Wine Chemistry and Biochemistry

9C Non-flavonoid Phenolic Compounds 517

OH

HO

R

R OH

OH

1 R OH

3 R OGlc

2 R OH

4 R OGlc

OH

HO

HO

OH

5

OH

H 3 CO

H 3 CO

6

HO

O OH

HO

OH

OH

OH

7

HO

O

OH

OH

HO

8 OH

HO

O

OH

OH

O

OH OH

O

HO

9

O OH

HO

HO

OH

OH

OH

HO O

OH

OH

OH

10

Fig. 9C.6Chemical structures of stilbenes:trans-resveratrol (1),cis-resveratrol (2),trans-piceid
(3),cis-piceid (4),trans-piceatannol (5),trans-pterostilbene (6),trans-δ-viniferin (7),trans-ε-
viniferin (8), -viniferin (9), hopeaphenol (10)

HO

HO

OH

+

HO OH

OH

HO

HO

OH

+

O OH

OH

. HO

O

OH

OH

HO

OH

H

.

HO

O

OH

OH

HO

OH

• H

Fig. 9C.7Biosynthesis oftrans-ε-viniferin

and the resveratrol tetramer hopeaphenol (Guebailia et al. 2006) have

been identified in grapevine and wine. In addition, some oligomeric glucosides like

cis-andtrans-ε-viniferin diglucosides and pallidol-3-3′′-diglucoside could be iso-

lated and characterized from Riesling wine (Baderschneider and Winterhalter 2000).

The content of stilbenes in wine varies considerably and depends on several fac-

tors including climate, grape variety, fungal infections (Perrone et al. 2007; Jeandet

et al. 1995), UV light, heavy metal ions (P ̈ussa et al. 2006) and enological methods