Methylation of Cyanidin-3-O-Glucoside with Dimethyl Carbonate

Straßmann, Sarah; Brehmer, Tillman; Passon, Maike; Schieber, Andreas

doi:10.3390/molecules26051342

Cited by 6 publications

(2 citation statements)

References 34 publications

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“…Even if it is a challenge to obtain glucuronidated, sulfated and O-methylated anthocyanins some methodologies can be used and are reported in the literature. For example methylation of cyandin-3-O-glucoside can be carried out by the reaction with dimethylcarbonate [115]. Regarding the hemisynthesis of sulfated derivatives several approaches are possible by bringing the anthocyanins into contact with chlorosulfonic acid [116] or even with sulfur trioxide-N-triethylamine [117].…”

Section: Anti-neuroinflammatory Effects On Anthocyanins and Their Metabolitesmentioning

confidence: 99%

Anthocyanins: Dietary Sources, Bioavailability, Human Metabolic Pathways, and Potential Anti-Neuroinflammatory Activity

Hornedo-Ortega¹,

Rasines-Perea²,

Cerezo³

et al. 2022

Biochemistry

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The objectives of this chapter are to summarize and discuss (i) the anthocyanins structure and content in foodstuffs and their dietary intake (ii) the anthocyanins bioavailability and human metabolic pathways and (iii) the in vitro and in vivo potent anti-neuroinflammatory effects of anthocyanins and their metabolites. Indeed, anthocyanins are polyphenolic compounds belonging to the group of flavonoids, and are one of the most commonly consumed polyphenols in a normal diet. They are responsible of red, blue and purple color of several fruits and vegetables and their intake has been related with several human health benefits. The anthocyanins structures diversities as well as their content in various fruits, vegetables and cereals is addressed. Moreover, despite the growing evidence for the protective effects of anthocyanins, it is important to highlight that the in vivo bioavailability of these compounds is relatively low in comparison to their more stable metabolites. Indeed, after consumption, these bioactives are subjected to substantial transformations in human body. Phase I and II metabolites generated by intestinal and hepatic enzymatic reactions, and phenolic acids produced by gut microbiota and their metabolized forms, are the most important metabolic anthocyanins forms. For this reason, the study of the biological properties of these circulating metabolites represents a more in vivo realistic situation. Although the anthocyanin bioavailability researches in humans are limited, they will be discussed together with a global metabolic pathway for the main anthocyanins. Moreover, several works have demonstrated that anthocyanins can cross the blood brain barrier, and accumulate in brain endothelial cells, brain parenchymal tissue, striatum, hippocampus, cerebellum and cortex. Consequently, the study of anthocyanins as potent therapeutic agents in neurodegenerative diseases has gained relevance and the principal and the most recent studies are also discussed in the book chapter.

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Section: Anti-neuroinflammatory Effects On Anthocyanins and Their Metabolitesmentioning

confidence: 99%

Anthocyanins: Dietary Sources, Bioavailability, Human Metabolic Pathways, and Potential Anti-Neuroinflammatory Activity

Hornedo-Ortega¹,

Rasines-Perea²,

Cerezo³

et al. 2022

Biochemistry

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“…Anthocyanins are natural plant dyes and are found in fruits and vegetables in the human diet [ 430 ]. Anthocyanins are known antioxidants and are positively charged with respect to the oxygen atom of the C-ring of the main structure of flavonoids ( Figure 9 ) [ 431 ], which distinguishes them from other groups of flavonoids. In the last few years, increased attention has been paid to the study of cyanidin 3-glucoside as antioxidant mediators of the Nrf2 pathway.…”

Section: Natural Compounds and Important Targets Associated With Chronic Inflammation And Oxidative Stress In Cancer Treatmentmentioning

confidence: 99%

Therapeutic Influence on Important Targets Associated with Chronic Inflammation and Oxidative Stress in Cancer Treatment

Neganova

Liu

Aleksandrova

et al. 2021

Cancers

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Chronic inflammation and oxidative stress are the interconnected pathological processes, which lead to cancer initiation and progression. The growing level of oxidative and inflammatory damage was shown to increase cancer severity and contribute to tumor spread. The overproduction of reactive oxygen species (ROS), which is associated with the reduced capacity of the endogenous cell defense mechanisms and/or metabolic imbalance, is the main contributor to oxidative stress. An abnormal level of ROS was defined as a predisposing factor for the cell transformation that could trigger pro-oncogenic signaling pathways, induce changes in gene expression, and facilitate accumulation of mutations, DNA damage, and genomic instability. Additionally, the activation of transcription factors caused by a prolonged oxidative stress, including NF-κB, p53, HIF1α, etc., leads to the expression of several genes responsible for inflammation. The resulting hyperactivation of inflammatory mediators, including TNFα, TGF-β, interleukins, and prostaglandins can contribute to the development of neoplasia. Pro-inflammatory cytokines were shown to trigger adaptive reactions and the acquisition of resistance by tumor cells to apoptosis, while promoting proliferation, invasion, and angiogenesis. Moreover, the chronic inflammatory response leads to the excessive production of free radicals, which further aggravate the initiated reactions. This review summarizes the recent data and progress in the discovery of mechanisms that associate oxidative stress and chronic inflammation with cancer onset and metastasis. In addition, the review provides insights for the development of therapeutic approaches and the discovery of natural substances that will be able to simultaneously inhibit several key oncological and inflammation-related targets.

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Semisynthesis of anthocyanins

Majhi,

Manickam

2024

Semisynthesis of Bioactive Compounds and Their Biological Activities

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Methylation of Cyanidin-3-O-Glucoside with Dimethyl Carbonate

Cited by 6 publications

References 34 publications

Anthocyanins: Dietary Sources, Bioavailability, Human Metabolic Pathways, and Potential Anti-Neuroinflammatory Activity

Anthocyanins: Dietary Sources, Bioavailability, Human Metabolic Pathways, and Potential Anti-Neuroinflammatory Activity

Therapeutic Influence on Important Targets Associated with Chronic Inflammation and Oxidative Stress in Cancer Treatment

Semisynthesis of anthocyanins

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