Structure–activity relationships of anthocyanidin glycosylation

Zhao, Chang Ling; Chen, Zhong Jian; Bai, Xue; Can, Ding; Long, Ting Ju; Wei, Fu; Miao, Kang Ru

doi:10.1007/s11030-014-9520-z

Cited by 112 publications

(56 citation statements)

References 78 publications

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“…The pancreatic lipase inhibitory activity of anthocyanidins depends on the number and position of the phenolic hydroxyl groups as well as the degree of polymerization at the 3‐hydroxyl group in the C‐ring (Wu et al, ; Zhao et al, ). The polyphenolic structure of the B‐ring increases the hydrophobic characteristics of the compounds, thus enhancing higher affinity toward lipases.…”

Section: Resultsmentioning

confidence: 99%

Cyanidin and cyanidin-3-glucoside derived from Vigna unguiculata act as noncompetitive inhibitors of pancreatic lipase

2019

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The consumption of legumes positively correlated with the reduction of body weight. In the present study, we identified and evaluated pancreatic lipase inhibitors from Vigna unguiculata and unraveled their mode of inhibition. The highly sensitive fluorometric method was adopted to access the pancreatic lipase activity and the ethanolic extract of Vigna unguiculata showed the maximum inhibition (IC50 of 15.2 µg/ml). Cyanidin and cyanidin‐3‐glucoside are the major anthocyanins observed in Vigna unguiculata. The IC50 value of cyanidin was 28.29 µM which was 6.5‐fold higher than the cyanidin‐3‐glucoside (188.28 µM). We determined an apparent Ki of 27.28 µM for cyanidin and cyanidin‐3‐glucoside (88.97 µM) with noncompetitive inhibition. Collectively, these results suggest that the glycosylation of the anthocyanidins significantly reduces lipase inhibition. The noncompetitive inhibition of pancreatic lipase by Vigna unguiculata anthocyanins may exert significant pharmacological activities toward obesity complications by calorie restriction. Practical applications The results of this study emphasize the importance of legumes in our diet to combat obesity‐related complications. Consumption of legumes minimizes fat absorption by inhibiting the action of the fat‐digesting enzyme.

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Section: Resultsmentioning

confidence: 99%

Cyanidin and cyanidin-3-glucoside derived from Vigna unguiculata act as noncompetitive inhibitors of pancreatic lipase

2019

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“…3. Zhao et al (2014) have also demonstrated in their recent review that the glycosylation of anthocyanidins usually lessen their antioxidant activity but may also enhance activity depending on the anthocyanidin type and the experimental method.…”

Section: Structure Activity Relationship (Sar)mentioning

confidence: 99%

Antiradical and reductant activities of anthocyanidins and anthocyanins, structure–activity relationship and synthesis

2016

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“…As the degree of hydroxylation is high, blue shades are produced, while the higher methoxylation degree produce red shades (VARGAS Y VARGAS et al, 2013). Under light exposure, anthocyanins glycosides were considered more stable than monoglycosides (ZHAO et al, 2014).…”

Section: Resultsmentioning

confidence: 99%

Stability of Anthocyanins From Agroindustrial Residue of Isabel Grape Grown in São Francisco Valley, Brazil

et al. 2017

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-Grape by-products are promising and sustainable sources of anthocyanins. Considering the factors related to degradation of those pigments, spectrophotometric and kinetic analyzes were carried out with the aim to evaluate the light and heat stability of anthocyanins from Isabel grape residue. We found that the exposure to luminosity (80W; 2500 lux) and high temperature (≥ 70ºC) significantly affected the absorption and content of those compounds (p <0.05), whose the most stable condition was obtained at 50°C (t 1/2 : 37.7h; k: 1.84 x 10 -2 h -1 ) and protected from light (t 1/2 : 3,320.6h; k: 2.09 x 10 -4 h -1 ). Therefore, the anthocyanins from the agroindustrial residue of Isabel grape are an alternative of natural colorants for food that can be packaged in opaque packaging and not subjected to severe heat treatment during processing. Index Terms: Vitis labrusca; Kinetics; Thermal degradation; Light. ESTABILIDADE DE ANTOCIANINAS DO RESÍDUO AGROINDUSTRIALDA UVA ISABEL CULTIVADA NO VALE DO SÃO FRANCISCO RESUMO -Subprodutos da uva são fontes promissoras e sustentáveis de antocianinas. Considerando os fatores envolvidos no processo de degradação desses pigmentos, análises espectrofotométricas e cinéticas foram realizadas com o objetivo de avaliar a estabilidade à luz e ao calor de antocianinas do resíduo da uva cv. Isabel. Constatou-se que a exposição à luminosidade (80 W; 2500/lux) e à temperatura elevada (≥ 70ºC) afetou significativamente a absorbância e o teor desses compostos (p <0,05), cuja condição mais estável foi obtida a 50ºC (t 1/2 : 37,7 h; k: 1,84 x 10 -2 h -1 ) e protegida da luz (t 1/2 : 3.320,6 h; k: 2,09 x 10 -4 h -1 ). Portanto, as antocianinas extraídas do resíduo da uva Isabel são uma alternativa de corante natural para produtos alimentícios que sejam acondicionados em embalagens opacas e não sejam submetidos a tratamentos térmicos severos durante o processamento. Termos para Indexação: Vitis labrusca, Cinética, Degradação térmica, Luz.

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Structure–activity relationships of anthocyanidin glycosylation

Cited by 112 publications

References 78 publications

Cyanidin and cyanidin-3-glucoside derived from Vigna unguiculata act as noncompetitive inhibitors of pancreatic lipase

Cyanidin and cyanidin-3-glucoside derived from Vigna unguiculata act as noncompetitive inhibitors of pancreatic lipase

Antiradical and reductant activities of anthocyanidins and anthocyanins, structure–activity relationship and synthesis

Stability of Anthocyanins From Agroindustrial Residue of Isabel Grape Grown in São Francisco Valley, Brazil

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