Acylated Flavone Glucosides: Synthesis, Conformational Investigation, and Complexation Properties

Alluis, Bertrand; Dangles, Olivier

doi:10.1002/(sici)1522-2675(19991215)82:12<2201::aid-hlca2201>3.0.co;2-4

Cited by 39 publications

(30 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…HSA has two primary hydrophobic binding sites commonly referred to as site I and site II, located at domains IIA and IIIA, respectively 25. 7‐Hydroxyflavone was found to bind to the inter‐domain IIA‐IIIA in close proximity to Trp214 26 and chrysin was found to bind to sub‐domain IIA of HSA 27, which resulted in the dramatic shifts (about 5 and 4 nm) of the maximum λ em of HSA fluorescence. Compared with BSA molecule (residue located in the first sub‐domain IB and Trp‐212 in sub‐domain IIA), the residue in HSA is more sensitive to the flavones, which was illustrated by the lager shifts of the maximum λ em .…”

Section: Resultsmentioning

confidence: 99%

Structure–affinity relationship of flavones on binding to serum albumins: Effect of hydroxyl groups on ring A

Xiao

Cao

Wang

et al. 2010

Molecular Nutrition Food Res

102

View full text Add to dashboard Cite

Four flavones (flavone, 7-hydroxyflavone, chrysin, and baicalein) sharing the same B- and C-ring structure but a different numbers of hydroxyl groups on the A-ring were studied for their affinities for BSA and HSA. The hydroxylation on ring A of flavones increased the binding constants (K(a)) and the number of binding sites (n) between flavones and serum albumins. The affinities of 7-hydroxyflavone for BSA and HSA were about 800 times and 40 times higher than that of flavone, respectively. It appears that the optimal number of hydroxyl groups introduced to the ring A of flavones is one. As more hydroxyl groups were introduced to positions at C-5, C-6, and/or C-7 of flavones, the affinities for serum albumins decrease. The critical energy transfer distances (R(0)) between the hydroxylated flavones (1-3 OH on the ring A) and serum albumins decreased with the increasing affinities for serum albumins.

show abstract

Section: Resultsmentioning

confidence: 99%

Structure–affinity relationship of flavones on binding to serum albumins: Effect of hydroxyl groups on ring A

Xiao

Cao

Wang

et al. 2010

Molecular Nutrition Food Res

102

View full text Add to dashboard Cite

show abstract

“…Synthesis of glycosylated flavonoids, especially with the use of biological catalysts, may be an attractive method of receiving these compounds in amounts sufficient for the research concerning influence of sugar residue in flavonoid molecules on their properties and subsequent application of these compounds as dietary supplements or pharmaceuticals (Alluis and Dangles, 1999). …”

Section: Microbial Glycosylation Of Flavonoidsmentioning

confidence: 99%

Microbial Glycosylation of Flavonoids

Sordon

Popłoński

Huszcza

2016

Polish Journal of Microbiology

View full text Add to dashboard Cite

A b s t r a c tFlavonoids constitute a large group of polyphenolic compounds naturally found in plants, which have a wide range of biological activity. Although flavonoids are beneficial to human health, their application is limited by their low bioavailability and poor water-solubility. Therefore, recently there has been a particular interest in glycosylated forms of flavonoids, which usually are better soluble, more stable, and more functional compared to their aglycones. Microbial transformation of natural flavonoids may be an attractive way of receiving their glycosylated derivatives in amounts sufficient for the research on the effect of glycoside group on compound properties and for further application of these compounds as ingredients of dietary supplements and pharmaceuticals.K e y w o r d s:

show abstract

“…Flavonoid acylation with aromatic acids was reported to improve physiological activities, such as UV-absorbing capacity, radical scavenging ability (Delazar et al, 2005;Harborne & Williams, 2000;Alluis & Dangles 1999;Jungblut et al, 1995) pigment stabilization (especially anthocyanins) , and interaction with cellular targets (Ferrer et al, 2008).…”

Section: Wwwintechopencommentioning

confidence: 99%

“…Some acylated flavonoids have been found to be involved in plant-insect interactions; they act as phytoalexins, oviposition stimulants, pollinator attractants (Iwashina, 2003), and insect antifeedants (Harborne & Williams, 1998). With respect to novel biological activities, acylation of flavonoids can result in changes in pigmentation (Bloor, 2001), insect antifeedant activity (Harborne & Williams, 1998) and antioxidant properties (Alluis & Dangles, 1999).…”

Section: Introductionmentioning

confidence: 99%