 ]. Consequently, aurones are emerging as privileged scaffolds in the search for new lead compounds, as evidenced by the increasing number of review papers published in recent decades [ 5 , 6 , 7 , 8 , 10 , 11 , 12 , 13 ].…”

Section: Introductionmentioning

confidence: 99%

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Scaffold-Hopping Strategies in Aurone Optimization: A Comprehensive Review of Synthetic Procedures and Biological Activities of Nitrogen and Sulfur Analogues

La Monica,

Alamia,

Bono

et al. 2024

Molecules

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Aurones, particular polyphenolic compounds belonging to the class of minor flavonoids and overlooked for a long time, have gained significative attention in medicinal chemistry in recent years. Indeed, considering their unique and outstanding biological properties, they stand out as an intriguing reservoir of new potential lead compounds in the drug discovery context. Nevertheless, several physicochemical, pharmacokinetic, and pharmacodynamic (P3) issues hinder their progression in more advanced phases of the drug discovery pipeline, making lead optimization campaigns necessary. In this context, scaffold hopping has proven to be a valuable approach in the optimization of natural products. This review provides a comprehensive and updated picture of the scaffold-hopping approaches directed at the optimization of natural and synthetic aurones. In the literature analysis, a particular focus is given to nitrogen and sulfur analogues. For each class presented, general synthetic procedures are summarized, highlighting the key advantages and potential issues. Furthermore, the biological activities of the most representative scaffold-hopped compounds are presented, emphasizing the improvements achieved and the potential for further optimization compared to the aurone class.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Scaffold-Hopping Strategies in Aurone Optimization: A Comprehensive Review of Synthetic Procedures and Biological Activities of Nitrogen and Sulfur Analogues

La Monica,

Alamia,

Bono

et al. 2024

Molecules

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“…A substância também é descrita como um componente de pesticidas para plantas, indicando que em nosso caso não se trata de um produto natural, mas um artefato 42,43 As cinco substâncias discutidas a seguir compreendem formas C-glicosiladas da apigenina, portanto possuem padrões de íons em MS 2 muito semelhantes entre si, assim como seus mecanismos de fragmentação, sendo reportadas estruturas muito semelhantes na espécie de bambu P. pracecox 47 . No tempo de retenção 13,9-14,7 minutos em AcH, DiG e nButC, referente ao íon pseudo molecular 563,1385 m/z, foram propostas as estruturas de isoschaftosídeo (22), neoeixosídeo (23) e Vicenina-3 (24). Os fragmentos analisados foram 563,14 m/z, 473,10 m/z, 443,09 m/z, 383,07 m/z e 353,07 m/z, que estão de acordo com os resultados descritos para esta série de compostos 48 , não sendo encontradas propostas para um mecanismo de fragmentação especificamente para as mesmas.…”

Section: Clae-dadunclassified

11º Workshop do Programa de Mestrado Profissional Tecnologia em Química e Bioquímica da USP – AMPT

Moreno,

Baptista,

Petri

2024

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Resumo: Extraíveis orgânicos são compostos que podem ser extraídos de elastômeros, plásticos e revestimentos do material de embalagem do medicamento, na presença de solvente(s) e/ou condição(ões) apropriado(s). A importância dos extraíveis está relacionada à sua identidade, concentração e toxicidade, pois pertencem a uma categoria de impurezas denominadas lixiviáveis, que podem estar presentes no medicamento, afetando sua segurança, qualidade e eficácia. Este artigo analisou padrões de referência conhecidos como extraíveis de materiais de embalagem por cromatografia à gás acoplada à espectrometria de massas (GC-MS), e suas identidades foram obtidas comparando-se o tempo de retenção, índice de retenção linear, os espectros de massas obtidos com a biblioteca instalada no equipamento e com a literatura, quando disponível. A partir dos padrões de referência dos extraíveis analisados, foi confirmada a identificação de um total de 17 compostos, os principais compostos presentes foram antioxidantes, plastificantes, monômeros e ácido esteárico. Seguindo a metodologia proposta, é possível utilizar os índices de retenção linear determinados neste artigo como referência em um novo experimento, visto que os índices de retenção linear aqui obtidos também foram comparados com os valores disponíveis na NIST e na literatura. Esta correlação possibilita a classificação da identificação de um extraível de uma categoria provisória, para confiável quando o padrão de referência não estiver disponível.

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Visible-Light-Driven Synthesis of Dihydroaurones from Aromatic Diazo Compounds

Duan,

Zheng,

Xiao

2024

J. Org. Chem.

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Dihydroaurones, which are derivatives of aurones, exhibit similar biological activity. Although there are many synthetic methods for dihydroaurones, ecofriendly methodologies that circumvent the use of precious metals still need to be explored. In this work, a catalyst-free, visible-light-driven synthesis of dihydroaurones has been developed through the cyclization of aromatic diazo compounds. The reaction proceeded smoothly under mild conditions, resulting in a series of dihydroaurones in moderate to high yields. Mechanistic investigation suggests that this process involves a radical-pair Stevens rearrangement.

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An update of aurones: food resource, health benefit, biosynthesis and application

Cited by 3 publications

References 101 publications

Scaffold-Hopping Strategies in Aurone Optimization: A Comprehensive Review of Synthetic Procedures and Biological Activities of Nitrogen and Sulfur Analogues

Scaffold-Hopping Strategies in Aurone Optimization: A Comprehensive Review of Synthetic Procedures and Biological Activities of Nitrogen and Sulfur Analogues

11º Workshop do Programa de Mestrado Profissional Tecnologia em Química e Bioquímica da USP – AMPT

Visible-Light-Driven Synthesis of Dihydroaurones from Aromatic Diazo Compounds

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