This document discusses wine pigments, including anthocyanins and their derivatives found in wine. It provides chemical structures of common anthocyanins like malvidin, peonidin, delphinidin and their conjugates. The document also summarizes research on wine pigments during aging and storage, finding losses of certain pigments over time, as well as correlations between some pigments.

1. titolo della presentazione

3. Wine chemistry

4. cyanidindelphinidin
pelargonidin
malvidin peonidinpetunidin
Wine pigments

5. O
+
OH
OH
O
OH
O
OO
OH
OH
OH
OH
O O
OH
OH
OH
OH
O
+
OH
O
OH
O
OO
OH
OH
OH
OH
OH
O
+
OH
O
OH
O
OO
OH
OH
OH
O
O
OH
OH
O
+
OH
O
OH
O
OO
OH
OH
OH
O
O
OH
OH
OH
O
+
OH
O
OH
O
OO
OH
OH
OH
O
O
OH
O
+
OH
O
OH
O
OH
malvidin
Wine pigments

6. OH
OOH
OH
OH
OH
OH
O
+
OH
O
OH
O
OO
OH
OH
OH
OH
O
+
O
OH
OH
O
O OH
OH
OH
OH
OH
O
OH
O
OH
OH
OH
OH
O
+
O
OH
OH
O
O
OH
OH
OH
OH
O
OH
OH
O
OH
OH
OH
OH
O
+
OH
OH
O
OH
O
OO
OH
OH
OH
OH
flavanol
flavanol
flavanol
acetaldehyde
Wine pigments

7. O
+
OH
OH
O
OH
O
OO
OH
OH
OH
OH
O
+
O
OH
OH
O
O OH
OH
OH
OH
O
O
O
+
O
OH
OH
O
O OH
OH
OH
OH
O
O OH
O
acetaldehyde
pyruvic
acid
O
+
OH
O
OH
O
OO
OH
OH
OH
OH
OH
p-coumaric acid
pyranovitisin
(vitisin B-type)
carboxypyranovitisin
(vitisin A-type)
Pinotin type
Wine pigments

8. Oliveira et al (2014) Dyes and Pigments
Wine pigments

9. Wine pigments
Chassaing et al (2015) Tetrahedron

11. Time
0.00 1.00 2.00 3.00 4.00 5.00 6.00 7.00 8.00 9.00 10.00
%
0
100
Sg_10_04_C5_02uL 13: MRM of 2 Channels ES+
493.22 > 331.12 (Mv 3-glu)
6.79e7
Dp glu
Mv glu
Cy glu
Pn glu
Pt glu
O
+
R
OH
OH
OH
O
O OH
OH
OH
OH
R
Mv : malvidin
Pn : peonidin
Pt : petunidin
Cy : cyanidin
Dp : delphinidin
Wine pigments UPLC-MS/MS

12. O
+
R
OH
OH
OH
O
O OH
OH
OH
O
O
OH
R
Pn pc glu
cis
trans
Cy pc glu
Pt pc glu
Mv pc glu
Wine pigments UPLC-MS/MS

13. O
+
R
OH
OH
O
O OH
OH
OH
OH
O
R
Dp pr glu
Pt pr glu
Pn pr glu
Mv pr glu
vitisins B-type
Wine pigments UPLC-MS/MS

14. O
+
R
OH
OH
O
O OH
OH
OH
OH
O
O OH
R
Dp pr glu
Pt cbpr glu
Mv cbpr glu
Pn cbpr glu
vitisins A-type
Wine pigments UPLC-MS/MS

15. Mv glu ethyl C/EC
Pt glu ethyl C/EC
Pn glu ethyl C/EC
O
+
O
OH
OH
O
O OH
OH
OH
OH
OH
O
OH
O
OH
OH
OH
OH
ethyl-linked
flavano-anthocyanins
Wine pigments UPLC-MS/MS

16. Mv glu C/EC
Pt glu C/EC
Pn glu C/EC
Cy glu C/EC
O
+
O
OH
OH
O
O
OH
OH
OH
OH
O
OH
OH
O
OH
OH
OH
OH
direct linked
flavano-anthocyanins
Wine pigments UPLC-MS/MS

18. Jen Christiansen

20. Cabernet Sauvignon
Chardonnay
Riesling
Sauvignon B.
Gewürztraminer
Grape pigments

21. malvidin 3-O-glu
vitisin type-A
vitisin type-B
O
+
O
OH
O
OH
O
O
glu
CH3
CH3
O OH
O
+
O
OH
O
OH
O
O
glu
CH3
CH3
O
+
OH
OH
O
OH
glu
OH
OH
vitisin type-A
vitisin type-B
malvidin 3-O-glu
Grape pigments

22. 2011 2012 2011 2012 2011 2012
Dp 3-glu 142.325 (16) 84.507 (19) 323.664 (10) 118.683 (10) 135.812 (15) 116.543 (20)
Cy 3 glc 85.017 (15) 43.041 (17) 23.463 (19) 5.071 (12) 26.263 (17) 8.584 (23)
Pt 3-glu 77.391 (11) 48.817 (13) 134.140 (9) 33.842 (6) 58.784 (16) 35.580 (13)
Pn 3-glc 66.499 (11) 54.577 (17) 129.499 (19) 34.979 (6) 87.036 (16) 27.852 (13)
Mv 3-glc 163.243 (10) 126.62 (13) 815.296 (14) 193.910 (8) 285.486 (18) 137.371 (14)
Pl 3-glc 0.403 (6) 0.349 (23) 1.190 (14) 0.281 (12) 0.813 (13) 0.114 (30)
B-type vitisin 0.035 (16) 0.003 (28) 0.053 (6) nd 0.042 (18) nd
A-type vitisin 4.286 (20) 0.509 (17) 29.607 (7) 0.451 (11) 6.421 (18) nd
total acylated 55.220 (12) 16.465 (14) 1607.174 (7) 299.997 (10) 882.531 (14) 267.493 (9)
Total 594.419 (11) 374.888 (16) 3064.086 (12) 687.214 (8) 1483.188 (11) 593.537 (17)
Dp: delphinidin; Cy: cyanidin; Pt: petunidin; Pn: peonidin; Mv: malvidin; Pl: pelargonidin; glu: glucoside; nd: not
detected
mg/Kg (%CV) mg/Kg (%CV) mg/Kg (%CV)
Table 2. Anthocyanins concentration in red berries expressed in mg/Kg of grape
Sangiovese Cabernet Sauvignon Merlot
Grape pigments

23. Sternad Lemut et al (2013) Journal of the Science of Food and Agriculture

25. O
+
R
OH
OH
OH
O
O OH
OH
OH
OH
R
O
+
R
OH
OH
OH
O
O OH
OH
OH
O
R1
R
Experimental wines Commercial wines
R1 = p-cumaroyl or acetyl
Wine pigments during aging

26. O
+
R
OH
OH
O
O OH
OH
OH
OH
O
R
vitisins B-type
O
+
R
OH
OH
O
O OH
OH
OH
OH
O
O OH
R
vitisins A-type
Experimental wines Commercial wines
Wine pigments during aging

27. O
+
R
OH
OH
O
O OH
OH
OH
OH
O
OH
O
R
pinotins
Experimental wines Commercial wines
Wine pigments during aging

28. O
+
O
OH
OH
O
O OH
OH
OH
OH
OH
O
OH
O
OH
OH
OH
OH
ethyl-linked
flavano-anthocyanins
Experimental wines Commercial wines
Wine pigments during aging

29. O
+
O
OH
OH
O
O
OH
OH
OH
OH
O
OH
OH
O
OH
OH
OH
OH
direct linked
flavano-anthocyanins
Experimental wines Commercial wines
Wine pigments during aging

30. O
+
O
OH
OH
O
O OH
OH
OH
OH
OH
O
OH
O
OH
OH
OH
OH
sum of ethyl-linked
flavano-anthocyanins
O
+
R
OH
OH
O
O OH
OH
OH
OH
O
R
Sum of vitisins B-type
Correlations
2004-2010: 0.726
2008-2010: 0.835
Wine pigments during aging

31. O
+
O
OH
OH
O
O OH
OH
OH
OH
OH
O
OH
O
OH
OH
OH
OHO
+
O
OH
OH
O
O OH
OH
OH
OH
O
O
?
O
+
O
OH
OH
O
O OH
OH
OH
OH
OH
O
CH3
H
O
+ flavanol
+
malvidin 3-glucoside
vitisin B-type
Correlations
2004-2010: 0.726
2008-2010: 0.835
Sum of vitisin B type
Sumflavano-ethyl-anthocyanins
Wine pigments during aging

32. O
+
O
OH
OH
O
O OH
OH
OH
OH
OH
O
OH
O
OH
OH
OH
OHO
+
O
OH
OH
O
O OH
OH
OH
OH
O
O
?
vitisin B-type
Arapitsas et al (2012) PLoS ONE
Correlations
2004-2010: 0.726
2008-2010: 0.835
Sum of vitisin B type
Sumflavano-ethyl-anthocyanins

33. O
+
R
OH
OH
OH
O
O OH
OH
OH
OH
R
O
+
R
OH
OH
O
O OH
OH
OH
OH
O
R
O
+
R
OH
OH
O
O OH
OH
OH
OH
O
O OH
R
O
+
R
OH
OH
O
O OH
OH
OH
OH
O
OH
O
R
O
+
O
OH
OH
O
O OH
OH
OH
OH
OH
O
OH
O
OH
OH
OH
OH
O
+
O
OH
OH
O
O
OH
OH
OH
OH
O
OH
OH
O
OH
OH
OH
OH
time
time
time
time
time
time
Arapitsas et al. J Agric Food Chem 2012
Wine pigments during aging

36. O
+
O
OH
OH
O
OH
O
OH
O
OH
OH
OH
OH
R
O
+
OH
OH
OH
O R
O
O
O
+
O
OH
OH
O
O
OH
OH
O
R
cellar
domestic
cellar
domestic
Wine pigments during storage

37. cellardomestic
time zero
cellar
domestic
cellar
domestic
cellar
domestic
Wine pigments during storage

38. cellardomestic
time zero
cellar
domestic
Wine pigments during storage

39. Wine pigments during storage

40. O
+
O
OH
OH
O
OH
O
OH
O
OH
OH
OH
OH
R
O
+
OH
OH
OH
O R
O
O
O
+
O
OH
OH
O
O
OH
OH
O
R
cellar
domestic
Domestic storage  loss of red color
Pinotins  possible markers of bad storage
O
+
O
OH
OH
O
OH
O
R
OH
O
OH
OH
OH
OH
CH3
O
+
O
OH
OH
O
O
R
O CH3
Wine pigments during storage

41. Consorzio
Brunello di Montalcino
Tomas Roman
Mario Malacarne
Giorgio Nicolini
Daniele Perenzoni
Andrea Angeli
Giuseppe Speri
Winery
Fondazione E. Mach
CREA-NUT
Joana Oliveira Melita Sternad Lemut
Fulvio Mattivi

42. fondazionebanfi.it