The

Flavonoids
ADVANCES IN RESEARCH
SINCE 1986
 The
Flavonoids
ADVANCES IN RESEARCH
SINCE 1986

Edited by

J. B. HARBORNE

0
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The Flavonoids: advances in research since

1986/edited by J .B. Harborne. --1st ed.
p. ern.
Includes bibliographical references and index.
ISBN 0-412-48070-0
l. Flavonoids. I. Harborne, J.B. (Jeffery B.)
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 Contents

List of contributors page ix

Preface xi

THE ANTHOCYANINS
Dieter Strack and Victor Wray
l.l Introduction 1
1.2 Analytical procedures 3
1.3 Chemistry 6
1.4 Distribution 12
Acknowledgements 19
References 19

2 FLA VANS AND PROANTHOCY ANIDINS 23

Lawrence J. Porter
2.1 Introduction 23
2.2 Nomenclature 23
2.3 Structure and distribution 25
2.4 Methods of isolation and purification 46
2.5 Structural elucidation 47
2.6 Synthesis and reactions 50
2.7 Biosynthesis 52
References 53

3 C-GLYCOSYLFLAVONOIDS 57
Mauricelay
3.1 Natural sources and main taxonomic implications 57
3.2 Naturally occurring C-glycosylflavonoids 63
3.3 Identification of C-glycosylflavonoids 84
3.4 Biological properties 86
Acknowledgements 87
References 87
vi Contents
4 BIFLAVONOIDS AND TRIFLA VONOIDS 95
Hans Geiger
4.1 Introduction 95
4.2 Methods of identification 95
4.3 Synthesis 95
4.4 Natural occurrence ll5
References 115

5 ISOFLA VONOIDS 117

Paul M. Dewick
5.1 Introduction 117
5.2 Recent developments in isolation techniques 118
5.3 lsoflavones 120
5.4 lsoflavanones 154
5.5 Rotenoids 159
5.6 Pterocarpans 166
5.7 lsoflavans 180
5.8 Isoflavanols 184
5.9 Isoflav-3-enes 185
5.10 3-Arylcoumarins 185
5.11 Coumestans 189
5.12 Coumaronochromones 193
5.13 Coumaronochromene 195
5.14 a-Methyldeoxybenzoins 195
5.15 2-Arylbenzofurans 195
5.16 lsoflavonoid oligomers 197
5.17 Miscellaneous structures 202
5.18 Biosynthesis 202
5.19 Microbial transformations of isoflavonoids 206
References 212
Appendix A. Checklist of known natural isoflavonoid aglycones 217
Appendix B. Trivial name index for isoflavonoids 232

6 NEOFLAVONOIDS 239
Dervilia M.X. Donnelly and Gerard Boland
6.1 Introduction 239
6.2 Spectroscopic identification of neoflavonoids 239
6.3 4-Arylcoumarins 242
6.4 Oxidation of 4-phenylcoumarins: formation of quinones 248
6.5 3,4-Dihydro-4-arylcoumarins 250
6.6 Neoflavenes 253
6.7 X-ray crystal structures 253
6.8 Open-chain neoflavonoids 255
6.9 Conclusions 257
References 257

7 FLA VONES AND FLA VONOLS 259

E. Wollenweber
7.1 Introduction 259
7.2 Flavonoids with hydroxyl and/or methoxyl substitution 260
7.3 Flavonoids with complex substitution 285
7.4 Revisions and problematical structures 329
 Contents vii
7.5 Occurrence and localization of flavonoid aglycones 329
7.6 Comments of flavonoids in medicinal plants 330
Acknowledgements 330
References 330

8 FLAVONE AND FLAVONOL GL YCOSIDES 337

Christine A. Williams and Jetfrey B. Harborne
8.1 Introduction 337
8.2 Separation and purification 338
8.3 Identification 339
8.4 Sugars and other conjugates 339
8.5 New reports of flavone glycosides 344
8.6 New reports of flavonol glycosides 351
8. 7 Prenylated flavonol glycosides 360
8.8 Distribution patterns 360
References 365
Appendix A. Checklist of known flavone and flavonol glycosides 370

9 THE MINOR FLA VONOIDS 387

Bruce A. Bohm
9.1 General introduction 387
9.2 Chalcones 387
9.3 Aurones (including auronols) 399
9.4 Dihydrochalcones 401
9.5 Flavanones 406
9.6 Dihydroflavonols 419
9.7 Biological activity of selected minor flavonoids 426
9.8 Chemical synthesis of minor flavonoids 427
References 433

10 1H NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY OF

FLA VONOIDS AND THEIR GLYCOSIDES IN HEXADEUTERO-
DIMETHYLSULFOXIDE 441
K.R. Markham and H. Geiger
10. I Introduction 441
10.2 The solvent, DMSO-d 6 441
10.3 Two-dimensional nuclear magnetic resonance techniques for
structure assignment 442
10.4 The flavonoid nucleus 446
10.5 The glycosyl moiety 463
Acknowledgements 471
References 471
Appendix A. Examples of spectra 473

ll BIOSYNTHESIS OF FLA VONOIDS 499

Werner Helier and Gert Forkmann
11.1 Introduction 499
11.2 General overview 500
11.3 Enzyme acronyms 501
11.4 Pathways to precursors of flavonoid formation 504
11.5 Major steps of the flavonoid pathway 508
viii Contents
11.6 Steps to flavonoid modification 514
11.7 Formation of isoflavones and pterocarpans 526
References 531

12 GENETICS OF FLAVONOIDS 537

Gert Forkmann
12.1 Introduction 537
12.2 General genetics 538
12.3 Molecular genetics 552
References 558

13 FLA VONOIDS AND FLOWER COLOUR 565

Raymond Brouillard and Olivier Dangles
13 .1 Introduction 565
13.2 Yellow to colourless flavonoids 566
13.3 Anthocyanins 569
13.4 Molecular complexes 575
13.5 Investigations in vivo 585
References 586

14 FLAVONOIDS AND INSECTS 589

Jeffrey B. Harborne and Renee J. Grayer
14.1 Flavonoids in pollination biology 589
14.2 Flavonoids and insect feeding 598
14.3 Flavonoids and insect oviposition 608
14.4 Sequestration of flavonoids by insects 610
14.5 Flavonoids and insect pest management 613
References 617

15 THE IMPACT OF PLANT FLAVONOIDS ON

MAMMALIAN BIOLOGY: IMPLICATIONS FOR
IMMUNITY, INFLAMMATION AND CANCER 619
Elliott Middleton Jr and Chithan Kandaswami
15.1 Introduction 619
15.2 Effects of flavonoids on mammalian enzyme systems 620
15.3 Flavonoid modulation of immune and inflammatory cell functions 624
15.4 Effects of flavonoids on smooth muscle 635
15.5 Antitoxic and hepatoprotective effects of flavonoids 635
15.6 Effects of flavonoids on other cells 636
15.7 Antiviral effects of flavonoids 636
15.8 Endocrine effects of flavonoids 638
15.9 Effects of flavonoids on lipid peroxidation and oxyradical production 638
15.10 Cancer-related properties of flavonoids 639
15.11 Metabolism and disposition of flavonoids 645
References 645

PLANT SPECIES INDEX 653

SUBJECT INDEX 661

 Contributors

B.A. Bohm
Department of Botany, University of British Columbia, Vancouver, Canada

G. Boland
Department of Chemistry, University College Dublin, Eire

R. Brouillard
lnstitut de Chimie, Universite Louis Pasteur, Strasbourg, France

0. Dangles
lnstitut de Chimie. Universite Louis Pasteur, Strasbourg, France

P.M. Dewick
Department of Pharmaceutical Sciences, University of Nottingham, UK

D.M.X. Donnelly
Department of Chemistry, University College Dublin, Eire

G. Forkmann
Max-Planck-lnstitut fur Zuchtungsforschung, Koln, Germany

H. Geiger
Botanik, Universitiit des Saarlandes, Saarbrucken, Germany

R.J. Grayer
Department of Botany, University of Reading, UK

J.B. Harborne
Department of Botany, University of Reading, UK

W. Helier
GSF-BIOP, Neuherberg, Germany

M. Jay
Laboratoire de Biologie, Universite Claude Bernard, Villeurbanne, France

C. Kandaswami
Department of Medicine, University of Buffalo, New York, USA
X Contributors
K.R. Markham
Industrial Research Ltd, Lower Hutt, New Zealand

E. Middleton Jr
Department of Medicine, University of Buffalo, New York, USA

L.J. Porter
Chemistry Division, DSIR, Petone, New Zealand

D. Strack
lnstitut fur Pharmazeutische Biologie, Technische Universitiit Braunschweig, Germany

C.A. Williams
Department of Botany, University of Reading, UK

E. Wollenweber
lnstitut fur Botanik, Technische Hochschule, Darmstadt, Germany

V. Wray
lnstitutfor Pharmazeutische Biologie, Technische Universitiit Braunschweig, Germany
 Preface

This new work in The Flavonoids series provides a comprehensive review

of the primary scientific literature published between 1986 and 1991. It can
also be regarded as a third supplement to the original Flavonoids volume
published in 1975 under joint editorship with T.J. and H. Mabry. The first
supplement Advances in Research appeared in 1982 and covered the 1975-80
literature, while the second supplement Advances in Research Since 1980
was published in 1988 and covered the 1981-85 literature. All the chapters
in this volume are self-contained and provide a treatment of the most recent
literature against the background of what has gone before. Methodology of
flavonoid analysis has been largely omitted, since two key works have
recently been published in this area: Methods in Plant Biochemistry, vol. 1,
Plant Phenolics edited by J.B. Harborne (Academic Press, 1989) and
Carbon-13 NMR of Flavonoids edited by P.K. Agrawal (Elsevier, 1989).
There is, however, a chapter on 1 H nuclear magnetic resonance spectro-
scopy, since this has not been covered in recent years.
Chapters 1-9 review the chemistry of the new structures reported during
1986-91, in relationship to earlier known structures, and the authors discuss
the natural distribution of each class of flavonoid. Function is considered
here in relationship to the role of flavonoids in flower colour (Chapter 13),
their effect on man and other mammals (Chapter 15) and their effects on
insects (Chapter 14). Biosynthesis is discussed in Chapter 11, and recent
experiments in the molecular biology of flavonoids are included. An
important review of the genetics of flavonoid production (Chapter 12)
provides the first modern up-to-date account of the mode of inheritance of
anthocyanin pigments in plants.
As editor, I am once again deeply indebted to the contributors, who have
carried out their demanding assignments in an exemplary fashion. The pace
of flavonoid research has not slackened at all in recent years, and it is hoped
to produce a fourth supplement, probably in modified form, before the turn
of the century. l would therefore welcome comments, criticisms and
xii Preface
suggestions from readers about this continuing series. In the meantime, I am
most grateful to the staff of Chapman & Hall for their generous support and
interest in this endeavour.

JEFFREY B. HARBORNE
December, 1992
 1
The anthocyanins
DIETER STRACK and VICTOR WRA Y
l.l Introduction
1.2 Analytical procedures
1.3 Chemistry
1.4 Distribution
Acknowledgements
References
I. I INTRODUCTION
l.l.l Occurrence
Anthocyanins are the most important group of water-
soluble plant pigments visible to the human eye. With a
few exceptions, e.g. the betalains, they are universal
plant colorants and largely responsible for the cyanic
colours of flower petals and fruits. They may also occur
in roots, stems. leaves and bracts, accumulating in the
vacuoles (Wagner, 1982) of epidermal or subepidermal
cells. They are also found infrequently in the petal
mesophyll, e.g. in most members of the Boraginaceae
(Harborne, 1988b). In a recent study on the histological
distribution of anthocyanins in spathes of various
Anthurium species, specific distributions of
anthocyanin-containing cells of the ad- and abaxial
epidermis, hypodermis and mesophyll were observed
(Wannakrairoj and Kamemoto, 1990). The authors
suggest that these specific distributions might even be
of value in establishing intrasectional species relation-
ships. An interesting tissue compartmentation has been
reported by Miyazaki et al. (1991 ), who identified
different patterns of hydroxybenzoyl and hydroxy-
cinnamoyl acylated anthocyanins in the tuber periderm
and flesh, respectively, of two cultivars of ipomoea
batatas.
The Flavonoids: Advances in research since 1986. Edited by J.B. Harborne.
Published in 1993 by Chapman & Hall, London. ISBN 0412480700.
The anthocyanins are usually in solution within the
vacuole, although they may sometimes be located in
spherical vesicles, called 'anthocyanoplasts' (Pecket and
Small, 1980), in which structural modifications of the
C 15 nucleus may occur (Merlin et al., 1985). Develop-
ment of these vesicles, involving light-dependent antho-
cyanin accumulation, has been observed in cells of
Ipomoea batatas suspension cultures (Nozue and
Yasuda, 1985). They were also detected in vacuoles
from Vitis vinifera suspension cultures (Cormier et al.•
1990). Anthocyanoplasts are usually detected in
vacuoles, although they may also appear as mem-
branous vesicles in the cytoplasm (Nozzolillo and
Ishikura, 1988). The presence or absence of antho-
cyanoplasts in vacuoles can provide additional data
useful to taxonomic studies (Nozzolillo and McNeill,
1985), and has been exemplified with seedlings from 31
taxa of Phaseolus and Vigna. Anthocyanoplasts were
found in all tested members of the Vigna subgenus
Ceratotropis.
i.1.2 Biosynthesis
The enzymology of the late steps in anthocyanin forma-
tion is still incomplete. The compounds involved are
collectively named 'flavonoids'. More than 4000 known
flavonoid structures are divided into 12 classes on the
basis of the oxidation level of the central pyran ring.
In the pivotal step of flavonoid biosynthesis, ordinarily
4-coumaroyl-coenzyme A, derived from L-phenyl-
alanine in the 'general phenylpropanoid metabolism'
(Hahlbrock and Grisebach. 1975), enters a stepwise
condensation reaction with three molecules of malonyl-
coenzyme A to form the C 15 chalcone intermediate, the
tetrahydroxychalcone (naringenin chalcone). In the
following well known 'flavonoidal metabolism', the
2 The anthocyanins
actual precursor for anthocyanin formation, the flavan-
3,4-cis-diol (leucoanthocyanidin), is formed, which then
appears to be converted to the anthocyanidin flavylium
cation by a hydroxylation at C-2 followed by two
dehydrations. The enzymic conversion of leucoantho-
cyanidins to anthocyanidins, however, has not yet been
demonstrated, and nor has it been for the analogous
reaction with the flavan-4-ol leading to 3-desoxy-
anthocyanidins (Forkmann, 1991, this volume).
1.1.3 Function
Anthocyanins play a definite role in the attraction of
animals as pollination and seed dispersal factors, and
hence they are of considerable value in the coevolution
of these plant-animal interactions. Thus, anthocyanin
patterns in a given plant family might be more closely
correlated with the pollinator class than with taxonomy,
as has recently been discussed in the case of floral
anthocyanins among 87 Penstemon species (Scrophul-
ariaceae) (Scogin and Freeman, 1987).ln particular, the
aglycones may be related to pollination ecology, since
they constitute the chemical basis of flower colour in
angiosperms along with other colour-modifying factors
(Harborne, 1988a; Brouillard and Dangles, this
volume). Scogin (1988) found, in a survey of antho-
cyanidins of 146 species of bird-visited flowers, that
a 'bird-visitation pigment syndrome' was generally
uniform across wide geographical distances. The pig-
ment syndromes of perching and hovering birds were
distinct. There was no evidence for pelargonidin enrich-
ment in tropical floras, as suggested by Harborne
(1976), at least for hummingbird-visited flowers. The
author discusses, from advancement indices and pig-
ment frequencies, that floral adaptation for bird
visitation may not be accompanied by great evolutionary
advancement in pigment composition. In another survey
on anthocyanins of the genus Erythrina (Fabaceae), no
correlation between floral pigments and class of avian
pollinators could be detected (Scogin, 1991).
In contrast to flower pigmentation, the transient
appearance of anthocyanins in certain seedcoats, seed-
lings, leaves, stems and roots does not find an easy
explanation. Several speculations on the perception or
filtration oflight and response to stress factors, including
microbial attack, await further thorough studies.
Nicholson and coworkers (Nicholson et al., 1987, 1988;
Hipskind et al., 1990) found the 3-desoxyantho-
cyanidins apigeninidin and luteolinidin, as well as the
caffeic acid ester of apigeninidin 5-arabinoside, as
phytoalexins produced in response to microbial infec-
tion. Anthocyanins may also be important factors -
with other flavonoids (Harborne, 1988a)- in the resis-
tance of plants in insect attack. Cyanidin 3-glucoside was
shown to protect cotton leaves against the feeding of
tobacco budworm (Hedin et al., 1983). Several physio-
logical functions for anthocyanins in the general
metabolism of plants described in the literature
(McClure, 1975; Hrazdina, 1982) are still rather
obscure.
1.1.4 Application
Apparently harmless to health, anthocyanins have con-
siderable potential in the food industry as safe and effec-
tive food additives (Markakis, 1982). Their annual
world production has been estimated to reach 10000
tons from grapes alone (Timberlake, 1980). Compared
to the synthetic colorants, however, anthocyanins have
not been extensively used because of their instability
towards a variety of chemical and physical factors
(Markakis, 1982; Timberlake and Henry, 1986). The
increasing number of new polyacylated anthocyanins,
displaying marked stability, may prove to be of par-
ticular importance for food technology. There will be,
however, limitations in the supply of the respective plant
materials. Future successful biotechnological processes
using cell cultures for the production of these stable
anthocyanins is promising, since it can be assumed that
such cultures retain the capacity for production of their
'in vivo'-specific anthocyanins (Seitz and Hinderer,
1988). There are several reports over the last five years
supporting this assumption.
1.1.5 Research interests
Anthocyanins still evoke a challenge to the imagination
of (bio )chemists (Harborne and Grayer, 1988), who
continue to investigate the final steps of anthocyanidin
biosynthesis and the mechanisms of anthocyanin
deposition. The relationship between biosynthesis and
the occurrence of 'anthocyanoplasts' should also be
considered.
Anthocyanins played an important role in the classical
work of plant genetic studies (Aiston, 1964). And they
are still important markers for geneticists, as discussed
for example in a review on the inheritance of antho-
cyanin pigmentation in the cultivated Solanum
tuberosum (De Jong, 1991). Anthocyanins are also of
increasing interest to molecular geneticists and plant
breeders in the fascinating field of modern molecular
biology. A series of regulatory genes acting upon the
structural genes of enzymes involved in anthocyanin
biosynthesis have been identified (Dooner et al., 1991).
The techniques of gene transfer have allowed manipula-
tion of flower colour, e.g. the noted experiments with
Petunia (Forkmann, 1991). However, there are
numerous limitations, the most crucial being the
phenomenon of variegation and unstable expression of
the newly introduced genes (Forkmann, 1991 ), and con-
siderable effort is still required to elucidate the
mechanism of gene expression in plants.
There is also a growing interest in anthocyanin-
 Analytical procedures
producing cell cultures (Seitz and Hinderer, 1988), e.g.
cultures from Daucus (Dougall and Vogelien, 1990;
Hopp and Seitz, 1987; Ozeki and Komamine, 1986;
Ozeki et al., 1987, 1989; Takeda, 1988, 1990; Vogelien
et al., 1990; Zwayyed et al., 1991), Catharanthus (Hall
and Yeoman, 1986, 1987), Centaurea (Kakegawa et al.,
1987, 1991; Takahashi et al., 1991), Euphorbia
(Bahadur and Reddy, 1987), Perilla (Zhong et al., 1991;
further cell-culture references are also found here),
Petunia (Hagendoorn et al., 1991) and Vitis (Hirasuna
eta!., 1991; Table 1.3). In general, 'it is without question
that plant cell cultures have become a central, indis-
pensable vehicle in secondary metabolic research'
(Zenk, 1991).
1.1.6 Recent advances
The classical techniques in anthocyanin analysis are
still important (Strack and Wray, 1989). However,
methodological advances have been considerable within
the review period (1986-91, including some work from
1992). They include further developments of sophisti-
cated nuclear magnetic resonance (NMR) techniques, in
particular the use of two-dimensional (2D) homonuclear
and heteronuclear correlation techniques, mass spectro-
metry (MS), where the exploitation of the newer ioniz-
ation techniques of fast atom bombardment and ion
spray have been particularly successful, and its on-line
application in high-performance liquid chromatography
(HPLC).
The objective of the following sections is to
summarize the recent advances in analytical pro-
cedures, in structure elucidation and in work on
anthocyanin occurrence. In addition, some selected
earlier classic work will be cited in connection with
recent problems.
1.2 ANALYTICAL PROCEDURES
1.2.1 Extraction and chromatography
(a) Extraction and stability
Increasing numbers of reports on labile highly acylated
anthocyanins, especially those with aliphatic acids,
make it necessary to perform mild pigment extractions
with methanol or ethanol containing weak acids such as
acetic (Harborne and Boardley, 1985), tartaric (Philip,
1974) or citric (Main et al., 1978; Strack et al., 1986)
instead of HCI, the most widely used acidic component
in earlier work. Also, small amounts of more volatile
stronger acids, e.g. 0.5-3% trifluoroacetic acid (TFA)
for extractions of the most complex polyacylated antho-
cyanins found by Goto and coworkers, are applicable.
TFA can easily be removed during pigment concen-
3
tration. Generally this should be performed with care
to avoid acid-dependent pigment degradation, and it is
recommended that the genuine structures be confirmed
after concentration procedures and isolation of indi-
vidual compounds by cochromatography with the crude
ext•·'lcts.
tn short preparative extractions, the addition of an
acidic component is not always necessary. However, for
quantitative analysis, the extraction method should be
thoroughly checked for the particular plant material and
the particular pigments. In each case, the extraction
procedure for structure elucidation or for analyticaU
quantitative purposes has to be optimized and adapted
to the problem under consideration, including aware-
ness of possible artifactual results (Strack and Wray,
1989). Factors affecting anthocyanin stability during
extraction and purification, such as pH, temperature,
oxygen, light, enzymes, nucleophilic agents, sugar
derivatives and copigments, have recently been dis-
cussed by Jackman and Smith (1993).
(b) High-performance liquid chromatography
Classical chromatographic techniques, such as layer
chromatography (paper chromatography (PC) and thin-
layer chromatography (TLC)) and open column
chromatography (CC), which still play a major role in
analytical analyses of anthocyanin patterns and isolation
procedures, have recently been reviewed by us (Strack
andWray, 1989).
HPLC of anthocyanins in both analyticaVquantitative
and (semi)preparative applications is now standard.
Apart from the improved resolution of anthocyanin
patterns compared with other separation methods, the
simultaneous rapid monitoring of qualitative and
quantitative data is its own recommendation in a wide
range of applications, e.g. identification of cultivars
(HPLC fingerprints) or in biochemical work on antho-
cyanin metabolism.
There is no HPLC system that can solve all problems.
In each case the solvents and gradient profiles,
especially when dealing with complex natural mixtures
with a wide range of anthocyanin polarity, should be
optimized (Strack and Wray, 1989). Goiffon et al.
(1991) have studied the various parameters affecting
the retention of anthocyanins on a reversed-phase
column (C 18 ). They were able to establish rules
governing the chromatographic behaviour of antho-
cyanins that allow the prediction of non-overlapping
elutions.
From the vast number of published HPLC data, some
essential features are noteworthy (compare Harborne
and Grayer, 1988; Strack and Wray, 1989). The overall
polarity and the stereochemistry of the anthocyanins are
the key factors for separation on the most popular
reversed-phase materials (C 18-derivatized silica column
4 The anthocyanins
supports). The following separation factors are well
documented.
(i) Substitution (hydroxyl and methoxyl groups) of
the anthocyanidin. B-ring substitutions of the common
structures give the elution order delphinidin <
cyanidin < petunidin < pelargonidin< peonidin <mal-
vidin; hydroxyl groups increase, while methoxyl
groups decrease mobility. Depending on the solvent
system used, cyanidin/petunidin and peonidin/malvidin
are critical pairs to resolve.
(ii) Nature, position and number of sugars attached
to the anthocyanidins. In general, glycosylation
increases mobility in the order 3,7-diglycosides <
3,5-diglycosides < 3-glycosides (compare HPLC of
cyanidin diglucosides from orchid petals; Strack et al.,
1989). This is not a strict rule, since the nature of the
sugars can markedly affect pigment mobility, e.g.
3-galactosides elute earlier than 3-glucosides followed
by the 3-rutinosides. That HPLC successfully separates
3-glucosides and 3-galactosides, which is difficult to
achieve by PC or TLC, has made it possible to correct
some earlier misidentifications (Sakata et al., 1986).
(iii) Sugar acylation with phenolic acids (hydroxy-
cinnamic acids or hydroxybenzoic acids) or aliphatic
acids (e.g. malonic acid). Acylation increases retention
time. The polarities ofthese acids determine the order of
elution. Thus a caffeoyl conjugate elutes earlier than a
4-coumaroyl one. A malyl conjugate should elute earlier
than the corresponding malonylated pigment. And,
again, this is not a strict rule. Pigment conformation,
e.g. intramolecular copigmentation, has a strong effect
on retention times. This has recently been demonstrated
with hydroxycinnamic acid-acylated anthocyanins from
Daucus carota (Glassgen et al., 1992a). The unusual
elution sequence sinapoyl < feruloyl < 4-coumaroyl
trisaccharide of cyanidin observed by these workers
must be ascribed to intramolecular copigmentation.
HPLC coupled with a new sophisticated detection
system is shown in applications of photodiode-array
detection of anthocyanins (Andersen, 1985; Hebrero
et al., 1988, 1989; Hong and Wrolstad, 1990). This has
been one of the most important advances in HPLC in the
last ten years. Using this method, the sample is scanned
every few milliseconds, generating ultraviolet/visible
(UVNis.) spectral data and calculating the absorbance
maximum. In addition, the purity of each peak can be
examined, providing different spectra for the possible
impurity and the pure component. HPLC-photodiode-
array detection has recently been successfully used
in analyses of the anthocyanins from cell suspension
cultures of Daucus carota (Glassgen et al., 1992a),
applying the classical strategy of UVNis. spectroscopic
interpretations (Strack and Wray, 1989).
Another recent methodological development is the
direct coupling of HPLC to a mass spectrometer
{HPLC-ion spray mass spectrometry, see below).
Loading samples up to 5 ,ul with flow rates up to
200 ,ul min - l on narrow-bore reversed-phase columns
(e.g. 100 X 2mm) and using ion spray for interfacing
HPLC with MS gave excellent results for the structure
determination of anthocyanin mixtures (Glassgen et al.,
1992b).
1.2.2 General identification and
miscellaneous methods
Non-spectroscopic methods such as hydrolysis and
HPLC are valuable tools (Strack and Wray, 1989),
which are even applicable when dealing with highly
complex pigments (Shi et al., 1992a). These authors
identified a cyanidin triglucoside with three molecules
of ferulic acid and an extra terminal glucose; the ratios
of acyl groups to cyanidin were determined by quanti-
tative HPLC using internal standards. HPLC analysis of
polyacylated (hydroxycinnamic acids) anthocyanins
with a photodiode-array detector enables the deter-
mination of the ratios of the absorbance between the
maxima of the UV and visible regions and thus allows
the estimation of the number of acyl groups of individual
pigments from the chromatogram (ldaka et al., 1987a).
Although few new data on methods other than NMR
spectroscopy and MS have become available in the
review period, the use of infrared (IR) spectroscopy,
resonance Raman (RR) spectrometry and circular
dichroism (CD) absorption spectroscopy has been
reviewed {IR, RR, CD- Strack and Wray, 1989; RR-
Merlin et al., 1987; CD- Goto et al., 1986; Goto, 1987).
CD spectra have been obtained from living flower petals
and offer an insight into details of the association and
conformational properties of the anthocyanin pigments
in situ (Hoshino, 1986). Isotachophoresis has been
applied for the analysis of anthocyanins with very similar
structures (Hiraoka and Yoshitama, 1986; Tsuda and
Fukuba, 1989). Merlin (1990) reports on developments
of IR and RR from improvements in Fourier-transform
spectrometers.
1.2.3 Spectroscopic methods
(a) Nuclear magnetic resonance spectroscopy
The continuing rapid developments in instrumentation,
in particular those involving nuclear magnetic resonance
(NMR) spectroscopy and mass spectrometry (MS), over
the last five years, have given considerable impetus to
structural elucidation in all fields of natural product
chemistry. For the anthocyanins this has meant that
structures as large and complex as the heavenly blue
anthocyanin from Ipomoea tricolor or ternatin A 1 from
Clitoria ternatea (see (1 .6)) have been determined. In
general, such determinations do not require either
 Analytical procedures
lengthy derivatizations or degradations, although some
of the classic techniques allow ready structure con-
firmation.
We have reviewed elsewhere the physical techniques
currently available for structural elucidations, and
emphasis was placed on the type of information avail-
able from the various types of spectroscopy (Strack and
Wray. 1989). Here we consider the more recent
advances. Modern one- and two-dimensional (ID and
2D) NMR spectroscopy continues to be the most power-
ful method for structural elucidation in solution. The
increasing availability of high-field superconducting
magnets (up to 14 T; T =testa) allows detection of ever-
decreasing amounts of compounds, and, providing pure
samples can be obtained, the unambiguous structures of
compounds in the low milligram range can be success-
fully investigated. Spectra from lD and 2D 1 H
homonuclear correlation spectroscopy (COSY) are now
routinely used for characterization of spin systems and,
in conjunction with the newer 2D total correlation
spectroscopy (TOCSY), also known as homonuclear
Hartmann-Hahn spectroscopy (HOHAHA) (Summers
et al., 1986), allow ready identification of the number
and nature (substitution pattern, configuration and/or
conformation) of sugar moieties and the aromatic
system of substituents and aglycones (Van Calsteren
et al., 1991). Often the 1 H shift assignments can be con-
firmed by the observation of characteristic long-range
couplings in the 2D COSY spectrum; in particular, H-6
can be distinguished from H-8 as the latter shows a small
coupling to H-4 (Glassgen et al., 1992a). Substituent
positions on the aglycones and sequential fragment
information have been obtained in numerous cases
by the use of lD 1H nuclear Overhauser difference
spectroscopy (Kondo et al., 1987; Strack and Wray,
1989) or from 2D nuclear Overhauser enhancement
spectroscopy (NOESY) (Terahara et al., 1990c).
More recently, in those cases where larger amounts of
compound were available. lD 13 C and 2D heteronuclear
correlation spectroscopy have been used to gain such
information. The 13C shifts belonging to protonated
carbons have been assigned b~ 2D correlation with the
1 H shifts via 1J(CH) using 3 C detection (Andersen
et al., 199la, b) or the more sensitive inverse 1H detec-
tion (Van Calsteren et al., 1991). Subsequent long-range
correlations via 2J(CH) and 3J(CH), again via 13 C detec-
tion (COLOC; e.g. Andersen et al., 199la) or the more
satisfactory 1 H detection (Van Calsteren et al., 1991),
usually provide an overdetermined system of corre-
lations from which the unambiguous structure can be
deduced. As a consequence of these and other investi-
gations, a considerable number of valuable 13 C shift data
for various substituted anthocyanidins are now avail-
able, and these are summarized in Table 1.1.
Fast interconversion of the quinonoidal bases and
carbinol pseudobases, via the flavylium cation, with
5
subsequent ring opening to give the Z- and £-chalcone
pseudobases, was demonstrated by 1H NMR spectro-
scopy for malvidin 3-glucoside (Cheminat and
Brouillard, 1986; Mistry et al., 1991) and 3,5-diglucoside
(Santos et al., 1992). Variation of the 1 H chemical shifts
of malvidin 3,5-diglucoside with pH and concentration
has been used to study the self-association of the
quinonoidal bases (Hoshino, 1991). The observation of
negative nuclear Overhauser effects (NOEs) for H-4
and H-6 at room temperature upon irradiation of the
anomeric protons, and normal positive NOEs at 60°C
was ascribed to destacking of the anthocyanin with
subsequent increased tumbling at the higher tempera-
ture. A similar phenomenon has been observed in 2D
NOESY spectra (Nerdal and Andersen, 1991).
Although various models appear to be compatible with
the NMR chemical shift and CD spectroscopic data,
recent quantitative 2D NOESY data, used as distance
constraints in a distance geometry algorithm, indicate
a head-to-tail model (Nerdal and Andersen, 1991) in
contrast to previously proposed models (Go to et al.,
1986; Goto, 1987). Direct evidence of intramolecular
stacking has been afforded by the observation of long-
range NOEs between the anthocyanidin and aromatic
acid moieties in diacylated (Goto et al., 1986) and
monoacylated compounds (GUissgen et al.. 1992a;
Yoshida et al., l99Ia). 1 H chemical shift changes and
UVNis. spectroscopy have been used to investigate a
comprehensive number of intermolecular copigmen-
tation interactions between anthocyanins and a variety
of natural phenolics, caffeine, theophylline, adenosine
5'-triphosphate (ATP), deoxyribonucleic acid (DNA)
and ribonucleic acid (RNA) (Mistry et al., 1991). and
the self-association of anthocyanidin 3,5-diglucosides
(Hoshino, 1992). Further details of these processes will
be found in Chapter 13.
(b) Mass spectrometry
Fast atom bombardment mass spectrometry (FAB-MS)
is currently the method of choice for mass deter-
mination of the anthocyanins (for review see Strack
et al., 1989). It is particularly useful in those situations
where the NMR method encounters characterization
difficulties with substituents such as malonyl and oxalyl
groups (Strack et al., 1986). The recent introduction
of the alternative ion spray (aerospray) (Bruins et al.,
1987) soft-ionization technique (IS-MS) also produces
[M]+ ions in high abundance directly from solutions
of anthocyanins, which allows rapid determination of
the molecular mass of the pigment. In combination with
tandem MS (MS/MS), it allows a fast and convenient
method for the determination of the anthocyanin
aglycone; and additionally. combined with liquid
chromatography (HPLC), provides a rapid and sensitive
method for the identification of a series of anthocyanins
 6 The anthocyanins
Table 1.1 Representative 13C chemical shifts•t of the anthocyanidin moieties of anthocyanins 1-8 in two mixed solvents: deuterated
dimethylsulfoxide (DMSO-d 6 )/HCI (i) and CD3 0D/CF3 C0 2 H (ii)
Cpdlsolv. 2 3 4 5 6 7 8 9

1/(i) 161.3 143.7 134.3 157.6 102.7 169.0 94.0 156.0

2/(i) 161.4 144.1 134.7 157.7 102.5 168.6 94.1 155.7
2/(ii) 164.36 145.64 137.03 159.55* 103.50 170.56 95.19 157.75"
3/(ii) 164.81 145.82 135.8 156.83* 106.03 169.62 97.50 156.90*
4/(i) 161.1 144.1 134.4 157.6 102.5 168.4 94.0 155.7
5/(ii) 164.19 145.49 137.35 159.29 103.42 170.7 95.24 157.86
6/(ii) 163.79 146.09t 134.08 156.89* 105.54 169.73 97.55 156.61*
7/(ii) 164.55 146.79 136.16 156.91 105.86 169.73 97.61 157.37
8/(ii) 163.29 145.74 138.22 158.12 103.66 171.3 95.76 159.46
Compounds 1-8 are shown below

Cpd C-3 C-5 C-7 C-3' C-4' C-5'

l 0-Sugar OH OH H OH H
2 0-Sugar OH OH OH OH H
3 0--Sugar 0-Sugar OH OH OH H
4 0-Sugar OH OH OH OH OH
5 0-Sugar OH OH OMe OH H
6 0-Sugar 0-Sugar OH OMe OH OH
7 0-Sugar 0-Sugar OH OMe OH OMe
8 0-Sugar OH OH 0-Sugar OH 0-Sugar
•t Assignment of signals in row interchangeable.
:j: I, Andersen (1988b); 2, Andersen, O.M., Aksnes, D.W., Nerdal, W. and Johansen, 0.-P. (private communication); 3, Van Calsteren,
M.-R., Cormier, F., Do, C. B. and Laing, R.R. (private communication); 4, Strack et al. (1986); 5, Johansen et al. (1991); 6, Andersen,
O.M., Opheim, S., Aksnes, D.W. and Froystein, N.A. (private communication); 7, Terahara eta/. (1990c).

in complex mixtures (Gliissgen et al., 1992a, b). Ion
spray techniques appear to be ideal for thermolabile
compounds such as anthocyanins - and also for the
analogous pigments, the betalains in members of the
Caryophyllales (Heuer et al., 1992). The alternatives
of electrospray {Whitehouse et al., 1985) and thermo-
spray (Biakeley and Vestal, 1983) are also of interest in
analysis of natural products.
Two MS/MS experiments are useful in IS-MS situ-
ations. A daughter-ion spectrum of each individual peak
in the spectrum is recorded to identify the anthocyanin
peaks in the spectrum by the detection of [antho-
cyanidin]+ fragments; and parent-ion spectra of the
[anthocyanidint are recorded to detect selectively
all anthocyanins containing this aglycone. These
methods have been successfully used to identify a series
of cyanidin-containing anthocyanins from Daucus
carota (Giiissgen et al., 1992b) and two gallic acid-
containing anthocyanins from Victoria amazonica
(Strack et al., 1992). Tandem FAB-MS of anthocyanins
with crude extracts from cell cultures of Vitis vinifera
(Laing and Cormier, 1990) has been employed for the
identification of anthocyanins (Table 1.3) without
chromatographic purification of the individual
components.
1.3 CHEMISTRY
1.3.1 General aspects
Anthocyanins are water-soluble glycosides and acyl-
glycosides of anthocyanidins, which are polyhydroxyi
and polymethoxyl derivatives of 2-phenylbenzo-
pyrylium (flavylium cation). They belong to the
phenolic class of flavonoids with the typical A-ring
benzoyl and B-ring hydroxycinnamoyl systems, with the
carbon numbering system shown in the structures of
Table 1.2. There are almost 300 naturally occurring
structures.
Besides the basic flavylium cation, the 'primary
structure', anthocyanins occur in aqueous acidic
solution as 'secondary structures', a mixture of the
quinonoidal base(s), the carbinol pseudobase and the
chalcone pseudobase (Brouillard, 1982). In addition,
there are four possible stabilization mechanisms leading
 Chemistry 7

10 I, 2' J' 4' 5' 6' Ref.:t

111.7 119.2 134.4 117.0 164.3 117.0 134.4 I

111.8 119.5 117.4* 146.2 154.4 116.8* !26.7 1
! !3.45 !2!.31 118.56 147.41 155.78 117.48 128.22 2,3,4
113.13 121.13 118.71 147.78 156.73* 117.66 129.71 5
111.7 118.3 111.2 146.5 143.1 146.5 I I 1.2 I
113.63 121.14 115.19 149.51 156.37 117.55 128.84 3
113.03 119.58 109.52 149.76t 147.55t 146.16t 114.03 6
I 13.60 119.66 111.07 149.86 147.19 149.R6 11!.07 3
114.33 120.27 117.30 147.69 147.19 147.69 117.30 7

Compound

Pelargonidin 3-0-f:l-o-glucopyranoside
Cyanidin 3-0-f:l-o-glucopyranoside
Cyanidin 3- 0-/3-( 6- 0-( E-4-cou maroy I)-2 -(/3-o-xy lopyranosyl )-/3-o-gl ucopyranosi de 1-5- 0-/3-o-glucopyran aside
Delphinidin 3-0-,8-o-glucopyranoside
Peonidin 3-0-f:l-o-glucopyranoside
Pe tunidin 3-0-,8-16-0-(4-0-.E-4-coumaroyl-a-L.-rhamnopyranosy1 )-/3-o-gl ucopyranoside j-5-0-,8-o-g1 ucopyranoside
Ma1vidin 3,5-0-di-f:l-o-glucopyranoside
De1phinidin 3,3' ,5' -tri-O-f3-o-g1ucopyranoside

to 'tertiary structures', such as self-association, inter-
and intramolecular copigmentation, and metal complex
formation. Copigmentation is probably the most
efficient protection mechanism, avoiding nucleophilic
attack of the quinonoidal structures by water in the
slightly acidic medium of most vacuoles.
In addition to the 17 anthocyanidins listed previously
(Harborne and Grayer, 1988), o· • new 6-hydroxyl
derivative has been found. Besides the known
6-hydroxypelargonidin (aur"ntinidin) and 6-hydroxy-
cyanidin, the delphinidin analogue has been shown to
occur (Saito et al., 1988a). In an investigation of various
cultivars of Alstroemeria species, it was found that
6-hydroxydelphinidin 3-rutinoside eo-occurs only in
pink-purple coloured flower petals with the 3-rutino-
sides of delphinidin, cyanidin and 6-hydroxycyanidin.
According to the anthocyanin types present, two other
groups of cultivars could be defined. These are one
group composed of cyanidin and 6-hydroxycyanidin
glycosides (ivory to orange-red in colour) and a second
composed of cyanidin and delphinidin glycosides
(crimson-pink).
The different colour variations of anthocyanins are
only partly due to their substitution patterns. The basic
chromophores are the scarlet pelargonidin, the crimson
cyanidin and the purple delphinidin (Harborne, 1988b).
In an HPLC screening of anthocyanins in varieties of Iris
ensata, Yabuya (1991) found that the formation of
purple, red-purple. blue-purple, light purple and pink
flowers depends upon the contributions of malvidin,
petunidin and delphinidin to the major anthocyanins.
Recent results on the possible in situ structures of
anthocyanins derived from stabilization mechanisms
such as self-association, inter- or intramolecular eo-
pigmentation, and complex metallo structures give a
more realistic view of the contribution of anthocyanin
structure to colour (Goto and Kondo, 1991). Lu et al.
(1992a) showed that the flower colour of Pharbitis nil
gradually shifts to the blue region with increasing
numbers of caffeic acid residues in polyacylated
pelargonidin glycosides.
1.3.2 Glycosides
Anthocyanins occur as 3-monosides, 3-biosides and
3-triosides as well as 3,5-diglycosides and more rarely
3,7-diglycosides associated with the sugars glucose,
galactose, rhamnose, arabinose and xylose. Glycosides
containing the latter two pentoses have now been
described in about a dozen new reports (Table 1.3). The
complex substitutions of the polyacylated lobelinins (see
(1.5)) and ternatins (see (1.6)) are noteworthy. A few
more reports of the more rarely found substitution at
the 7-hydroxyl have appeared from members of the
Commelinaceae and Orchidaceae (Table 1.3).
8 The anthocyanins
Table 1.2 Structures of naturally occurring anthocyanidins

(!I)

Substitution pall ern •

Anthocyanidin 3 5 6 7 3' 5'

Common basic structures

Pelargonidin (Pg)t OH OH H OH H H
Cyanidin ( Cy) OH OH H OH OH H
Delphinidin (Dp) OH OH H OH OH OH
Common methylated structures
Peonidin (Pn) OH OH H OH OMe H
Petunidin (Pt) OH OH H OH OMe OH
Malvidin (Mv) OH OH H OH OMe OMe
Rare 3-desoxy structures
Apigeninidin (Ap) H OH H OH H H
Luteolinidin (Lt) H OH H OH OH H
Tricetinidin (Tr) H OH H OH OH OH
Rare hydroxy/ated structures
Aurantinidin (Au) OH OH OH OH H H
6-Hydroxy-Cy(60HCy) OH OH OH OH OH H
6-Hydroxy-Dp (60HDp) OH OH OH OH OH OH
Rare methylated structures
5-Methyl-Cy ( SM Cy) OH OMe H OH OH H
Rosinidin (Rs) OH OH H OMe OMe H
Pulchellidin (Pl) OH OMe H OH OH OH
Europinidin (Eu) OH OMe H OH OMe OH
Hirsutidin (Hs) OH OH H OMe OMe OMe
Capensinidin (Cp) OH OMe H OH OMe OMe

*Numbering according to the anthocyanidin carbon numbering system in (1.1).

tAbbreviation (used in Table 1.3).

A new monoglycoside, cyanidin 3-xyloside, has been
found in fruits of Aronia melanocarpa (Rosaceae)
and eo-occurs with the major components, cyanidin
3-galactoside and 3-arabinoside (Oszmianski and Sapis,
1988). Cyanidin 3-xyloside has also been found recently
in the fruits of apple (Mazza and Velioglu, 1992). In the
anthocyanins, rhamnoglucosides usually occur as
the rutinoside (rhamnosyl-1,6-glucoside); however,
Andersen ( 1988b, 1989b) reported the neohesperido-
side (rhamnosyl-1 ,2-glucoside) as a new disaccharide
found in pigments of the receptacles of members of the
Podocarpaceae.
There is one new report on the occurrence of rare
glucuronosyl derivatives, namely cyanidin 3-malonyl-
glucuronosylglucoside in Bellis perennis (Saito et al. ,
1988b). This pigment, along with cyanidin 3-malonyl-
glucoside, is more stable in neutral solution than
cyanidin 3-glucoside, but less stable than cyanidin
3-glucuronylglucoside.
1.3.3 Acylglycosides
Recent advances in analytical procedures (Strack and
Wray, 1989) have resulted in numerous reports on
anthocyanins variously acylated with hydroxycinnamic
acids, hydroxybenzoic acids, acetic acid and some
aliphatic dicarboxylic acids, such as malonic, malic,
oxalic and succinic acids (Harborne and Grayer, 1988).
 Chemistry
(a) Acylation with phenolic acids
The common aromatic acyl groups most widely found
are the hydroxycinnamic acids, 4-coumaric, caffeic,
ferulic and sinapic acids. The latter has been found more
often recently, as have also the hydroxybenzoic acids.
The unsubstituted cinnamic acid, which is rarely
found in natural products, has now been found for the
first time as the acyl moiety of peonidin 3-sophoroside
(Bobbio et al., 1988). This cinnamoyl derivative has
been isolated from flowers of Tabebuia impetiginosa
(Bignoniaceae), but awaits complete spectroscopic
characterization.
Cyanidin 3- (sinapoylxylosylglucosylgalactoside),
which has been described as being the major pigment in
Daucus carota (Afghan carrot cultivar) cell suspension
cultures (Harborne et al., 1983), has been identified
by FAB-MS (Harborne and Self, unpublished) as a
branched trisaccharide with the sinapoyl moiety located
on the glucose residue. This structure has now been sub-
stantiated and unambiguously elucidated by NMR and
IS-MS {Gliissgen et al., 1992a,b) to be cyanidin 3-0-
[2"-0-{J-xylopyranosyl-6"- 0-(6' '' -0-sinapoyl-{J-gluco-
~yranosyl)-{J-galactopyranoside] along with the respec-
tive feruloyl and 4-coumaroyl derivatives as minor con-
stituents. Using on-line HPLC/IS-MS and tandem MS,
the presence of these pigments, along with some other
components, has been demonstrated in the roots of the
Afghan carrot cultivar and in the central flowers of
wild carrot (Gliissgen et al. , 1992b).
Three new mono- and disinapoylglucosides of
cyanidin, alatanins A, Band C (Fig. 1.1), were isolated
from the tuber of purple Dioscorea alata (Yoshida et al.,
OR 1
OH
(J .2)
Fig. 1.1 Structures of alatanins A, Band C:
R' R2 R'
AlataninA Glc-6-Sin Glc Glc
AlataninB Glc-6-Sin Glc H species and cultivars (Ji et al., 1992). Gallic acid-acylated
AlataninC H H H delphinidin and cyanidin 3-galactosides have been found
The abbreviations used in the structures in this chapter are:
Ara = arabinose; Caf = caffeic acid; Coum = 4-coumaric
acid; Glc = glucose; 4HBA = 4-hydroxybenzoic acid;
Rha = rhamnose; Sin = sinapic acid.
9
1991b). These pigments were very stable in neutral
aqueous solution, which is ascribed to the intra-
molecular stacking of sinapic acid and to the chiral self-
association of the anthocyanidin nuclei (Yoshida et a!
1991a). ·'
Usually, the hydroxycinnamic acid moieties of secon-
dary products are present in the rrans or E form. This
comes directly from the phenylalanine ammonia-lyase
(PAL) derived non-oxidative elimination of NH 3 from
L-phenylalanine involving the pro-3S hydrogen (Hanson
and Rose, 1975) with the formation of a double bond to
give £-cinnamic acid. This product is subject to a series
of hydrox~lation and methylation reactions, resulting in
the formation of the common E-( 4-coumaric), £-caffeic
E-ferulic and E-sinapic acids. During the extraction pro~
cedures of hydroxy cinnamic acid conjugates, there is the
possibility of EIZ isomerization, which can easily be
demonstrated by irradiation with UV light (366 nm) of
the respe~tive pigments in vitro (Yoshida et al., 1990).
Whereas Isolated polyacylated anthocyanins are found
predominantly esterified with E-hydroxycinnamic acids,
the monoacylated ones give in addition appreciable
portions of the Z form, obviously as a result of EIZ
isomeriz~tion (Goto and Kondo, 1991). A possible
explanatiOn for the lack of isomerization in the former
case might be_ the more rigid conformation of the high-
molecular-weight polyacylated anthocyanins.
Anthocyanins acylated with hydroxy benzoic acids are
rarely fo~n_d. A 3-soph<_Jroside-5-glucoside of cyanidin
and peomd_m acylated With 4-hydroxybenzoic acid along
With caffeic and ferulic acids was identified from
Ipomoea batatas cell cultures (Nozue et al., 1987). A
delphinidin derivative containing four molecules of
4-hydroxybenzoic acid (cyanodelphin, see {l.JO)) has
been found m flowers of Delphinium hybridum (Kondo
et al., 1991 ). Two complex pelargonidin and delphinidin
derivatives containing five molecules of sugar and two
molecules of 4-hydroxybenzoic acid, the latter linked
through the 4-hydroxy group and the carboxylic group to
the sugar moieties, in flowers of Campanula medium,
ha~e been identified by thorough spectroscopic investi-
gations (Terahara et al., 1990a). From the periderm
of lp~moea bata~as_, 4-hydroxybenzoylated caffeoyl-
glycosldes of cyamdm were identified (Miyazaki et al. ,
1991). A cyanidin 3-glucosyllathyroside (branched)
acylated with 4-hydroxybenzoic acid has been found in
suspension cultures of Daucus carota (Gliissgen et al.,
1992a). Recently cyanidin 3-glucoside and 3-rutinoside
acylated with gallic acid (3,4,5-trihydroxybenzoic acid)
have been found in red spring leaves of various Acer
in leaves of Victoria amazonica (Strack et al., 1992).
Other galloylated flavonoids, e.g. flavonol galloyl-
glycosides, are well known (Harbome and Grayer
1988). '
10 The anthocyanins
(b) Acylation with acetic acid OGtc...L Caf

Anthocyanins acylated with acetic acid have been found ~ OH

in the skin of grapes (Vitaceae) (see previous editions of
The Flavonoids), and more recently in the leaves of Vitis
~I
vinifera (Dame and Glories, 1988) as well as in berries
of Eurya japonica (Theaceae) (Terahara et al., 1988).
Yamaguchi et al. (1990) reported the first observation OH
,,
OGtc...L Ara 2... Caf

of an acetylated anthocyanin in plants of the Asteraceae,
in flowers of Zinnia elegans. Very recently, Toki et al.
(199lc) found not only pelargonidin 3-acetylglucoside in
flowers of a Verbena hybrida cultivar (Verbenaceae),
but also, for the first time, an anthocyanin diacetate,
delphinidin 3,5-di-(6-acetylglucoside), in another
Verbena cultivar (Toki et al., 199la).
(c) Acylation with aliphatic dicarboxylic acids
Takeda et al. {1989) discovered a new malonylated
anthocyanin in flowers of Malva sylvestris, i.e. malvidin
3-( 6"-malonylglucoside )-5-glucoside (malonylmalvin).
Thus the classic source of malvin actually contains this
pigment in a malonylated form. An electrophoretic
survey showed that flower pigments in other species of
Malvaceae are also zwitterionic. The first description of
malylated anthocyanins in flowers of Dianthus species
(Terahara et al., 1986) has now been extended to various
cultivars, proving the wide occurrence of pelargonidin
and cyanidin 3-malylglucoside in these plants, along
with pelargonidin and cyanidin 3-glucosides and 3,5-
diglucosides (Ledeme, 1991). Further studies on the
occurrence of oxalylglucosides in European orchids
(Strack et al., 1986, 1989) have led to the tentative
identification of cyanidin oxalyl 3,5-diglucoside, oxalyl
3,7-diglucoside and the copigmented cyanidin oxalyl
3,5-diglucoside-kaempferol 7-glucoside.
Caf
(I 3) Zebrimn
3,5-diglucosides bearing in addition 4-coumaric or
caffeic acid (Fig. 1.2).
Another complex 'heteroacylated' pigment from
bluish violet petals of Lobelia erinus (Kondo et al.,
l989c) has been shown to be acylated with two and three
different hydroxycinnamic acids and additionally
acylated with one malonic acid {lobelinin A and B
(1.5)).
The structures of four of the six known blue ternatins
from flowers of Clitoria ternatea (Saito et al., 1985),
tematins Al, A2, B l and Dl, have now been un-
ambiguously identified (Terahara et al., t 989a, 1990b-e;
Kondo et al., 1990a). Among these, ternatin Al (1.6)
is the largest monomeric anthocyanin known to date
(Terahara et al., l990e). It is composed of delphinidin
with seven molecules of glucose, four molecules of
R'
OH
HO
,,
R 1 ~Gic0

R4 (/ 4)
1.3.4 Polyacylglycosides
Fig. 1.2 Structures of Salvia anthocyanins:
The heavenly blue anthocyanin has now been com-
pletely characterized by means of the 1 H NMR spectro- R'
scopy NOE method, which enabled unambiguous
assignment of all proton signals of the sugar moieties. Salvianin H OH Malonyl Malonyl
This was not possible by the previously applied 2D Monardaein H H Malonyl Malonyl
COSY method (Kondo et al. , 1987). Monodemalonyl- H OH Malonyl H
salvianin
From violet leaves of Zebrina pendula (Idaka et al., H
Bisdemalonylsalvianin H OH H
1987d) a complex pigment, zebrinin (1.3), has been Monodemalonyl- H H Malonyl H
isolated, which is composed of cyanidin with three monardaein
molecules of glucose, one molecule of arabinose and Salviadelphin OH OH Malonyl Malonyl
four molecules of caffeic acid. Among the typical Monodemalonyl- OH OH Malonyl H
pigments acylated with both aliphatic and phenolic salviadelphin
acids, such as malonylawobanin, monardaein or Bisdemalonyl- OH OH H H
cinerarin (Harborne and Grayer, 1988), are those salviadelphin
isolated from scarlet, purple and blue flowers of Salvia Dimalonylawobanin OH H Malonyl Malonyl
Malonylawobanin OH H Malonyl H
splendens (Kondo et al., 1989b). These are mono- and H Malonyl H
Salviamalvin OMe
dimalonylated pelargonidin, delphinidin and malvidin
 Chemistry 11
OG!c-Lcar

HO

Malonyl .E.. GlcO

(1.5) Lobe linin A. R = H

Lobelinin B, R =OMe

OGle 2-Coum..:!.. Glc 11... Coum 4

OH

HO
@)
OGic2-Coum..:Loic

OH
'-----+@
(I 6) Tematin A I

OMe
4-coumaric acid and one molecule of malonic acid, with
a molecular-ion peak at mlz 2107 as a flavylium ion
corresponding to C96 H 107 0 53 +in its FAB-MS spectrum.
Four acylated anthocyanins were isolated from HO
flowers of red-purple (Lu et al., 1992a) and violet-blue
cultivars (Lu et al., 1992b) of Pharbitis nil and identified
as mono-, di- and tricaffeoylglucosides of pelargonidin
and peonidin 3-sophoroside-5-glucoside, respectively
(Figs 1.3 and 1.4}. The caffeic acid residues were shown
to be responsible for the stability of these pigments, with
increasing stability in the order of increasing acyl sub-
stitution.
Two new anthocyanins, campanin and rubro- (1.8)
campanin (1.9}, were isolated from the flowers of
Campanula medium (Terahara et al., 1990f) and Fig. 1.4 Pigments in violet-blue cultivars of Pharbitis nil
(structure 5 = 'heavenly blue anthocyanin').
identified as trihydroxybenzoylated 7-tri-glucosides
of delphinidin and pelargonidin 3-rutinosides. A similar,
but more complex, polyhydroxybenzoylated antho- cyanin, cyanodelphin (1.10), was isolated from blue
petals of Delphinium hybridum (Kondo et al., 1991)
OH
and identified as delphinidin containing four molecules
of 4-hydroxybenzoic acid, six molecules of glucose and
HO
R

OGle

R
Gk ..Lcar..2...o1~ +
-·----0 OH
OGfc...LRha

(I 7) (1 9) Campanin, R =OH
Fig. 1.3 Pigments in red-purple cultivars of Pharbitis nil. Rubrocampanin. R H=
12 The anthocyanins
OH
DH
Glc..i.. 4HBA..!!... GlcO
I• ll
4HBA Glc
4 b 11
Glc- 4HBA- Glc OH
I•
4HBA
(l I 0) Cyanodelphin
one molecule of rhamnose. This compound was very
stable in neutral aqueous solution.
1.3.5 Metalloanthocyanins
The earlier discussed anthocyanin metal chelates
(Shibata et al., 1919) are highly associated complexes of
metalloanthocyanins containing flavones as copigments
(Goto, 1987). However, other phenolics may also occur
as copigments, such as caffeoylquinic acid in the
aluminium complex with delphinidin 3-glucoside in
Hydrangea macrophylla (Takeda et al., 1985a, b).
The complex metalloanthocyanins reach M, values
near 10000, as in the case of commelinin, which occurs
in the deep blue petals of Commelina communis and is
a chelate complex of two atoms of magnesium and six
molecules each of malonylawobanin, i.e. delphinidin
3-[6"-(4-coumaroyl)glucoside)-5-(6"-malonylglucoside),
and flavocommelin, i.e. 7-methylisovitexin 4' -gluco-
side. K+ is possibly the in vivo counter-cation. Its M,
is about 9100 (Tamura et al., 1986).
Another metalloanthocyanin was found in the blue
cornflower, Centaurea cyanus, called protocyanin
(Bayer, 1958, 1966). This pigment has been purified by
Go to et al. ( 1986) and proposed to be composed of six
molecules of cyanidin 3-(6" -succinylglucoside)-5-gluco-
side, six molecules of apigenin 4' -(6"-malonylglucoside )-
?-glucoside, and Fe and Mg ions (M, 8500), with a struc-
ture similar to that of commelinin (Goto, 1987).
1.4 DISTRIBUTION
Anthocyanins identified during 1986-91, including some
that were identified in 1992, are collected in Table 1.3.
For 1986 only those are included which were not listed
in the previous edition. As was pointed out there
(Harborne and Grayer, 1988), it is still difficult to use
anthocyanins with complete confidence as taxonomic
markers because only relatively few plants have been
properly surveyed. In the following section some recent
results on the systematic distribution of anthocyanins
will be summarized.
Anthocyanins occur rarely in gymnosperms (Timber-
lake and Bridle, 1975), which is consistent with a
different flower biology compared to the angiosperms.
Andersen (1988b, l989b), who found new anthocyanins
based on neohesperidose in the receptacles of Dacry-
carpus dacrydioides and three Podocarpus species,
which have never been found so far outside the Podo-
carpaceae, discussed these glycosides as possible
chemotaxonomic markers that link the genus Dacry-
carpus to Podocarpus within the Podocarpaceae. The
possible function of these pigments, giving the recept-
acle the appearance of an angiosperm fruit, could be an
aid in animal dispersion of the seeds (Andersen, 1988b).
The first complete identification of malonylated
anthocyanins in Poaceae has been reported by Harborne
and Self ( 1987) for Zea mays. Re-examination by paper
electrophoresis for zwitterionic pigments in Poaceae,
e.g. Alopecurus pratensis, Dactylis glomerata and a
Bromus sp., proved positive. Therefore, it is likely that
malonylated anthocyanins, e.g. cyanidin 3-(6"-
malonylglucoside), are widespread in grasses.
In European Orchidaceae, some cyanidin glycosides
acylated with oxalic acid have been described. Besides
the complete elucidation of cyanidin 3-(6-oxalylgluco-
side) (Strack et al., 1986), cyanidin oxalyl 3,5-digluco-
side, cyanidin oxalyl 3,7-diglucoside and the co-
pigmented cyanidin oxalyl 3,5-diglucoside-kaempferol
?-glucoside were tentatively identified. A survey of 79
species from 14 genera of the Orchidaceae (Strack et al.,
1989) showed the widespread occurrence of these pig-
ments and revealed genus-specific patterns. On the basis
of these results and in conjunction with earlier non-
chemical descriptions, some taxonomic and phylo-
genetic conclusions could be drawn. Thus a new
Dactylorhiza section, 'Dactylorhiza Sectio Romanae',
and the new orchid genus, 'Anteriorchis', have been
defined.
An unusual single new blue-coloured anthocyanin
present in flowers of the non-European orchid
Phalaenopsis schilleriana has been identified as cyanidin
3-trisinapoylglucoside-7 ,3 '-diglucoside ( Griesbach,
1990). The position of the three sinapoyl moieties on the
3-glucose has yet to be determined. Preliminary analysis
of flower extracts from Doritis pulcherrima also indi-
cated the presence of 3' -substituted cyanidin derivatives
(Griesbach, 1990).
In Asteraceae, the number of anthocyanins acylated
with aliphatic dicarboxylic acids increased to 14 after
elucidation of pelargonidin 3-( 6"-succinylglucoside )-
5-glucoside, only the second anthocyanin known to
carry succinate; the first was the cyanidin analogue in
Centaurea species (Harborne and Grayer, 1988). This
new anthocyanin came from pink Centaurea cyanus
flowers (Takeda et al., 1988a) and seems to be restricted
to the tribe Cynareae of the Asteraceae. All other tribes
in this family contain malonic acid esters (Takeda et al.,
1986).
Table 1.3 Natural occurrence of anthocyanins
Taxon
GYMNOSPERMAE
Podocarpaceae
Dacrycarpus dacrydioides
Podocarpus 3 spp.
ANGIOSPERMAE MONOCOTYLEDONEAE
Amaryllidaceae
Alstroemeria 4 spp., 11 cvs. Flower
Araceae
Philodendron hastum
Commelinaceae
Tradescantia pallida
Zebrina pendula
Dioscoreaceae
Dioscorea a/ata
D. alata
Musaceae
Musa acuminata vars.
Orchidaceae
Phalaenopsis schil/eriana
Anacamptis pyramidalis,
Barlia 2 spp., Cephalanthera
2 spp., Dactylorrhiza 16 spp.,
Epipactis atrorubens,
Gymnadenia 2 spp.,
Himantoglossum adriaticum,
Limodorum abortivum,
Neottianthe cucullata,
Nigritella 5 spp., Ophrys
l3 spp., Orchis 20spp.,
Serapias 8 spp., Traunsteinera
globosa
Poaceae
Sorghum bicolor
Zea mays
ANGIOSPERMAE DICOTYLEDONEAE
Aceraceae
Acer, various spp. Leaf
Organ Pigment' References
Receptacle Pg 3-neohesperidoside • Andersen (I 988b)
Receptacle Cy and Dp 3-neohesperidoside*, Andersen (I 989b)
Cy 3-glucoside, Cy 3-rutinoside
Cy 3-rutinoside; limited distribution ofDp, Saitoetal. (1988a)
60HCy and 60HDp 3-rutinoside*
Spathe Cy 3-glucoside, Cy 3-rutinoside Alfaetal. (1987)
Flower Cy(3 x feruloyl, I x terminal glucose; Shi et al. (199la)
3 x feruloyl) 3,7,3'-triglucoside
Leaf Cy 3-[ (2" ,5"-dicaffeoylarabinosyl)glucoside]- Idaka et al. (l987d)
7 ,3' -di-(6' '' -caffeoylglucoside) (zebrinin)*
Tuber Cy 3-gentiobioside, Cy• and Pn • 3-glucosyl- Shoyama et al. (! 990)
( 4"-sinapoylglucoside) • ~
t,;;·
Tuber Alatanin A*, B*, c• Yoshidaetal. (l991b)
....~
~
Bract Cy, Pn, Dp, Pt and Mv 3-rutinoside Horry and Jay (1988)
....0s::
Flower Cy 3-trisinapoylglucoside-3' ,7-diglucoside* Griesbach (1990) ::I
Flower Widespread occurrence of Cy 3-glucoside, Strack et al. (1989)
Cy 3,5-diglucoside, Cy 3,7-diglucoside,
Cy 3-(6"-oxalylglucoside )'
Leafb, mesocotylb Ap, Lt; Apcaffeoy15-arabinoside* Nicholsonetal. (1987, 1988), Hipskind
et al. (1990)
Leaf, seed coat Cy 3-(6"-malonylglucoside), Cy 3-(dimalonyl- Harborne and Self ( 1987)
glucoside)
Cy 3-(2" -galloylglucoside) •, Cy 3-{2"-galloyl- Ji eta/. (1992) .....
( rhamnosyl )glucosideJ* w
(Contd.)
 ~
-
Table 1.3 (Contd.)

Taxon Organ Pigment' References

Apiaceae
Daucus carota Cell culture, root, Cy 3-[ (6"-sinapoylglucosyl )xylosylgalactoside I, Glassgen et al. (1992a), Gliissgen et al.
central flower Cy 3-[ (6"-( 4-coumaroyl)glucosyl)xylosyl- (1992b)d
galactoside], Cy 3-[ ( 6"-feruloylglucosyl )-
xylosylgalactoside], Cy 3-[ ( 6"-(4-hydroxy-
benzoyl )glucosyl)xylosylgalactoside],
Cy-3-xylosylgalactoside, 3-xylosylglucosyl-
galactoside
Araliaceae
Panax ginseng Cell culture Pn 3-glucoside In-Ok eta/. (1989)
Asteraceae
Bel/is perennis Flower Pg 3-(6"-malonylglucoside ), Cy 3-(6"-malonyl- Saitoetal. (1988b), Tokietal. (l99lb)
glucoside), Cy 3-[ ( 6"-malonylglucuronyl)-
glucoside]*, Cy 3-glucuronylglucoside*,
Cy 3-[(6"-malonylglucosyl)glucoside }* ~
~
Centaurea cyanus Flower Pg 3-(6"-succinylglucoside )-5-glucoside* Takedaeta/. (1988a) 1::)
Cell culture Cy 3-(6" -malonylglucoside) Kakegawaeta/. (1987) ~
Dendranthema morifolium Flower Cy 3-(6" -malonylglucoside), Cy 3-dimalonyl- Saitoetal. (1988b) s.
glucoside <:l
Echinacea 2 spp. Flower Cy 3-glucoside, Cy 3-(6"-malonylglucoside) Cheminat eta/. (1989) ~
f:l
Zinnia elegans Flower Pg and Cy acetyl-3,5-diglucoside Yamaguchietal. (1990)
Bignoniaceae
....;:::
~
Arrabidaea 2 spp. Corolla Cy 3-glucoside, Cy 3-rutinoside Scogin ( 1985)
Clytostoma callistegioides Corolla Cy 3,5-diglucoside, Cy 3-(4-coumaroyl)- Scogin ( 1985) "'
glucoside-5-glucoside
lncarvillea delavayi Corolla Cy 3-rutinoside Scogin (1985)
l. olgae Corolla Cy 3-glucoside, Cy 3-rutinoside Scogin (1985)
Mansoa verrucifera Corolla Cy 3,5-diglucoside, Cy 3-( 4-coumaroyl)- Scogin (1985)
glucoside-5-glucoside
M. alliacerum Corolla Cy 3-rutinoside Scogin (1985)
Paragonia pyramidata Corolla Cy 3-glucoside, Cy 3-rutinoside Scogin (1985)
Podranea ricasoliana Corolla Cy 3-rutinoside Scogin (1985)
Tabebuia impetiginosa Flower Pn 3-cinnamoylsophoroside* Bobbio et al. (1988)
Bombacaceae
Bombax malabaricum Petal Cy 3-glucoside, Cy 3,5-diglucoside Scogin (1986)
Ceiba acuminate Petal Cy 3-glucoside Scogin (1986)
Chorisia speciosa Petal Cy 3-glucoside, Cy 3,5-diglucoside Scogin ( 1986)
Ochroma pyramidale Calyx Cy 3-glucoside Scogin ( 1986)
Pachira aquatica Stamen, filament Cy 3-glucoside, Cy 3-rutinoside Scogin (1986)
Pseudobombax ellipticum Stamen, filament Cy 3-glucoside, Cy 3,5-diglucoside Scogin ( 1986)
P. grandiflorum Petal Cy 3-glucoside, Cy 3,5-diglucoside Scogin ( 1986)
 JJrass1ca oleracea Leaf Cy 3-{6"-(4-coumaroyl)glucosylglucoside ]- ldakaetal. (J987b.c)
5-glucoside, Cy 3-(6"-feruloylglucosyl-
glucoside )-5-glucoside, Cy 3-(6''-sinapoyl-
glucosylglucoside)-5-glucoside, Cy 3-
[6"-( 4-glucosyl-( 4-coumaroyl)glucosyl-
glucosidej-5-glucoside*, Cy 3-[6"-(4-glucosyl)-
feruloylg\ucosylglucoside)-5-glucoside•.
Cy 3-16"-( 4-coumaroyl)glucosyl-(2'' '-sinapoyl-
glucoside)]-5-glucoside*, Cy 3-{6"-feruloyl-
glucosyl-(2' ''-sinapoylglucoside) J-
5-glucoside*, Cy 3-((6"-sinapoylglucosyl)-
(2' '' -sinapoylglucoside)]-5-glucoside
Sinapis alba Seedling Cymalonyl4-coumaroyl sinapoyl Takeda eta/. ( 1988b)
3-sambubioside-5-glucoside*. Cy malonyl
feruloyl sinapoyl3-sambubioside-
5-glucoside•, Cy malonyl4-coumaroyl
sinapoy13-sambubioside-5-sophorosicte•,
Cy malonyl feruloyl sinapoy13-sambubioside-
5-sophoroside •
Campanulaceae
Campanula medium Flower Campanin•, rubrocampanin • Teraharaeta/. (!990f}
Caprifoliaceae
Sambucus canadensis Cy 3-( xylosy 1-(6"-(4-coumaroyl )glucoside) 1- Johanseneta/. (1991)
5-glucoside, Cy 3-sambubioside- \:j
5-glucoside*, Cy 3-sambubioside, ~:;·
Cy 3-glucoside ....
"'t
Caryophyllaceae ~
Dianthus caryophyllus Flower Pg 3-glucoside, Pg 3-malylglucoside; Ledeme(l99!) E.
various cvs. Cy 3-glucoside, Cy 3-malylglucoside, s·
Cy 3,5-diglucoside ;:'$
Convolvulaceae
Ipomoea batatas 4 cvs. Periderm Cy and Pn 3 ,5-glucoside; Cy and Pn Miyazakietal. (!991)
3-diglucoside-5-glucoside; Cy* and Pn •
4-hydroxybenzoy13-diglucoside-S-glucoside;
Cy* and Pn· caffeoy14-hydroxybenzoyl
3-diglucoside-5-glucoside; Pn caffeoyl
3 ,5-diglucoside •; Cy and Pn * caffeoyl
3-diglucoside-5-glucoside; Pn caffeoyl
feruloyl3-diglucoside-5-glucoside •;
Pn feruloyl3-diglucoside-5-glucoside
Root Pn(3 x feruloyl.l x caffeoylor2 x feruloyl, Shiecal. (1991b)
1 x caffeoyl) 3-diglucoside-5-glucoside
Cell culture Cy and Pn 4-hydroxybenzoyl4-coumaroyl Nozueetal. (1987)
caffeoyl feru!oyl3-sophoroside-5-glucoside
Pharbitis nil Flower, bluecvs. Pn 3-sophoroside-5-glucoside, Pn 3-[6"- Luetal. (1991)
(4-glucosylcaffeoyl )sophoroside l-
5-glucoside •
Flower, red- Pg 3-sophoroside-5-glucoside and its mono-, Luer a/. (1992a)
purplecvs. di-* and tricaffeoylglucosides*f (Fig. 1.3)
Flower. violet- Pn 3-sophoroside-5-glucoside and its mono- •, Luetal. (1992b)
blue CVS di-* and tricaffeoylglucosides (heavenly .....
VI
blue anthocyanin; Kondo et al., 1987)
(Fig. 1.4) (Contd.)
 .......
0\
Table 1.3 (Contd.)

Taxon Organ Pigment• References

Ericaceae
Arbutus unedo
Gay/ussacia 4 spp.
Vaccinium japonicum
V. macrocarponcvs.
V. oxycoccus
V. uliginosum
Vaccinium 20 spp.
Fabaceae
Clitoria ternatea
Erythrina 21 spp.
Millettia zechiana
Vigna2spp.
Gentianaceae
Eustoma grandiflorum
Lamiaceae
A juga rep tans
Peril/afrutescens var. crispa
Fruit Dp 3-galactoside; Cy 3-galactoside, Maccarone et al. (1990)
Cy 3-glucosylgalactoside
Fruit Cy, Pn, Dp, Pt and Mv 3-glucosides, Ballingtonetal. (1988a)
3-galactosides, 3-arabinosides; G. brachycera
lacks Pn 3-arabinoside
Fruit Pg and Cy 3-arabinoside. Pg and Cy Andt.rsen (1987a)
3-galactoside
Fruit Cy and Pn 3-galactoside, Cy and Pn Sapers and Hargrave (1987)
3-arabinoside
Fruit Cy and Pn 3-glucoside, Cy and Pn 3-galactoside, Andersen (1989a)
Cy and Pn 3-arabinoside; Dp, Pt and Mv
3-glucoside
Fruit Cy, Pt, Dp and Mv 3-glucosides, Andersen ( 1987b)
3-arabinosides, 3-galactosides
Fruit Cy, Pn, Dp, Pt and Mv 3-glucosides, Ballington eta!. (1987 ,1988b, c) ~
~
3-galactosides, 3-arabinosides; limited
distribution in V. stamineum, V. erythro- §
carpum; exclusively the Cy glycosides in
V. parvifo/ium
s-e
~
Flower TernatinsAl*, A2*, Bl* and Dl* Teraharaeta/. (1989a, 1990b-e), 1::1
~
Kondoeta/. (1990a)
Pg and Cy 3-glucoside, Pg and Cy 3-sophoroside, Scogin (1991)
~-
Flower
Pg and Cy 3,5-diglucoside (variously)
Flower Pg 3-rhamnoside; Cy and Mv 3,5-diglucoside Parvez and Ogbeide ( 1990)
Seedcoat, hypocoty! Dp 3-glucoside Pandey et al. (1989)
Flower Pg and Dp 3-( 4-coumaroylrhamnosyl- Asen et al. (1986)
galactoside )-5-glucoside, Pg and Dp
3-rhamnosylgalactoside-5-glucoside, Pg and
Dp 3-( 4-coumaroylgalactoside)-5-glucoside,
Pgand Dp 3-galactoside-5-glucoside;
Pg 3-feruloylrhamnosylgalactoside-
5-glucoside, Pg 3-feruloylgalactoside-
5-glucoside
Cell culture Cy (4-coumaroyl, feruloyl, malonyl) glucoside Callebaut era!. (1990)
Cell culture Cy 3-(6"-(4-coumaroyl)glucoside J-5-glucoside, Tamuraera/. (1989a)
Cy 3-[6"-(4-coumaroyl)glucoside]-5-
( 6"-malonylglucoside), Cy 3-(6"-feruloyl-
glucoside )-5-glucoside, Cy 3-(6"-feruloyl-
glucoside )-5-( 6"-malonylglucoside) •
 P. ocimoidesvar. crispa Leaf Cy 3-(6"-( 4-coumaroyl)glucosidej-5- Kondoetal. (1989a), Yoshidaeta/. (1990)
( 6" '-malonylglucoside), Cy 3-(6" -caffeoyl-
glucoside )-5-( 6" -malonylglucoside),
Cy 3-[6"-( 4-coumaroyl)glucoside )-5-
(6"-malonylglucoside ), Cy 3-(6"-caffeoyl-
glucoside)-5-glucoside, Cy 3-[6"-
(4-coumaroyl)glucoside ]-5-glucoside
Salvia 2 spp. Flower Pg 3-caffeoylglucoside-5-dimalonylglucoside •, Tomas-Barberan et al. (1987)
monardaein, Pg3-caffeoylglucoside-
5-malonylglucoside, Pg 3-caffeoylglucoside-
5-glucoside, Pgmonodemalonylmonardaein*,
Pg 3-( 4-coumaroyl)glucoside-5-glucoside
Salvia coccinea Calyx Cy 3-caffeoylglucoside-5-dimalonylglucoside- Tomas-Barberan et al. ( 1987)
Cy 3-( 4-coumaroyl)glucoside-5-dimalonyl-
glucoside
S. spfendens Scarlet flower Salvianin*, monardaein, monodemalonyl Kondoetal. (1989b)
salvianin*, bisdemalonylsalvianin, mono-
demalonylmonardaein •
Purple flower Salviadelphin*, monodemalonylsalviadelphin•, Kondoetal. (l989b)
bisdemalonylsalviadelphin, dimalonyl-
awobanin*
S. farinacea (blue) Flower/stem Malonylawobanin, salviamalvin • Kondoetal. (1989b)
Lobeliaceae
Lobelia erinus Flower Lobelinin A • and B* Kondoetal. (1989c)
Malvaceae
Cell culture Cy glucosides Mizukami(l991)
Hibiscus sabdariffa
0c::;·
H. syriacus Flower Pg, Cy, Pn. Dp, PtandMv 3-(6"-malonyl- Kim et al. (1989) ::;-
glucoside) &
Malva sylvestris Flower Mv 3-(6"-malonylglucoside )-5-glucoside • Takeda et al. (1989) l::::
Myrtaceae iS·
Metrosideros 8 spp. Flower Cy and Pn 3-glucoside; Dp, Pt and Mv Andersen (1988a) ;:::
3-glucoside (limited); Pn, Cy, Dp, Pt and Mv
3,5-diglucoside (limited)
Nymphaeaceae
Victoria amazonica Leaf Cy and Dp 3-(2"-galloylgalactoside) * Stracketal. (1992)
Polygonaceae
Polygon urn 9 spp. Sepal, stem, Cy 3-g!ucoside, Cy 3-galactoside, Cy 3-rhamno- Yoshitamaeta/. (1987)
propagule sylglucoside, Cy 3-rhamnosylgalactoside;
Dp 3-glucoside, Dp 3-rhamnosylglucoside;
M v 3 ,5-diglucoside
Primulacea
Cyclamen persicum Flower Pn and Mv monoglucoside; Pn rutinoside; Miyajimaeta/. (1990)
Mv dig!ucoside
Ranunculaceae
Delphinium hybridum Flower Cyanodelphin •• Kondoetal. (1991)
Rosaceae
Aronia melanocarpa Fruit Cy 3-glucoside, Cy 3-galactoside, Oszmianski andSapis (1988)
Cy 3-arabinoside, Cy 3-xyloside •
Malus sylvestris Fruit Cy 3-galactoside, Cy 3-glucoside, Mazza and Velioglu (1992)
Cy 3-arabinoside, Cy 3-xyloside
Prunus8spp. Fruit Cy 3-glucoside. Cy 3-rutinoside; Pg and Pn Werner et al. (1989)
3-glucoside; Pn 3-rutinoside -...l
Prunus x yedoensis Cell culture Cy 3-glucoside Ishikura er al. (1989)
(Comd.)
-
Table 1.3 ( Contd.)

Taxon Organ Pigment• References .....

00
Sax1fragaceae
Saxifraga 31 spp. Bulbil. stem, Cy 3-glucoside; Dp, Pt, Pn and Mv Andersen and Ovstedal ( 1988)
flagellae, leaf, 3-glucoside; Dp, Cy, Pt, Pnand Mv
ovary. petal 3,5-diglucoside; Cy 3-galactoside,
Cy 3-arabinoside
Tolmiea menziesii Flower Cy, Dp and Mv 3-glucoside Soltis and Soltis ( 1986)
Scrophulariaceae
Penstemon 87 spp. Flower Pg, Cy and Dp 3-glucosides, 3,5-diglucosides, Scogin and Freeman (1987)
3-arabinosides
Solanaceae
Petunia hybrida various cvs. Flower Pn, Pt and Mv 3-caffeoylrutinoside-5-glucoside Griesbach eta/. (I 991)
Solanum americanum Fruit Mv 3-sophoroside-5-glucoside, Bobbio et al. (1987)
Mv 3-( dicaffeoylsophoroside )-5-glucoside
S. tuberosum Tuber Pt3-( 6"-( 4-coumaroyl)rhamnosyl]g1ucoside * Andersen et al. (1991 b)
Theaceae
Camellia Japonica ssp. rusucana Cy 3-glucoside, Cy3-galactoside, Sakataetal. (1986)
Cy 3-arabinoside, Cy 3,5-diglucoside
Camellia spp. Flower Cy 3-glucoside, Cy 3-galactoside, Cy 3-[ 6"- Sakata and Arisumi (1985), Sakata eta/.
(4-coumaroyl)glucoside J (1987), Saitoetal. (1987)
Eurya japomca Fruit Cy 3-( 4"-acetylrhamnosyl)glucoside Teraharaeta/. (1988) ;;a
Verbenaceae ~

Verbena hybrida Flower Pg and Dp* 3-(6"-malonylglucoside); Teraharaetal. (1989b), Tokietal. §

Vitaceae
Ampelopsis brevipedunculata
Vitis vinifera 3 cvs.
V. vimfera 54 vars.
V. vinifera
Dp 3-( 6"-acetylglucoside )-5-( 6" -acetyl- (J991a, c) s.
glucoside)*; Pg and Cy 3-( 6"-acetyl- <;::)
glucoside )-5-glucoside; Pg 3-(6"-acetyl- ~
glucoside) •; Pg and Cy 3-( 6"-malonylglucoside) 1:)
;::
Fruit Dp, Mv and Pt 3-rhamnoside-5-glucoside; Yoshitamaeta/. (1991) ~-
Mv 3,5-diglucoside
Leaf Cy, Pn, Dp, Pt and Mv 3-glucoside; Cy, Pn, Dame and Glories (1988)
Dp and Mv 3-acetylglucoside; Pn and Mv
3-(4-coumaroyl)glucoside; Cy and Mv
3-caffeoylglucoside
Fruit Cy, Pn, Pt and Mv 3-glucosides, 3-acetyl- Roggeroetal. (1988)
glucosides, 3-( 4-coumaroyl)glucosides;
Mv 3-caffeoylglucoside
Cell culture Pg, Cy, Pn andMv 3-glucosides, Tamura et al. ( 1989b), Laing and Cormier
3-( 4-coumaroyl)glucosides, 3 ,5-diglucosides; (1990), Do and Cormier (1991),
Mv 3-[6"-( 4-coumaroyl)glucoside]- Tamura and Sugisawa (1991 ),
5-glucoside Van Calsteren et al. (1991)

•see also structures illustrated in text. Where not indicated, position of acyl
moieties is not completely determined. Only a few selected references are
listed in which the attachment of sugars to the anthocyanidin were not
identified. In systematic names, the sugar-sugar bonds are not specified.
*New pigment; not listed in the previous editions (Timberlake and Bridle,
1975; Hrazdina, 1982; Harborne and Grayer, 1988); not indicated in cases of
rossibly new anthocyanins with incomplete structure elucidation.
Phytoalexin oc~'!rring _after inoculati~n with isolates of Col/etotrichum
cFurther oxalyl derivatives were tentatively identified, i.e. Cy oxalyl 3,5-
diglucoside, Cy oxalyl 3,7-diglycoside and the copigmented anthocyanin Cy
oxalyl3,5-diglucoside-kaempferol 7-glucoside.
dSee Note added in proof.
•cyanodelphin may be identical with violdelphin, which has previously been
identified as Dp 3-rutinoside substituted at C-7 with two glucoses and two
4-hydroxybenzoic acids (Kondo et al., 1990b).
1Reported also at a Japanese meeting by Kondo et al.
 References
An acylated anthocyanin, cyanidin 3-(4-coumaroyl-
glucoside)-5-glucoside, was reported for the first time
in flowers of members of the Bignoniaceae (exclusively
in the tribe Bignonieae), along with some non-acylated
cyanidin glycosides (Table 1.3) (Scogin, 1985). From the
anthocyanin patterns, the author discusses a phyto-
chemical similarity between Bignoniaceae and the
closely related Scrophulariaceae, from which acylated
anthocyanins have also been reported (Timberlake and
Bridle, 1975). However, the distribution of these
anthocyanins ('Hennigian cladogram') among tribes of
the Bignoniaceae only poorly supports the phylogenetic
affinities discussed on the basis of general taxonomic
characters (Scogin. 1985).
In vegetative organs from members of the Brassic-
aceae, acylated anthocyanins with hydroxycinnamic
acids are frequently found (Table 1.3, and previous
editions). Takeda et al. ( 1988b) recently found in Sinapis
alba seedlings new complex polyacylated anthocyanins
containing malonic acid and two different hydroxy-
cinnamic acids. This is only the second report on
malonyl moieties in anthocyanins from Brassicaceae,
although the first in such complex pigments. Their
definite structures have yet to be elucidated.
Fruits of members of the Ericaceae are characterized
by the regular presence of monoglycosides of the six
common anthocyanidins (Table 1.3). Analyses of the
anthocyanin patterns seem to be useful in taxonomic
studies of Vaccinium (Ballington et al., 1988b). Such
studies support a recent origin for North American
sections of the genus Vaccinium (Ballington et al.,
l988c).
A study of the anthocyanin patterns of 31 European
Saxifraga species (Andersen and Ovstedal, 1988) does
not support sectional division in this genus, although
there was good agreement with subsectional classi-
fication. In another study of a member of the Saxi-
fragaceae, namely of 16 diploid and tetraploid cyto-
types of Tolmiea menziesii (Soltis and Soltis, 1986),
the patterns of 3-glucosides are in agreement with other
systematic data, which indicate that tetraploid Tolmiea
is of autopolyploid origin. This is a significant obser-
vation since differences in anthocyanin patterns can
reveal species of hybrid origin, as shown by Andersen
and Ovstedal ( 1983) among Saxifraga species.
In various cultivars of Camellia species (Theaceae),
cyanidin 3-galactoside, along with some other antho-
cyanins, seems to be a characteristic pigment (Sakata
et al., 1986). Quantitative patterns and relative amounts
of the galactoside may be used as a chemical marker for
the classification of Camellia cultivars. On the basis
of the proportion of cyanidin 3-galactoside in the total
anthocyanin fraction, it was possible to show phylo-
genetic differentiations between two Camellia groups,
namely wild forms of Japanese and Formosan origin
(Sakata et al., 1987).
19
ACKNOWLEDGEMENTS
Work from D.S.'s laboratory was supported by the
Deutsche Forschungsgemeinschaft (Boon) and the
Foods der Chemischen Industrie (Frankfurt).
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Note added in proof:
The cell culture, as well as root and central flower of
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Flavones and flavonols

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The minor flavonoids

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