Chemical fact sheet: Peonidin 3-glucoside

Peonidin 3-glucoside

Basics

Category
Anthocyanidin derivatives
IUPAC-name
5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(((3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)chromenylium chloride
Formula
No formula stored
Exact mass
498.09289 g/mol
Molecular weight
No weights stored
Structure
Chemical structure of peonidin 3-glucoside
Figure 1.1: Chemical structure of peonidin 3-glucoside

Sources

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

Chrozophora tinctoria  (L.) A. Juss.
1st
Ribes nigrum 'Ben Alder'
1st
Ribes nigrum 'Ben Nevis'
1st
Ribes nigrum 'Ben Lomond'
1st
Ribes nigrum 'Ben Tirran'
1st
Ribes nigrum 'Titania'
1st

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

References

  1. P. Nabais, J. Oliveira, F. Pina, N. Teixeira, V. de Freitas, N. Brás, A. Clemente, M. Rangel, A. Silva, and M. Melo, "A 1000-year-old mystery solved: Unlocking the molecular structure for the medieval blue from Chrozophora tinctoria, also known as folium.," Science Advances , vol. 6 , no. 16 , pp. eaaz7772 , DOI: 10.1126/sciadv.aaz7772 .
  2. X. Wu, L. Gu, R. Prior, and S. McKay, "Characterization of anthocyanins and proanthocyanidins in some cultivars of Ribes, Aronia, and Sambucus and their antioxidant capacity," Journal of Agricultural and Food Chemistry , vol. 52 , no. 26 , pp. 7846–7856 , DOI: 10.1021/jf0486850 .

Analysis results

Analysis result 1

Detection technique Values Units
M⁺ 463 m/z
MS²⁺ 301 m/z
STD
False
TLC
False
UV/Vis detector description
UV/Vis
Mass spectrometer description
HPLC-DAD-ESI-MS, API-LC-ESI-MS/MS
Organism
Chrozophora tinctoria  (L.) A. Juss.
fresh
Collection dates
2016-7, 2016-8, 2016-9, 2017-7, 2017-8, 2017-9, 2018-7, 2018-8, 2018-9
Sample note
The researchers (A. Clemente, F. Pina, M.J. Melo, P. Nabais) collected the fruits between July and September in 2016, 2017 and 2018. In the 2hour-extraction of fruits, care was taken to not grind the seeds that are kept inside, as mentioned in medieval treatises which present thorough instructions not to break the fruits and free the seeds treatises which present thorough instructions not to break the fruits and free the seeds. After this period, the solution presented a deep blue color. period, the solution presented a deep blue color.
Extraction solvents
MeOH: water (70:30, v/v)
Extraction mass/volume-ratio
40 mg/mL
Extraction repeats
1
Extraction time
2 h
Extract drying method
evaporation under vacuum
Analysis solvents
water; ACN in 1 % HCOOH (v/v)
References

P. Nabais, J. Oliveira, F. Pina, N. Teixeira, V. de Freitas, N. Brás, A. Clemente, M. Rangel, A. Silva, and M. Melo, "A 1000-year-old mystery solved: Unlocking the molecular structure for the medieval blue from Chrozophora tinctoria, also known as folium.," Science Advances , vol. 6 , no. 16 , pp. eaaz7772 , DOI: 10.1126/sciadv.aaz7772 .

Analysis result 2

Detection technique Values Units
M⁺ 463 m/z
MS²⁺ 301 m/z
STD
True
TLC
False
UV/Vis detector description
HPLC-DAD
Mass spectrometer description
ion-trap, HPLC-DAD-ESI-MS/MS
Organism
Ribes nigrum 'Ben Alder'
cultivated
dried, powdered
Sample note
The black currants (cultivar Ben Alder) were obtained from Wisley Gardens, Royal Horticultural Society, England.Fresh berry samples were frozen and stored at -20 C until transferred to the Arkansas Children's Nutrition Center, at which time the frozen samples were freeze-dried and ground into powder. The powder was kept at -70 C until analysed.
Drying methods
freeze-dried
Dried material storage temperature
-70 °C
Extraction solvents
MeOH:water:acetic acid (85:15:0,5, v/v)
Extraction mass/volume-ratio
40 mg/mL
Extraction repeats
2
Extraction time
52 min
Analysis solvents
methanol; water; acetic acid
Detection note
Only traces were detected.
References

X. Wu, L. Gu, R. Prior, and S. McKay, "Characterization of anthocyanins and proanthocyanidins in some cultivars of Ribes, Aronia, and Sambucus and their antioxidant capacity," Journal of Agricultural and Food Chemistry , vol. 52 , no. 26 , pp. 7846–7856 , DOI: 10.1021/jf0486850 .

Analysis result 3

Detection technique Values Units
M⁺ 463 : ND m/z
STD
True
TLC
False
UV/Vis detector description
HPLC-DAD
Mass spectrometer description
ion-trap, HPLC-DAD-ESI-MS/MS
Organism
Ribes nigrum 'Ben Nevis'
cultivated
dried, powdered
Sample note
The black currants (cultivar Ben Nevis) were obtained from Wisley Gardens, Royal Horticultural Society, England.Fresh berry samples were frozen and stored at -20 C until transferred to the Arkansas Children's Nutrition Center, at which time the frozen samples were freeze-dried and ground into powder. The powder was kept at -70 C until analysed.
Drying methods
freeze-dried
Dried material storage temperature
-70 °C
Extraction solvents
MeOH:water:acetic acid (85:15:0,5, v/v)
Extraction mass/volume-ratio
40 mg/mL
Extraction repeats
2
Extraction time
52 min
Analysis solvents
methanol; water; acetic acid
References

X. Wu, L. Gu, R. Prior, and S. McKay, "Characterization of anthocyanins and proanthocyanidins in some cultivars of Ribes, Aronia, and Sambucus and their antioxidant capacity," Journal of Agricultural and Food Chemistry , vol. 52 , no. 26 , pp. 7846–7856 , DOI: 10.1021/jf0486850 .

Analysis result 4

Detection technique Values Units
M⁺ 463 : ND m/z
STD
True
TLC
False
UV/Vis detector description
HPLC-DAD
Mass spectrometer description
ion-trap, HPLC-DAD-ESI-MS/MS
Organism
Ribes nigrum 'Ben Lomond'
cultivated
dried, powdered
Sample note
The black currants (cultivar Ben Lomond) were obtained from Wisley Gardens, Royal Horticultural Society, England.Fresh berry samples were frozen and stored at -20 C until transferred to the Arkansas Children's Nutrition Center, at which time the frozen samples were freeze-dried and ground into powder. The powder was kept at -70 C until analysed.
Drying methods
freeze-dried
Dried material storage temperature
-70 °C
Extraction solvents
MeOH:water:acetic acid (85:15:0,5, v/v)
Extraction mass/volume-ratio
40 mg/mL
Extraction repeats
2
Extraction time
52 min
Analysis solvents
methanol; water; acetic acid
References

X. Wu, L. Gu, R. Prior, and S. McKay, "Characterization of anthocyanins and proanthocyanidins in some cultivars of Ribes, Aronia, and Sambucus and their antioxidant capacity," Journal of Agricultural and Food Chemistry , vol. 52 , no. 26 , pp. 7846–7856 , DOI: 10.1021/jf0486850 .

Analysis result 5

Detection technique Values Units
M⁺ 463 : ND m/z
STD
True
TLC
False
UV/Vis detector description
HPLC-DAD
Mass spectrometer description
ion-trap, HPLC-DAD-ESI-MS/MS
Organism
Ribes nigrum 'Titania'
cultivated
dried, powdered
Sample note
The black currants (cultivar Titania) were obtained from Wisley Gardens, Royal Horticultural Society, England.Fresh berry samples were frozen and stored at -20 C until transferred to the Arkansas Children's Nutrition Center, at which time the frozen samples were freeze-dried and ground into powder. The powder was kept at -70 C until analysed.
Drying methods
freeze-dried
Dried material storage temperature
-70 °C
Extraction solvents
MeOH:water:acetic acid (85:15:0,5, v/v)
Extraction mass/volume-ratio
40 mg/mL
Extraction repeats
2
Extraction time
52 min
Analysis solvents
methanol; water; acetic acid
References

X. Wu, L. Gu, R. Prior, and S. McKay, "Characterization of anthocyanins and proanthocyanidins in some cultivars of Ribes, Aronia, and Sambucus and their antioxidant capacity," Journal of Agricultural and Food Chemistry , vol. 52 , no. 26 , pp. 7846–7856 , DOI: 10.1021/jf0486850 .

Analysis result 6

Detection technique Values Units
M⁺ 463 : ND m/z
STD
True
TLC
False
UV/Vis detector description
HPLC-DAD
Mass spectrometer description
ion-trap, HPLC-DAD-ESI-MS/MS
Organism
Ribes nigrum 'Ben Tirran'
cultivated
dried, powdered
Sample note
The black currants (cultivar Ben Tirran) were obtained from Wisley Gardens, Royal Horticultural Society, England.Fresh berry samples were frozen and stored at -20 C until transferred to the Arkansas Children's Nutrition Center, at which time the frozen samples were freeze-dried and ground into powder. The powder was kept at -70 C until analysed.
Drying methods
freeze-dried
Dried material storage temperature
-70 °C
Extraction solvents
MeOH:water:acetic acid (85:15:0,5, v/v)
Extraction mass/volume-ratio
40 mg/mL
Extraction repeats
2
Extraction time
52 min
Analysis solvents
methanol; water; acetic acid
References

X. Wu, L. Gu, R. Prior, and S. McKay, "Characterization of anthocyanins and proanthocyanidins in some cultivars of Ribes, Aronia, and Sambucus and their antioxidant capacity," Journal of Agricultural and Food Chemistry , vol. 52 , no. 26 , pp. 7846–7856 , DOI: 10.1021/jf0486850 .