1985 - Vetschera - C - Glycosylflavones As An Accumulation Tendency A Critcal Review

THE BOTANICAL REVIEW
VOL. 51 JANUARY-MARCH,
1985 No. 1
C-Glycosylflavones as an Accumulation Tendency:

A Critical Review
KARIN MARIA VALANT-VETSCHERA

Institute of Botany
University of Vienna
Rennweg 14, A-1030 Vienna
Austria
Abstract .................................................................................................................................................................... I
Z u s a m m e n f a s s u n g ............................................................................................................................................ 2
I. Introduction .......................................................................................................................................................... 3
II. Distribution o f C-Glycosylflavones in the C o m p o s i t a e ....................................................... 7
III. C-Glycosylflavones as a Part o f the F l a v o n o i d C o m p l e m e n t
in the C o m p o s i t a e ............................................................................................................................................ 13
IV. C-Glycosylflavones as a Part o f the F l a v o n o i d C o m p l e m e n t
in Selected A n g i o s p e r m Families ......................................................................................................... 20
V. Specialization T r e n d s in C-Glycosylflavone A c c u m u l a t i o n ............................................. 40
VI. C-Glycosylflavones as a T a x o n o m i c Character ......................................................................... 44
VII. Concluding R e m a r k s ...................................................................................................................................... 45
VIII. A c k n o w l e d g m e n t s ............................................................................................................................................ 46
IX. Literature Cited .................................................................................................................................................. 46
X. Appendix: Structures o f C-Glycosylflavones ............................................................................... 51
Abstract
C-Glycosylflavones represent a special group of flavonoid glycosides
both with respect to their chemical structure and presumed different bio-
genetic origin. Their accumulation and distribution in various plant groups
has frequently been interpreted systematically; however, the application
of chemotaxonomic congruence sometimes has led to'incoherent results.
This indicates the necessity for studying C-glycosylflavones primarily as
an accumulation tendency before using them as systematic markers. Tak-
ing this into account, the distribution of C-glycosylflavones within the
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2 THE BOTANICAL REVIEW
Compositae has been compiled and, on the basis of available data, their
integration into the complete flavonoid complement analyzed. These re-
sults have been compared to those from other selected angiosperm groups,
with special regard to the occurrence of certain combinations of different
flavonoid glycosides with C-glycosylflavones. Despite the lack of detailed
systematic surveys, the biosynthetic capacity of C-glycosylflavone accu-
mulation in the Compositae was found to be relatively high. Mono- and
di-C-glycosylflavones, including some with complex structures, are ac-
cumulated in the tribes Anthemideae, Heliantheae, Cynareae and Lac-
tuceae. The genera of the Anthemideae and Heliantheae exhibited a very
similar C-glycosylflavone profile, thus suggesting possible affinities. The
tribes Eupatorieae, Astereae, Inuleae, Vemonieae and Senecioneae ap-
parently accumulated only a small number of less complex C-glycosylfla-
vones. Strikingly, di-C-glycosylflavones were often combined with a series
of flavonoid O-glycosides, whereas predominantly C-glycosylflavone pro-
files showed a low percentage of co-occurring flavonoid O-glycosides.
These combination trends could possibly serve as additional chemical
characters. Various combination trends have been found within the an-
giosperms surveyed here. Mostly C-glycosylflavones co-occurred with fla-
vonol 3-O-glycosides and (or) flavone 7-O-glycosides. Mutual exclusivity
appeared to be very rare. A predominantly C-glycosylflavone pattern
frequently contained a few flavonoid O-glycosides only. By comparison,
the Compositae seemed to accumulate di-C-glycosylflavones as a part of
a flavonol- or flavone-dominated pattern to a greater extent than the other
taxa studied here. Taxa accumulating C-glycosylflavones as a main ten-
dency exhibited different degrees of specialization with respect to the
substitution patterns of individual compounds. These patterns are much
more conclusive than the mere presence/absence criterion. The available
data suggest a reconsideration of the present dogma on flavonoid evo-
lution. There is little evidence that C-glycosylflavones truly represent an
intermediate stage in the reduction trend from flavonols to flavones. More
knowledge on the biosynthesis and function(s) of C-glycosylflavones would
be helpful for their interpretation as systematic features.
Zusammenfassung
C-Glykosylflavone unterscheiden sich strukturchemisch, wahrschein-
lich aber auch biogenetisch yon den tibrigen Flavonoidglykosiden. Daher
wurde ihre Verbreitung und Akkumulation h~ufig systematisch interpre-
tiert. Die Anwendung der "chemotaxonomischen Kongruenz" als Inter-
pretationsmodell erscheint jedoch problematisch. Zum besseren Ver-
st~indnis des Merkmals C-Glykosylflavon-Akkumulation w~re daher eine
Analyse der Akkumulationstendenz per se notwendig. Dies beriicksich-
C-GLYCOSYLFLAVONES 3
tigend, wurde die Verbreitung von C-Glykosylflavonen bei den Composi-

tae analysiert, wobei besonders auch ihre Integration im gesamten Fla-
vonoidprofil diskutiert wird. Die Ergebnisse wurden mit ~ihnlichen
Analysen bei verschiedenen Angiospermen-Gruppen verglichen und die
Kombination mit verschiedenen Flavonoid-O-Glykosiden eingehender
studiert. Trotz der geringen Zahl vergleichender Untersuchungen bei den
Compositae erscheint ihre Biosynthesekapazit~it relativ hoch: in den Tri-
ben Anthemideae, Heliantheae, Cynareae und Lactuceae kommt es zur
Akkumulation yon auch komplexeren mono- und di-C-Glykosylflavonen.
Dabei zeigen vor allem Gattungen der Anthemideae und Heliantheae
weitgehend fibereinstimmende C-Glykosylflavon-Profile. Dagegen wer-
den in den Triben Eupatorieae, Astereae, Senecioneae, Vernonieae und
Inuleae nur die biogenetisch einfacheren Derivate in geringerem Ausmass
akkumuliert. Auffallenderweise kommen di-C-Glykosylflavone h~iufig in
Kombination mit dominierenden Flavonoid-O-Glykosiden vor, w~ihrend
in Profilen mit dominierender C-Glykosylflavon-Ausstattung die ent-
sprechenden Flavonoid-O-Glykoside mengenm~issig stark zurficktreten.
Diese Kombinationstendenzen k6nnten sich als zus~itzliches chemisches
Merkmal erweisen. Unterschiedliche Kombinationstendenzen wurden bei
anderen Angiospermen-Gruppen beobachtet. Meistens wurden C-Gly-
kosylflavone mit Flavonol-3-O-Glykosiden und (oder) Flavon-7-O-Gly-
kosiden co-akkumuliert. Dabei kommt es selten zum wechselseitgen Aus-
schluss von C-Glykosylflavonen und Flavonoid-O-Glykosiden. Meist
enth~ilt ein dominierendes C-Glykosylflavon-Muster wenige Flavonoid-
O-Glykoside. Im Vergleich dazu scheint die Kombination von di-C-Gly-
kosylflavonen und dominierenden Flavonoid-O-Glykosiden bei den
Compositae haufiger zu sein als bei den tibrigen hier untersuchten An-
giospermen. Taxa mit dominierenden C-Glykosylflavon-Profilen zeigen
vielfach ein unterschiedliches Ausmass an Spezialisierung im Substitu-
tionsmuster der einzelnen Derivate. Diese Muster erscheinen als che-
mische Merkmale bedeutsamer als das Merkmal "Vorkommen versus
Fehlen." Aufgrund der bisherigen Daten erscheint daher eine Revision
des bestehenden Dogmas der Flavonoid-Evolution erforderlich, da es
wenig Hinweise auf die postulierte Rolle der C-Glykosylflavone als Zwi-
schenstufe im Flavonol-Flavon Reduktionstrend gibt. Mehr Informatio-
nen fiber Biosynthese und Funktion yon C-Glykosylflavonen k~Snntenzu
einem besseren Verst~indnis dieses chemischen Merkmals beitragen.
I. Introduction
Flavonoids are secondary plant constituents proven to be useful for
taxonomic purposes (Gornall et al., 1979; Harborne, 1967, 1977; Rich-
ardson, 1983a; Richardson & Young, 1982). The availability of standard
4 T H E B O T A N I C A L REVIEW
procedures for their analysis (Mabry et al., 1970) has increased their use
in biological laboratories enormously. Thus we have gotten more insight
into the distribution of flavonoids within the plant kingdom. However,
there is still need for further detailed structural determinations. Structures
based only on simple UV-spectroscopy become more and more suspect,
especially since many complex structures have now been reported to occur
naturally (Harborne & Mabry, 1982). Their structural identification re-
quires much more sophisticated spectroscopic methods. These difficulties
are especially important when dealing with C-glycosylflavones. Progress
has been made during the last decade by Prof. Chopin and co-workers
(Chopin & Bouillant, 1975; Chopin et al., 1982a), who have developed
methods for C-glycosylflavone identification on the microscale level. This
is very important for botanists, since in most cases the yield of a purified
flavonoid may be quite low. This improvement in methodology may be
one reason why reports on C-glycosylflavone accumulation in plants are
increasing--a fact that might change our present view of their position in
the evolutionary path of flavonoids (Harborne, 1977; for basic structures
of flavonoid glycosides see Fig. 1).
The C-glycosylflavones appear to be a unique group of flavonoids,
basically because of structural and biogenetic differences from other fla-
vonoids. They differ from the flavonoid O-glycosides by having their
sugars attached via a carbon atom at the C-6 and/or the C-8 position of
the molecule. Furthermore, data obtained from Lemnaceae cultures
(Hahlbrock & Grisebach, 1975 and references cited therein) and those of
Gentianaceae (Chopin et al., 1982a and references cited therein) indicate
that C-glycosylation takes place at the chalcone/flavanone stage--an early
step in flavonoid biosynthesis--and prior to oxidation to the flavone. So
far there is no evidence for sugar attachment at the (oxidized) flavone
stage. Flavones, however, as well as C-gylcosylflavones, serve as good
substrates for subsequent O-glycosylation. Since enzymes responsible for
C-glycosylation have not yet been isolated and described, the exact mech-
anisms of sugar attachment remain unknown (Franz & Griin, 1983). It
can be assumed that C-glycosylating enzymes are not identical with those
involved in O-glycosylation.
The use of C-glycosylflavones as chemical characters was based on their
different biosynthetic origin from other flavonoid glycosides. Their oc-
currence was interpreted as being intermediate in the reduction series
from flavonols to flavones (Harborne, 1977). Although other authors were
in doubt about the value of some proposed flavonoid evolution series
(Gornall & Bohm, 1978), they still considered the C-glycosylflavones to
represent a "semiadvanced" character status. All these ideas are based
mainly on absence/presence analysis. However, C-glycosylflavones occur
as a series of derivatives differing both in substitution pattern (e.g., hy-
O~/OH
FLAVONOL 3-O-GLYCOSIDES FLAVONE 7-O-GLYCOSIDES
OH OH
OH
H O ~
GLO
OH 0 OH O
QUERCETIN 3-0-GLYCOSIDE LUTEOLIN 7-O-GLYCOSIDE
C-GLYCOSYLFLAVONES
OH
OH O
ISOORIENTIN
Fig. 1. Basic structures of flavonoid glycosides.
droxyl and methoxyl groups at the ring A and B) and structural diversity
of sugars attached to the flavonoid nucleus (e.g., glucose, arabinose, xylose,
rhamnose, etc.). Thus these compounds represent different levels of com-
plexity. It may be more important to consider which derivatives are
present or absent and their relative amounts. Furthermore, C-glycosyl-
flavones often co-occur with flavonoid O-glycosides, and these combi-
nations could serve as additional chemical characters.
C-glycosylflavones have been studied not only for taxonomic purposes.
Metabolic data have also been obtained. In Avena sativa (Effertz & Weis-
senbSck, 1976, 1980; Popovici & WeissenbSck, 1976, 1977; WeissenbSck,
1970), notable qualitative differences were found during the ontogenetic
process. Moreover, certain derivatives were found to be tissue- or organ-
specific. These findings indicate that, in systematic surveys, plant tissues
of similar developmental age should be utilized. Additionally, infraspecific
variability should be taken into account. In a recent survey on Achillea

flavonoids (Valant-Vetschera, 1981) it appeared that infraspecific varia-
tion was high when C-glycosylflavones represented the main accumulation
tendency, but it was very low when only a few such compounds were
present together with various flavonoid O-glycosides.
As with most of the secondary plant products (Gershenzon & Mabry,
1983), C-glycosylflavones probably have a function for the plant. Since
most C-glycosylflavones absorb in the range of 270-340 nm, their action
as an UV screen for protection of the coenzymes N A D and N A D P has
been postulated (Swain, 1975). In addition, they could prevent dimeri-
zation of the thymine units of the D N A molecule. These functions could
have been a prerequisite for the conquering of dry land habitats by aquatic
plants, and could serve as an explanation for the occurrence of C-glyco-
sylflavones in Algae (Characeae; see Swain, 1975). Apart from these still
hypothetical considerations, an O-glycosylated C-glycosylflavone isolated
from Zea mays has been shown to inhibit insect development (Elliger et
al., 1980). Furthermore, a stabilizing function for other essential com-
pounds as well as an enhancement of their function by acting synergis-
tically is feasible. For a better understanding of C-glycosylflavone accu-
mulation, it would certainly be very helpful to know more about their
function(s).
Regardless of the problems discussed before, the accumulation of C-gly-
cosylflavones might still be a valuable chemical character. There are,
however, some aspects to be considered before their distribution and
accumulation may be interpreted systematically. In particular, an in-
creased knowledge of their accumulation behavior is a basic requirement.
This would include studies on the accumulation of C-glycosylflavones
versus flavonoid O-glycosides and other classes of flavonoids, as well as
the accumulation of special derivatives and their relative amounts. With
regard to combination trends, accumulation behavior would further in-
clude features such as the predominance of either the one or the other
class of flavonoids, a switchover to another class and the omnipresence
of several classes. As already pointed out, infraspecific variability and
tissue specific accumulation have to be taken into account as well. Thus
the process of studying accumulation behavior corresponds largely to the
analyzing of morphological features and their development. There would
be no primary taxonomic inferences resulting from these studies, but more
information would accumulate, thus helping the interpretation of C-gly-
cosylflavone formation as a chemical character.
The present survey was inspired by the results of detailed investigations
of the flavonoid pattern of the genus Leucocyclus (Valant-Vetschera, 1982b)
and the Achillea ptarmica group (Valant-Vetschera, in press a). Both
groups show a similar accumulation behavior of C-glycosylflavones: al-
though these compounds dominate the flavonoid profile of most taxa, a

flavonol dominated pattern was observed in a few samples. This switch-
over in flavonoid profile occurs at the level of subspecies (as in Leuco-
cyclus) or between closely related species, as in Achillea ptarmica and A.
salicifolia. On one hand these differentiations might carry taxonomic
significance; on the other hand, they suggest that caution is to be applied
in interpreting flavonoid data. To estimate the significance of these dif-
ferentiations, other genera in the Compositae were surveyed with regard
to both their C-glycosylflavone content and their combination trends.
Similarly, selected angiosperm families were analyzed for their combi-
nation trends. For this purpose only leaf flavonoid data were considered,
for reasons already discussed here.
II. Distribution of C-Glycosylflavones in the Compositae

According to earlier surveys C-glycosylflavones appeared to be of re-
stricted distribution within the Compositae (Chopin & Bouillant, 1975;
Heywood et al., 1978). In a more recent survey (Chopin et al., 1982a)
additional reports were included, thus suggesting that these compounds
might be more widespread than originally believed. It has to be stressed
that there is still a need for detailed studies of the flavonoid distribution
in many tribes (Harborne, 1978), since there are still only scattered records
of C-glycosylflavone occurrence in the genera and tribes of this family.
Data on the occurrence of individual compounds in genera and tribes are
listed in Table I. Main emphasis has been put on the compounds isolated
from leaf tissue; other sources are indicated separately.
In Achillea (Anthemideae) C-glycosylflavones are one of the major
accumulation trends (Valant, 1978; Valant-Vetschera, 1982a, in press a).
They occur as a series of mono-C-glycosylflavones such as vitexin (1),
isovitexin (2), swertisin (7), orientin (5), isoorientin (6), and swertiaja-
ponin (11), as well as a series of di-C-glycosylapigenins and -luteolins.
[See Appendix I for these structures.] Some more complicated structures
such as isoorientin 2"-arabinoside or isoorientin 7,Y-dimethyl ether (14)
are of restricted distribution. O-Glycosides of C-glycosylflavones (vitexin
7-O-glucoside) have been reported for A. fragrantissima (Forsk.) Schultz-
Bip. (Shalaby et al., 1965), but this could not be confirmed by recent
studies (Valant-Vetschera, 1981). A preliminary analysis of root material
indicated the presence of swertisin (7), di-C-glycosylapigenins, isoorientin
(6) and swertiajaponin (11) in A. fragrantissima, whereas A. lycaonica
Boiss. & Heldr. roots accumulated vitexin (I), di-C-glycosylapigenins,
orientin (5), isoorientin (6) and di-C-glycosylluteolins (Valant-Vetschera,
in press b). The flavonoid complement of the roots corresponded largely
to that observed in aerial parts (Table I). By contrast, A. spinulifolia Fenzl
THE BOTANICALREVIEW
Table I
Distribution o f C-glycosylflavones in the Compositae"
Tribe, genus,
species C-glycosylflavones References
Anthemideae
Achillea spp. vitexin, isovitexin, swertisin, vicenins, Valant, 1978
oftentin, isoorientin, swertiajaponin
A. leptophylla M.B. swertisin, swertiajaponin Valant et al.,
1978
A. setacea W. & K. vicenin-2, vicenin-3, schaftoside, isoschaf- Valant et al.,
toside 1978
A. setacea group vitexin, isovitexin, swertisin, di-C-glyco- Valant-Vetschera,
sylapigenins, oftentin, isoorientin, swer- 1984
tiajaponin
A. cretica L. isoorientin 7,3'-dimethyl ether Valant et al.,
1980
A. ptarmica L. vitexin, "glycosyl vitexin, di-C-glycosyl- Valant-Vetschera,
(group) apigenins, oftentin, isoorientin, isoor- 1982a, in
ientin 2"-arabinoside, di-C-glycosyllu- press a
teolins
A. fragrantissima vitexin 7-O-glucoside Shalaby et al.,
(Forsk.) Sch.-Bip. 1965
swertisin, di-C-glycosylapigenins,iso- Valant-Vetschera
orientin, swertiajaponin m press b
A. fragrantissima swcrtisin, di-C-glycosylapigenins,swertia- Valant-Vetschera
(roots) japonin m press b
A. lycaonica Boiss. & vitexin, di-C-glycosylapigenins,oftentin, Valant-Vctschera
Heldr. isoorientin, di-C-glycosylluteolins in press b
A. lycaonica (roots) vitexin, di-C-glycosylapigcnins,orientin Valant-Vetschera
m press b
A. spinulifolia Fenzl di-C-glycosylapigenins,isoschafiosidc, Valant-Vetschera
ex Boiss. orientin, isoorientin, swertiajaponin m press b
A. aleppica DC. di-C-glycosylapigenins,orientin, isoorien- Valant-Vetscbera
tin, swcrtiajaponin, di-C-glycosylluteo- m press b
lins
Leucocyclus formosus isovitexin, schafioside, isoschafioside, Valant-Vetschera,
Boiss. vicenin-3, isoorientin + 2"-arabinoside, 1982b
isoorientin caffeoyl ester, luccnin-2
Otospermum glabrum isovitexin, di-C-glycosylapigenins,often- Greger, unpubl.
(Lag.) Willk. tin, isoorientin
Ajania fastigiata 6,8-di-C-glucopyranosylapigen- (~umbalov & Zu-
(Winkl.) Poljak. in + rotation isomer baeva, 1976
Table I
Continued
Tribe, genus,
Artemisia transilien- vicenins Cumbalov & Fa-
sis Poljak. deeva, 1970
Heliantheae
Gaillardia pulchella vitexin, isovitexin, swertisin, orientin Wagner et al.,
Foug. 1972a
Balduina spp. isovitexin, orientin, isoorientin Bohm, 1978
Helenium spp. vitexin, isovitexin, swertisin, vicenin-1, Biemer, 1973
vicenin-2, orientin, isoorientin, swertia-
japonin
Helenium 4 spp. vitexin, isovitexin, isovitexin 4'-O-gluco- Biemer et al.,
side, swertisin, oilentin, isooilentin, 1977
swertiajaponin
Flourensia cernua vicenin-1, vicenin-2, schaftoside, isoschaf- Dillon et al.,
DC. toside, neoschaftoside 1976
Dahlia spp. di-C-glycosylapigenins Giannasi, 1975
Cynareae
Carlina biebersteinii unidentified Wagner, 1978
Bernh. ex Hornem.
C. vulgaris L. schaftoside, orientin, isoorientin, carlino- Raynaud & Ra-
side solojaona,
1976; Rasolo-
jaona & Ray-
naud, 1979
C. macrocephala schafloside, isoorientin Dombris & Ray-
Moils naud, 1980
C. macrocephala schafioside, orientin, isoorientin Dombris & Ray-
(flowers) naud, 1981a
C. acaulis L. vitexin, isoschaftoside, orientin, isoorien- Raynaud & Ra-
tin solojaona,
1979
C. acanthifolia L. schaftoside, isoschafioside, orientin, iso- Raynaud & Ra-
orientin solojaona,
1978
C. corymbosa L. schaftoside, orientin, isooilentin, Dombris & Ray-
lucenin-2 naud, 1977,
1981b
C. corymbosa (roots) corymboside Besson et al.,
1979
10 THE BOTANICALREVIEW
Table I
Continued
Tribe, genus,
species C-glycosylttavones References
Atractylis gummifera isoschaftoside, orientin, isoorientin Raynaud &
L. Dombfis, 1978
Staehelina dubia L. isoorientin Raynaud etal.,
1971
Centaurea solstitialis schaftoside, orientin, isoorientin Kamanzi & Ray-
L. naud, 1976
C. solstitialis L. schaftoside, orientin, isoorientin Kamanziet al.,
(flowers) 1983a
C. melitensis L. isovitexin, vicenin-2, schaftoside, often- Kamanziet al.,
(flowers) tin, isoorientin 1983b
Lactuceae
Tragopogon spp. vitexin, isovitexin, O-xylosylisovitexin, Be~er & Own-
swertisin, vicenin-l, vicenin-2, orientin, bey, 1971;
isoorientin, swertiajaponin, lucenin-1, Kroschewsky
lucenin-2 et ~., 1969
Catananche caerulea schafloside, neoschaftoside, carlino- Proliac etal.,
L. side + isomer 1973; Proliac
&Raynaud,
1977
Eupatorieae
Eupatorium seroti- vicenin-2 Wagner ~ ~.,
num Michx. 1972b
Liatris spp. vicenin- 1, vicenin-2 Wagner ~ ~.,
1973
Astereae
Hazardia spp. C-8-glycosylapigenin, di-C-glycosylapigen- Clark & Mabry,
ins 1978
Hazardia
sect. Hazardia C-8-glycosylapigenin, di-C-glycosylapigen- Clark et al., 1980
ins
sect. Bracteofolia di-C-glycosylapigenins Clark et al., 1980
Stenotus di-C-glycosylapigenins Clark et al., 1980
Ericameria di-C-glycosylapigenins Clark et al., 1980
Asiris C-8 -glycosylapigenin, C-6-glycosylapigen- Clark et al., 1980
in, di-C-glycosylapigenins
Haplopappus sericeus vitexin, isovitexin, vicenin-2 Ares et al., 1982
Phil.
C-GLYCOSYLFLAVONES I1
Table I
Continued
Tribe, genus,
H. scrobiculatus vitexin, isovitexin,vicenin-2, schafioside A t e s et al., 1982
(Nees) DC.
Inuleae
Helichrysum bractea- orientin, isoorientin Rimpler et al.,
turn Andr. 1963
Senecioneae
Senecio radicans di-C-rhamnosylapigenins Glennie et al.,
complex 1971
Vernonieae
Vernonia cinerea (L.) i s o o r i e n t i n Gunasingh & Na-
Less. (flowers) garajan, 1981
a If not indicatedotherwise,compoundswere isolatedfrom leafmaterial.
ex Boisss. and A. aleppica DC. showed no C-glycosylflavones in the roots

which might have one basis in the different root morphology and growth
form. The latter two species develop secondary roots, whereas A. fra-
grantissima and A. lycaonica have a strong primary root system (tap root;
Valant-Vetschera, in press b).
The closely related genus Leucocyclus was found to contain isovitexin
(2) and a series ofisoorientin derivatives (isoorientin [6], its 2"-arabinoside
and caffeoyl ester) together with di-C-glycosylapigenins (vicenin-3 [17],
schaftoside [19], isoschaftoside [20]) and di-C-glycosylluteolins (lucenin-
2 [23]) in the leaves (Valant-Vetschera, in press b). Otospermum glabrum
(Lag.) Willk. affords another (monotypic) genus with a predominantly
C-glycosylflavone pattern although the more complex structures seem to
be not present (Greger, 1978; unpubl.). This genus is not allied to Achillea
or Leucocyclus by any morphological or chorological characters. Di-C-
glycosylflavones are occasionally accumulated in species of Artemisia
(Cumbalov & Fadeeva, 1970; Valant-Vetschera & Rficker, in prep.) and
Ajania (Cumbalov & Zubaeva, 1976).
A similar variety of C-glycosylflavones occurs in some genera of the
Heliantheae (Table I). In particular, the genera Gaillardia (Wagner et al.,
1972a), Balduina (Bohm, 1978) and Helenium (Bierner, 1973; Bierner et
al., 1978) of the subtribe Gaillardiinae (Stuessy, 1978) are characterized
by the predominance of mono- and di-C-glycosylflavones, including the
7-O-methyl ethers swertisin (7) and swertiajaponin (11). By contrast,
Flourensia (Helianthinae; Dillon et al., 1976) and Dahlia (Coreopsidinae;
Giannasi, 1975) accumulate mainly di-C-glycosylapigenins. Although these

data are of limited value for systematic conclusions, the similarity in the
chemistry of the tribes Anthemideae and Heliantheae is striking. Fur-
thermore, both tribes are characterized by the common occurrence of
isobutyl amides (Greger, 1982; Sorensen, 1978), which are, however, not
correlated with the occurrence of C-glycosylflavones in the same genera.
Additionally, certain types of S-substituted polyacetylenes (Sorensen, 1978)
have been reported for both tribes, thus suggesting another possible affinity
amongst members of both tribes.
Almost the same set of C-glycosylflavones (vitexin [1], isovitexin [2],
orientin [5], di-C-glycosylapigenins and -luteolins) is typical of the genera
Carlina, Atractylis, Staehelina and Centaurea of the Cynareae (Table I).
Some of these compounds are not only found in the leaf tissue, but also
in the roots of Carlina corymbosa L. (Besson et al., 1979), and flower
heads of Centaurea melitensis L. (Kamanzi et al., 1983b). Earlier reports
on the occurrence of isoswertisin (8) as part of the blue pigment complex
in flowers of C. cyanus L. (Asen & Jurd, 1967) could not be verified in a
second study (Asen & Horowitz, 1974). The flavone glycoside part of the
pigment complex was identified as apigenin-4'-O-B-D-glucoside 7-O-~-
D-glucuronide. Thus there is no evidence for the occurrence of C-gly-
cosylflavones in the cornflower pigment. Generally, the C-glycosylflavone
profile of the respective genera does not appear to be uniform. This might
be due to limited systematic studies on the distribution of individual
compounds. The occurrence of the di-C-glycosylflavones corymboside
(22) and carlinoside (25) as well as the lack of the 7-O-methyl ethers
swertisin (7) and swertiajaponin (11) distinguish the Cynareae from some
of the other tribes.
Within the Lactuceae, the genus Tragopogon shows a complex C-gly-
cosylflavone pattern (Belzer & Ownbey, 197 l; Kroschewsky et al., 1969).
Apart from vitexin (1), isovitexin (2), orientin (5), isoorientin (6), vicenins
(16, 18) and lucenins (23, 24), the occurrence of the 7-O-methyl ethers
swertisin (7) and swertiajaponin (I1) and that of O-xylosylvitexin as a
minor constituent has been reported. By contrast, Catananche caerulea
L. contains carlinoside (25; Proliac & Raynaud, 1977) and other di-C-
glycosylflavones such as schaftoside (19), isoschaftoside (20) and the cor-
responding di-C-glycosylluteolins (Proliac et al., 1973). The structure pro-
posed for isoschaftoside (20) was later revised to correspond to that of
neoschaftoside (Chopin et al., 1982a; Dillon et al., 1976). A detailed
structural investigation ofneoschaftoside was carried out recently and the
correct structure assigned to it (Besson et al., 1984). In most of the other
tribes, the accumulation of C-glycosylflavones appears to be a minor trend.
Most genera lack variability in substitution patterns, accumulating either
di-C-glycosylflavones (e.g., Eupatorieae, Astereae p.p.; Senecioneae) or
simple mono-C-glycosylflavones (Inuleae, Vernonieae). Within the As-

tereae, the generic assemblage of Haplopappus and Hazardia shows a
greater diversity in the formation of apigenin-derived C-glycosylflavones
(Clark & Mabry, 1978; Clark et al., 1980). The presence of vitexin (1),
isovitexin (2), vicenin-2 (16) and isoschaftoside (20) has been confirmed
for some Haplopappus species (Ates et al., 1982). In the tribe Vernonieae,
isoorientin (6) has been reported as a fower constituent of Vernonia
cinerea (L.) Less. (Gunasingh & Nagarajan, 1981), which appears to be
the only record for the tribe.
Although the data on C-glycosylflavone accumulation in the Compos-
itae are limited, they illustrate the biogenetic capacity of several tribes
and genera. It appears that some derivatives are of restricted distribution
(e.g., swertisin [7], swertiajaponin [11], and carlinoside [25]), which might
turn out to be of systematic value. Moreover, combined accumulation of
different di-C-glycosylapigenins, such as vicenins (16, 17, 18) with schaf-
toside (19) and isoschaftoside (20), could serve as a chemical character.
Future studies on both distribution and detailed structure might be helpful
in establishing the value of C-glycosylflavones as chemical features within
the Compositae.
III. C-Glycosylflavones as a Part of the Flavonoid

Complement in the Compositae
In the Compositae, C-glycosylflavones often co-occur with other fla-

vonoids and their O-glycosides, even if they should represent the main
accumulation tendency. Naturally, there are quantitative and qualitative
differences in the accumulation of different types of glycosides, thus cre-
ating various combination trends. These combination trends were ana-
lyzed with special regard to the co-occurrence with different C-glycosyl-
flavone derivatives (Table II). The correlation of co-occurrence between
C-glycosylflavones and flavonoid O-glycosides is expressed as a percent-
age of taxa containing C-glycosylflavones. Main emphasis was put on the
correlation between C-glycosylflavone formation and that offlavonol 3-O-
glycosides and flavone 7-O-glycosides, which are the main characteristics
of the flavonoid profile of the Compositae (Harborne, 1978).
Recent research on Achillea (Valant, 1978; Valant-Vetschera, 1982a,
in press a) and Leucocyclus (Valant-Vetschera, 1982b) has revealed several
interesting aspects of flavonoid diversification. Both genera are charac-
terized not only by the predominance of C-glycosylflavones, but also by
the predominance offlavonol 3-O-glycosides. Flavone 7-O-glycosides are
accumulated as a minor trend. Regarding the combination of these three
tendencies, two combinations were observed: either C-glycosylflavones
oo
;> ;> ;> >
0 8
O o
tr~ O
0
6
+
0
8 S r,.~
~ 9~ 9
0
0 ~ 8~
.=.
0
>
o 0
=_
o >
0 o +
=
"r~
d
e~
?
0
oo
v
e~
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+
f~
o
o
r O O r'- O 0o
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~ ~.~ 8
~o ~ a e,a e,
~~ ~ ~
,'4
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~~ 9~..~~
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O~
g
r~
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a~
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g
o~
O
O. 6 6 ~, O. -~ ~O. O.O.
6 "~
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Y~
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r r
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III
o~ ~o ~o~o o~ ~ ~o~o~o~o~
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6 o ~ .~ ~ ~ ~~~ .~.~
~ ~ ~',~
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~ ~ ~ ~ ~o,'~~ i
.!
0
represented the main accumulation tendency with the additional for-

mation of only a few flavonol 3-O-glycosides, or vice versa. Flavone 7-O-
glycosides occurred occasionally in both flavonol- and 1C-glycosylfla-
vone-dominated profiles. Apart from these more general trends, specific
compounds also characterized groups within Achillea, thus having the
role of marker compounds. The systematic significance of these trends
was discussed earlier (Valant-Vetschera, 1982a). Although the distinction
between flavonol 3-O-glycoside-dominated and C-glycosylflavone-dom-
inated patterns proved to be a valuable systematic criterion, doubts arose
as these differentiations began to be found at lower taxonomic levels. In
particular, the two subspecies of Leucocyclus formosus Boiss. (Valant-
Vetschera, 1982b) and the closely related pair of species A. ptarmica L.
and A. salicifolia Besser (Valant-Vetschera, in press a) exhibited this switch-
over in flavonoid profile. In both cases only one C-glycosylflavone
remained in an otherwise flavonol dominated complement. The direction
of this evolution is not clear. According to the current dogma C-glyco-
sylflavones should represent an intermediate stage in the flavonol-flavone
reduction series (Gornall & Bohm, 1978; Harborne, 1977). There is, how-
ever, little support for this theory on the basis of the flavonoid diversi-
fication in Achillea and Leucocyclus. From the biogenetic point of view,
such a changeover would involve a series of different enzymes acting,
assuming that the biosynthesis of C-glycosylflavones is that much different
from that of the O-glycosides, as is generally believed. On the other hand,
almost nothing is known about the different functional role(s)--if there
is a n y - - o f C-glycosylflavones versus flavonol 3-O-glycosides or flavone
7-O-glycosides. They could also be interchangeable with respect to their
ecological adaptive value.
The numerical data from the A. ptarmica group and the genus Leu-
cocyclus, as well as those of other Achillea groups studied so far, are listed
in Table II. The correlation of C-glycosylflavones with flavonol 3-O-
glycosides is frequently below 50%. In those cases where di-C-glycosyl-
flavones only are being accumulated, the percentage of flavonol 3-O-
glycosides increases, but individual flavonol 3-O-glycosides show different
values (e.g., quercetin 3-O-rhamnoglucoside up to 100%, and kaempferol
3-O-glycosides far lower). Correlations with flavone 7-O-glycosides ap-
pear to be very low and do not differ with various C-glycosylflavone
derivatives. Similarly, the genus Leucocyclus shows a low percentage of
additional flavonol 3-O-glycoside accumulation when C-glycosylflavones
predominate; a high percentage of correlation is observed with the pres-
ence of di-C-glycosylflavones. Flavone 7-O-glycoside correlate to 100%
with C-glycosylflavones, but they are accumulated in trace amounts only.
The question then arises as to how far this accumulation behavior of C-
glycosylflavones is typical only of Achillea and Leucocyclus, or if similar

biochemical trends can be found in other genera of the Compositae as
well. Therefore, the comparison of combination trends was extended to
some other genera (Table II).
Flavonoid distribution studies have been carried out only in a few
genera (e.g., Tragopogon, Hazardia, Helenium, Dahlia). The structures
of the C-glycosylflavones accumulated have, however, not been identified
for all of them. Tragopogon provides an example of accumulation trends
similar to Achillea: a series o f m o n o - and di-C-glycosylflavones correlates
highly with quercetin 3-O-glucoside and luteolin 7-O-glucoside (Kro-
schewsky et al., 1969; Table II). By contrast, the genus Helenium; showing
a similar C-glycosylflavone profile, additionally accumulates apigenin 7-0-
glucoside in a very low percentage (Bierner, 1973). One species of Cen-
taurea contains several C-glycosylflavones together with quercetin 3-0-
glucoside (Kamanzi & Raynaud, 1976), but further distribution has so
far not been investigated. Typical constituents of some Hazardia species
are mainly di-C-glycosylapigenins and one 1C-8-glycosylapigenin (Clark
& Mabry, 1978). The correlation both with flavonol 3-O-glycosides and
with flavone 7-O-glycosides is relatively high. All the other genera listed
here (Liatris, Dahlia, Senecio) apparently accumulate di-C-glycosylapi-
genins as the only glycoflavones. Most of the O-glycosides show a high
percentage of co-occurrence with these compounds (Table II).
Due to the limited information on flavonoid diversification within the
Compositae, these results cannot be used presently as taxonomic char-
acters at the family or tribal level. However, they appear to be useful
chemical characters at the generic or infrageneric level. These results
suggest that much more attention be paid to the C-glycosylflavone ac-
cumulation both with regard to the predominance of special derivatives
and to their combination trends. Moreover, these data indicate that di-
C-glycosylflavones occur more frequently than other derivatives, espe-
cially in combination with flavonoid O-glycosides (Table II). This feature
is not only of interest as a possible chemical character, but also from the
biogenetic point of view: assuming that C-glycosylflavones are interme-
diates in the biochemical evolution from flavonols to flavones, why should
di-C-glycosylflavones in particular represent this stage in the fairly ad-
vanced Compositae? This problem remains unsolved at present. From
the many possible reasons for this behavior, the functional role of C-gly-
cosylflavone accumulation as such or that of special derivatives should
be taken into consideration. Besides, it has to be determined if this feature
could also be a purely biochemical one, being dependent on enzymatic
reaction sequences which are not primarily correlated with taxonomic
relationships.
Table III
List of families surveyed
Dicotyledoneae
MAGNOLIIDAE Magnoliales Idiospermaceae, Winteraceae,
Lauraceae
Ranunculales Ranunculaceae
DILLENIIDAE Dilleniales Dilleniaceae
Theales Clusiaceae (Hypericaceae p.p.)
CARYOPHYLLIDAE Caryophyllales Amaranthaceae, Basellaceae,
Chenopodiaceae, Didiereaceae,
Nyctaginaceae, Phytolaccaceae,
Portulacaceae, Caryophyllaceae,
Molluginaceae
ROSIDAE Fabales Fabaceae
ASTERIDAE Tubiflorae Polemoniaceae, Lamiaceae, Solanaceae
Gentianales Gentianaceae
Monocotyledoneae
COMMELINIDAE Cyperales Cyperaceae
LILIIDAE Zingiberales Zingiberaceae,
Marantaceae
Orchidales Orchidaceae
ARECIDAE Arales Lemnaceae
IV. C-Glycosylflavones as a Part of the Flavonoid Complement

in Selected Angiosperm Families
This section is devoted mainly to a similar analysis o f selected angio-
sperms, with special regard to combination trends. Little attention, how-
ever, is paid to the impact on systematics, for reasons already discussed.
This survey does not claim to be complete, mainly because only the more
recent literature is incorporated and secondly, m u c h o f this literature
consists o f general systematic surveys o f flavonoid occurrence and the
C-glycosylflavones per se have not always been fully characterized. For
further information on the distribution o f C-glycosylflavones the surveys
o f Chopin et al. (1982a) and o f Bandjukova and Jugin (1981) are rec-
o m m e n d e d . Table III gives a list o f families considered in this chapter.
T h e data on combination trends are s u m m a r i z e d in Table IV, organized
similarly to Table II.
Dicotyledoneae:
IDIOSPERMACEAE." Surprisingly, C-glycosylflavones (di-C-glycosylapigen-
ins) and flavone 7-O-glycosides o f apigenin and luteolin were detected in
one m e m b e r o f a more primitive angiosperm group (Young & Sterner,
0 0
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0
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6 + -- ,.~ + ooo, oo, 6

e~ 9 ~ ~ .~ .~
o
0
+
0
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rd
7, 7~
2, ~ -d
.~ .~ o
o,
+
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5 o .- o
~o, o, o o, ~ 6 ~ , . o o
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e~
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0
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9~ ~ ~-~ .~~ .~ .~ .~ § .~
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I=
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I I I
6 6
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§
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9 9. 666 ~§
0
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e~
r r r o
O
0o
e~
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ox
0 0
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o~
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0 0 0
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8 0
o o o
e~
0
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n:l ~,~ + + 0 6,
i
06
0
0 0
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~+
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8
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8
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8~ 9~ o~
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~o
&
8~
1981). In Idiospermum these compounds correlated 100%, but only one

taxon has been analyzed.
WINTERACEAE: This family of the Magnoliales affords another example of
the occurrence of C-glycosylflavones and flavones (Williams & Harvey,
1982). In particular, seven samples of Tasmannia piperita (Hook.) Miers
and one of Drimys winteri J. R. & G. Forster contained unidentified
C-glycosylflavones together with quercetin (100% correlation). Kaemp-
ferol correlated far less (28%), whereas the flavones correlated differently
in these two genera. It would be interesting to know more about the
structures of the C-glycosylflavones present in this family.
LAURACEAE" Within this family, C-glycosylflavones are typical of some
Persea species (Wofford, 1974). Vitexin (1), isovitexin (2), orientin (5)
and isoorientin (6) occur together with quercetin- and kaempferol 3-0-
glycosides and correlate 100%.
RANUNCULACEAE"The accumulation of C-glycosylflavones appears to be
a rare feature in this family, with only a few genera (e.g., Adonis, Ranun-
culus p.p., Chopin & Bouillant, 1975; Chopin et al., 1982a) accumulating
them. Recently, a comparative study carried out on Clematis (Dennis &
Bierner, 1980) indicated that beside the mono- and di-C-glycosylflavones,
a series of flavonol and flavone O-glycosides were characteristic features
of the flavonoid complement. Five species accumulated isoorientin (6)
and isovitexin (2) which correlated highly with most of the other glyco-
sides present. In one taxon, vicenin-2 (16) was accumulated instead of
the mono-C-glycosyl derivatives, and this particular compound seems
also to be highly correlated both with the flavonols and the flavones.
DILLENIACEAE"In this family several apigenin mono-C-glycosides (vitexin
[1], isovitexin [2], isovitexin 7-O-glucoside) have been reported to occur
(Gurni & Kubitzki, 1981). In Doliocarpus, correlation was observed with
myricetin 3-O-rhamnoside, being 76% when all three C-glycosylflavones
were present, but only 14% when only one or two C-glycosylflavones were
present. One species of Dillenia contained C-glycosylflavones, which nat-
urally gave a correlation of 100% with the flavonol 3-O-glycoside present.
CLUSIACEAE"The genus Hypericum affords mono-C-glycosides of luteolin
and apigenin (Calie et al., 1983). In the two species with C-glycosylfla-
vones, a 100% correlation was found with the flavonol 3-O-glycosides
and the flavone 7-O-glycosides. Another five species were found not to
contain C-glycosylflavones.
AMARANTHACEAE"This family was surveyed, together with other families
of the Caryophyllales, by comparison of hydrolyzed leaf extracts (Rich-
ardson, 1978). The presence of orientin (5) and isoorientin (6), possibly
Wessely-Moser isomers, correlates with quercetin (100%) and kaempferol

(100%). Unidentified glycoflavones correlate with quercetin (100%) as
well. Earlier reports indicated the presence of flavonol 3-O-glycosides
(quercetin and kaempferol based) in this family (Mabry et al., 1972 and
references cited therein). Thus it may be assumed that the four taxa
containing flavonols also accumulate them as the 3-O-glycosides.
BASELLACEAE:NO correlation was observed in one taxon of the Basellaceae
shown to be accumulating C-glycosylflavones (Richardson, 1978), al-
though quercetin was found in the same species earlier (Mabry et al.,
1972).
CHENOPODIACEAE" Orientin (5), isoorientin (6) and unidentified C-glyco-
sylflavones correlate with quercetin and kaempferol to the extent of 50%
in this family (Richardson, 1978). Flavonols and their 3-O-glycosides
appear to be the main constituents in this family, occurring also as
6-substituted derivatives in Spinacea oleracea L. (Mabry et al., 1972).
DIDIEREACEAE" Four taxa of this family accumulate unidentified C-gly-
cosylflavones together with quercetin (50%) and myricetin (25%; Rich-
ardson, 1978). In a systematic survey (Burret et al., 1981) the presence
of vitexin (I) and isovitexin (2) and of the flavonols myricetin, quercetin
and kaempferol as well as of C-methylated and O-methylated derivatives
was indicated. Some genera (e.g., Decaryia) contained polymethoxyfla-
vones as free aglycones (Rabesa & Voirin, 1980). In these publications,
reference is frequently made to the doctoral thesis of Rabesa (University
of Lyon, 1980), which should contain more information about the fla-
vonoid profile of this family, but it was not available to the author.
NYCTAGINACEAE; A 100% correlation between quercetin and unidentified
C-glycosylflavones is found in the Nyctaginaceae (Richardson, 1978). No
reports on the nature of the flavonol glycosides have been given.
PHYTOLACCACEAE"In contrast to the former families, C-glycosylflavones
in Phytolaccaceae appear to be correlated with the accumulation of
kaempferol only (Richardson, 1978). Some genera, such as Phytolacca,
contain a range of flavonol 3-O-glycosides (Mabry et al., 1972; Richard-
son, 1978). The glycosides of the genus Trichostigma, which accumulates
orientin (5) and isoorientin (6), have not been fully analyzed.
PORTULACACEAE" Three taxa of this family show accumulation of C-gly-
cosylflavones, but no correlation with any other flavonoid glycoside, al-
though flavonol 3-O-glycosides are present in several members of this
family (Mabry et al., 1972, Richardson, 1978).
CARYOPHYLLACEAE" This family has proven to be a rich source of C-gly-
cosylflavones including several complex derivatives (Chopin & Bouillant,

1975; Chopin et al., 1982a). This may be one reason for the difficulties
encountered in isolating and identifying these compounds in the course
of a broad survey (Richardson, 1978). Apart from the widespread mono-
C-glycosylflavones orientin (5), isoorientin (6), vitexin (1) and isovitexin
(2), the C-6-arabinosylapigenin, isomollupentin (4) was reported to occur
in this family (Chopin et al., 1982a). Furthermore, di-C-glycosylflavones
such as schaftoside (19) and lucenin-2 (23) and some complex cinnamoyl
derivatives of vicenin-2 (16) and schaftoside (19) are accumulated (Cho-
pin et al., 1982a). Flavonols appear to be common constituents and are
also present as 3-O-glycosides (Mabry et al., 1972). As could be expected
from a predominantly C-glycosylflavone pattern, flavonol 3-O-glycosides
(or flavonols) show a relatively low correlation, mostly far below 50%.
Apparently, most of the biosynthetic activities are involved in the for-
mation of C-glycosylflavones, giving rise to many complex derivatives.
MOLLUGINACEAE"Several complex C-glycosylflavones have been reported

for Mollugo species (Chopin et al., 1982a). Mono-C-glycosyl derivatives
appear to be mainly 7-O-methylated and are apigenin-based (isoswertisin
[8], molludistin [10] and their 2"-rhamnosides). Furthermore, di-C-gly-
cosylapigenins were isolated from one species and identified as 6-C-/~-D-
xylopyranosyl-8-C-a-L-arabinopyranosylapigenin (Chopin et al., 1982b).
A different species has been analyzed by Richardson (1978) and was found
to accumulate vitexin (1) and isovitexin (2), correlating 100% with quer-
cetin and kaempferol. The flavonols are probably glycosylated at the
3-position (Mabry et al., 1972). The occurrence of C-arabinosylflavones
appears to be a common feature of the Caryophyllaceae and the Mollu-
ginaceae, which could turn out to be of taxonomic significance.
FABACEAE:This family is particularly known for the occurrence of C-gly-

cosylated compounds which also occur as isoflavones (see Chopin &
Bouillant, 1975; Chopin et al., 1982a). Of this large family, only two
genera will be discussed here. The genus Prosopis was found to contain
apigenin di-C-glycosides and a range of flavonol and flavone O-glycosides
(Bragg et al., 1978). The correlation with both of them was high, the
flavonols amounting to 100% and the flavones a little lower (83% and
98%). In contrast to many other papers, the relative occurrence of indi-
vidual compounds was expressed as a percentage already, which accounts
for the figures given in Table IV.
A survey of flavonoid accumulation in Old and New World Lupinus
species reveals that C-glycosylflavones and flavonol 3-O-glycosides are
apparently mutually exclusive (Williams et al., 1983). Although the gly-
coflavones have not been completely identified, there are indications that
mono-C-glycosylflavones may occur. Vitexin (1), orientin (5), cytisoside

(12) and C-8-glucosyldiosmetin (13) have been reported as constituents
of Lupinus arboreus Sims. (Nicholls & Bohm, 1979). Additional C-gly-
cosylflavones were found to occur in geographical collections of the same
species and the quantitative differences were determined (Nicholls & Bohm,
1982). Furthermore, the presence of flavonol 3-O-glycosides and flavone
7-O-glycosides observed earlier (Nicholls & Bohm, 1979) was confirmed.
Therefore it may be assumed that the aglycones found by Williams et al.
(1983) occur as flavonol 3-O-glycosides and flavone 7-O-glycosides, re-
spectively. How far the same C-glycosylflavones present in L. arboreus
are distributed in this genus is not clear on basis of the published data.
POLEMONIACEAE: In the course of a survey on the flavonoid patterns of
the Polemoniaceae (Smith et al., 1977), seven genera were reported to
accumulate C-glycosylflavones. Of these, the genus Phlox has been known
for a long time to be a rich source for C-glycosylflavones, with some
species aggregates forming no less than 28 derivatives (Levy, 1983 and
references cited therein). Whereas the earlier survey (Smith et al., 1977)
gave no indication as to the nature of the C-glycosylflavones present, the
two genera Linanthus and Leptodactylon were later analyzed in detail
(Smith et al., 1982). A series of flavonol O-glycosides and some flavone
7-O-glycosides were found to co-occur with different C-glycosylttavones.
Generally, the correlation is relatively high, even with the more complex
derivatives such as isovitexin 4'-O-arabinoside in Leptodactylon and the
O-glucoside ofisovitexin 7,4'-dimethyl ether (15) in Linanthus. The ear-
lier survey gave figures easier to summarize, but they seem to be less
conclusive, since the C-glycosylflavone structures were not fully analyzed.
LAMIACEAE: During a survey of the occurrence of vicenin-2 (16) in this
family, Origanum, Thymus and Hyssopus were found to contain this
compound (Husain & Markham, 1981). Earlier, vicenin-2 (16) had been
isolated from leaf extracts of Teucrium and its structure determined (Ray-
naud & Chourikha, 1976). Furthermore, C-glycosylflavones are accu-
mulated in the genera Ajuga and Phlomis (Chopin et al., 1982a). Any
correlation with the formation of flavonoid O-glycosides in Origanum,
Thymus and Hyssopus has not been reported upon.
SOLANACEAE"Within this family, the flavonoid complement of the genus
Solanum sect. Androceras has been studied intensively (Whalen, 1978).
Most of the species contain a range of flavonol 3-O-glycosides including
8-substituted derivatives. Two C-glycosylflavones were identified as an
C-8-glycosylapigenin and a di-C-glycosylapigenin. The co-occurrence
with flavonol 3-O-glycosides (quercetin, kaempferol and isorhamnetin)
was found to be 100% with both glycoflavones; 8-hydroxyflavonol 3-0-
glycosides correlated 100% with mono-C-glycosylapigenin, but only 50%

with the di-C-glycosylapigenin. Flavone 7-O-glycosides were found cor-
related to an extent of 33% with the di-C-glycosylapigenin.
GENTIANACEAE: Some genera of this family prove to be rich sources for
C-glycosylflavones (Chopin et al., 1982a). Based mainly on isoorientin
(6) and isovitexin (2), several complex structures including cinnamoyl
esters have been isolated from the genus Gentiana (Jacot-Guillarmod et
al., 1975; Luong et al., 1977). Moreover, O-glycosides of these complex
derivatives also accumulate. Little is known, however, about co-occur-
rence with other flavonoid glycosides, since most reports concentrate on
the isolation and identification of the C-glycosylflavones. Flavonols and
their glycosides seem to be of restricted distribution (Bellmann & Jacot-
Guillarmod, 1973 and references cited therein), which also applies to the
occasional accumulation of flavone O-glycosides (Chulia & Debelmas,
1977). For the latter the correlation with the occurrence of C-glycosylfla-
vones is relatively high. Possibly minor amounts offlavonols and flavones
might occur in Gentiana species, but reports on complete flavonoid pat-
terns are scant to date. There are, however, several records on the additional
accumulation of O- and C-glycosylated xanthones (Hostettmann-Kaldas
& Jacot-Guillarmod, 1978; Massias et al., 1982). These compounds are
generally believed to be biosynthetically related to the flavonoids (Har-
borne, 1977). The formula of the C-glucosyl xanthone, mangiferin, is
illustrated in Figure 2.
Monocotyledoneae:
CYPERACEAE" C-glycosylflavones are one of the main accumulation ten-
dencies in the Cyperaceae (Williams & Harborne, 1977a). In a recent
survey of 60 species containing these compounds, no flavonols could be
found, indicating that these two groups of flavonoids are mutually exclu-
sive here. On the other hand, flavones were found to co-occur in 70% of
the species. Similar results were obtained earlier (Harborne, 1971). In
that study, the C-glycosylflavone was identified as isoorientin (6), whereas
Williams and Harborne (1977a) additionally found an isoorientin 3'-0-
glucuronide in one of the Cyperaceae species. Apparently, several other
C-glycosylflavones are also accumulated and structure elucidation is under
way by this group. Recent studies on Australian Cyperaceae (Harborne
et al., 1982) reveal that the genus Cyperus is obviously rather poor in
C-glycosylflavones, but contains a series of flavone glycosides.
ZINGIBERACEAE: Within this family, C-glycosylflavones are accumulated--
together with flavonols--in the genus Costus (Williams & Harborne,
1977b). The correlation with quercetin (70%) appears to be far higher
HOjoOH
GLc- y v -o=
OH 0
Fig. 2. Formula of mangiferin.
than that with kaempferol (28%). Apigenin di-C-glycosides (schaftoside

[19], isoschaftoside [20]) were isolated from Costus sanguineus Donne,
together with a quercetin 3-O-galactosylrhamnoside. According to these
data, flavonols occur as 3-O-glycosides in most of the species investigated.
C-glycosylflavones of a different substitution pattern, including vitexin
(1), isovitexin (2), orientin (5) and isoorientin (6) as well as vitexin and
isovitexin sulfates and 7-O-glycosides, occur in the related Marantaceae
(Williams & Harborne, 1977b). They proved to be mutually exclusive
with flavonol 3-O-glycosides of quercetin, kaempferol and myricetin and
showed hardly any correlation with flavone O-glycosides.
ORCHIDACEAE: Like many monocot families, the Orchidaceae also accu-
mulate C-glycosylflavones (Williams, 1979). Di-C-glycosylapigenins, a
C-glycosylchrysoeriol 7-O-glycoside, vitexin (1), isovitexin (2) and vitexin
7-O-glucoside have been siolated from various species. Their distribution
in the whole family, however, has not been determined. Flavonols and
flavones show a very low correlation (under 10%), which really seems to
be a significant trend.
LEMNACEAE: A detailed survey on Lemnaceae flavonoids (McClure &
Alston, 1966) revealed that C-glycosylflavones were frequently present in
Lemna and Spirodela, only to a lesser extent in Wolffia and were com-
pletely lacking in Wolffiella. A series of flavonol 3-O-glycosides and fla-
vone .7-O-glycosides was accumulated as well. Very little correlation,
however, was found between the accumulation of C-glycosylflavones and
flavonol 3-O-glycosides, whereas flavone glycosides appeared to score
higher. In Table IV the occurrence of acylated C-glycosyl derivatives was
not taken into account, since they were restricted to a few species of Lemna
only.
Keeping in mind that the data presented here cannot be fully conclusive,
the attempt is made to summarize the contents of Tables II and IV with
respect to the more general aspects of accumulation behavior of
C-glycosylflavones versus flavonoid O-glycosides (Table V). Genera and
families are listed according to their taxonomic position, and the C-
Table V
A summary o f combination trends in some angiosperm taxa
Group A Group B
Magnoliidae Drimys* F3, F7 Idiospermum F7

Tasmannia* F3, F7
Persea F3
Clematis F3, F7
Diileniidae Doliocarpus F3
Dillenia F3
Hypericum F3, F 7 -
Caryophyllidae Amaranthaceae F3
Chenopodiaceae F3
Phytolaccaceae F3
Caryophyllaceae F 3 - Caryophyllaceae F3
Molluginaceae F3 Molluginaceae F3
Rosidae Lupinus F7 Prosopis F3, F7
Asteridae I Phlox F3
Leptodactylon F3, F7
Linanthus F3, F5, F3,7, F 7 -
Solanum
sect. Androceras F3, F 7 -
Gentiana F7
Asteridae II Achillea F3-, F7- Achillea F3
Leucocyclus F3-, F7- Leucocyclus F3
Tragopogon F3, F 7 - Liatris F3
Helenium F7 Hazardia F3, F7
Dahlia F3, F7
Senecio F3
Liliidae Marantaceae F 7 - Zingiberaceae:
Orchidaceae F 3 - , F 7 - Costus F3
Commelinidae Cyperaceae F7
Arecidae Lemnaceae F3, F7
Group A: mono-C-glycosylflavone dominated.
Group B: di-C-glycosylflavones accumulated only.
F3: flavonol 3-O-glycosides; FS: flavonol 5-O-glycosides; F3, 7: flavonol 3,7-di-O-gly-
cosides; F7: flavone 7-O-glycosides.
- indicates minor tendency.
* Structures not identified.
glycosylflavone patterns have been distinguished as either (group A) mono-

C-glycosylflavone dominated, or (group B) accumulating only di-C-gly-
cosylflavones. It must be emphasized that although plants are listed tax-
onomically, there is no primary intention to draw systematic conclusions.
It appears that the general tendency is that o f a C-glycosylflavone dom-
inated profile together with a more or less reduced set of either flavonol-
or flavone O-glycosides, which is typical of a series of subclasses. However,
some taxa have apparently shifted from group A to group B either within
the same genus or the same family. Whereas this phenomenon seems to
be rare in some subclasses, it becomes more frequent in the Compositae.
In this particular family the taxa of group B are more numerous than
those of group A at present. Another important feature could be the
correlation with flavonoid O-glycosides: in group A, flavonol 3-O-gly-
cosides and flavone 7-O-glycosides equally co-occur with the C-glyco-
sylflavones, but in group B the flavonol 3-O-glycosides predominate as a
combination. It remains unclear whether the direction of biochemical
evolution may be read as going from group A to group B or vice versa
or even other less obvious ways. These patterns, however, do not support
the theory of C-glycosylflavones being intermediates in the flavonol-fla-
vone reduction trend (Harborne, 1977).
V. Specialization Trends in C-Glycosylflavone Accumulation
In many of the plant groups analyzed in this study, C-glycosylflavones
occur as a series of derivatives. The major substitution trends of C-gly-
cosylflavones are listed in Table VI. Substitution occurs not only at the
flavonoid molecule but also on the C-glycosyl sugar component. The
various substitution patterns appear to be specific at different taxonomic
levels. Some genera and families accumulating C-glycosylflavones as a
major tendency have been chosen to illustrate various substitution pat-
terns. Since detailed quantitative studies have generally not been carried
out, only the relative amounts of the different derivatives can be indicated
(Fig. 3a-g).
A comparison of the genera Achillea (including Leucocyclus) and He-
lenium of the Compositae reveals that specialization trends are quite
similar (Fig. 3a and b). However, Achillea and Leucocyclus also produce
small amounts of O-glycosylated or acylated derivatives, and fewer C-8-
glycosyl derivatives than Helenium. Other aspects offlavonoid production
in these genera have been discussed earlier (Section II). By contrast, spe-
cialization appears to be high in Gentiana (Fig. 3c), showing a distinctive
tendency to form C-6-glycosylated flavones and a variety of O-glycosides
and acylated derivatives based upon these. In the Caryophyllaceae, there
is apparently a major trend to produce O-glycosylated apigenin derivatives
C-GLYCOSYLFLAVONES 4i
Table VI
Major substitution patterns of C-glycosylflavones
A. ON THE FLAVONOID NUCLEUS
A.I. hydroxylation
A.I.1. on ring A
A. 1.2. on ring B
A.2. methoxylation
A.2.1. on ring A
A.2.2. on ring B
A.3. C-glycosylation
A.3.1. variation in sugar component
A.3.2. variation in sugar attachment at C-6 and/or C-8-position
A.4. O-glycosylation
A.5. sulfates
A.5.1. on hydroxyl group
A.5.2. on O-glycosyl component
B. ON THE C-GLYCOSYL SUGAR COMPONENT
B.1. O-glycosylation
B.2. acylation
B.2.1. acetylation
B.2.2. benzoyl substitution
B.2.3. cinnamoyl substitution
(e.g., in Silene [Melandrium], Chopin et al., 1982a) but, generally speaking,

this family appears to be less specialized with respect to substitution trends
(Fig. 3d) than members of the Gentianaceae. The genera Leptodactylon
and Linanthus of the Polemoniaceae accumulate a series of derivatives,
including the rare 7,4'-dimethylated C-glycosylapigenins. Thus both
A-ring and B-ring substitution appear to be equal trends here (Fig. 3e).
The C-glycosylflavone pattern seems to be less specialized, especially when
compared with that of Gentiana. Finally, the monocots can be examined
for their substitution patterns, and the Lemnaceae and Orchidaceae have
been chosen as representatives. There appears to be little specialization
in either family and the relative amounts are similar. One notable dif-
ference is the tendency to produce sulfates in Orchidaceae. The Lemna-
ceae, however, accumulate acylated di-C-glycosylflavones.
Since in most cases the C-glycosylflavones are only part of the flavonoid
complement, the co-occurrence of other flavonoid glycosides should also
be discussed here. When comparing the genera of Compositae, Achillea
is seen to be characterized by the predominance of C-glycosylflavones
and flavonol 3-O-glycosides, whereas Helenium accumulates C-glycosyl-
flavones with flavone 7-O-glycosides as a minor trend (for correlation see
Table II). Similarly, the Caryophyllaceae co-accumulate flavonol 3-0-
glycosides and species of Gentiana co-accumulate flavone 7-O-glycosides
and flavonols as minor tendencies. The Polemoniaceae genera, on the

contrary, show a greater diversity in the flavonol O-glycoside pattern,
accumulating not only the widespread 3-O-glycosides but also 3,7-di-O-
glycosides and 5-O-glycosides. Furthermore, flavone 7-O-glycosides rep-
resent a minor tendency in these genera. Both the Orchidaceae and Lem-
naceae accumulate several flavonol 3-O-glycosides, but the latter family
shows an additional flavone 7-O-glycoside production trend. In all these
examples the correlation is not always high between the formation of
C-glycosylflavones and any flavonoid O-glycoside, but the different glyco-
sidic types are not mutually exclusive. However, there are some taxa
which accumulate either C-glycosylflavones or flavonol 3-O-glycosides,
such as Lupinus or some Cyperaceae genera. Strikingly, no mutual ex-
clusivity offlavone O-glycoside and C-glycosylflavone synthesis has been
observed in these taxa.
Based upon the data discussed before, a hypothetical scheme of accu-
mulation behavior of C-glycosylflavones has been developed (Fig. 4). The
presence of all three types of glycosides (flavonoid O-glycosides FXt and
FX2; C-glycosylflavones CGL) in a plant, as opposed to the predominance
of C-glycosylflavones (CGL) may be explained via increase and decrease
factors. In taxa where C-glycosylflavones predominate the flavonoid pro-
file, there is either a large number of derivatives or specialization with
regard to the substitution patterns ("Increase"). Concomitantly, the co-
occurrence with flavonoid O-glycosides (FX~ and FX2) would be decreas-
ing ("Decrease"). The available data indicate that the probability of both
the flavonoid O-glycosides and the C-glycosylflavones showing the same
degree of specialization is relatively low. It would be tempting to assume
that the direction of biochemical evolution proceeds along the line from
omnipresence to predominance, thus representing a reduction trend. This,
however, has not been verified so far and the reverse process cannot be
excluded. Moreover, there could also be different lines of evolution within
different groups of plants. The mutual exclusiveness of C-glycosylflavones
and flavonoid O-glycosides appears to be of restricted distribution within
the angiosperms and the reported cases could be an artifact. If large
amounts of plant material are analyzed, it is possible to identify trace
Fig. 3a-3g. Substitution patterns in some angiosperm taxa. a) Achillea and Leucocyclus
(Compositae-Anthemideae); b) Helenium (Compositae-Heliantheae); c) Gentiana (Gen-
tianaceae);d) Caryophyllaceae; e) Leptodactylon and Linanthus (Polemoniaceae); f) Orchi-
daceae; g) Lemnaceae. C6 = C-6-glycosylated flavones; C8 = C-8-glycosylated flavones; C6,8 =di-
C-glycosylflavones; CA = A-ring substituted C-glycosylflavones; CB = B-ring substituted
C-glycosylflavones; Co = O-glycosylated C-glycosylflavones; CAr = acylated C-glycosylfla-
vones; Csu = C-glycosylflavone sulfates; + indicates relative amounts.
Fig. 4. Hypothetical scheme of accumulation behavior of C-glycosylflavones in related

taxa.
compounds that would not be detectable in smaller samples. Therefore

predominance and mutual exclusiveness may be identical phenomena.
VI. C-Glycosylflavones as a Taxonomic Character
The previous considerations lead to the final discussion about the eval-
uation of C-glycosylflavone accumulation as a character in systematics.
Current literature reveals that these compounds are used as chemical
characters in various ways. Generally, the presence/absence feature is used
and projected on the taxonomy of the plant group under study, based on
the hypothesis of chemotaxonomic congruence (Harris & Bisby, 1980).
However, it is clear that in the light of increasing knowledge, this approach
is much too simplistic (Poppendieck, 1983). Consequently, molecular
structures and substitution patterns of flavonoids are used as models for
interpretation of their evolution (e.g., Gottlieb et al., 1982). A problem
arises, however, with the assignment of polarity, i.e., the decision as to
whether the given structure or pattern is primitive or advanced. As Gor-
nail and Bohm (1978) have pointed out, complexity is not necessarily
advanced since, in some cases, reduction trends may have occurred. Thus
a biogenetically simple flavonoid can represent an advanced stage as well.

Similar difficulties are inherent in cladistic analysis (Humphries & Rich-
ardson, 1980). Most of the problems arise from the attempt to arrive at
generalizations for flavonoid data analysis leading to reproducible results
(for discussion of this see Richardson, 1983a, 1983b). Reproducibility,
however, does not start at the level of data interpretation, but it has to
be achieved in obtaining the data, which still seems to be somewhat of a
problem. Especially in the case ofC-glycosylflavones, a detailed structural
analysis as well as the establishment of the limits ofinfraspecific variability
are prerequisite to their use as chemical features.
There is no doubt that only consideration of as many characters as
possible is the basis for a more natural grouping of taxa. Transferred to
the flavonoids, this implies the use of as many chemical characters as
possible. Flavonoids are only a small part of the polyphenolic pathway,
which in itself is only part of the complete biogenetic pool of a plant.
Taking this into account, it becomes obvious that a certain group of
compounds may be much more correlated with other biogenetic activities
rather than with morphological characters such as leaf shape, fruit length,
etc. Therefore, more insight into the biosynthetic activities of a plant
group is required before the character status can be established (for a
critique of the present approaches see also Harris & Bisby, 1980). Re-
garding the evolutionary status of C-glycosylflavones, their proposed
"semiadvanced" character status (Harborne, 1977) becomes less con-
vincing in view of increasing numbers of reports on their occurrence.
Therefore their putative position as intermediates in the flavonol-flavone
reduction series is not necessarily valid for all of the angiosperms, espe-
cially if the only link to this series is "primitive" woodiness or "advanced"
herbaceous habit. To obtain definite proof for one theory or another seems
impossible at the moment, so our position is that we should strive for
high probability, rather than absolute certainty. As long as we cannot
establish the functional role for C-glycosylflavone accumulation contra
flavonoid O-glycoside formation, we may not be able to recognize the
physiological importance for the plant. It is felt that the evaluation of a
chemical character will be more reasonable when such considerations are
taken into account. There is still a long way to go.
VII. Concluding Remarks

1) We have to find new ways for analyzing chemical data for taxonomic
purposes, trying especially to increase the reproducibility of results.
2) Many disadvantages can be overcome by focusing primarily on ac-
cumulation trends as such and by critical analysis of the variability of the
chemical feature, analogous to the analysis of morphological phenomena.
3) Chemical data should be c o m p a r e d to other chemical data prior to

comparison with morphological characters, etc., avoiding overestimation
o f congruence with the latter.
4) Within the C-glycosylflavones, the use o f absence/presence features
should be replaced by actual molecular features and substitution trends.
5) More attention should be attributed to the co-occurrence o f different
flavonoid types rather than to the single, distinctive c o m p o u n d s often
used as group characters.
6) More information on biosynthetic sequences and the possible func-
tion o f C-glycosylflavone accumulation would be helpful.
7) The pathway o f C-glycosylflavone differentiation is not easy to gen-
eralize; there appears to be a high degree o f individuality in the different
plant groups. This, however, does not apply to general trends observed,
as with the correlation with formation o f flavonoid O-glycosides.
VIII. Acknowledgments
The idea for this study arose during a nine m o n t h s stay at the Harding
Laboratory, New York Botanical Garden, and was highly stimulated by
discussions with Drs. F. C. Seaman and P. M. Richardson. Their help in
carrying out this project is gratefully acknowledged. M y special thanks go
to Dr. P. M. Richardson for his critical revision o f the manuscript. T h a n k s
are also due to Prof. Dr. H. Greger (Institute o f Botany, University o f
Vienna) for unpublished data and to the staff o f the New York Botanical
G a r d e n for their support in getting access to laboratory and library fa-
cilities.
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X. Appendix
STRUCTURES OF C-GLYCOSYLFLAVONES
OH
R2 ~.,fOH R2 ~OH
fyy
OH 0 OH 0
RI=H, R2=GLUCOSYL:VITEXIN i_ RI=H, R2= GLUCOSYL:ORIENTIN5
RI=GLUCOSYL,R2=H: ISOVITEXIN2 RI=GLUCOSYL, R2=H: ISOORIENTIN ~
RI=H, R2=ARABINOSYL:MOLLUPENTIN3_
RI=ARABINOSYL, R2=H: ISOMULLUPENTIN4-
OH
R2 ~OH R2 h OH
c"y y R;yy
OH 0 OH O
RI=GLUCOSYL,R2=H: SWERTISIN 7_ RI=GLUCOSYL,R2=H: SWERTIA-
RI=H, R2=GLUCOSYL:ISOSWERTISIN 8_ JAPONIN iI
R2 ~ O H
HO~~ R1 ~OCH3
OH 0 OH 0
RI=ARABINOSYL,R2=H: RI= GLUCOSYL, R2=H'.CYTOSOSIDE 12
ISOMOLLUDISTIN RI=GLUCOSYL, R2=OH:
RI=H, R2=ARABINOSYL: 8-C-GLUCOSYLDIOSMETIN 1__3
MOLLUDISTIN 1_.00
OCH3
~ ~ 1 o c H3
OH 0 OH 0
R=GLUCOSYL: ISOORIENTIN R=GLUCOSYL:ISOVITEXIN
7,3'-DIMETHYL ETHER 14 7,4'-DIMETHYL ETHER 1--5
OH
HO oy ,R2 f~.~OH R2 F~ OH
R f TOHy 0 R{ "~ "~

OH 0
RI=R2=GLUCOSYL: VICENIN-2 16 RI=R2=GLUCOSY:LLUCENIN-2

RI=GLUCOSYL, R2=XYLOSYL'VICENIN-317 Rz=XYLOSYL,R2=GLUOCSYL:LUCENIN-I 2~
RI=XYLOSYL, R2=GLUCOSYL:VICENIN-1i__8 RI=GLUCOSYL, R2=ARABI NOSYL:
CARLINOSIDE 25
RI=GLUCOSYL,R2=(x-L-ARABINOSYL:
SCHAFTOSIDE 19
RI=ARABINOSYL, R2=GLUCOSYL:ISO-
SCHAFTOSIDE 20
RI=GLUCOSYL,R2=~-L-ARABINOSYL:
NEOSCHAFTOSIDE 21
RI=ARABINOSYL, R2=GALACTOSYL:
CORYMBOSIDE 2__22

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THE BOTANICAL REVIEW

C-Glycosylflavones as an Accumulation Tendency:

KARIN MARIA VALANT-VETSCHERA

Copies o f this issue [51 (1)] m a y be obtained f r o m the Scientific Publications

The Botanical Review 51: 1-52, January-March, 1985

tigend, wurde die Verbreitung von C-Glykosylflavonen bei den Composi-

variability should be taken into account. In a recent survey on Achillea

though these compounds dominate the flavonoid profile of most taxa, a

II. Distribution of C-Glycosylflavones in the Compositae

ex Boisss. and A. aleppica DC. showed no C-glycosylflavones in the roots

Giannasi, 1975) accumulate mainly di-C-glycosylapigenins. Although these

simple mono-C-glycosylflavones (Inuleae, Vernonieae). Within the As-

III. C-Glycosylflavones as a Part of the Flavonoid

In the Compositae, C-glycosylflavones often co-occur with other fla-

;> ;> ;> >

represented the main accumulation tendency with the additional for-

glycosylflavones is typical only of Achillea and Leucocyclus, or if similar

IV. C-Glycosylflavones as a Part of the Flavonoid Complement

6 + -- ,.~ + ooo, oo, 6

1981). In Idiospermum these compounds correlated 100%, but only one

Wessely-Moser isomers, correlates with quercetin (100%) and kaempferol

cosylflavones including several complex derivatives (Chopin & Bouillant,

MOLLUGINACEAE"Several complex C-glycosylflavones have been reported

FABACEAE:This family is particularly known for the occurrence of C-gly-

mono-C-glycosylflavones may occur. Vitexin (1), orientin (5), cytisoside

glycosides correlated 100% with mono-C-glycosylapigenin, but only 50%

than that with kaempferol (28%). Apigenin di-C-glycosides (schaftoside

Magnoliidae Drimys* F3, F7 Idiospermum F7

glycosylflavone patterns have been distinguished as either (group A) mono-

(e.g., in Silene [Melandrium], Chopin et al., 1982a) but, generally speaking,

and flavonols as minor tendencies. The Polemoniaceae genera, on the

Fig. 4. Hypothetical scheme of accumulation behavior of C-glycosylflavones in related

compounds that would not be detectable in smaller samples. Therefore

VI. C-Glycosylflavones as a Taxonomic Character

a biogenetically simple flavonoid can represent an advanced stage as well.

VII. Concluding Remarks

3) Chemical data should be c o m p a r e d to other chemical data prior to

Asen, S. and R. M. Horowitz. 1974. Apigenin 4'-O-~-D-glucoside 7-O-~-D-glucuronide:

Bierner, M . W . 1973. Chemosystematic aspects of flavonoid distribution in twenty-two

, and B. Voirin. 1983a. Les C-glycosyl flavonoides des fleures de Centaurea

9 1983a. Flavonoids and phylogenetic systematics. Pages 115-123 in N. I. Platnick

R f TOHy 0 R{ "~ "~

RI=R2=GLUCOSYL: VICENIN-2 16 RI=R2=GLUCOSY:LLUCENIN-2

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