204
NOTIZEN
F l a v o n o i d Pigments and Plant P h y l o g e n y :
T h e Case of the Hand-flower tree
Chiranthodendron pentadactylon
J. B. HARBORNE
P h y t o c h e m i c a l Unit, Botany Dept., T h e University, R e a d i n g ,
England,
a n d DALE M . SMITH
D e p t . of B i o l o g i c a l Sciences, University of California,
Santa Barbara, U S A
(Z. Naturforsch. 27 b, 210 [1972]; received December 14, 1971)
Continuing studies of flavonoid distribution patterns
in plants have indicated that flavonoid pigments are
useful phyletic markers, providing new information on
the relative primitiveness or advancement of particular
plant taxa 2 . One class of flavonoid of especial
interest are the desoxyanthocyanins, pigments lacking
the 3-hydroxyl present in ordinary anthocyanins and
which are presumably biosynthetically simpler. That
they are primitive characters is borne out by the fact
that they occur primarily in certain mosses 3 and as
pigments in juvenile fronds of ferns 4 . The same pig-
ments do, however, occur regularly in one higher plant
family, the Gesneriaceae. Production here is cor-
related with selection for orange red flower colour
favoured by hummingbird pollinators and this is con-
firmed by the fact that they are completely confined
to one subfamily, the Gesnerioideae, which is geogra-
phically restricted to the New World where humming-
birds are common pollinators 4 ' 5 .
Against this background, the isolated report by
PALLARES and G A R Z A in 1 9 4 9 6 of the desoxyantho-
cyanidin apigeninidin in the flowers of the Hand-
flower tree Chiranthodendron pentadactylon (Sterculi-
aceae) is anomalous. Although this plant has been the
focus of a religious cult because the stamens of the
flowers strikingly resemble a red hand, there is no
reason phyletically why the red pigment should be
unusual. While the pigment was isolated in quantity
and analysed by classical procedures by the Mexican
workers, it was not compared directly with authentic
material so that the identification could have been in
R e q u e s t f o r reprints should sent to Dr. J. B . HARBORNE,
T h e University of R e a d i n g , Department of Botany, T h e
University, L o n d o n R o a d , Reading (England).
1 J. B . HARBORNE, " C o m p a r a t i v e Biochemistry of the Flavo-
n o i d s " , A c a d e m i c Press, L o n d o n 1 9 6 7 .
2 J. B . HARBORNE, i n : " R e c e n t A d v a n c e s in Phytochemi-
s t r y " , v o l . I V , ed. V . C. RUNECKLES, Appleton-Century-
C r o f t , N e w Y o r k 1 9 7 1 , in press.
3 G . BENDZ, O . MARTENSSON, and L . TERENIUS, A c t a C h e m .
Scand. 1 6 , 1 1 8 3 [1962].
4 J. B. HARBORNE, Phytochem. 5, 589 [ 1 9 6 6 ] .
5 J. B . HARBORNE, Phytochem. 6 , 1 6 4 3 [ 1 9 6 7 ] .
6 E . S. PALLARES and H . M . GARZA, Arch. Biochem. 2 1 , 377
[1949].
7 W . G. C. FORSYTH and V . C. QUESNEL, Biochem. J. 6 5 ,
177 [ 1 9 5 7 ] .
error. We therefore decided to reinvestigate it. Freshly
collected purplish sepals and red calyces were ana-
lysed separately using modern procedures 1 and yielded
only one pigment, the commonest of all anthocyanins,
cyanidin 3-glucoside; no trace of desoxyanthocyanin
could be detected. This finding is expectable since
cyanidin glycosides have been reported in Theohroma
cacao, the only other member of the Sterculiaceae to
have been examined for anthocyanins 7 .
In order to be quite sure that desoxyanthocyanins
were indeed absent from the plant, the leaves which
contain yellowish brown hairs on the underside were
also examined. The yellow brown hair pigment was
completely insoluble and clearly not flavonoid in
nature. However, the leaf was rich in flavonoids, con-
taining in addition to much leucocyanidin, luteolin
7-glucoside, luteolin 7-glucuronide and quercetin 3-glu-
coside. It also yielded a quantity of the relatively un-
common yellow flavonol gossypetin, which was present
in a new glycosidic combination as the 3-glucuronide.
Phyletically, the most significant discovery is the pre-
sence of gossypetin, since the Sterculiaceae are in-
cluded in the Malvales and the first report of gos-
sypetin in Nature was in the yellow flowers of Gos-
sypium8. Furthermore, CRONQUIST 9 derives the Mal-
vales together with the Primulales and Ericales from
the Theales. It is highly significant that these other
two derived orders are major sources of gossypetin;
it is present in Primula10 and Dionysia11 (Primu-
laceae) and in Rhododendron12 and many related
Ericaceae 13 and in Empetraceae 14. Indeed, the finding
of gossypetin in the Sterculiaceae provides phyto-
chemical evidence for preferring Cronquists's arrange-
ment 9 of the above orders over that recently put for-
ward by T A K H T A J A N 1 5 .
Although this is the first definitive report of gossy-
petin in this family, BATE-SMITH 16 in his leaf s u r v e y
of the dicotyledons detected gossypetin-like compounds
in several other Sterculiaceae, notably in Fremontia,
and the more frequent occurrence of gossypetin in the
group is being explored further. However, the above
results with the Hand-flower tree do demonstrate to a
remarkable degree the predictive value of flavonoids
as phyletic markers among higher plant groups.
8 A . G. PERKIN, J. chem. Soc. [ L o n d o n ] 7 5 , 825 [ 1 8 9 9 ] .
9 A . CRONQUIST, " T h e Evolution and Classification of
Flowering Plants", Nelson, London 1968.
10 J. B. HARBORNE, P h y t o c h e m . 7 , 1 2 1 5 [ 1 9 6 8 ] .
11 J. B . HARBORNE, Phytochem. 10, 4 7 2 [ 1 9 7 1 ] .
12 J. B . HARBORNE and C. A . WILLIAMS, Phytochem. 10, 2727
[1971].
13 J. B . HARBORNE and C. A . WILLIAMS, Bot. J. Linn. Soc., in
press.
14 D . M . MOORE, J. B. HARBORNE, and C. A . WILLIAMS, Bot.
J. L i n n . S o c . 6 3 , 2 7 7 [ 1 9 7 0 ] .
15 A . TAKHTAJAN, " F l o w e r i n g Plants, Origin and Dispersal",
Oliver & B o y d , E d i n b u r g h 1968.
16 E. C. BATE-SMITH, Bot. J. Linn. S o c . 5 8 , 39 [ 1 9 6 2 ] .