cyanidin-3-sambubioside and cyanidin

Thirteen anthocyanins were isolated from the flowers of two Aeschynanthus species, A. fulgens and A. pulcher, and six cultivars, 'Mahligai', 'Mona Lisa', 'SoeKa', 'Redona', 'Freshya' and 'Bravera', and identified as pelargonidin and cyanidin 3-O-sambubiosides and their malonates, succinates, p-coumarates and caffeates, and pelargonidin 3-O-glucoside by acid hydrolysis, HR-MS and NMR. Of their anthocyanins, pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-malonylglucoside)] (2), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-succinylglucoside)] (3), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-E-p-coumaroylglucoside)] (4), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-Z-p-coumaroylglucoside)] (5), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-E-caffeoylglucoside)] (6) and cyanidin 3-O-[xylosyl-(1 → 2)-(6''-succinylglucoside)] (9) were reported in nature for the first time.

Topics: Anthocyanins; Disaccharides; Flowers

Excessive Ultraviolet (UV) irradiation induces skin damage. In the present study, the potential protective activity of anthocyanins (cyanidin-3-O-sophoroside and cyanidin-3-O-sambubioside) from black peanut against skin damage induced by UV-B was evaluated in vitro and in vivo. Treatment with anthocyanins significantly reversed UV-B induced oxidative damage and following apoptotic death in human HaCaT cells. Nuclear-factor-E2-related factor 2 (Nrf 2) was activated by anthocyanins through Nrf 2 protein stabilization and nuclear translocation, along with the expressions of antioxidant responsive element (ARE)- related genes (HO1, GCLC and NOQ1). Nrf 2 knockdown in HaCaT cells by targeted-shRNA plasmid markedly abolished the protective activity of anthocyanins against UV-B irradiation. Additionally, topical application of anthocyanins (5 mg cm-2) inhibited UV-B induced oxidative stress and cell apoptosis in BALB/c mouse skin tissues. The protective effect of anthocyanins can be explained by the regulation of oxidative-stress and the suppression of cell apoptosis through the activation of Nrf-2 by interaction with the MAPK and NF-κB signaling pathways. Our results suggested that anthocyanins from black peanut skin might be used as a potential photochemo-protective agent against UV-B induced skin damage.

Topics: Animals; Anthocyanins; Antioxidants; Apoptosis; Arachis; Caspase 3; Cell Line; Disaccharides; Female; Gene Knockdown Techniques; Humans; Keratinocytes; Mice; Mice, Inbred BALB C; NF-E2-Related Factor 2; NF-kappa B; Oxidative Stress; Protective Agents; Reactive Oxygen Species; Signal Transduction; Skin; Ultraviolet Rays

Peanut testae are potent sources of polyphenols. When the water extracts and acid hydrolysates of five different-colored testae were analyzed by HPLC, chromatograms monitored at 280 nm varied remarkably, whereas two major peaks in the chromatograms monitored at 530 nm were detected only in kernels having completely or partially black color. After acid hydrolysis of the extracts, cyanidin was detected in each of the hydrolysates. By respectively subjecting the black testae of raw and roasted (175 degrees C for 20 min) kernels of a black colored cultivar to water extraction and HPLC analysis, a prominent peak was detected in both extracts. The structure of the substance under those peaks was identified by mass and NMR spectrometry as cyanidin 3-sambubioside in peanut testae for the first time. Subjection of cyanidin 3-sambubioside to antioxidation and anti-inflammation assessments revealed that it was a potent antioxidant and inhibitor of nitric oxide production.

Topics: Animals; Anthocyanins; Antioxidants; Arachis; Cell Line; Chromatography, High Pressure Liquid; Disaccharides; Hot Temperature; Macrophages; Magnetic Resonance Spectroscopy; Mice; Nitric Oxide; Pigments, Biological; Seeds