47888-56-2Relevant academic research and scientific papers
The fate of acylated anthocyanins in mildly heated neutral solution
Collins, Thomas M.,Dangles, Olivier,Fenger, Julie-Anne,Robbins, Rebecca J.
, (2020)
In neutral solution, anthocyanins acylated by hydroxycinnamic acids typically exhibit attractive blue colors and a higher resistance to color loss compared to their nonacylated homologs. However, they remain vulnerable to a poorly understood combination of oxidative and hydrolytic reactions that strongly contribute to color loss and limits their industrial applications. In this work, the thermal degradation of isolated red cabbage anthocyanins (0, 1 or 2 acyl groups) at pH 7 was investigated by UPLC-DAD-MS (low- and high-resolution). Non-oxidative alterations, including deacylation and intramolecular acyl transfer, were observed and found very dependent on the number and position of the acyl group(s) as well as on the presence of iron ions. At intermediate and advanced thermal degradation, several oxidative mechanisms were evidenced that lead to protocatechuic acid, phloroglucinaldehyde 2-O-glucoside, acylglycosides and derivatives of 2,4,6-trihydroxyphenylacetic acid and 3,5,7-trihydroxycoumarin. Based on the product distribution observed and on the impact of added Fe2+ ions and H2O2, possible degradation mechanisms are discussed. They likely start with a one- or two-electron transfer from the anionic base (a major colored form in neutral solution) to O2. The hydrogen peroxide produced could then further react as an electrophile with the anionic base and/or the hemiketal (major colorless hydrated form). This contribution to understanding the degradation mechanisms of anthocyanins around neutrality can open up new stabilization strategies to extend the range of their food applications to neutral media.
A tetra-acylated cyanidin 3-sophoroside-5-glucoside from the purple-violet flowers of Moricandia arvensis (L.) DC. (Brassicaceae)
Tatsuzawa, Fumi,Ito, Shun,Sato, Motoki,Muraoka, Hiroki,Kato, Kazuhisa,Takahata, Yoshihito,Ogawa, Satoshi
, p. 170 - 173 (2013/08/25)
A novel tetra-acylated cyanidin 3-sophoroside-5-glucoside was isolated from the purple-violet flowers of Moricandia arvensis (L.) DC. (Family: Brassicaceae), and determined to be cyanidin 3-O-[2-O-(2-O-(4-O-(6-O-(4-O- (β-glucopyranosyl)-trans-caffeoyl)-β-glucopyranosyl)-trans-caffeoyl) -β-glucopyranosyl)-6-O-(trans-caffeoyl)-β-glucopyranoside] -5-O-[6-O-(malonyl)-β-glucopyranoside] by chemical and spectroscopic methods.
Tetra-acylated cyanidin 3-sophoroside-5-glucosides from the flowers of Iberis umbellata L. (Cruciferae)
Saito, Norio,Tatsuzawa, Fumi,Suenaga, Eri,Toki, Kenjiro,Shinoda, Koichi,Shigihara, Atsushi,Honda, Toshio
experimental part, p. 3139 - 3150 (2009/05/09)
The structures of 11 acylated cyanidin 3-sophoroside-5-glucosides (pigments 1-11), isolated from the flowers of Iberis umbellata cultivars (Cruciferae), were elucidated by chemical and spectroscopic methods. Pigments 1-11 were acylated with malonic acid,
Triacylated anthocyanins from Ajuga reptans flowers and cell cultures
Terahara, Norihiko,Callebaut, Alfons,Ohba, Riichiro,Nagata, Tadahiro,Ohnishi-Kameyama, Mayumi,Suzuki, Masahiro
, p. 199 - 203 (2007/10/03)
Four anthocyanins were isolated from Ajuga reptans flowers and one from the cell cultures. By FAB mass spectrometry measurements, the structures of these pigments were determined as delphinidin and cyanidin glucosides acylated with two cinnamic acids, while three of them were also malonylated. A delphinidin-based pigment in the crude extract from cell cultures was identical to the major flower pigment as shown by HPLC co-chromatography. Moreover, by application of 1H and 13C NMR consisting of DQF-COSY, NOESY, ROESY, 2D-HOHAHA, HSQC and HMBC methods, the structures of two new anthocyanins were identified as delphinidin and cyanidin 3-O-(2-O-(6-O-(E)-p-coumaryl-β-D-glucopyranosyl)-(6-O-(E)-p-coumaryl)- β-D-glucopyranosyl)-5-O-(6-O-malonyl-β-D-glucopyranoside). The deacylated anthocyanins were confirmed as delphinidin and cyanidin 3-sophoroside-5-glucosides. Copyright
