The document provides biographical and contact information for Panagiotis Arapitsas. It lists his educational background including degrees from TEI of Athens - Greece, Erasmus University of Turin, Italy, University of Florence, Italy, and University of Uppsala, Sweden. It also lists his work experience including as a researcher at Fondazione E. Mach since 2010 and as a lecturer at several universities. The document includes his contact information and links to his website and the FEM metabolomic platform website.

2. Panagiotis Arapitsas
Oenology and Beverage Technology (TEI of Athens - Greece)
Erasmus University of Turin, Italy
Master in Methods of Synthesis in Organic Chemistry (University of Florence, Italy)
PhD in Food Polyphenols Chemistry (University of Florence, Italy)
Marie Curie – University of Uppsala, Sweden
Researcher at Fondazione E. Mach since 2010
Lecturer at University of Trento since 2019
Lecturer at University of Nova Gorica (Slovenia) since 2021
Lecturer at University of West Attika since 2016
University of Gent, Belgium
University of Perugia, Italy
I.E.K. of Athens, Greece
Araldica Winery, Asti, Italy
Sigalas Winery, Santorini, Greece
panagiotis.arapitsas@fmach.it
https://sites.google.com/a/fmach.it/wine-metabolomics/

9. www.fmach.it

10. FEM metabolomic platform: instruments
Targeted analysis
Untargeted metabolomics
Isolation
FEM metabolomic platform: methods
www.fmach.it

11. University of West Attica
April 2021
Χημεία Οίνων
Wine Chemistry

12. Metabolomics: definitions
What can the cell potentially do?
What is currently being turned on?
What enzymes are currently active?
What is being produced/consumed?
System biology

13. Wine Chemistry – Wine Composition
How big is the wine metabolome?

14. Metabolomic: what is and what is not
How big is the metabolome?
Sigma-Aldrich has ~55K commercial available chemicals
Kegg contains 18K metabolites
HMDB is based in ~42K metabolites
Plant metabolome is estimated to cover 200K metabolites
PubChem ID contains more than 10M entries
CAS contains over 90M unique organic
and inorganic chemicals
ChemSpider contains over 57M
compounds from 530 data sources

15. Plant metabolome is estimated to cover
200 000 metabolites
#
of
metabolites
5-21% ethanol
g/L
mg/L
µg/L
ng/L
pg/L
fg/L
How big is the metabolome?
Wine Chemistry – Wine Composition

16. #
of
metabolites
5-21% ethanol
g/L
mg/L
µg/L
ng/L
pg/L
fg/L
Plant metabolome is estimated to cover
200 000 metabolites
How big is the metabolome?
Wine Chemistry – Wine Composition

17. Wine Chemistry – Wine Composition
Waterhouse, Understanding wine chemistry, 2016

18. Wine Chemistry – Grape
Koutroumanidis et al

19. Wine Chemistry – Phenolics

20. Wine Chemistry – Phenolics
Kayama et al JASH 2008
shikimic acid
phenylalanine

21. Wine Chemistry – Phenolics – Classification according the skeleton
C6 C6-C3
O
OH
O
OH
C6-C2-C6
phenolic acids cinnamics acids stilbenoids
O
OH
O
H
O
OH
O
H
OH
O
OH
O
H
OH
O
H
O
H
OH
O
H
O
OH
O
H
O
H
O
OH
O
H
O
OH
O
H
OH
OH
O
H
OH
OH
OH
O
OH
OH
OH
O
OH
OH
O
OH
C6-C3-C6
flavanoids
O
A C
B
7
2
3
4
5
6
2'
8
3'
4'
5'
6'
2' : 2 prime (not apostrophe)

22. Wine Chemistry – Phenolics – Classification according the skeleton
C6 C6-C3
O
OH
O
OH
C6-C2-C6
phenolic acids cinnamics acids stilbenoids
C6-C3-C6
flavanoids
O
A C
B
7
2
3
4
5
6
2'
8
3'
4'
5'
6'
António Teixeira
Phenols concentration depends
1. Grape cultivar (genetics)
2. Climate, sun, soil (environment)
3. Vine, cluster, berry

23. Wine Chemistry – Phenolics – Phenolic acids
shikimic acid
O
OH
O
H
O
OH
O
H
OH
O
OH
O
H
OH
O
H
gallic acid
UV-Vis spectrum
nm
250 300 350 400 450 500 550
270 nm
nm
250 300 350 400 450 500 550
280 nm
• Wooden barrel
• Non vinifera
• Hydrolysable tannins
gallic acid
O
HO
HO
OH
O
HO
O
OH
OH
OH
glucogallin
p-OH-benzoic acid protocatechic acid

24. Wine Chemistry – Phenolics – Phenolic acids
shikimic acid
O
OH
O
H
O
OH
O
H
OH
O
OH
O
H
OH
O
H
gallic acid
p-OH-benzoic acid protocatechic acid
O
O
O
O
O
H
O
H
OH
OH
ellagic acid
castalagin
70 mg/L
10 mg/L
2-20 mg/L hydrolysable tannins
Muscadine (V. Rotundifolia)

25. flowering
veraison
ripening
Cinnamates
Wine/Grape Chemistry – Phenolics - Cinnamates

26. Romeyer et al JAFC 2983
Wine/Grape Chemistry – Phenolics - Cinnamates

27. Wine Chemistry – Phenolics - Cinnamates
shikimic acid phenylalanine cinnamic acid
coumaric acid
coutaric acid
fertaric acid caftaric acid
caffeic acid
ferulic acid

28. Wine/Grape Chemistry – Phenolics - Cinnamates
grape reaction product (GRP, GRP1 or 2-S-glutathionyl caftaric acid)

29. Wine Chemistry – Phenolics - Cinnamates
coutaric acid
Wine 15 mg/L
Hydroxycinamates: White wines main phenolics

30. fertaric acid
Wine Chemistry – Phenolics - Cinnamates
Wine 4 mg/L
Hydroxycinamates: White wines main phenolics

31. Wine Chemistry – Phenolics - Cinnamates
nm
250 300 350 400 450 500 550
caffeic acid
UV-Vis spectrum
324 nm

32. fertaric acid
Wine Chemistry – Phenolics - Cinnamates
coutaric acid 4-vinyl phenol
4-vinyl guaicol 4-ethyl guaicol
4-ethyl phenol
OH
O
O
O
H
O
OH
OH
O
OH
O
O
O
H
O
OH
OH
O
O CH3
OH
C
H2
O CH3
OH
C
H3
O CH3
OH
C
H3
OH
C
H2

33. flowering
veraison
ripening
stilbenoids

34. Wine/Grape Chemistry – Phenolics - Stilbenoids
shikimic acid phenylalanine cinnamic acid coumaric acid
O
H
OH
OH
OH
OH
OH
OH
O
OH
O
OH
OH
OH
O
H
OH
O
O
OH
OH
OH
O
H
O
H
trans-resveratrol
cis-resveratrol
trans-piceid
cis-piceid
O
O
O
H
OH
OH
O
O
H
OH
O
H
H
H
trans-pterostilbene
cis-epsilon-viniferin
hv

35. Wine/Grape Chemistry – Phenolics - Stilbenoids
O
H
OH
OH
OH
OH
OH
OH
O
OH
O
OH
OH
OH
O
H
OH
O
O
OH
OH
OH
O
H
O
H
trans-resveratrol
cis-resveratrol
trans-piceid
cis-piceid
O
O
O
H
OH
OH
O
O
H
OH
O
H
H
H
trans-pterostilbene
cis-epsilon-viniferin
hv
biosynthesis
UV
Antifungal activity
Biological activities in human
~ 7 mg/L red wines
~ 0,5 mg/L white wines

36. Wine/Grape Chemistry – Phenolics – Experiment I
Regent
Cabernet Cortis
Solaris
Johanniter
Phoenix
Regent
Phoenix
Regent
Phoenix
Cabernet
Cortis
Johanniter
Solaris
Ehrhardt et al J Mass Spec 2014

37. Wine/Grape Chemistry – Phenolics – Experiment I
Ehrhardt et al J Mass Spec 2014

38. Wine/Grape Chemistry – Phenolics – Experiment I
Ehrhardt et al J Mass Spec 2014

39. Wine/Grape Chemistry – Phenolics – Experiment II
Savoi et al BMC Plant Biology 2016
Results indicate that water deficit conditions can potentially
impact the quality of white wines by increasing the accumulation
of potential antioxidant and flavor compounds (e.g., derivatives
of benzoic and cinnamic acids, zeaxanthin, and
monoterpenes) in the grapes.

40. Wine/Grape Chemistry – Phenolics – Experiment III
Malita Sternad Lemut, PhD Thesis, Nova Gorica, 2014

41. Wine/Grape Chemistry – Phenolics – Experiment III
Malita Sternad Lemut, PhD Thesis, Nova Gorica, 2014

42. Wine/Grape Chemistry – Phenolics – Experiment III
Malita Sternad Lemut, PhD Thesis, Nova Gorica, 2014

43. flowering
veraison
ripening
flavonols
Wine/Grape Chemistry – Phenolics - Flavonols

44. Wine/Grape Chemistry – Phenolics - Flavonols

45. Wine Chemistry – Phenolics - Flavonols
quercetin
quercetin 3-rabinoside
quercetin 3-glucuroside
quercetin 3-galactose quercetin 3-rhamnoside
quercetin 3-glucose

46. Wine/Grape Chemistry – Phenolics - Flavonols
UV-Vis spectrum

47. Wine/Grape Chemistry – Phenolics – Experiment I

48. Martínez-Lüscher et al Frontiers 2019

49. Wine/Grape Chemistry – Phenolics – Experiment IV
Mattivi et al ACS Books 2015,Photo by Daniele Perenzoni
OH
R
O
O
H
OH
R
O
O
OH
O
H
OH
O
O
O
OH
OH
O
H
OH
OH
O
O
OH
OH
O
H
OH
O
O
glu
Hydrolysis of tartarate esters and glucosidic
links occur faster in higher storage
temperatures

50. Wine/Grape Chemistry – Phenolics – Experiment IV
Mattivi et al ACS Books 2015,Photo by Daniele Perenzoni
In defective wine we observed that the flakes, consisted mainly of
quercetin (c. 57% of dry weight) and also contained other flavonols
(kaempferol, myricetin and isorhamnetin) in minor mounts. No evidences
that this precipitate could be associated with any metal were found. So
probably these disk-shaped, floating flakes appear to be mainly made up
of flavonol aglycones, compounds naturally present in wine but at
insufficient concentrations to adversely affect it, which could cause wine
defects in the case of an excessive concentration. This could be the case
with quercetin, which as we observed increased its concentration in wine
by >300% during the 24 months of storage, with a faster trend in wines
stored in domestic conditions.

51. flowering
veraison
ripening
anthocyanins
Wine/Grape Chemistry – Phenolics - Anthocyanins

52. Wine Chemistry – Phenolics - Anthocyanins

53. Wine/Grape Chemistry – Phenolics - Anthocyanins

54. Wine/Grape Chemistry – Phenolics - Anthocyanins
Walker et al Plant Mol Biol 2006
Αμπσισικό οξύ

55. Castellarin et al 2007 Planta

56. Wine Chemistry – Phenolics - Anthocyanins
O
+
O
H
OH
O
OH
O
O
O
O
H
OH
OH
OH
O O
OH
OH
O
H
O
H
O
+
O
H
O
OH
O
O
O
O
H
OH
OH
OH
O
H
O
+
O
H
O
OH
O
O
O
O
H
OH
OH
O
O
OH
O
H
O
+
O
H
O
OH
O
O
O
O
H
OH
OH
O
O
OH
OH
O
H
O
+
O
H
O
OH
O
O
O
O
H
OH
OH
O
O
O
H
O
+
O
H
O
OH
O
OH

57. epicatechin
malvidin glu
caftaric
A-E-T
A-T
A-type vitisin
B-type vitisin
pinotins
O
+
O
O
H
OH
O
OH
O
R
O
+
O
O
H
O
OH
O
R
O
OH
OH
O
+
O
O
H
O
OH
O
R
O
O
+
O
O
H
O
OH
O
R
O
O
O
H
O
O
OH
O
H
OH
OH
OH
O
+
O
O
H
OH
O
OH
O
R
O
OH
O
H
OH
OH
OH
O
+
O
O
H
OH
O
OH
O
R
O
OH
O
H
OH
OH
OH
O
O
O
OH
OH
O
O
R
1
R = glucose
R1 = tartate
Wine/Grape Chemistry – Phenolics - Anthocyanins

58. Wine Chemistry – Phenolics - Anthocyanins
UV-Vis spectrum
nm
250 300 350 400 450 500 550
O
OH
HO
OH
OH
OH
cyanidin

59. Wine/Grape Chemistry – Phenolics - Anthocyanins
Oliveria et al Synlett 2016

60. Wine/Grape Chemistry – Phenolics - Anthocyanins
Oliveria et al Synlett 2016

61. Wine/Grape Chemistry – Phenolics - Anthocyanins
Oliveria et al Synlett 2016

62. Wine/Grape Chemistry – Phenolics - Anthocyanins
Oliveria et al Synlett 2016

63. Wine/Grape Chemistry – Phenolics - Anthocyanins
Oliveria et al Synlett 2016

64. Wine/Grape Chemistry – Phenolics - Anthocyanins
Oliveria et al Synlett 2016

65. Wine/Grape Chemistry – Phenolics - Anthocyanins
Oliveria et al Synlett 2016

66. Wine Chemistry – Phenolics - Anthocyanins
Chassaing et al (2015) Tetrahedron

67. Wine Chemistry – Phenolics - Anthocyanins
Bobeica et al Frontiers 2016

68. Wine Chemistry – Phenolics - Anthocyanins
O
+
O
OH
OH
O
H
O
O OH
OH
OH
OH
O O
+
OH
OH
OH
O
H
O
O OH
OH
OH
OH
OH
O
+
O
OH
OH
O
H
O
O OH
OH
OH
OH
O
+
OH
OH
OH
O
H
O
O OH
OH
OH
OH
O
+
O
OH
OH
O
H
O
O OH
OH
OH
OH
OH
+
+ +

69. Myles et al PNAS 2011

70. Wine Chemistry – Phenolics – Anthocyanins – Experiment V

71. Analytical Chemistry – Mass Spectrometry
definitions
Mass spectrometer is an analytical instrument that produce a beam of gas ions from a sample, sorts the
resulting mixture of ions according to their mass-to-charge (m/z) ratios using electrical of magnetic fields,
and provides analog or digital output signals from which mass-to-charge ration and intensity (abundance) of
each detected ionic species may be determinate.
Sample
introduction
Ionization
Mass
separation* detection
vacuum
computer
*Mass analyzer

72. Analytical Chemistry – Mass Spectrometry
+ +
+
+
+
+
+
+ +
+
m/z
intensity
sample ions
mass analyzer detector
Single quadrupole MS
Scan mode MS

73. Analytical Chemistry – Mass Spectrometry
100%
relative
intensity
fragment ions
base peak
molecular ion
isotope ions
m/z
[M + H]+
[M - H]-
[M + Na]+
[M + Cl]-
[M + nH]n+

74. Analytical Chemistry – Mass Spectrometry
+ +
+
+
+
sample ions mass analyzer
detector
mass analyzer
fragmentor
Triple quadrupole MS
Full scan mode MS
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
m/z
intensity

75. Analytical Chemistry – Mass Spectrometry
+ +
+
+
+
+
m/z
intensity
sample ions mass analyzer
detector
mass analyzer
fragmentor
Triple quadrupole MS
SIM (Single ion monitoring) mode MS
+ +

76. Analytical Chemistry – Mass Spectrometry
+ +
+
+
+ +
+
+
m/z
intensity
sample ions mass analyzer
detector
mass analyzer
fragmentor
+
+
Triple quadrupole MS
Product ion scan mode MS

77. Analytical Chemistry – Mass Spectrometry
+ +
+
+
+ +
+
+
m/z
intensity
sample ions mass analyzer
detector
mass analyzer
fragmentor
+
Triple quadrupole MS
MRM (Multiple reaction monitoring) scan mode MS

78. Wine Chemistry – Phenolics – Anthocyanins – Experiment V

79. DAD trace at
520 nm
mlv 3-glu vitisin B
mlv p-coum 3-glu
pinotins
Wine Chemistry – Phenolics – Anthocyanins – Experiment V

80. Arapitsas et al Food Res Inter 2014
Wine Chemistry – Phenolics – Anthocyanins – Experiment V

81. 6.00 6.50 7.00 7.50
%
100
Cabernet
Sauvignon
Arapitsas et al Food Res Inter 2014
Wine Chemistry – Phenolics – Anthocyanins – Experiment V

82. 6.00 6.50 7.00 7.50
%
100
%
100
6.00 6.50 7.00
Chardonnay
Riesling
Sauvignon B.
Gewürztraminer
Muscateller
Cabernet
Sauvignon
Arapitsas et al Food Res Inter 2014
Wine Chemistry – Phenolics – Anthocyanins – Experiment V

83. Arapitsas et al Food Res Inter 2014
Wine Chemistry – Phenolics – Anthocyanins – Experiment V

84. Arapitsas et al Food Res Inter 2014
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
Wine Chemistry – Phenolics – Anthocyanins – Experiment V

85. Sternad Lemut et al (2013) Journal of the Science of Food and Agriculture
Wine Chemistry – Phenolics – Anthocyanins – Experiment VI

86. Wine Chemistry – Phenolics – Anthocyanins – Experiment VII

87. O
+
R
OH
OH
O
H
O
O OH
OH
OH
OH
R
O
+
R
OH
OH
O
H
O
O OH
OH
OH
O
R1
R
Experimental wines Commercial wines
R1 = p-cumaroyl or acetyl
Wine Chemistry – Phenolics – Anthocyanins – Experiment VII

88. O
+
R
OH
O
H
O
O OH
OH
OH
OH
O
R
vitisins B-type
O
+
R
OH
O
H
O
O OH
OH
OH
OH
O
O OH
R
vitisins A-type
Experimental wines Commercial wines
Wine Chemistry – Phenolics – Anthocyanins – Experiment VII

89. O
+
R
OH
O
H
O
O OH
OH
OH
OH
O
OH
O
R
pinotins
Experimental wines Commercial wines
Wine Chemistry – Phenolics – Anthocyanins – Experiment VII

90. O
+
O
OH
O
H
O
O OH
OH
OH
OH
OH
O
OH
O
O
H
O
H
OH
OH
ethyl-linked
flavano-anthocyanins
Experimental wines Commercial wines
Wine Chemistry – Phenolics – Anthocyanins – Experiment VII

91. O
+
O
OH
O
H
O
O
O
H
OH
OH
OH
O
OH
OH
O
O
H
O
H
OH
OH
direct linked
flavano-anthocyanins
Experimental wines Commercial wines
Wine Chemistry – Phenolics – Anthocyanins – Experiment VII

92. O
+
O
OH
O
H
O
O OH
OH
OH
OH
OH
O
OH
O
O
H
O
H
OH
OH
sum of ethyl-linked
flavano-anthocyanins
O
+
R
OH
O
H
O
O OH
OH
OH
OH
O
R
Sum of vitisins B-type
Correlations
2004-2010: 0.726
2008-2010: 0.835
Wine Chemistry – Phenolics – Anthocyanins – Experiment VII

93. O
+
R
OH
OH
O
H
O
O OH
OH
OH
OH
R
O
+
R
OH
O
H
O
O OH
OH
OH
OH
O
R
O
+
R
OH
O
H
O
O OH
OH
OH
OH
O
O OH
R
O
+
R
OH
O
H
O
O OH
OH
OH
OH
O
OH
O
R
O
+
O
OH
O
H
O
O OH
OH
OH
OH
OH
O
OH
O
O
H
O
H
OH
OH
O
+
O
OH
O
H
O
O
O
H
OH
OH
OH
O
OH
OH
O
O
H
O
H
OH
OH
Pigments & Wine ageing
Arapitsas et al J Agric Food Chem 2012

94. O
+
O
OH
OH
O
H
O
O OH
OH
OH
OH
O O
+
OH
OH
OH
O
H
O
O OH
OH
OH
OH
OH
O
+
O
OH
OH
O
H
O
O OH
OH
OH
OH
O
+
OH
OH
OH
O
H
O
O OH
OH
OH
OH
O
+
O
OH
OH
O
H
O
O OH
OH
OH
OH
OH
+
+ +
Pigments & Wine ageing
Arapitsas et al J Agric Food Chem 2012

95. O
+
R
OH
OH
O
H
O
O OH
OH
OH
OH
R
O
+
R
OH
O
H
O
O OH
OH
OH
OH
O
R
delphinidin
cyanidin
peonidin
petunidin
malvidin
Pigments & Wine ageing
Arapitsas et al J Agric Food Chem 2012

96. Trouillas et al Chem Rev 2016

97. Trouillas et al Chem Rev 2016

98. Gómez-Alonso et al 2012 JAFC

99. κοτσιφάλι
Μαυροτράγανο Μανδηλαριά Αγιοργίτικο Ξινόμαυρο
Kyraleou et al JFCA 2020

100. κοτσιφάλι
Μαυροτράγανο Μανδηλαριά Αγιοργίτικο Ξινόμαυρο
Kyraleou et al JFCA 2020

101. flowering
veraison
ripening
flavanols
Wine/Grape Chemistry – Phenolics - Flavanols

102. Wine Chemistry – Phenolics - Flavanols
cyanidin
delphinidin
pelargonidin
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
OH
O
O
H
OH
OH
OH
O
O
H
OH
OH
OH
+
+
+
epicatechin catechin
epigallocatechin gallocatechin
epiafzelechin afzelechin
O
O
H
OH
O
OH
O
OH
OH
OH
OH
O
O
H
OH
O
OH
O
OH
OH
OH
OH
OH
(epi)catechin-gallate
(epi)gallocatechin-gallate

103. Wine Chemistry – Phenolics – Flavanols (dimers)
(epi)catechin
epigallocatechin
O
O
H
OH
O
OH
O
OH
OH
OH
OH
O
O
H
OH
O
OH
O
OH
OH
OH
OH
OH
(epi)catechin-gallate
(epi)gallocatechin-gallate
O
O
H
OH
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
O
OH
OH
OH
OH
O
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
O
OH
OH
O
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
O
OH
OH
OH
O
OH
OH
OH
More in seeds

104. Wine Chemistry – Phenolics – Flavanols (oligomers)
(epi)catechin
epigallocatechin
O
O
H
OH
O
OH
O
OH
OH
OH
OH
O
O
H
OH
O
OH
O
OH
OH
OH
OH
OH
(epi)catechin-gallate
(epi)gallocatechin-gallate
O
O
H
OH
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH

105. Wine Chemistry – Phenolics – Flavanols (oligomers)
(epi)catechin
epigallocatechin
O
O
H
OH
O
OH
O
OH
OH
OH
OH
O
O
H
OH
O
OH
O
OH
OH
OH
OH
OH
(epi)catechin-gallate
(epi)gallocatechin-gallate
O
O
H
OH
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH

106. Wine Chemistry – Phenolics – Flavanols (polyomers)
(epi)catechin
epigallocatechin
O
O
H
OH
O
OH
O
OH
OH
OH
OH
O
O
H
OH
O
OH
O
OH
OH
OH
OH
OH
(epi)catechin-gallate
(epi)gallocatechin-gallate
O
O
H
OH
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
O
OH
OH
OH
OH
O
OH
OH
OH

107. Wine Chemistry – Phenolics – Flavanols (degree of polymerization)
terminal unit
4 upper units
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
O
OH
OH
OH
O
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
O
O
H
OH
OH
OH
OH
terminal unit
4 upper units

108. Database – Phenol explorer
http://phenol-explorer.eu/