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STILBENOID CHEMISTRY
FROM WINE AND THE GENUS VITIS,
A REVIEW

Alison D. PAWLUS, Pierre WAFFO-TÉGUO, Jonah SHAVER


and Jean-Michel MÉRILLON*

GESVAB (EA 3675), Université de Bordeaux, ISVV Bordeaux - Aquitaine,


210 chemin de Leysotte, CS 50008, 33882 Villenave d'Ornon cedex, France

Abstract Résumé
Stilbenoids are of great interest on account of their many promising Les stilbénoïdes présentent un grand intérêt en raison de leurs nombreuses
biological activities, especially in regards to prevention and potential activités biologiques prometteuses, en particulier dans la prévention et le
treatment of many chronic diseases associated with aging. The simple traitement de diverses maladies chroniques liées au vieillissement. Le
stilbenoid monomer, E-resveratrol, has received the most attention due to E-resvératrol, monomère stilbénique, a suscité beaucoup d'intérêt de par
early in vitro and in vivo biological activities in anti-aging assays. Since ses activités biologiques in vitro et in vivo. Une des principales sources
Vitis vinifera, primarily in the form of wine, is a major dietary source of alimentaires en stilbénoïdes est Vitis vinifera, principalement sous forme
these compounds, there is a tremendous amount of research on resveratrol de vin. De nombreux travaux de recherche ont été menés sur le resvératrol
in wine and grapes. Relatively few biological studies have been performed dans le vin et le raisin. À ce jour, relativement peu d'études ont été réalisées
on other stilbenoids from Vitis, primarily due to the lack of commercial sur les stilbènes du genre Vitis autre que le resvératrol, principalement en
sources of many of these compounds. The diverse stilbenoids from this raison de leur absence de commercialisation. Ce genre est une source
economically important genus are an untapped source of health promoting inexploitée de stilbénoïdes d'intérêt potentiel pour la santé et c'est pourquoi
compounds and because of this, numerous efforts for isolation, identification de nombreux efforts pour l'isolement, l'identification et la quantification
and quantification of additional stilbenoids have been ongoing. Additionally, d'autres stilbénoïdes sont en cours. Comme les espèces proches sont
due to their role as phytoalexins, stilbenoids play an important role in the susceptibles de présenter des voies métaboliques similaires, une meilleure
defense against pathogens. Therefore, the compounds produced by highly connaissance de la diversité chimique du genre Vitis peut être utile dans
resistant strains are of great interest for the development of resistant crops, cette tâche. Nous avons effectué une revue bibliographie des stilbénoïdes
natural spray reagents, and as new dietary supplements or pharmaceuticals. de ce genre économiquement important afin de promouvoir la chimie des
Since closely related species are likely to have similar metabolic pathways, stilbénoïdes du vin et des espèces de Vitis, plus particulièrement V. vinifera.
a more thorough understanding of the chemical diversity of stilbenoids En outre, nous abordons la quantification et la distribution de tous ces
within Vitis is useful in this endeavor. In this review, we focus on stilbenoids stilbénoïdes.
found in the Vitis genus with the aim of aiding future stilbenoid chemistry,
particularly in V. vinifera and wine. Additionally, we discuss the efforts Mots clés: oligostilbénoïde, resvératrol, Vitis, Vitis vinifera, vin
to quantify stilbenoids in Vitis, with a focus on non-resveratrol stilbenoid
compounds.

Key words: oligostilbenoid, resveratrol, Vitis, Vitis vinifera, wine

manuscript received 13 July 2012 - revised manuscript received 24th October 2012

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A.D. PAWLUS et al.

INTRODUCTION (Bavaresco and Fregoni, 2001). Stilbenoids are, therefore,


of great interest due to their activity against many
Epidemiological studies have attributed moderate devastating vine diseases and pests. Multiple avenues
consumption of red wine to numerous health benefits to exploit this activity are being investigated. One potential
such as the prevention of age-related diseases, including use of stilbenoids is as a naturally occurring pesticide for
some cancers, neurodegenerative diseases, and most non-resistant species, such as Vitis vinifera L., the major
strongly, cardiovascular diseases (Anstey et al., 2009;
Chao et al., 2008; Larrieu et al., 2004; Orgogozo et al.,
wine grape. Such usage could reduce reliance on traditional

1997; Renaud and de Lorgeril, 1992; Wang et al., 2006).


pesticides. In addition to producing stilbenoid rich products
such as natural spray reagents, wine, or dietary
What accounts for such activity? A single glass of wine supplements, another avenue of research involves the use
contains the fermented extract of 100 to 140 grape berries, of known induction mechanisms to promote disease
which produces, depending on variety and vinification resistance (Cantos et al., 2003). There is also interest in
methods, up to 500 mg of polyphenolic compounds selectively breeding high stilbenoid producing Vitis species
(Lopez et al., 2001; Stervbo et al., 2007; Waterhouse and by crossing V. vinifera with disease resistant, wild Vitis
Teissedre, 1997). These polyphenols include a number (Malacarne et al., 2011).
of known beneficial compounds, the majority being
flavonoids, such as anthocyanins and tannins, phenolic In all, a more thorough knowledge of the chemistry
acids and stilbenoids. While many of these compounds and biology of these molecules can provide multiple
are found in widely consumed fruits and vegetables, wine health, environmental, and economic benefits. In this
review we summarize the current knowledge of stilbenoids
found in the Vitis genus in addition to recent data on
is the dominant dietary source of stilbenoids.
Stilbenoids have received considerable attention due stilbenoid quantitation in Vitis and wine.
to their promising biological activities. The stilbenoid
monomer, resveratrol (1), 3,5,4'-trihydroxy-trans-stilbene, STILBENOIDS IN THE VITIS GENUS
in particular, has undergone extensive biological testing.
Both in vitro and in vivo animal studies of resveratrol Over 1000 stilbenoids have been structurally
have demonstrated promising activities in regards to characterized throughout the plant kingdom and their
disease prevention, progression, and treatment (Baur and distribution and structural variations have been reviewed
Sinclair, 2006; Howitz et al., 2003; Jang et al., 1997; (Cichewicz and Kouzi, 2002; Lin and Yao, 2006; Shen
Pezzuto, 2011). Due to these biological activities, it has et al., 2009; Sotheeswaran and Pasupathy, 1993). They
been concluded that resveratrol could be part of the are found in a number of plant families, including
explanation for the French Paradox and other Celastraceae, Cyperaceae, Dipterocarpaceae, Fabaceae,
epidemiological studies supporting the moderate Gnetaceae, Iridaceae, Moraceae, Paeoniaceae and
consumption of red wine for the prevention of diseases Vitaceae. The Vitaceae family encompasses approximately
such as cardiovascular disease (Renaud and de Lorgeril, 900 species within 14 to 17 genera, primarily in tropical
1992; Renaud et al., 1998; Sun et al., 2002). Since the regions (Keller, 2010; Soejima and Wen, 2006). Of these
genera, stilbenoids have been found primarily in only five,
the Ampelopsis, Cissus, Cyphostemma, Parthenocissus
numerous biological activities reported for resveratrol are
and Vitis genera. Due to their economic importance as the
outside the scope of this article, we refer the reader to
existing biologically focused reviews (Anekonda, 2006;
major table and wine making grape around the world, the
species in the Vitis genus have been studied the most.
Bishayee, 2009; Szkudelska and Szkudelski, 2010). More
Species from Vitis also have a long history of use as
recently, promising biological activities have been shown
with other stilbenoids found in Vitis species, including
piceatannol (2), piceid (3), pterostilbene (4), scirpusin A medicinal plants, particularly V. amurensis, V. coignetiae,
(5), vaticanol C, α-viniferin (6), and vitisin A (7). These and V. vinifera, the later also being used by the modern
activities include mechanisms related to the prevention nutraceutical and cosmeceutical industries. Vitis has, until
of cancers, neurological diseases, and cardiovascular recently, been divided into two subgenera, the Euvitis and
diseases (Chung et al., 2010; Joseph et al., 2008; Oshima the Muscadinia. Muscadinia is composed of three
et al., 1995b; Richard et al., 2011; Shibata et al., 2007; American species, including the species formerly known
Son et al., 2010; Tsukamoto et al., 2010), demonstrating as V. rotundifolia, the most important economic species
potential health benefits of additional stilbenoids, many of Muscadinia. Due to differences in chromosome number
and other characteristics, Muscadinia is now considered
its own genus and V. rotundifolia is now named
of which are known constituents of wine.
As phytoalexins, stilbenoids are induced by infections Muscadinia rotundifolia (Michx.) Small (Bouquet et al.,
and mechanical stress, such as that caused by UV damage 2008; Keller, 2010; Péros et al., 2011). Since it is still
or insects. Their production affords protection against of interest in the wine industry, we included this species
many Vitis pathogens, such as Plasmopara viticola in our review.

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Within Vitis, stilbenoids have been identified in around susceptible Vitis species have shown that disease resistant
20 species, including hybrid species, of the approximate species produce stilbenoids more readily and in higher
60 to 70 species found in Vitis. In table 1, we have listed concentration when exposed to pathogens such as downy
the Vitis species and the specific plant parts the stilbenoids mildew, Plasmopara viticola, and gray mold, Botrytis
were isolated from. The remaining two-thirds of the Vitis cinerea (Bavaresco et al., 1997; Bavaresco and Fregoni,
species most likely contain stilbenoids, but have yet to be 2001; Pezet et al., 2004). Stilbenoid production can also
examined for these compounds. Despite this lack of be induced by abiotic stress such as UV irradiation,
research in all Vitis species, approximately 100 stilbenoid mechanical injury, and certain chemicals (Bavaresco and
monomers, dimers, and oligomers have been found, and Fregoni, 2001; Bavaresco et al., 2009). In fact, the major
nearly 20 are known constituents of wine. stilbenoids from V. vinifera were first identified in leaves
after induction by abiotic and biotic stresses (Langcake
STILBENOID PRODUCTION and Pryce, 1976; Langcake and Pryce, 1977a; Langcake
and Pryce, 1977b ; Langcake and McCarthy, 1979 ;
The metabolism of stilbenoids and regulatory Langcake, 1981). The production of stilbenoids is highly
interactions are complex and not all mechanisms are variable among the different plant parts in regards to types
currently understood. However, we do know that produced, concentrations, and response to outside stimuli.
stilbenoids are downstream secondary metabolic products For example, resveratrol is induced in both leaves and
of the phenylpropanoid pathway and diverge from the berries in response to external stimuli, but is constitutively
flavonoid pathway through the stilbene synthase (STS) expressed and accumulated in stems and roots where it,
enzymes. According to recent analysis of the grapevine along with other stilbenoids, are believed to protect against
genome, there is an estimated 20 to 40 STS genes, many wood rot. Other stilbenoids, such as piceid, have been
of which have shown to be expressed when exposed to shown to be constitutively expressed in various tissues,
biotic stress (Chong et al., 2009). including berries (Gatto et al., 2008).
Since a number of stilbenoids are induced by infections Due to their biological activities, both in the plant and
and have antifungal activity, they are considered to be in humans, the possibility to artificially manipulate
phytoalexins. Comparisons between disease resistant and stilbenoid levels is of great interest. Research into post-
Table 1. Vitis species and plant part where stilbenoids have been reported. References are found in Table 2.
a
Plant Species Plant Part(s) Studied
Muscadinia rotundifolia (Michx.) Small Berries and wine
(previously V. rotundifolia Michx.)
V. acerifolia Raf. (reported as V. longii) Roots
V. amurensis Rupr. Leaves, stems and roots
V. berlandieri Planch. Roots
V. betulifolia Diels & Gilg Stems
V. chunganensis Hu Whole plant
V. cinerea (Engelm.) Engelm. ex Millard Roots
V. coignetiae Pulliat ex Planch. Berries, leaves, stems, and whole plant
V. davidii (Rom. Caill.) Foëx Stems
V. flexuosa Thunb. Stems
V. heyneana Roem. & Schult. (also includes V. Stems
pentagona Diels & Gilg)
V. labrusca L. (Concord grape) Berries, stems, leaves and wine
V. riparia Michx. Leaves and roots
V. riparia x V. berlandieri SO4 (Oppenheim Roots
selection no. 4)
V. rupestris Scheele Roots
V. solonis longii Roots
V. solonis richter Roots
V. thunbergii Sieb. & Zucc. Roots and stems
V. vinifera L. Berries, cell suspension cultures, leaves,
roots, stems and wine
V. wilsoniae H. J. Veitch Stems
This table is to meant to provide an up-to-date survey of which Vitis species stilbenoids have been reported from. In these studies, many
a
!
different clones, cultivars, and hybrids have been used, particularly with V. vinifera. This information can be found in the original manuscript,
however, in many studies, this information was lacking.

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A.D. PAWLUS et al.

harvest abiotic stresses, such as UV irradiation and ozone while only nine are currently known in wine. Among
treatment, is currently ongoing for the production of high- these is the more unusual 2,4,6-trihydroxyphenanthrene
stilbenoid containing wines and grape-derived products 2-O-glucoside (10), isolated from a Riesling wine
(Cantos et al., 2003 ; Gonzalez-Barrio et al., 2006 ; (Baderschneider and Winterhalter, 2000). There are
Guerrero et al., 2010). Efforts are also being made to 35 reported dimers in Vitis, 24 having been identified in
utilize stilbenoid induction as natural pesticides through V. vinifera and its cell cultures, and nine in wine. The
known elicitors, such as ethephon and methyl jasmonate dimers found in wine are mostly resveratrol dimers,
(Belhadj et al., 2008a; Belhadj et al., 2008b; Faurie et derivatives of viniferin and pallidol, with ε-viniferin (8)
al., 2009). This research could lead ways to safely induce being the most common.
There are 16 known trimers in Vitis species. Six of
naturally occurring stilbenoids on an industrial scale or
these trimers have been reported in various V. vinifera
use them as spray reagents against disease, which could
help reduce or eliminate the need for the currently used
pesticides. plant parts, including the roots, leaves, and stems, although,
to date, none of these have been reported in wine. The
STRUCTURAL DIVERSITY presence of trimers, based on molecular weight using
OF VITIS STILBENOIDS HPLC-MS-MS, has, however, been suggested in grapes
treated with UV light and ozone (Gonzalez-Barrio et al.,
Structural variations in stilbenoids typically involve 2006). Additionally, there are a total of 26 known
tetramers, including a tetramer breakdown product,
(-)-viniferal (11). While only one of these compounds,
stilbenoid monomer polymerization, glycosylation,

hopeaphenol (12), has been reported in wine, 14 others


prenylation, methoxylation, and various hydroxylation
patterns. There have been several attempts to delineate
and improve the classification of these various derivatives are known V. vinifera plant part constituents. Finally, there
(Lin and Yao, 2006; Shen et al., 2009; Sotheeswaran and are two known Vitis stilbenoid pentamers and one
Pasupathy, 1993). The proposed classification initially hexamer, none of which have been found in wine or any
separates the monomers from the oligomers. Oligomers V. vinifera plant part.
undergo further classifications based on their monomer
unit composition and heterogeneous coupling, i. e. Several notable points exist in the literature, relating
resveratrol (1), piceatannol (2), gnetol (2,3', 5',6- to stilbenoid nomenclature and structure, which complicate
tetrahydroxy-trans-stilbene), isorhapontigenin (3,4', 5- matters of identification and classification. There are a
trihydroxy-3'-methoxy-trans-stilbene), and oxyresveratrol. number of instances where common names given to
These are further separated into groups with oxygen particular stilbenoids can lead to confusion. In 2009, two
containing heterocycles (group A), such as ε-viniferin independent research groups published the isolation and
(8), or those without (group B), such as pallidol (9). The identification of two new different stilbenoid dimers, one
few remaining compounds that do not fit within this from V. vinifera stembark and one from V. thunbergii roots.
scheme are assigned to a small miscellaneous category. These groups published concurrently and chose the same
Resveratrol is the predominant monomer subunit in Vitis, name for their newly identified compounds, vitisinol E
with multiple patterns of oligomerization and (13,14) (Chiou et al., 2009 ; Choi et al., 2009). The
glycosylation. The resveratrol dimer, ε-viniferin (8), is opposite situation occurred in 1999, when two groups
considered the major oligomer intermediate in Vitis isolated the same stilbenoid dimer but gave it two different
common names, amurensin H and viniferifuran (15)
(Huang et al., 1999a; Ito et al., 1999). Another area of
species.
In order to better understand the chemical diversity
of stilbenoids in Vitis species, we have delineated the
confusion with nomenclature comes from the use of the
common name “vitisin” », which refers to either the well-
known stilbenoid compounds with their plant name and characterized pyranoanthocyanin pigments in wine, vitisin
part, including those found in wine, in Table 2. Of the
approximately 100 stilbenoids identified in Vitis, 18 are
A and B, or to a series of stilbenoid oligomers, vitisins A
through E.
monomers. These are primarily methoxylated and
glycosylated derivatives of resveratrol and piceatannol Another potential point of confusion lies in the
along with their Z (cis) and E (trans) isomers. A large structure and naming of the ε-viniferins. The compound
portion of these monomers are glycosides, many of which itself is a simple resveratrol dimer, however, there are two
were isolated and identified in V. vinifera cell culture stereochemical centers, at positions 7a and 8a on the
studies, a method developed in our laboratory for further dihydrofuran ring, allowing for four potential
biological studies and potential industrial production of stereoisomers (see compound 8 in Table 2 for numbering).
these compounds (Krisa et al., 1999; Waffo-Téguo et al., The trans configuration of the two hydrogens in this
1996a). Seventeen of these 18 monomers have been saturated ring system, meaning one alpha and one beta
identified in parts of the V. vinifera vine or in cell cultures, hydrogen, is most common in Vitis.

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Table 2. Compounds reported in Vitis species.

Monomers
a b
Compound Structure M.W. Plant Name References
Name and Part
Z-Astringin HO 406.38 V. vinifera cell (Buiarelli et al.,
suspension 2007; Waffo-Téguo
cultures and et al., 1998)
wine
OGlc
OH
OH
E-Astringin (18) OH 406.38 V. coignetiae (Buiarelli et al.,
OH berries 2007; Carando et al.,
V. vinifera cell 1999; Kim et al.,
HO suspension 2009; Krisa et al.,
cultures, and 1999; Naugler et al.,
red and white 2007; Ribeiro de
OGlc
wine Lima et al., 1999;
Vitrac et al., 2002;
Vitrac et al., 2005;
Waffo-Téguo et al.,
1996a; Waffo-Téguo
et al., 1998)
E-Piceatannol (astringinin) (2) OH 244.24 V. amurensis (Bavaresco et al.,
OH leaves and 2002; Buiarelli et
stems al., 2007; Delaunay
HO V. coignetiae et al., 2002; Ha et
berries al., 2009b; Kim et
V. vinifera al., 2009; Kulesh et
OH
stems, berries, al., 2006; Zga et al.,
and wine 2009)
Z-Piceid HO 390.38 V. labrusca (Adrian et al., 2000;
berries Baderschneider and
M. rotundifolia Winterhalter, 2000;
berries Buiarelli et al.,
OGlc V. vinifera 2007; Krisa et al.,
berries, leaves, 1999; Larronde et
OH cell cultures al., 2005; Leblanc et
and red and al., 2008; Mattivi et
white wine al., 1995; Naugler et
al., 2007; Pezet et
al., 2003; Ribeiro de
Lima et al., 1999;
Santamaria et al.,
2010; Vitrac et al.,
2001; Vitrac et al.,
2002; Waffo-Téguo
et al., 1998)

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A.D. PAWLUS et al.

E-Piceid (3) OH 390.38 V. amurensis (Adrian et al., 2000;


leaves and Baderschneider and
HO stems Winterhalter, 2000;
V. coignetiae Buiarelli et al.,
berries 2007; Guebailia et
OGlc V. labrusca al., 2006; Ha et al.,
berries 2009a; Ha et al.,
M. rotundifolia 2009b; Jean-Denis et
berries al., 2006; Kim et al.,
V. vinifera 2009; Krisa et al.,
berries, cell 1999; Landrault et
suspension al., 2002; Larronde
cultures, et al., 2005; Leblanc
leaves, stems et al., 2008; Mattivi
and red and et al., 1995; Naugler
white wine et al., 2007; Ribeiro
de Lima et al., 1999;
Santamaria et al.,
2010; Vitrac et al.,
2001; Vitrac et al.,
2002; Vitrac et al.,
2005; Waffo-Téguo
et al., 1996a; Waffo-
Téguo et al., 1996b;
Waffo-Téguo et al.,
1998; Waterhouse
and Lamuela-
Raventós, 1994; Yan
et al., 2001)

E-Pterostilbene (4) OH 256.30 V. coignetiae (Adrian et al., 2000;


berries Kim et al., 2009;
H3CO V. vinifera Langcake et al.,
leaves and 1979; Pezet and
berries Pont, 1988; Pezet et
OCH3 al., 2003)

Z-Resveratrol HO 228.24 V. labrusca (Buiarelli et al.,


wine 2007; Delaunay et
M. rotundifolia al., 2002; Jeandet et
wine al., 1995; Krisa et
OH V. vinifera al., 1999; Lamikanra
leaves, stems, et al., 1996; Mattivi
OH cell suspension et al., 1995; Naugler
cultures and et al., 2007; Pezet et
red and white al., 2003; Ribeiro de
wine Lima et al., 1999;
Vitrac et al., 2001;
Vitrac et al., 2002;
Vitrac et al., 2005)

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E-Resveratrol (1) OH 228.24 V. amurensis (Adrian et al., 2000;


leaves, stems, Amico et al., 2009;
HO and roots Baderschneider and
V. betulifolia Winterhalter, 2000;
stems Barjot et al., 2007;
OH V. Bisson et al., 2011;
chunganensis Buiarelli et al.,
whole plant 2007; Dourtoglou et
V. coignetiae al., 1999; Ector et
berries and al., 1996; Gambuti
leaves et al., 2004;
V. davidii Gerogiannaki-
stems Christopoulou et al.,
V. labrusca 2006; Guebailia et
berries, leaves, al., 2006; Ha et al.,
stems, and 2009a; Ha et al.,
wine 2009b; He et al.,
V. pentagona 2009; Huang and
stems Lin, 1999; Jean-
V. riparia Denis et al., 2006;
leaves Jeandet et al., 1991;
V. riparia x V. Jeandet et al., 1995;
berlandieri Krisa et al., 1999;
roots Kulesh et al., 2006;
M. rotundifolia Lamikanra et al.,
berries and 1996; Landrault et
wine al., 2002; Langcake
V. thunbergii and Pryce, 1976;
stems Langcake, 1981;
V. vinifera Leblanc et al., 2008;
berries, cell Li et al., 1996; Li et
suspension al., 1998a; Lou et
cultures, stems, al., 2004; Mattivi et
leaves, and red al., 1995; Naugler et
and white wine al., 2007; Pezet et
al., 2003; Ribeiro de
Lima et al., 1999;
Siemann and
Creasy, 1992; Vitrac
et al., 2001; Vitrac
et al., 2002; Vitrac
et al., 2005; Wang et
al., 2011;
Waterhouse and
Lamuela-Raventós,
1994)

Z-Resveratrol-3,4'-O-!- HO 552.52 V. vinifera cell (Decendit et al.,


diglucoside suspension 2002; Larronde et
cultures al., 2005)
OGlc

OGlc

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A.D. PAWLUS et al.

E-Resveratrol-3,4!-O-!- OGlc 552.52 V. vinifera cell (Decendit et al.,


diglucoside suspension 2002; Larronde et
(mulberroside E) HO cultures al., 2005)

OGlc
E-Resveratrol 2-C-glucoside OH 390.38 V. vinifera (Baderschneider and
stems and Winterhalter, 2000;
HO wine, Riesling Yan et al., 2001)

Glc
OH
Z-Resveratrol GlcO 552.52 V. vinifera cell (Larronde et al.,
3,5-O-!-diglucoside suspension 2005)
cultures
OGlc

OH
E-Resveratrol OH 552.52 V. vinifera cell (Larronde et al.,
3,5-O-!-diglucoside suspension 2005)
GlcO
cultures

OGlc
Z-Resveratrol GlcO 714.67 V. vinifera cell (Larronde et al.,
3,5,4'-O-!-triglucoside suspension 2005)
cultures
OGlc

OGlc
Z-Resveratroloside HO 390.38 V. vinifera cell (Krisa et al., 1999;
suspension Waffo-Téguo et al.,
cultures 1998)
OH

OGlc
E-Resveratroloside OGlc 390.38 V. vinifera cell (Krisa et al., 1999;
suspension Waffo-Téguo et al.,
HO cultures 1998)

OH
E-Rhapontigenin OH 258.27 V. coignetiae (Adrian et al., 2000)
OCH3 berries

HO

OH
2,4,6-Trihydroxyphenanthrene OH 388.37 V. vinifera (Baderschneider and
2-O-glucoside (10) wine, Riesling Winterhalter, 2000)
OH

OGlc

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!
Dimers
a b
Compound Structure M.W. Plant Name References
Name and Part

(+)-Ampelopsin A HO 470.47 V. amurensis (Chen and Wang,


H leaves, stems, and 2009; Chiou et al.,
O OH roots 2009; Ha et al.,
V. betulifolia stems 2009a; Ha et al.,
HO V. coignetiae 2009b; Huang and
H whole plant Lin, 1999; Kulesh et
OH V. heyneana stems al., 2006; Li et al.,
V. thunbergii roots 1996; Li et al.,
OH
and stems (var. 1998b; Lou et al.,
taiwaniana) 2004; Oshima et al.,
V. vinifera stems 1995b; Reniero et
al., 1996; Wang et
OH al., 2011; Yan et al.,
2001; Zga et al.,
2009)

Ampelopsin D OH 454.47 V. amurensis roots (Huang and Lin,


V. vinifera leaves 1999; Mattivi et al.,
OH 2011)
H
HO

OH
H
HO

HO
(+)-Ampelopsin F OH 454.47 V. amurensis (Chiou et al., 2009;
HO
leaves and stems Ha et al., 2009a; Ha
V. coignetiae et al., 2009b;
whole plant Oshima et al.,
HO OH V. thunbergii roots 1995b; Yan et al.,
V. vinifera stems 2001)

OH
OH
Amurensin A HO 472.49 V. amurensis roots (Huang and Lin,
HO OH 1999)
H
H
H
HO
HO

OH OH

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A.D. PAWLUS et al.

Betulifol A H O
OH 452.45 V. betulifolia stems (Li et al., 1998b)
HO
H H
OH
O H
HO
Gnetin A OH 454.47 V. flexuosa stems (Li et al., 1998c; Li
V. wilsoniae stems et al., 1998d)

OH

H
HO
O

H O
HO
Isoampelopsin F HO OH 454.47 V. amurensis stems (Kulesh et al., 2006)

HO OH
H

OH
OH
(-)-Malibatol A HO 468.45 V. vinifera stems (Yan et al., 2001)

H OH
OH
HO

O
HO

HO
c
Pallidol (9) OH 454.47 V. amurensis (Delaunay et al.,
OH
stems 2002; Guebailia et
V. vinifera cell al., 2006; Kulesh et
H suspension al., 2006; Landrault
HO cultures, leaves, et al., 2002; Mattivi
OH stems and red wine et al., 2011; Naugler
H (Bergerac) et al., 2007; Vitrac et
al., 2001; Vitrac et
HO OH al., 2002; Waffo-
Téguo et al., 2001)

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Pallidol 3,3!- OH 778.75 V. vinifera wine, (Baderschneider and


OGlc
diglucoside Riesling Winterhalter, 2000)

HO
OH

HO OGlc
Pallidol 3-O- OH 616.61 V. vinifera wine, (Baderschneider and
OH
glucoside Riesling Winterhalter, 2000)

HO
OH

HO OGlc
Parthenocissin A HO 454.47 V. vinifera wine, (Vitrac et al., 2001)
OH
H red Bergerac

HO
OH
H
H
OH

OH
Quadrangularin A HO 454.47 V. vinifera leaves (Mattivi et al., 2011)
OH
H

HO
OH
H
H
OH

HO
Scirpusin A (5) OH 470.47 V. vinifera stems (Kong et al., 2010)
HO

O OH

HO

OH

OH

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A.D. PAWLUS et al.

(+)-Viniferether A OH 486.51 V. vinifera roots (Fujii et al., 2005)

OH
H
HO

H OH
H
HO
H3CO H
OH
(+)-Viniferether B OH 486.51 V. vinifera roots (Fujii et al., 2005)
OH
H
HO

H OH
H
HO H
H3CO
OH
Viniferifuran (15) HO 452.45 V. amurensis roots (Chiou et al., 2009;
(Amurensin H) V. thunbergii roots Huang et al., 1999a;
O OH
V. vinifera stems Ito et al., 1999)
HO

OH

OH
E-"-Viniferin (19) HO 454.47 V. vinifera cell (Breuil et al., 1998;
(E-Resveratrol suspension Jean-Denis et al.,
O cultures, leaves, 2006; Pezet et al.,
dehydrodimer)
and wine 2003; Vitrac et al.,
HO
2005; Waffo-Téguo
OH et al., 2001)

OH
OH
E-"-Viniferin 11- HO 616.61 V. vinifera cell (Waffo-Téguo et al.,
O-!-D- H suspension cultures 2001)
O
glucopyranoside
(resveratrol HO OH
dehydrodimer 11- H
O-!-D-
glucopyranoside) OGlc OH
E-"-Viniferin 11!- HO 616.61 V. vinifera cell (Waffo-Téguo et al.,
O-!-D- H
O
suspension cultures 2001)
glucopyranoside
(E-Resveratrol HO OH
dehydrodimer 11!- H
O-!-D-
glucopyranoside) OH OGlc

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Z-"-Viniferin HO 454.47 V. vinifera leaves (Pezet et al., 2003)


after UV-
O
irradiation
HO
HO

OH
OH
Z-#-Viniferin HO 454.47 V. vinifera leaves (Amira-Guebailia et
H and wine al., 2009; Mattivi et
O OH al., 2011; Pezet et
HO OH al., 2003)
H

OH
(+)-E-#-Viniferin HO 454.47 V. heyneana stems (Huang and Lin,
H V. vinifera stems 1999; Ito and Niwa,
O OH
and leaves 1996; Li et al., 1996;
HO Mattivi et al., 2011)
H

OH

OH

E-#-Viniferin (8) HO 454.47 V. amurensis (Amico et al., 2009;


leaves, stems, Amira-Guebailia et
O OH and roots al., 2009; Barjot et
V. berlandieri roots al., 2007; Bisson et
HO V. betulifolia stems al., 2011; Chiou et
V. chunganensis al., 2009; Guebailia
whole plant et al., 2006; Ha et
OH V. cinerea roots al., 2009b; He et al.,
V. coignetiae 2009; Huang et al.,
whole plant 2005; Jean-Denis et
V. davidii stems al., 2006; Kulesh et
OH V. flexuosa stems al., 2006; Landrault
V. longii roots et al., 2002;
V. riparia leaves Langcake and Pryce,
and roots 1977a; Langcake,
V. riparia x V. 1981; Li et al.,
berlandieri roots 1998a; Li et al.,
V. rupestris roots 1998b; Li et al.,
V. solonis longii 1998c; Li et al.,
roots 1998d; Mattivi and
V. solonis richter Reniero, 1992;
roots Oshima et al.,
V. thunbergii roots 1995b; Ourtoule et
and stems (var. al., 1996; Pezet et
taiwaniana) al., 2003; Vitrac et
V. vinifera leaves, al., 2005; Wang et
roots, stems, and al., 2011; Yan et al.,
red wine 2001; Zga et al.,
V. wilsoniae stems 2009)

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A.D. PAWLUS et al.

Z-$-Viniferin HO 454.47 V. vinifera leaves (Mattivi et al., 2011)


(7a,8a-cis-Z-#- H
O OH
viniferin 17)
HO
H
OH
OH
E-$-Viniferin HO 454.47 V. vinifera leaves (Mattivi et al., 2011)
(7a,8a-cis-E-#-
viniferin 16) H
O OH

HO
H

OH

OH
Z-#-Viniferin HO 778.75 V. vinifera wine, (Baderschneider and
diglucoside Riesling Winterhalter, 2000)
O OH

GlcO OH

OGlc
E-#-Viniferin HO 778.75 V. vinifera wine, (Baderschneider and
diglucoside Riesling Winterhalter, 2000)
O OH

GlcO

OGlc

OH
#-Viniferin diol HO 488.49 V. betulifolia stems (Li et al., 1998b;
(Betulifol B) H V. coignetiae stems Oshima et al.,
O OH 1995a)
HO
H
HO
OH
OH

OH

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Vitisinol A HO H H OH 452.45 V. thunbergii roots (Huang et al., 2005)


O

H H

HO OH

O
Vitisinol B HO 574.58 V. thunbergii roots (Huang et al., 2005)
H
O OH

HO OH
H

OH
CHO

OH
Vitisinol C HO 428.48 V. thunbergii roots (Huang et al., 2005)
O

H
H

HO
OH
OH
Vitisinol D HO 454.47 V. thunbergii roots (Huang et al., 2005)
O

O
HO

OH

OH
(+)-Vitisinol E O 486.51 V. vinifera (Choi et al., 2009)
(13) HO H stembark
H
HO
O OCH3
OH
OH
Vitisinol E (14) OH 444.48 V. thunbergii roots (Chiou et al., 2009)

HO O
HO

OH

OH

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A.D. PAWLUS et al.

Vitisinol G HO 452.45 V. thunbergii roots (Chiou et al., 2009)


O
OH

HO

OH OH
!
Trimers
a b
Compound Structure M.W. Plant Name References
Name and Part
Ampelopsin C OH OH 680.70 V. betulifolia stems (Chiou et al.,
HO V. coignetiae 2009; Huang et
HO
whole plant al., 2005; Li et
H V. davidii stems al., 1996; Li et
H V. heyneana stems al., 1998a; Li et
H V. thunbergii roots al., 1998b;
HO OH
and stems (var. Oshima et al.,
H
H taiwaniana) 1995b; Wang et
al., 2011)
HO O
H

HO
Ampelopsin E HO OH 680.70 V. amurensis roots (Huang and Lin,
H H V. davidii stems 1999; Li et al.,
O O V. wilsoniae stems 1998a; Li et al.,
1998d)
HO OH
H H

OH OH

OH
Z-Ampelopsin E HO
OH 680.70 V. thunbergii roots (Chiou et al.,
2009)
H H
O O OH
HO
H H
OH
OH OH

Z-Amurensin B HO OH 680.70 V. amurensis (Ha et al.,


H H leaves and stems 2009a)
O O

HO OH
H H

OH OH
OH

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E-Amurensin B HO OH 680.70 V. amurensis (Ha et al.,


H H leaves, stems, and 2009a; Ha et al.,
O O roots 2009b; He et
OH V. chunganensis al., 2009;
HO
whole plant Huang and Lin,
H H 1999)

OH OH

OH
Amurensin C HO OH 678.68 V. amurensis roots (Huang et al.,
H 2000)
O O

HO OH
H

OH OH

OH
Amurensin D OH 678.68 V. amurensis roots (Huang et al.,
OH 2000)
H
O O
HO
OH
H
HO
OH

OH
Amurensin G HO OH 680.70 V. amurensis (Ha et al.,
leaves, stems, and 2009b; He et
OH roots al., 2009;
V. chunganensis Huang et al.,
OH H whole plant 1999b)
H
HH OH
HO OH
H
O
H
HO

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A.D. PAWLUS et al.

Gnetin H HO OH 680.70 V. amurensis (Ha et al.,


H H leaves and stems 2009a; Ha et al.,
O O V. berlandieri 2009b; He et
OH roots al., 2009;
HO
V. chunganensis Mattivi and
H H whole plant Reniero, 1992)
V. cinerea roots
OH OH V. longii roots
V. riparia roots
V. rupestris roots
V. solonis longii
OH
roots
V. solonis richter
roots
V. vinifera roots
E-trans- OH 680.70 V. vinifera leaves (Barjot et al.,
Miyabenol C and stems 2007; Mattivi et
HO al., 2011)
H
O OH

HO
H H

HO O OH
H
HO
E-cis- OH 680.70 V. vinifera leaves (Mattivi et al.,
Miyabenol C 2011)
HO
H
O OH

HO
H H

OH O OH
H
HO !
Z-trans- HO 680.70 V. vinifera leaves (Mattivi et al.,
Miyabenol C H 2011)
O OH

HO
H H
OH

HO O OH
H
HO

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%-Viniferin (6) OH 678.68 V. riparia leaves (Langcake,


V. vinifera leaves 1981; Mattivi et
al., 2011; Pryce
H and Langcake,
O OH 1977)
H
HO
H O
H
HO H O H

OH
OH
(+)-Viniferol D OH 680.70 V. vinifera stems (Takaya et al.,
2003)
OH

OH H
H H
OH
H
HO
H
O OH OH
H
HO
Vitisin E OH 680.70 V. coignetiae (Shinoda et al.,
stems 1997)

OH OH
H
H H
HO OH

O O
H H
HO OH
Vitisinol F HO 654.70 V. thunbergii roots (Chiou et al.,
H 2009)
O OH
OH

HO H H

H
OH O

OH

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A.D. PAWLUS et al.

!
Tetramers
a b
Compound Structure M.W. Plant Name References
Name and Part
Ampelopsin H OH 906.93 V. vinifera leaves (Mattivi et al.,
HO HO O
H 2011)
H
OH
OH
H
H H
H
HO HO
H
O OH OH
H

HO
Amurensin I HO H
O OH
902.89 V. amurensis roots (Huang et al.,
HO 2001)
HO H H O
H
H
H
HO
OH
HO OH
HO HO
Amurensin J HO OH 906.93 V. amurensis roots (Huang et al.,
H
O O
H 2001)

HO OH
H H

H
OH HO O
H

OH
OH
OH
Amurensin K OH 920.91 V. amurensis roots (Huang et al.,
2001)
H
HO O

OH
O
H

OH
OH
HO H
H
HO
O
H
HO H

OH
OH

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Amurensin L HO 904.91 V. amurensis roots (Huang et al.,


OH
2001)
O
HO

OH
OH
HO
HO H
H
H O
O H

OH
OH
Amurensin M OH 902.89 V. amurensis roots (Huang et al.,
2001)

HO

OH

HO
HO O
O OH
OH
HO

OH

OH
Davidol A O
OH HO O 906.93 V. davidii stems (Li et al.,
(hypothesized HO OH 1998a)
structure)

HO OH HO OH

OH OH
Flexuosol A OH 906.93 V. flexuosa stems (Li et al.,
1998c)
HO
H HO
O OH

HO
H OH
H H

OH O O
H H
HO OH

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A.D. PAWLUS et al.

Heyneanol A HO
OH 906.93 V. amurensis roots (Huang et al.,
H
H
HO O V. betulifolia stems 2001; Jang et
O OH
OH V. heyneana stems al., 2007; Li et
HO H al., 1996; Li et
H H
al., 1998b; Li et
OH
OH al., 2000)
H O
HO
Hopeaphenol HO 906.93 V. amurensis roots (Guebailia et
(12) H
O OH V. betulifolia stems al., 2006; He et
OH
V. chunganensis al., 2009;
whole plant Huang et al.,
HO H V. flexuosa stems 2001; Ito et al.,
H HO
V. vinifera leaves, 1997; Li et al.,
H
stems, roots, and 1998b; Li et al.,
OH
H
OH red wine 1998c; Reniero
et al., 1996;
OH Yan et al.,
HO O 2001)
H
OH
Isohopeaphenol HO 906.93 V. amurensis roots (Huang et al.,
H
O OH V. vinifera leaves 2001; Ito et al.,
OH
and stems 1997; Mattivi et
al., 2011; Yan
HO H et al., 2001)
H HO
H
OH OH
H

OH
HO O
H
OH
Miyabenol A HO 922.92 V. thunbergii roots (Chiou et al.,
2009; Huang et
HO al., 2005)
H H
O OH O OH

HO
H H
H

OH
HO H O
OH

OH
Vaticanol C HO
OH
906.93 V. vinifera leaves (Mattivi et al.,
isomer H
2011)
HO
(tentative O
OH
structure) H OH
H H H H
HO
H OH
O OH OH
H
HO

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(+)-Viniferol A OH 906.93 V. vinifera stems (Yan et al.,


OH 2001)

HO H
OH O
H

OH H H OH
H
H H
HO OH

O OH
H
HO
(+)-Viniferol B OH 906.93 V. vinifera stems (Yan et al.,
OH HO 2002)
OH
OH H H OH
H H
HO H H H
O

O OH
H
HO OH
(+)-Viniferol C HO 906.93 V. vinifera stems (Yan et al.,
H 2002)
O OH
HO
H OH
H
H
OH
H O
HO H
H
H
OH
HO HO
OH
(+)-Viniferol E OH
HO OH
OH
924.94 V. vinifera roots (Fujii et al.,
H H
O 2005)
H H
HO H H OH

O OH HO O
H H
HO OH
(+)-Vitisifuran HO 904.91 V. amurensis roots (Huang et al.,
A O OH V. vinifera stems 2001; Ito et al.,
1999)
HO OH

OH HO
H H

H OH
OH

HO O
H
OH

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A.D. PAWLUS et al.

(-)-Vitisifuran B HO 904.91 V. vinifera stems (Ito et al., 1999)


O OH

HO
OH
HO OH

OH
H
H
H O
O
H

OH

OH
Vitisin A (r-2- HO 906.93 V. amurensis (Chen and
Viniferin) (7) H
O OH leaves, roots, and Wang, 2009;
stems Chiou et al.,
HO V. betulifolia stems 2009; Ha et al.,
H
OH V. chunganensis 2009b; He et
whole plant al., 2009;
OH V. coignetiae Huang et al.,
OH
H stems and whole 2001; Huang et
H plant al., 2005; Ito et
H OH V. davidii stems al., 1998; Jang
HO V. flexuosa stems et al., 2007;
O OH V. thunbergii roots Korhammer et
H and stems al., 1995; Li et
HO V. vinifera stems al., 1998a; Li et
V. wilsoniae stems al., 1998b; Li et
al., 1998c; Li et
al., 1998d;
Oshima et al.,
1993; Oshima et
al., 1995b;
Wang et al.,
2011; Yan et
al., 2001)

Z-Vitisin A HO OH 906.93 V. coignetiae (Ito et al., 1998;


OH stems and whole Oshima et al.,
H plant 1993; Oshima et
OH al., 1995b)
H
O

OH
H H
OH
H
OH
HO

O OH
H
HO

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E-Vitisin B HO 906.93 V. amurensis roots (dBisson et al.,


H
(r-Viniferin) O OH V. berlandieri 2011; Chen and
HO roots Wang, 2009; Ito
d
H
V. riparia x V. and Niwa, 1996;
berlandieri roots Korhammer et
OH HO OH V. cinerea roots al., 1995; Lou et
V. coignetiae al., 2004;
H
OH stems Mattivi and
O
H V. longii roots Reniero, 1992;
H O H V. riparia roots Oshima et al.,
V. rupestris roots 1995a; Wang et
HO V. solonis longii al., 2011; Zga et
OH roots al., 2009)
V. solonis richter
roots
V. thunbergii var.
taiwaniana stems
and roots
V. vinifera stems
and roots
Z-Vitisin B OH 906.93 V. amurensis roots (Lou et al.,
HO OH V. coignetiae 2004; Oshima et
H
O OH stems al., 1995a)
HO H
HO H O
H
H
OH
OH
O
H
OH
E-Vitisin C HO 906.93 V. thunbergii roots (Huang et al.,
H
O OH V. vinifera stems 2005; Ito and
HO Niwa, 1996)
H

HO HO OH

H
OH
H
O
H O H

HO
OH

However, a recent study found the cis configuration dihydrobenzofuran form were isolated with both cis (Z)
in downy mildew infected V. vinifera leaves, meaning and trans (E)-double bond configurations. The authors
both hydrogens arein the alpha or both in the beta position named these two cis-dihydrobenzofuran forms, E-ω-
(Mattivi et al., 2011). This naming of cis and trans viniferin (16) and Z-ω-viniferin (17), despite having
conformation for these hydrogens is an area of confusion the same planar structure as ε-viniferin, while other authors
when dealing with stilbenoids, which often contain a trans have referred to this compound as 7a, 8a-cis-ε-viniferin
(E) or cis (Z) double bond as well. The E/Z nomenclature, (Huang et al., 2000; Lin and Yao, 2006; Mattivi et al.,
for the trans and cis double bond, respectively, is more 2011). It should also be noted that in the relative
precise, yet less commonly used in stilbenoid literature. conformation, the difference between the cis-
The study by Mattivi et al. (2011) illustrates this problem, dihydrobenzofuran form and the trans-dihydrobenzofuran
where both the trans-ε-viniferin and the cis- form can be determined by comparison of their NMR

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A.D. PAWLUS et al.

Vitisin D OH 906.93 V. coignetiae (Shinoda et al.,


H stems 1997)
HO O

OH
H
OH
H
OH

OH
H
OH
H
HO

O OH
H
HO
!
Breakdown Product from Tetramer
a b
Compound Structure M.W. Plant Name References
Name and Part
(-)-Viniferal HO 574.58 V. thunbergii roots (Chiou et al.,
(11) H
V. vinifera stems 2009; Huang et
O OH al., 2005; Ito
and Niwa,
HO 1996)
H OH
H

H
OH O

OHC
!
data. Determining the absolute configuration, however, QUANTIFICATION OF STILBENOIDS
1 Quantification methods
is more challenging, i. e. the difference between (+) and
(-)-ε-viniferin. For known compounds, their [α]D values
can be compared with the literature. Currently, only the
(+)-ε-viniferin form has been proven to be in Vitaceae,
Numerous techniques have been used for the
whereas (-)-ε-viniferin can be found in other plant families quantification of stilbenoids with varying degrees of
(Lin and Yao, 2006). Nevertheless, there have been success. The primary techniques used include liquid
isolated reports of (-)-ε-viniferin in Vitis, though the chromatography with ultraviolet detection (LC-UV), LC-
complete spectroscopic data set was not provided (Amico fluorescence detection, gas chromatography-mass
et al., 2009; Kulesh et al., 2006). A careful discussion on spectrometry (GC-MS) and LC-MS, in conjunction with
the difficulties in determining the relative and absolute numerous sample preparation techniques, see Table 3.
configurations of the viniferins and other stilbenoids, is The majority of the initial studies utilized GC-MS,
provided in the publication by Mattivi et al. (2011). Due however, this method has drawbacks, such as derivation
to the difficulties in assigning absolute configurations to requirements and destruction of oligomers and glycosides
stilbenoid oligomers, many compounds have been prior to detection. These properties have a tendency to
reported with only their relative configurations assigned. promote artificially high aglycone monomer levels and
However, since (+)-ε-viniferin is considered a major E to Z-isomer conversions (Flamini, 2003; Soleas et al.,
stilbenoid intermediate for larger oligomers, the structures 1997). While HPLC-UV analysis does not have the same
containing viniferin moieties are normally presented as problems as GC-MS, other problems such as lack of
containing the same configuration when not otherwise baseline resolution, leading to overestimation of individual
determined. In the reports of many complex oligomers, stilbenoid levels, may exist, along with poor sensitivity.
only the relative configuration has been assigned. More selective techniques such as fluorescence detection

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!
Pentamers
a b
Compound Structure M.W. Plant Name References
Name and Part

Amurensin E OH 1132.14 V. amurensis roots (Huang et al.,


OH 2000)
H
O O
HO
OH
H
HO
HO OH

H
H OH
HO OH
H

HO O
H

HO
Amurensin F OH 1132.14 V. amurensis roots (Huang et al.,
OH 2000)
H
O O
HO
OH
H
HO
OH OH

HO
H O
H H
HO
H O

OH OH
!
can help overcome these drawbacks, whereas the high incomplete extraction due to poor solvent choice.
selectivity of LC-MS techniques can eliminate this Comparisons of multiple solvent extraction efficiencies
problem. However, matrix effects offer a particular have shown that 50 to 60 % ethanol in water was more
challenge in the quantitation of individual compounds in effective for E-resveratrol and E-ε-viniferin extraction in
complex samples such as wine. This may be overcome vine canes than a wide-range of other solvent systems
by sample cleaning techniques such as solid phase and ratios tested (Karacabey and Mazza, 2008; Rayne et
extraction (SPE), sample dilution, selective extraction, or al., 2008). In another study, comparing extraction rates
use of stable isotopes (Careri et al., 2004 ; Stark et al., of solvents with grape skins, a different set of solvents
was tested and acidified methanol was shown to be most
effective for resveratrol and piceid extraction (Sun et al.,
2011; Zotou and Frangi, 2008). The comparison of LC-
UV with LC-MS-MS has shown the later to have higher
sensitivity and selectivity (Careri et al., 2004). 2006). Higher temperatures and ultrasonication also
improve extraction efficiencies, but decomposition or
We have compiled quantitation studies of stilbenoids isomer conversion may occur more readily. Therefore,
in Vitis species, including wine, in Table 3. While useful, differences between studies may represent differences in
comparison between quantitation studies has some extraction efficiencies or changes occurring during the
drawbacks since additional, non-detector variables exist, extraction procedures. Additionally, there are variations
particularly when comparing solid materials such as grape in the preparation of plant material that need to be
skins or stems. One important problem may involve considered when comparing mul≤tiple studies. Some

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A.D. PAWLUS et al.

!
Hexamer
a b
Compound Structure M.W. Plant Name References
Name and Part

Chunganenol HO HO 1372.40 V. chunganensis (He et al., 2009)


OH whole plant
HO
OH
H HO
H
H
HO H OH H
O
H HO H

HO O
HO
H H
HO O
H
HO

OH

OH

!aMany reports of previously isolated known compounds were not confirmed using all spectroscopic techniques required for unambiguous
assignments. We included these to have a more complete list where stilbenoids have been identified. Additionally, due to the challenge of
assigning absolute stereochemistry to complex oligomers, only the relative configuration was reported in some cases. We drew the structures
as reported, but these may only reflect relative configurations. In the case of common compounds such as E-ε-viniferin, we attempted to
differentiate between reports where the configuration was determined from those where only the planar structure was determined.
b
All or most of the spectroscopic information can be found in underlined references.
c
This report of pallidol from V. amurensis (Kulesh et al., 2006) has recently been disputed due to discrepancies in NMR data (Mattivi et al.,
2011).
d
This report of vitisin B had an error in the original publication, the name of the structure was erroneously given as vitisin C.

researchers have used the fresh weight of the plant material isomer, Z-resveratrol, in addition to their glycosides, Z-
whereas others have used the dry weight, making and E-piceid, have become more common. The majority
comparison between these studies difficult. Using the of research has been performed on wine made from
fresh weight for quantitation studies may also be different cultivars of V. vinifera, including comparisons
complicated by amount of rainfall or lack of rainfall levels of wines made in different years, geographic locations,
immediately prior to collection. Due to the role of micro-climates, and using different methods of vinification,
stilbenoids as phytoalexins, quantitation of stilbenoids see Table 3 (Bavaresco, 2003; Moreno-Labanda et al.,
has been performed on different parts of infected 2004). A 2007 review by Stervbo et al. summarized the
grapevines. However, even within these studies, variations findings from 31 papers on the quantitation of E-resveratrol
exist in sample material. For example, some studies levels in a total of 511 individual monovarietal red wines,
examined only the infected parts of the leaves and others including 21 different varieties from 18 regions around
extracted the entire leaf that showed some degree of the world. Not all of these studies examined Z-resveratrol
infection. We have therefore attempted to include all and the piceids, but the authors included these data when
relevant information available in Table 2. available. The overall levels of E-resveratrol ranged from
2 Quantitation results undetectable levels to 14.3 mg/l, with an average of
1.9 mg/L. In this review no variety or region was found
A tremendous effort has been made to quantify levels to be clearly superior. Interestingly, varieties such as Pinot
of stilbenoids in wine of multiple varieties, vintages, noir tend to have higher levels, though this higher level
terroir, and growth conditions. Since the initial quantitation was not ubiquitous with every Pinot noir tested. No distinct
of resveratrol in wine by Siemann and Creasy in 1992, trends were observed with Z-resveratrol, which ranged
the quest to find which variables may produce wines with from undetectable levels to 5.1 mg/L, averaging 1.0 mg/L.
high concentrations has been ongoing (Siemann and The piceid isomers, which were typically higher than
Creasy, 1992). While E-resveratrol concentrations have resveratrol levels, averaged 5.4 and 1.4 mg/L for E- and
been the most widely reported, efforts to quantify its Z-piceid, respectively. A slight trend appeared when

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Table 3 - Summary of recent quantitation studies of different stilbenoids, in Vitis species.


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A.D. PAWLUS et al.

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J. Int. Sci. Vigne Vin, 2012, 46, n°2, 57-111


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J. Int. Sci. Vigne Vin, 2012, 46, n°2, 57-111


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J. Int. Sci. Vigne Vin, 2012, 46, n°2, 57-111


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*aRed wine unless otherwise specified. bUnits are based on weight of skins and seeds from 50 grapes, macerated with 50 ml of MeOH. cRecovery
for piceid was 73% and for resveratrol was 37%, based on spiking/recovery study. dVariety used was not specified further. fw=fresh weight,
dw=dry weight, ND=none detected, SD=standard deviation, trace=compound found, but not in quantifiable concentrations. « Doble pasta »
was made from additional solids from rosé production.

looking at latitude in the northern hemisphere, where also ambiguous, since levels between thin and thick varied
more northern locations contained higher resveratrol unpredictably (Stervbo et al., 2007).
content. One example of this is the higher concentrations
in Canadian red wines than those found in Greece or Additional efforts to quantify resveratrol in wine have
Japan. The authors also looked to see if a trend was occurred, which we included in Table 3. In addition to
apparent with thick and thin skinned grapes. This was examining wine samples, studies have quantified

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stilbenoids in separate plant parts, the berries themselves, E- and Z-resveratrol concentration in the berries of
and wine during the vinification process in order to gain Mencia, Albarello and Merenzao grapes. In this study,
a better understanding of the stilbenoid level dynamics. Mencia berry skins had approximately 10 times the
For example, in a study by Gatto et al. (2008), the concentrations of E-resveratrol than the other two varieties
E-resveratrol and Z- and E-piceid levels were examined tested (Moreno et al., 2008). These high levels of E-
in 78 V. vinifera white and red grape varieties grown in resveratrol in Mencia wine and grapes warrant further
the same research station in three different years. This investigation. It would also be interesting to determine if
study controlled for influences such as climate variability the levels of other stilbenoids were also high in this variety
and differences in vinification methods by studying the or if this monomer dominates.
berries directly, allowing genetic influences and ripening
phases on stilbenoid levels to be examined. The authors The main purpose of these quantitation studies has
evaluated the grapes at three different time points to generally been to determine the amount of these
determine the levels of the three different stilbenoids at biologically important molecules in wines and grapes
veraison, at technological ripeness, and at a post-ripening currently being consumed. Additional studies have aimed
phase, 20 days later. They simultaneously monitored at determining which factors, such as specific vinification
genetic expression between high and low resveratrol processes, variety used, and location, may contribute to
producers. The authors demonstrated that in high higher levels. However, this has proved challenging since
resveratrol producers, such as Pinot noir, Tarrango, stilbenoid content varies significantly in wines, even the
Franconia, Alicante Bouquette, and Carmenere, there was same types of wine produced in the same region can
stilbenoid accumulation in the berries throughout contain nontrivial differences. Numerous studies have
development. Both E- and Z-piceid were constitutively found that stilbenoid levels in grapes and leaves are
expressed, whereas resveratrol was confirmed to be an influenced by a number of factors, including genetic,
inducible stilbenoid (Gatto et al., 2008). They also nutritional, climatic, disease status, altitude, and latitude
supported the reoccurring finding that Pinot noir is one (Bavaresco, 2003; Bavaresco et al., 2007; Deluc et al.,
of the varieties with higher levels of resveratrol (Lamuela- 2011; Tinttunen and Lehtonen, 2001). For example, since
Raventos et al., 1997; Melzoch et al., 2001). In another resveratrol is induced in berries, levels of disease pressure
recent study, 186 Portuguese red wines of different varieties in the vineyard may influence resveratrol levels. This
and vintages were evaluated for their E- and Z-resveratrol relationship is not linear however, as a small amount of
content using HPLC-UV. E-resveratrol levels ranged from disease pressure increases stilbenoid production, while
0.05 to 10.9 mg/L, while the concentrations of Z- highly infected berries have lower levels (Adrian et al.,
resveratrol ranged from 0.04 to 8.7 mg/L. The identity of 2000). Similar non-linearity has been seen in resveratrol
all the varieties tested was not provided, since many were levels and increasing altitudes (Bavaresco et al., 2007).
blended wines, but wine made from Touriga Nacional In other studies, incubation of resveratrol and pterostilbene
variety in the Beira Interior denomination of origin with Botrytis cinerea, the causative organism of gray
contained the highest resveratrol content (Paulo et al., mold, showed oxidative dimerization of both compounds,
2011). demonstrating disease status may also influence overall
stilbenoid profiles (Breuil et al., 1998; Breuil et al., 1999).
Most studies have not been able to single out a wine Controlled studies using P. viticola infected leaves showed
variety with consistently higher stilbenoid levels, with the high year-to-year variability of a number of stilbenoids,
possible exception of Pinot noir, which many studies have demonstrating a need for multi-year studies (Vrhovsek
shown to have the highest average, and a lesser known et al., 2011). These factors, that play a role in stilbenoid
variety, Mencia. In a recent study focusing on resveratrol synthesis, have been reviewed and updated by Bavaresco
isomers, involving wines from 5 different Galician et al. (Bavaresco and Fregoni, 2001; Bavaresco et al.,
Controlled Denomination of Origin regions in 2009). Other factors such as influence of phylloxera
Northwestern Spain, the Mencia variety from Valdeorras
had one of the highest E-resveratrol concentrations
resistant rootstock have yet to be evaluated. Furthermore,
the process of vinification has influences on wine
currently known. In one monovarietal wine sample, the
E-resveratrol concentration was 36.1 mg/L. Mencia
stilbenoids, both qualitatively and quantitatively. Known
influential factors include maceration and fermentation
containing wines from Ribeira Sacra also contained high time and temperature, yeast and bacteria used for alcoholic
levels, up to 31.4 mg/L. However, the Mencia grown in and malolactic fermentation, and post-processsing factors
Ribeiro CDO were much lower, with levels ranging from such as wine bottle aging (Monagas et al., 2005; Poussier
2.5 to 5.8 mg/L. The concentration of Z-resveratrol in all et al., 2003; Vitrac et al., 2005).
wines was very low, with a maximum Z-resveratrol
concentration of 0.25 mg/L (Feijóo et al., 2008). The To further complicate matters, there is an observable,
relatively high concentration of resveratrol in Mencia dynamic relationship between the resveratrol monomers
berries was also demonstrated in a study comparing the with their corresponding glycosides and oligomers. For

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A.D. PAWLUS et al.

example, a study involving the UV irradiation of leaf Burgundy and a range of North African wines, with
discs showed resveratrol levels peaking at 18 hours, then concentrations up to 2.1 mg/L. Taken together, these
decreasing as ε-viniferin levels increased, peaking at studies show that the range of concentrations among and
36 hours (Langcake and Pryce, 1977b). This gradual between these compounds in different wines varies
accumulation of viniferins after exogenous induction has significantly, from below detectable levels to tens of
been confirmed in grape skins as well (Gonzalez-Barrio mg/mL, see Table 3 for references.
et al., 2006). During the wine making process itself,
glycoside levels typically fall while monomer levels rise. In addition to studies involving the quantitation of
This is due to the alcoholic and, to a lesser extent, the stilbenoids in wine and berries, there is a growing interest
malolactic fermentation processes, causing a decrease in in evaluating the stilbenoids in other parts of the grapevine.
glycoside levels via deglycosylation reactions, in addition Since roots, stems, canes, and rachis are a byproduct of
the wine industry, they are an untapped source of these
biologically active molecules (Bisson et al., 2011; Rayne
to increases in extraction efficiency of the aglycones from
the grape skins as alcohol levels increase (Bavaresco et
al., 1999 ; Vian et al., 2005 ; Vrhovsek et al., 1997). et al., 2008; Zhang et al., 2011). A recent comparison
However, as seen in the review article by Stervbo et al. of V. vinifera plant parts, examining resveratrol levels in
(2007), many wines still contain high levels of glycosides the shoot tips, petiole, leaves, stem phloem, stem xylem,
and low levels of aglycones. In the 2005 study by Vitrac and roots demonstrated highest levels in the stem phloem,
et al., a 1999 Brazilian Merlot contained 23 mg/L of axillary bud, and roots (Wang et al., 2010). Additionally,
E-astringin, a glycoside of piceatannol, and no detectable Vitis species other than V. vinifera have different stilbenoid
quantities of E-resveratrol (Vitrac et al., 2005). This profiles and may be rich sources of biologically active
suggests that in studies where only the levels of resveratrol stilbenoids. For example, in our laboratory, we found the
aglycones in wines have been determined, a substantial roots of a phylloxera resistant grapevine rootstock,
amount of glycosides may exist, however the reason is V. riparia x V. berlandieri SO4A, had significant levels
not known (Goldberg et al., 1995 ; Waterhouse and of the stilbenoid tetramer, E-vitisin B. The levels of
Lamuela-Raventós, 1994). In another example, wine stilbenoids in stems and roots also appear to be seasonally
made from Cabernet Franc has been reported in several dependent. For example, a 2002 study comparing the
studies to have one of the lowest levels of E-resveratrol concentrations of ε-viniferin and E-resveratrol in the stems
when compared to others such as Pinot noir, Cabernet- showed that there were significantly higher levels of these
Sauvignon, and Merlot (Gatto et al., 2008; Nikfardjam two compounds in October than in July and January
et al., 2006). However, in a study comparing several (Aaviksaar et al., 2003). Plant part, variety, and disease
Merlot and Cabernet-Sauvignon wines with a Cabernet pressure can influence the type and quantity of stilbenoids
Franc, E-astringin (18) was highest in Cabernet Franc, at found.

CONCLUSION
a concentration of 23.1 mg/L, which made its overall
stilbenoids quantity comparable to the other wines (Vitrac
et al., 2005). This demonstrates the usefulness of
quantifying a greater range of stilbenoids in wine when We have reviewed the current state of Vitis stilbenoid
chemistry and show that it is a very active area of research.
Eighteen of the approximately 60 species in Vitis have at
trying to determine stilbenoid levels.
So far, of the 19 currently known stilbenoids in wine, least one reported phytochemical study with a current
12 have been quantified in at least one study, as referenced
in Table 3. These compounds include the E and Z forms
total of around 100 known stilbenoids. The most studied
Vitis species is the primary wine producing species,
of astringin, piceid, resveratrol, and ε-viniferin, in addition V. vinifera, followed by other minor species used for wine,
to hopeaphenol, pallidol, E-piceatannol, and E-δ-viniferin
(19). The piceatannol glycoside, E-astringin, was
species used as phylloxera resistant rootstock for
V. vinifera, and species used as medicinal plants. Sixty-
quantified in wines from France, Brazil, Canada, Italy, one stilbenoids have been identified in various plant
and Portugal, where levels ranged from undetectable to tissues, cell cultures, and wine of V. vinifera with only 19
38.1 mg/L, in a French Bergerac wine. Its isomer,
Z-astringin was quantified in a number of Italian wines
currently known constituents of wine. The isolation and
structure elucidation of stilbenoids is not trivial, particularly
where it was found to have levels up to 1.3 mg/L, similar
to E-astringin levels which ranged from undetectable to
as the determination of absolute configurations becomes
1.8 mg/L. Several dimers, including pallidol, Z- and
more difficult as oligomer sizes and complexities increase.
E-ε-viniferin, and Z- and E-δ-viniferin were also Due to the interest in the health promoting and
examined, of these, δ-viniferin was found to have the antifungal properties of stilbenoids, we summarized recent
highest levels, 22.4 mg/L in a Brazilian Merlot. The only studies pertaining to their quantitation in different plant
known tetramer to be unambiguously identified in wine, parts and wine. The majority of studies have focused on
hopeaphenol, was quantified in Pinot noir wines from resveratrol and piceid levels, with more recent research

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Anstey K.J., Mack H.A. and Cherbuin N., 2009. Alcohol


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decline: Meta-analysis of prospective studies. Am. J. Geriatr.
Psychiatry, 17, 542-555.
oligomers. The metabolic pathways for stilbenoid synthesis
are complex and the relationship between stilbenoids is
dynamic since they are influenced by multiple Baderschneider B. and Winterhalter P., 2000. Isolation and
characterization of novel stilbene derivatives from Riesling
wine. J. Agric. Food Chem., 48, 2681-2686.
environmental and genetic factors. Wine presents an even
more complex case as viticultural and vinification
techniques may vary widely between varieties and regions. Balík J., Kyselákova M., Vrchotová N., Tríska J., Kumsta M.,
Therefore, studies quantifying only a small number of Veverka J., Híc P., Totusek J. and Lefnerová D., 2008.
Relations between polyphenols content and antioxidant
activity in vine grapes and leaves. Czech J. Food Sci., 26,
stilbenoids may be misleading in regards to overall
stilbenoid content.
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experimental methods, vary considerably in the literature, two vine stalk oligomers of resveratrol on a panel of
lymphoid and myeloid cell lines : Comparison with
resveratrol. Life Sci., 81, 1565-1574.
complicating comparisons between studies. A uniform
examination of plant material, including wine, using
Baur J.A. and Sinclair D.A., 2006. Therapeutic potential of
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5, 493-506.
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stilbenoid levels and allow better comparisons between
Vitis species and varieties. Bavaresco L., Petegolli D., Cantü E., Fregoni M., Chiusa G. and
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phytoalexins in grapevine berries infected by Botrytis
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A more thorough understanding of the stilbenoid
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in elucidating their biological importance, both in humans
and the plants themselves. Since the majority of stilbenoids,
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extensive biological testing, some may be found to have
an even greater biological importance as they become
Kluwer Academic Publishers, The Netherlands 500 p.
known and available for testing. An increased knowledge
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