Chemical fact sheet: Cyanidin 3-O-glucoside

Cyanidin 3-O-glucoside

Basics

Category
Anthocyanidin derivatives
IUPAC-name
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)chromenylium
Formula
No formula stored
Exact mass
449.10780 g/mol
Molecular weight
449.38400 g/mol
Structure
Chemical structure of cyanidin 3-O-glucoside
Figure 1.1: Chemical structure of cyanidin 3-O-glucoside

Sources

In summary, the chemical cyanidin 3-O-glucoside has been analyzed from following sources:

Allium cepa var. Ramata di Montoro  L.
1st
Allium cepa var. Tropea  L.
1st
Aronia melanocarpa 'Galicjanka'
1st 2nd
Punica granatum
1st
Ribes nigrum 'Titania'
1st
Sambucus nigra var. Haschberg  L.
1st 2nd

Note that an analysis result in the database may indicate either presence or lack thereof of a chemical in an analyzed sample.

References

  1. V. Di Stefano, R. Pitonzo, M. Novara, D. Bongiorno, S. Indelicato, C. Gentile, G. Avellone, R. Bognanni, S. Scandurra, and M. Melilli, "Antioxidant activity and phenolic composition in pomegranate (Punica granatum L.) genotypes from south Italy by UHPLC-Orbitrap-MS approach.," Journal of the Science of Food and Agriculture , vol. 99 , pp. 1038–1045 , DOI: 10.1002/jsfa.9270 .
  2. J. Oszmiański, and S. Lachowicz, "Effect of the production of dried fruits and juice from chokeberry (Aronia melanocarpa L.) on the content and antioxidative activity of bioactive compounds.," Molecules , vol. 21 , no. 8 , pp. 1098 , DOI: 10.3390/molecules21081098 .
  3. R. Slimestad, and H. Solheim, "Anthocyanins from black currants (Ribes nigrum L.).," Journal of Agricultural and Food Chemistry , vol. 50 , pp. 3228–3231 , DOI: 10.1021/jf011581u .
  4. L. Szaloki-Dorko, M. Steger-Mate, and L. Abranko, "Evaluation of colouring ability of main European elderberry (Sambucus nigra L.) varieties as potential resources of natural food colourants," Food Science and Technology , vol. 50 , no. 6 , pp. 1317–1323 , DOI: 10.1111/ijfs.12773 .
  5. I. Tedesco, V. Carbone, C. Spagnuolo, P. Minasi, and G. Russo, "Identification and quantification of flavonoids from two southern Italian cultivars of Allium cepa L., Tropea (red onion) and Montoro (copper onion), and their capacity to protect human erythrocytes from oxidative stress.," Journal of Agricultural and Food Chemistry , vol. 63 , pp. 5229–5238 , DOI: 10.1021/acs.jafc.5b01206 .

Analysis results

Analysis result 1

Detection technique Values Units
M⁺ 449.10699 m/z
MS²⁺ 287.05420 m/z
STD
True
TLC
False
UV/Vis detector description
UHPLC-DAD
Mass spectrometer description
ESI-MS, quadrupole Orbitrap MS
Organism
Punica granatum
cultivated
squeezed, fresh, frozen, juice
Sample note
The samples were identified and collected by the researchers.
Dried material storage temperature
-20 °C
Dried material storage notes
dark
Extract liquid storage temperature
-20 °C
References

V. Di Stefano, R. Pitonzo, M. Novara, D. Bongiorno, S. Indelicato, C. Gentile, G. Avellone, R. Bognanni, S. Scandurra, and M. Melilli, "Antioxidant activity and phenolic composition in pomegranate (Punica granatum L.) genotypes from south Italy by UHPLC-Orbitrap-MS approach.," Journal of the Science of Food and Agriculture , vol. 99 , pp. 1038–1045 , DOI: 10.1002/jsfa.9270 .

Analysis result 2

Detection technique Values Units
UV/Vis 517 nm
M⁺ 449 m/z
MS²⁺ 287 m/z
STD
True
TLC
False
UV/Vis detector description
UPLC-PDA
Mass spectrometer description
UPLC-PDA-ESI-MS/MS, UPLC-QTOF-MS
Organism
Aronia melanocarpa 'Galicjanka'
cultivated
ground, dried, passed through a strainer (1mm)
Sample note
The fruit samples (about 15kg) were obtained from a horticultural farm in Trzebnica, near Wroclaw, Poland. The raw material was collected at the optimum ripening stage recommended for consumption. The whole fruits were freeze-dried, so that the pressure was reduced to 0.0960 kPa. The temperature in the drying chamber was -60 C, and in the shelves 26C. The dried material was ground with laboratory mill (IKA A.11, Christ) and then passed through a strainer (1mm). The powder (code PDF) was ready for the analyses.
Drying methods
freeze-dried
Drying temperature
26 °C
Extraction solvents
methanol acidified with 2 % formic acid
Extraction mass/volume-ratio
40 mg/mL
Extraction repeats
2
Extraction time
30 min
Analysis solvents
methanol acidified with 2 % formic acid
References

J. Oszmiański, and S. Lachowicz, "Effect of the production of dried fruits and juice from chokeberry (Aronia melanocarpa L.) on the content and antioxidative activity of bioactive compounds.," Molecules , vol. 21 , no. 8 , pp. 1098 , DOI: 10.3390/molecules21081098 .

Analysis result 3

Detection technique Values Units
UV/Vis 517 nm
M⁺ 449 m/z
MS²⁺ 287 m/z
STD
True
TLC
False
UV/Vis detector description
UPLC-PDA
Mass spectrometer description
UPLC-PDA-ESI-MS/MS, UPLC-QTOF-MS
Organism
Aronia melanocarpa 'Galicjanka'
cultivated
pressed, dried, passed through a strainer (1mm), ground
Sample note
The fruit samples (about 15kg) were obtained from a horticultural farm in Trzebnica, near Wroclaw, Poland. The raw material was collected at the optimum ripening stage recommended for consumption. The whole, uncrushed fruits were pressed on a hydraulic press (SSRE, Waesaw, Poland). The obtained pomace was freeze-dried using an Alpha 1-4 LSC freeze dryer. The pressure was reduced to 0.960kPa. The temperature in the drying chamber was -60 C, and in the shelves 26C.Then, the material was ground, then passed through a strainer (1mm). After that the powder (code PPUF) was ready for the analyses.
Drying methods
freeze-dried
Drying temperature
26 °C
Extraction solvents
methanol acidified with 2 % formic acid
Extraction mass/volume-ratio
40 mg/mL
Extraction repeats
2
Extraction time
30 min
Analysis solvents
methanol acidified with 2 % formic acid
References

J. Oszmiański, and S. Lachowicz, "Effect of the production of dried fruits and juice from chokeberry (Aronia melanocarpa L.) on the content and antioxidative activity of bioactive compounds.," Molecules , vol. 21 , no. 8 , pp. 1098 , DOI: 10.3390/molecules21081098 .

Analysis result 4

Detection technique Values Units
UV/Vis 280
519 		nm
M⁺ 449 m/z
MS²⁺ 287 m/z
STD
False
TLC
False
UV/Vis detector description
HPLC-UV/Vis, photodiode array, HPLC-PAD
Mass spectrometer description
ESI-MS
Organism
Ribes nigrum 'Titania'
cultivated
frozen
Collection dates
2001-8
Sample note
The researchers collected black currant berries (Ribes nigrum, cv. Titania) and voucher specimens are deposited at Polyphenols Laboratories.
Dried material storage temperature
-10 °C
Extraction solvents
methanol, water, trifluoroacetic acid
Extraction mass/volume-ratio
250 mg/mL
Extraction repeats
2
Extraction time
2 d
Extract drying method
evaporation
Analysis solvents
methanol; water
References

R. Slimestad, and H. Solheim, "Anthocyanins from black currants (Ribes nigrum L.).," Journal of Agricultural and Food Chemistry , vol. 50 , pp. 3228–3231 , DOI: 10.1021/jf011581u .

Analysis result 5

STD
True
TLC
False
UV/Vis detector description
HPLC-DAD, HPLC-UV/Vis
Mass spectrometer description
HPLC-ESI-MS, Q-TOF-MS, quadrupole/fime-of-flight
Organism
Sambucus nigra var. Haschberg  L.
cultivated
homogenized, dried, frozen
Collection dates
2012-8
Sample note
Representative samples were collected from several plants by researchers. The clusters contained black, fully ripe berries and about 1.5kg of berries with stalks per sample were packed in plastic bags. The fully mature berries were frozen and stored for some days before further lyophilization.
Drying methods
lyophilized
Dried material storage temperature
-18 °C
Extraction solvents
60 % (v/v) methanol, 1 % (v/v) formic acid
Extraction mass/volume-ratio
20 mg/mL
Extraction repeats
1
Extraction time
35 min
Extraction temperature
35 °C
Analysis solvents
MeOH; water; formic acid
References

L. Szaloki-Dorko, M. Steger-Mate, and L. Abranko, "Evaluation of colouring ability of main European elderberry (Sambucus nigra L.) varieties as potential resources of natural food colourants," Food Science and Technology , vol. 50 , no. 6 , pp. 1317–1323 , DOI: 10.1111/ijfs.12773 .

Analysis result 6

STD
True
TLC
False
UV/Vis detector description
HPLC-DAD, HPLC-UV/Vis
Mass spectrometer description
HPLC-ESI-MS, Q-TOF-MS, quadrupole/fime-of-flight
Organism
Sambucus nigra var. Haschberg  L.
cultivated
homogenized, dried, frozen
Collection dates
2012-8
Sample note
Representative samples were collected from several plants by researchers. The clusters contained black, fully ripe berries and about 1.5kg of berries with stalks per sample were packed in plastic bags. The fully mature berries were frozen and stored for some days before further lyophilization.
Drying methods
lyophilized
Dried material storage temperature
-18 °C
Extraction solvents
60 % (v/v) methanol, 1 % (v/v) formic acid
Extraction mass/volume-ratio
20 mg/mL
Extraction repeats
1
Extraction time
35 min
Extraction temperature
35 °C
Analysis solvents
MeOH; water; formic acid
References

L. Szaloki-Dorko, M. Steger-Mate, and L. Abranko, "Evaluation of colouring ability of main European elderberry (Sambucus nigra L.) varieties as potential resources of natural food colourants," Food Science and Technology , vol. 50 , no. 6 , pp. 1317–1323 , DOI: 10.1111/ijfs.12773 .

Analysis result 7

Detection technique Values Units
M⁺ 449 m/z
MS²⁺ 287 m/z
STD
True
TLC
False
UV/Vis detector description
HPLC-UV/Vis
Mass spectrometer description
HPLC/ESI-ITMSn, electrospray ionization multistage ion trap mass spectrometry
Organism
Allium cepa var. Ramata di Montoro  L.
cultivated
chopped
Sample note
The variety is cultivated in a niche geographical area in southern Italy. The cultivated bulbs were provide by local committee promoters of Cipolla Ramata di Montoro located in Montoro (Campania, Italy).
Extraction solvents
80 % methanol
Extraction mass/volume-ratio
500 mg/mL
Extraction repeats
1
Extraction time
25 min
Extraction temperature
20±5 °C
Extract drying method
rotary evaporation
Dried extract storage temperature
-20 °C
Analysis solvents
1 % formic acid
References

I. Tedesco, V. Carbone, C. Spagnuolo, P. Minasi, and G. Russo, "Identification and quantification of flavonoids from two southern Italian cultivars of Allium cepa L., Tropea (red onion) and Montoro (copper onion), and their capacity to protect human erythrocytes from oxidative stress.," Journal of Agricultural and Food Chemistry , vol. 63 , pp. 5229–5238 , DOI: 10.1021/acs.jafc.5b01206 .

Analysis result 8

Detection technique Values Units
M⁺ 449 m/z
MS²⁺ 287 m/z
STD
True
TLC
False
UV/Vis detector description
HPLC-UV/Vis
Mass spectrometer description
HPLC/ESI-ITMSn, electrospray ionization multistage ion trap mass spectrometry
Organism
Allium cepa var. Tropea  L.
cultivated
chopped
Sample note
Tropea variety is a well known red onion in southern Italy. The researchers collected onion bulbs in Tropea, Calabria, Italy.
Extraction solvents
80 % methanol
Extraction mass/volume-ratio
500 mg/mL
Extraction repeats
1
Extraction time
25 min
Extraction temperature
20±5 °C
Extract drying method
rotary evaporation
Dried extract storage temperature
-20 °C
Analysis solvents
1 % formic acid
References

I. Tedesco, V. Carbone, C. Spagnuolo, P. Minasi, and G. Russo, "Identification and quantification of flavonoids from two southern Italian cultivars of Allium cepa L., Tropea (red onion) and Montoro (copper onion), and their capacity to protect human erythrocytes from oxidative stress.," Journal of Agricultural and Food Chemistry , vol. 63 , pp. 5229–5238 , DOI: 10.1021/acs.jafc.5b01206 .