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titolo della presentazione
Summer school Sanguis Jovis - Sangiovese anthocyanins and climate changes
Wine chemistry
cyanidindelphinidin
pelargonidin
malvidin peonidinpetunidin
Wine pigments
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
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
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
Oliveira et al (2014) Dyes and Pigments
Wine pigments
Wine pigments
Chassaing et al (2015) Tetrahedron
Summer school Sanguis Jovis - Sangiovese anthocyanins and climate changes
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
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
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
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
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
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
Summer school Sanguis Jovis - Sangiovese anthocyanins and climate changes
Jen Christiansen
Summer school Sanguis Jovis - Sangiovese anthocyanins and climate changes
Cabernet Sauvignon
Chardonnay
Riesling
Sauvignon B.
Gew端rztraminer
Grape pigments
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
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
Sternad Lemut et al (2013) Journal of the Science of Food and Agriculture
Summer school Sanguis Jovis - Sangiovese anthocyanins and climate changes
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
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
O
+
R
OH
OH
O
O OH
OH
OH
OH
O
OH
O
R
pinotins
Experimental wines Commercial wines
Wine pigments during aging
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
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
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
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
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
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
Summer school Sanguis Jovis - Sangiovese anthocyanins and climate changes
Summer school Sanguis Jovis - Sangiovese anthocyanins and climate changes
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
cellardomestic
time zero
cellar
domestic
cellar
domestic
cellar
domestic
Wine pigments during storage
cellardomestic
time zero
cellar
domestic
Wine pigments during storage
Wine pigments during storage
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
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
fondazionebanfi.it

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Summer school Sanguis Jovis - Sangiovese anthocyanins and climate changes