Cyanidin-3-O-glucoside: Physical-Chemistry, Foodomics and Health Effects
Abstract
:1. Introduction
2. Physical Chemistry of Cy3G
2.1. Chemical Structure
2.2. Color
2.3. Temperature
2.4. pH
2.5. Antioxidant Capacity
3. Cy3G in Plant Biochemistry
3.1. Biosynthesis
3.2. Dietary Sources
4. Foodomics
4.1. Oral Cavity
4.2. Stomach
4.3. Small Bowel
4.4. Large Bowel
4.5. Splanchnic Metabolism
5. Cy3G Health Effects
5.1. Human Studies
5.2. Cell Lines and Rodent Models
5.3. Physiologically-Relevant Molecular Mechanisms
6. Future Prospects
Acknowledgments
Author Contributions
Conflicts of Interest
Abbreviations
ΔA | Hyperchromic effect |
Δλ | Bathochromic shift |
ADME | Absorption, distribution, metabolism and excretion |
ANR | Anthocyanidin reductase |
ANS | Anthocyanidin synthase |
ACNs | Anthocyanins |
Å2 | Polar surface area |
AOX | Antioxidants |
ASSWV | Abrasive strip** square wave voltammetry |
βRA | β-Resorcylic acid |
BA | Benzoic acid-4-glucoronide |
BA-Gnd | Benzoic acid-4-glucoronide |
BRB | Black raspberry |
BSA | Bovine serum albumin |
CHI | Chalcone isomerase |
CHS | Chalcone synthase |
COMT | Catechol-O-methyltransferase |
CON | Unknown condensing enzyme(s) |
CT | Condensed tannins |
CV | Cyclic voltammetry |
CVD | Cardiovascular disease |
Cy | Cyanidin |
Cy3G | Cyanidin-3-O-glucoside |
DFR | Dihydroflavonol-4-reductase |
Dp | Delphinidin |
Dp3G | Delphinidin-3-O-glucoside |
Dp3Ga | Delphinidin-3-O-galactoside |
Dp3R | Delphinidin-3-O-rutinoside |
DPV | Differential of pulses voltammetry |
EHM | Entero-hepatic metabolism |
Epa | Anodic peak potential |
F3,5H | Flavanone-3,5-hidroxylase |
F3H | Flavanone-3-hidroxylase |
FA | Ferulic acid |
FLS | Flavonol synthase |
FNS | Flavone synthase |
GI | Gastrointestinal |
GLUT1,2,3 | Glucose transporter 1,2,3 |
HA | Hippuric acid |
HAS | Human serum albumin |
Hb | Hemoglobin |
IVA | Isovainillinic acid |
IVA-3-Gnd | IVA-3-glucoronide |
LAR | Leucoanthocyanidin reductase |
LDOW | Leucoanthocyanidin dioxigenase |
LogP | Octanol/water partition coefficient |
LPH | Lactase-phlorizin hydrolase |
Mb | Myoglobin |
MCP-1/CCL2 | Monocyte chemoattractant protein-1 |
MCT1 | Mono-carboxylated transporter 1 |
Mv | Malvidin |
Mv3G | Malvidin-3-O-glucoside |
MW | Molecular weight |
NCCD | Non-communicable chronic diseases |
OMT | Malvidin (Mv), O-methyltransferase |
Pas | Proanthocyanidins |
PC | Phenolic compounds |
PCA | Protocatechuic acid |
PCA-3-Gnd | PCA-3-glucoronide |
PCA-3-Gnd | PCA-4-glucoronide |
PCA-Sft | PCA-sulfate |
Pg | Pelargoddin |
PGA | Phloroglucinaldehyde |
PgANS | Pelargodin specific-anthocyanidin synthase |
Pn | Peonidin |
Pn3Ga | Peonidin-3-O-galactoside |
PST | Phenyl sulfotranferases |
Pt | Petunidin |
RE | Reference electrode |
ROS | Reactive oxygen species |
RSC | Radical scavenging capacity |
SGLT1 | Na+-glucose transporter |
UFGT | UDP-glucose-flavonoid-3-o-glucosyltransferase |
UGT | Uridine-5′-diphosphate glucoronosyltransferases |
VA | Vainillinic acid |
VA-3-Gnd | VA-3-glucoronide |
VA-Sft | VA-sulfate |
WE | Working electrode |
3,4-dOH-BA | Methyl-3,4-dihydroxybenzoate |
3RT | Anthocyanidin-3-glycoside rhamnosyl-transferase |
4-OH-BA | 4-Hydroxy-benzaldehyde |
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Code | Name | [M]+ (m/z) | MS/MS (m/z) | Solubility (mg/mL) | LogP | Å2 |
---|---|---|---|---|---|---|
Cy | Cyanidin (anthocyanidin) | 287 | 0.049 | 3.05 | 114.3 | |
Cy3A | Cy-3-arabinoside (pentose) | 419 | 287 | 0.41 | 1.06 | 173.21 |
Cy3X | Cy-3-xyloside | 419 | 287 | 0.41 | 1.06 | 173.2 |
Cy3G | Cy-3-glucoside | 449 | 287 | 0.6 | 0.39 | 193.4 |
Cy3Ga | Cy-3-galactoside | 449 | 287 | -- | 0.24 | 193.4 |
Cy3Aga | Cy-3-(6′′-acetyl)-galactoside | 491 | 287 | 0.39 | 0.82 | 199.5 |
Cy3Sa | Cy-3-sambubioside | 518 | 287 | -- | -- | -- |
Cy3,3′′MG | Cy-3-(3′′-malonyl)-glucoside | 535 | 287 | 0.47 | 0.68 | 236.8 |
Cy3,6′′MG | Cy-3-(6′′-malonyl)-glucoside | 535 | 449/287 | 0.45 | 0.68 | 236.8 |
Cy3Sa | Cy-3-sambubioside | 581 | 287 | 1.17 | -1.1 | 252.4 |
Cy3dOXG | Cy-3-(dioxaloyl)-glucoside | 593 | 287 | 0.17 | 2.55 | 280.2 |
Cy3R | Cy-3-rutinoside | 595 | 449/287 | 0.9 | −1.64 | 252.4 |
Cy3XR | Cy-3-xylosylrutinoside | 727 | 581/287 | 2.52 | −2.1 | 311.3 |
Cy3GR | Cy-3-glucosylrutinoside | 757 | 287/611 | 3.85 | −2.8 | 331.5 |
Cy3,5GG | Cy-3,5-diglucoside | 611 | 449/287 | -- | −2.3 | 272.6 |
Cy3So | Cy-3-sophoroside | 611 | 287 | -- | -- | 260 |
Cy3Sa5R | Cy-3-sambubioside-5-rhamnoside | 727 | 581/433/287 | -- | -- | -- |
Cy3So5R | Cy-3-sophoroside-5-rhamnoside | 757 | 611/433/287 | -- | -- | -- |
Molecule | pH | Epa/mV | Technique | Electrodes | Ref. |
---|---|---|---|---|---|
Cy3G | 3.5 | 490, 980 | DPV | WE: Glassy carbon RE: Ag|AgCl | [47] |
4.5 | 420, 815 | ||||
7.0 | 310, 500 | ||||
Cy3G | 2.2 | 548 | CV | WE: Glassy carbon RE: Ag|AgCl | [52] |
4.8 | 400 | ||||
5.9 | 310 | ||||
6.9 | 230 | ||||
Cy3G | 2.0 | 500 | ASSWV | WE: Paraffin rod impregnated RE: Ag|AgCl | [52] |
Cy | 403 | ||||
Cy3G | 1.0 | 617 | CV | WE: Platinum RE: SCE | [53] |
Group | Fruit/Vegetable | Cy3G 2 | Major ACNs 3 |
---|---|---|---|
Fruits/Berries | Black elderberry | 794.13 | Cy3G |
Blackberry raw | 138.72 | Cy3G | |
Black Aestivalis grape | 18.72 | Cy3G | |
Gooseberry | 2.95 | Cy3G | |
Nectarine peeled | 0.56 | Cy3G | |
Peach peeled | 0.28 | Cy3G | |
Blackcurrant raw | 25.07 | Dp3R (304.91) | |
Black chokeberry | 19.64 | Cy3A (252.76) | |
Blueberry | 14.2 | Dp3G (22.6) | |
Sweet cherry raw | 18.73 | Cy3R (143.27) | |
Red raspberry | 14.89 | Cy3So (37.61) | |
Raspberry pomace (dry) | 41.52 | Cy3So (100.1) | |
Plum fresh | 8.63 | Cy3R (33.85) | |
Lowbush blueberry | 7.5 | Mv3G (26.06) | |
Redcurrant | 3.37 | Cy3XR (11.22) | |
Strawberry | 2.88 | Pg3G (47.1) | |
Lingonberry | 1.42 | Cy3Ga (48.69) | |
Highbush blueberry | 1.37 | Dp3Ga (20.50) | |
Sour cherry | 1.12 | Cy3GR (43.63) | |
Black grape | 1.08 | Mv3G (39.23) | |
American Cranberry | 0.74 | Pn3Ga (22.02) | |
Cloudberry | 0.62 | Cy3R (1.86) | |
Juices/wine | Pomegranate pure juice | 3.43 | Cy3G |
Blood orange pure juice | 1.41 | Cy3MG (1.76) | |
Red wine | 0.21 | Mv3G (9.97) | |
Cereals/legumes | Black bean raw | 3.99 | Dp3G (20.50) |
Blue maize hybrid | 2.25 | Cy3G | |
Vegetables | Black Olive raw | 10.62 | Cy3R (72.35) |
Red lettuce raw | 0.62 | Cy3MG (2.91) |
Cell Line | Cy3G dose | Mechanism | Ref. |
---|---|---|---|
Erythrocytes | 10–100 μM | ↓ cholesterol and TBAR in cell membranes | [1] |
Human adherent macrophages (from U937 cells), oral epithelial cells (GMSM-K) and gingival fibroblasts (HGF-1) | 5–25 μg/mL | ↓ IL-6 level (macrophages), cytoprotection (GMSM-K, HGF-1) against nicotine toxicity | [4] |
Colon (Caco2), liver (HepG2), prostate (PC3) | Blue maize ACNs (189–500 μg/g)-extract | ↓ cell proliferation | [36] |
Gastric cancer (KATO III) | 12.5 μM | ↓ Helicobacter pylori VacA-induced cell death | [91] |
Adipocytes (3T3-L1) | 50 μM | ↓ FoxO1-mediated transcription of lipase | [123] |
Hepatome (HepG2) | 1–100 μM | ↑ fatty acid oxidation and AMPK activity | [124] |
Adipocyte | 0.5–50 μM + docosahexanoic acid | ↓ basal lipolysis , inflammatory markers | [127] |
Breast cancer (BT474m MD-MB231, MCF7) | 10 μM | ↓ invasion / increased expression of ErB2 | [133] |
Murine thymoma (EL-4T) | 2.5–5.0 μg/mL | ↓ Il-3 & IL-4 by GATA-3 inhibition | [134] |
Pheochromocytoma (PC-12) | IC50, 15.3 μg/mL | ↓ ATP-induced [Ca2+] increase | [135] |
Colon cancer (HT-29) | 25 μM | ↓ IL-8, nitrite, PGE2 | [136] |
human aortic epithelial cells | 0.5–50 μM | ↑ oxiesterol efflux, ↑ABCG1/ABCA1 expression | [137] |
Heart (isolated mitochondria) | 20 Μm | ↑ phosphorylation, ATP production, ↑e− carrier | [138] |
Adipocytes (steam cells) | 100 μg/mL | ↓ IL-6 level | [139] |
Ovarian cancer (HO-8910PM) | IC50, 13.8 μg/mL | ↑ apoptosis, ↓mucin 4 expression | [140] |
Model | Protocol (Dose) | Effects | Ref. |
---|---|---|---|
Mice (nude), SKH-1 | Oral | ↓ lipid per oxidation ↑ Glutathione | [3] |
Mice, C57BL/6 | Oral, 24 h before, (2 mg/kg) | ↓ Neuronal apoptosis reducing factor, superoxide level, infarct size | [5] |
Mice (obese), C57BL/6 | Oral, 5 w, 0.02% diet, (ad libitum) | Antidiabetic by modulating c-jun N-terminal kinase | [122] |
Mice, apoE (-) | Oral, 12 w, 0.06% diet, (ad libitum) | ↓ expression of hepatic cholesterol 7a-hydroxylase | [137] |
Mice, ovarian cancer | Oral, 2 w, (5 mg/kg) | ↓ Growth of ovarian xenograft tumors | [140] |
Mice, C57BL/6 | Oral, 12 w, (40–200 mg/kg) | ↓ weigh gain, insulin resistance, adiposity, leptin | [141] |
Mice, apoE (-) | Oral, 8 w, 0.2% diet (ad libitum) | ↓ atherogenesis, ↑endothelial repair | [142] |
Mice, with peritonitis/edema | Oral, 30–60 min before (40 mg/kg) | ↓ inflammation, expression COX-2/PGE2 | [143] |
Mice, diabetic | Oral, 4 w, (300 µg/10g) | ↓ blood glucose | [144] |
Mice, KK-Ay | Oral | ↓ visceral fat ↑ lipoprotein lipase | [145] |
Mice, C57BL/6 w/acute alcohol-induced liver injury | Oral, 24–48 h, (10 mg/kg) | ↓ plasma IL-6 ,TNF-α, ALT and AST and ↑ SIRT1 p-c-Jun and Bax expression | [146] |
Rats (retinal degeneration) | Oral, 5 w, 100 mg/kg | ↓ Loss of photoreceptors | [147] |
Mice (fetus) | Intra-peritoneal 10–30 mg/kg | ↓Neuronal damage by caspase 3 inhibition | [148] |
Rats (β-amyloidosis) | Oral, 30 day, 10 mg/kg | ↓ cognitive impairment induced by Aβ via the modulation of GSK-3β/tau | [149] |
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Olivas-Aguirre, F.J.; Rodrigo-García, J.; Martínez-Ruiz, N.D.R.; Cárdenas-Robles, A.I.; Mendoza-Díaz, S.O.; Álvarez-Parrilla, E.; González-Aguilar, G.A.; De la Rosa, L.A.; Ramos-Jiménez, A.; Wall-Medrano, A. Cyanidin-3-O-glucoside: Physical-Chemistry, Foodomics and Health Effects. Molecules 2016, 21, 1264. https://doi.org/10.3390/molecules21091264
Olivas-Aguirre FJ, Rodrigo-García J, Martínez-Ruiz NDR, Cárdenas-Robles AI, Mendoza-Díaz SO, Álvarez-Parrilla E, González-Aguilar GA, De la Rosa LA, Ramos-Jiménez A, Wall-Medrano A. Cyanidin-3-O-glucoside: Physical-Chemistry, Foodomics and Health Effects. Molecules. 2016; 21(9):1264. https://doi.org/10.3390/molecules21091264
Chicago/Turabian StyleOlivas-Aguirre, Francisco J., Joaquín Rodrigo-García, Nina Del R. Martínez-Ruiz, Arely I. Cárdenas-Robles, Sandra O. Mendoza-Díaz, Emilio Álvarez-Parrilla, Gustavo A. González-Aguilar, Laura A. De la Rosa, Arnulfo Ramos-Jiménez, and Abraham Wall-Medrano. 2016. "Cyanidin-3-O-glucoside: Physical-Chemistry, Foodomics and Health Effects" Molecules 21, no. 9: 1264. https://doi.org/10.3390/molecules21091264