The cancer preventive activity and mechanisms of prenylated resveratrol and derivatives

Zhou, Ting; Jiang, Yueming; Zeng, Bin; Yang, Bao

doi:10.1016/j.crtox.2023.100113

Cited by 4 publications

(4 citation statements)

References 51 publications

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“…Stilbenes, based on their lipophilic character showed high encapsulation efficiency into liposomes up to 98% as has been demonstrated for the reference stilbene resveratrol in phosphatidylcholine-cholesterol liposomes . The lipophilicity of phenolics further increases with methoxy- and prenyl- groups as shown for resveratrol-methoxylated derivative pterostilbene . Furthermore, the fluorescence results contribute to our understanding of the uptake dynamics of MF-loaded liposomes by monocytes .…”

Section: Resultsmentioning

confidence: 58%

Enhancing Solubility and Bioefficacy of Stilbenes by Liposomal Encapsulation─The Case of Macasiamenene F

Brezani,

Blondeau,

Kotouček

et al. 2024

ACS Omega

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Stilbenes in food and medicinal plants have been described as potent antiphlogistic and antioxidant compounds, and therefore, they present an interesting potential for the development of dietary supplements. Among them, macasiamenene F (MF) has recently been shown to be an effective anti-inflammatory and cytoprotective agent that dampens peripheral and CNS inflammation in vitro. Nevertheless, this promising molecule, like other stilbenes and a large percentage of drugs under development, faces poor water solubility, which results in trickier in vivo administration and low bioavailability. With the aim of improving MF solubility and developing a form optimized for in vivo administration, eight types of conventional liposomal nanocarriers and one type of PEGylated liposomes were formulated and characterized. In order to select the appropriate form of MF encapsulation, the safety of MF liposomal formulations was evaluated on THP-1 and THP-1-XBlue-MD2-CD14 monocytes, BV-2 microglia, and primary cortical neurons in culture. Furthermore, the cellular uptake of liposomes and the effect of encapsulation on MF anti-inflammatory effectiveness were evaluated on THP-1-XBlue-MD2-CD14 monocytes and BV-2 microglia. MF (5 mol %) encapsulated in PEGylated liposomes with an average size of 160 nm and polydispersity index of 0.122 was stable, safe, and the most promising form of MF encapsulation keeping its cytoprotective and anti-inflammatory properties.

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Section: Resultsmentioning

confidence: 58%

Enhancing Solubility and Bioefficacy of Stilbenes by Liposomal Encapsulation─The Case of Macasiamenene F

Brezani,

Blondeau,

Kotouček

et al. 2024

ACS Omega

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“…30 This compound previously was synthesised through a sequence involving O -alkylation followed by the O - to C -isomerisation. 31,32 The allylation with cinnamyl alcohol produced an unknown symmetrical isomer 3ac as a single product in a 60% yield (entry 4). The reason for such a switch in the regioselectivity is unknown but may relate to the formation of a more stabilised cation intermediate.…”

Section: Resultsmentioning

confidence: 99%

Catalytic prenylation of natural polyphenols

Du,

Korchi,

Rubtsov

et al. 2023

New J. Chem.

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“…For example, piceatannol is a hydroxylated compound from resveratrol, and it showed the highest cancer chemo-preventive activities [65]. Moreover, the prenylation of stilbenes showed good cancer preventive activities [66]. The physicochemical and biochemical properties of flavonoids could modulate through glycosylation reactions.…”

Section: Improving Intracellular Udp-sugar Level For Biosynthesis Of ...mentioning

confidence: 99%

Metabolic Engineering of Corynebacterium glutamicum for the Production of Flavonoids and Stilbenoids

Chu,

Tran,

Pham

et al. 2024

Molecules

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Flavonoids and stilbenoids, crucial secondary metabolites abundant in plants and fungi, display diverse biological and pharmaceutical activities, including potent antioxidant, anti-inflammatory, and antimicrobial effects. However, conventional production methods, such as chemical synthesis and plant extraction, face challenges in sustainability and yield. Hence, there is a notable shift towards biological production using microorganisms like Escherichia coli and yeast. Yet, the drawbacks of using E. coli and yeast as hosts for these compounds persist. For instance, yeast’s complex glycosylation profile can lead to intricate protein production scenarios, including hyperglycosylation issues. Consequently, Corynebacterium glutamicum emerges as a promising alternative, given its adaptability and recent advances in metabolic engineering. Although extensively used in biotechnological applications, the potential production of flavonoid and stilbenoid in engineered C. glutamicum remains largely untapped compared to E. coli. This review explores the potential of metabolic engineering in C. glutamicum for biosynthesis, highlighting its versatility as a cell factory and assessing optimization strategies for these pathways. Additionally, various metabolic engineering methods, including genomic editing and biosensors, and cofactor regeneration are evaluated, with a focus on C. glutamicum. Through comprehensive discussion, the review offers insights into future perspectives in production, aiding researchers and industry professionals in the field.

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The cancer preventive activity and mechanisms of prenylated resveratrol and derivatives

Cited by 4 publications

References 51 publications

Enhancing Solubility and Bioefficacy of Stilbenes by Liposomal Encapsulation─The Case of Macasiamenene F

Enhancing Solubility and Bioefficacy of Stilbenes by Liposomal Encapsulation─The Case of Macasiamenene F

Catalytic prenylation of natural polyphenols

Metabolic Engineering of Corynebacterium glutamicum for the Production of Flavonoids and Stilbenoids

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