Selective Iodination Enables Anthocyanin Synthesis to Be More General

Abstract

The current synthesis routes of anthocyanins are relatively complicated, which significantly hinders their development. We optimized the method by introducing a selective iodination reaction and also established a general scheme for preparing anthocyanin diglycosides. This method allows anthocyanin synthesis to require fewer steps and costs. Based on this, we prepared four common anthocyanins and two anthocyanin diglucosides and measured their antioxidant and anti-insulin resistance activities.

Covalent Interactions of Anthocyanins with Proteins: Activity-Based Protein Profiling of Cyanidin-3-O-glucoside

“…C3G and the B-ring intermediate 2b were obtained in previous work. 27 The following abbreviations were used in reporting spectra, br s (broad singlet), s (singlet), d (doublet), t (triplet), q (quartet), m (multiplet), dd (doublet of doublets). NMR spectra of intermediates and probe final products are in Supporting Information.…”

“…Insulin resistance HepG2 cell modeling was performed by fatty acids as previously reported. 27 Then the cells were treated with C3G or C3G-Probe for 24 h and cultured with DMEM containing 100 nM insulin for another 24 h. The glucose consumption was calculated using a glucose assay kit (Njjcbio; Nanjing, China). 50, 100, 200, and 400 μM of C3G-Probe were incubated with 8 × 10 4 HepG2 per well for 24 h, and then cytotoxicity was measured by CCK8 kit (beyotime; Shanghai, China).…”

“…26 Besides, our previous work found that C3G exhibits better activity in HepG2 cell insulin resistance and in vitro antioxidant effects compared to other anthocyanins. 27 Herein, we investigated the potential bioactive targets of anthocyanins and their interaction modes with electrophilic skeletons. Based on our previous work on anti-insulin resistance activity, we first revealed the protein profiling of C3G in the whole proteome of HepG2 cells and found its covalent binding to some target proteins.…”

“…In this work, the clickable alkynyl group was introduced into the A ring of C3G to avoid affecting the activity, 29,30 and the modification of the two phenolic hydroxyl groups was referred to Wang et al 31 As shown in Figure 1A, the covalent binding probe C3G-Probe and the noncovalent photoaffinity probe C3G-Diazirine were obtained based on the synthetic route we developed previously. 27 After the probe identifies the target proteins, the alkynyl reacts with the azide group attached with a fluorescent dye or biotin by click chemistry. 32 For noncovalent molecules, additional photoaffinity groups and irradiation are needed to form stable labeling.…”

Optimized Synthesis and Antioxidant Activity of Anthocyanins Delphinidin-3-O-glucoside and Petunidin-3-O-glucoside

“…In our earlier research, the strategy developed for synthesizing anthocyanins was only effective in producing four highly pure four anthocyanins: C3G, pelargonidin-3- O -glucoside (P3G), peonidin-3- O -glucoside (Pn3G), and malvidin-3- O -glucoside (M3G) . Besides, in the existing literature, successful chemical synthetic routes of Dp3G and Pt3G are scarce and cockamamie.…”