47705-70-4Relevant articles and documents
New acylated cyanidin glycosides extracted from underutilized potential sources: Enzymatic synthesis, antioxidant activity and thermostability
Fernandez-Aulis, Fernanda,Torres, Andrea,Sanchez-Mendoza, Ernesto,Cruz, Luis,Navarro-Ocana, Arturo
, (2019/11/26)
Interest in anthocyanins has increased remarkably in recent decades, although their wider application has been hampered by instability problems. Thus, this study aimed at developing a strategy to gain access to more stable anthocyanins via enzymatic esterification. For that purpose, three cyanidin derivatives were obtained from underutilized, but easily accessible sources, and their total anthocyanin content was quantified. The purity of cyanidins obtained ranged from 40% to 88% depending on their source. Subsequently, the critical enzymatic reaction conditions were established, and the best results were found using tert-butanol as a solvent, 20 g/L of lipase B from Candida Antarctica, and vinyl cinnamate as acyl donor at ratio 250:1 (acyl donor to anthocyanin). Finally, five new acylated anthocyanin derivatives were synthesized with improved antioxidant activity and thermostability, in comparison to the cyanidin-3-glucoside, which is an advantageous feature for industrial applications.
Highly Promiscuous Flavonoid 3- O-Glycosyltransferase from Scutellaria baicalensis
Wang, Zilong,Wang, Shuang,Xu, Zheng,Li, Mingwei,Chen, Kuan,Zhang, Yaqun,Hu, Zhimin,Zhang, Meng,Zhang, Zhiyong,Qiao, Xue,Ye, Min
supporting information, p. 2241 - 2245 (2019/03/19)
A highly regio-specific and donor-promiscuous 3-O-glycosyltransferase, Sb3GT1 (UGT78B4), was discovered from Scutellaria baicalensis. Sb3GT1 could accept five sugar donors (UDP-Glc/-Gal/-GlcNAc/-Xyl/-Ara) to catalyze 3-O-glycosylation of 17 flavonols, and the conversion rates could be >98%. Five new glycosides were obtained by scaled-up enzymatic catalysis. Molecular modeling and site-directed mutagenesis revealed that G15 and P187 were critical catalytic residues for the donor promiscuity. Sb3GT1 could be a promising catalyst to increase structural diversity of flavonoid 3-O-glycosides.
Color and antioxidant properties of cyanidin-based anthocyanin pigments
Stintzing, Florian C.,Stintzing, Angela S.,Carle, Reinhold,Frei, Balz,Wrolstad, Ronald E.
, p. 6172 - 6181 (2007/10/03)
A series of cyanidin-based anthocyanin pigments was investigated to determine the effect of structural variation on a number of chemical and physical properties: CIELAB color coordinates, visual detection thresholds, hydration constants (pKH), and in vitro antioxidant activities (ORAC). In addition to individual isolated compounds, purified total pigment isolates from blackberry, elderberry, black carrot, red cabbage, and sweet potato were also examined. Acylation with cinnamic acids shifted color tonality (hue angle) to purple, and markedly increased pKH and antioxidant activity, but lowered the visual detection threshold. Glycosidic substitution at the 5 position moved tonalities toward purple and decreased pKH, and tended to lower the ORAC value, but raised the visual detection threshold. Increasing the number of sugar substituents at the 3 position also affected all of these parameters, however, the extent was not predictable. Antioxidant levels of purified anthocyanin extracts were much higher than expected from anthocyanin content indicating synergistic effect of anthocyanin mixtures.
