Biochemical Systematics and Ecology, Vol. 9, No. 4, pp. 263-265, 19~1. 0305-1978/81/040263-03 $02.

00/0
Printed in Great Britain. © 1981 Pergamon Press Ltd.

Flavonoids and the Systematics of Luffa

EDWARD E. SCHILLING and CHARLES B. HEISER, JR.*

Department of Botany, University of Tennessee, Knoxville, TN 37916, USA;
*Department of Biology, Indiana University, Bloomington, IN 47405, USA

Key Word Index - Luffa; Cucurbitaceae; flavonoids; chemotaxonomy.

A b s t r a c t - Flavonoids were characterized from leaves and flowers of six species of Luffa. Each species had a distinct
flavonoid pattern. Based on leaf flavonoids, Luffa is separable into two groups of species: L. graveolens and L. operculata
contain only flavonols. L. acutangula, L. aergyptiaca, L. echinata and L. forskalii contain only flavones. Flavonoid data
indicate that the New World disjunct species, L. operculata, is most closely related to L. graveolens.

It~xludion the origin of the domesticated plants and

The genus Luffa comprises eight or so species
[1-3]. Two of the species, Luffa acutangula (L.)
Roxb. and L. aegyptiaca Miller (synonym: L. cyl-
indfca (L.) Roem.) include domesticated plants.
The fruits of the former are used for food, particu-
larly in south-eastern Asia; the fruits of the latter
are a minor source of food and are more important
for their use as sponges. One species, L.
operculata (L.)Cogn., is indigenous to tropical
America, whereas all of the other species are
native to the Old World. The greatest concentra-
tion of species is in India.
Flavonoid studies were initiated as part of a
biosystematic analysis of species relationships
within Luffa. Problems of particular interest are
TABLE 1. SOURCES OF LUFFA SAMPLES ANALYSED FOR
explanation of the disjunct distribution of L. oper-
culata. Living material of six species was available
for study (Table 1).
Ten flavonoid glycosides were isolated and
characterized from leaves and flowers of Luffa
(Fig. 1). Each species has a distinct flavonoid
pattern (Table 2). Of the three species for which
multiple samples were available, only L.
acutangula exhibits flavonoid variability (Table 2).
Except for L. acutangula var. amara, which lacks
detectable flavonoids, leaves of each species
have two compounds (Table 2). Flavonoid
patterns from flowers of a given species were

~
FLAVONOID CHEMISTRY
Taxon Country Collector
OR4
L. acutangula var. acutangula

L. acutangula var. amara

India
USA
USA
India
R. Maxwell
H. and J. Ritz
Heiser
M.M. Bhandari
RIO'~o~'~
L. aegyptzaca (domesticated) Colombia G. Anderson
Japan T. Sugiyama
Mexico T, W. Whitaker OH 0
USA Burpee Seed Co.
L. aegyptJaca (wild) Australia C.R. Dunlop 1. Apigenin 7-glucoside (Rt: glucose; R2, R3, R4: H).
Fiji S. Vodonaivalu
2. Luteolin 7-glucoside (R l: glucose; R2, R4: H; R3: OH).
L. echtnata India B. Dutt 3. Apigenin 7,4'-diglucoside (Rt, R4: glucose; R?, R3: H).
L. forskah/ Yemen Arab S. A Chaudhary 4. Luteolin 7,4'-diglucoside (R1, R4: glucose; R2: H; R3: OH).
Republic 5. Chrysoeriol 7-glucoside (RI: glucose; R2, R4: H; R3: OCH3).
L. graveolens Australia C.R. Dunlop 6. Kaempferol 3-glucoside (R1, R3, R4: H; R2: -O-glucose).
L. opercu/ata Brazil J. Coleman 7. Quercetin 3-glucoside (R1, R4: H; R2: -O-glucose; R3: OH).
Brazil W. Rodrigues 8. Quercetin 3-diglucoside (R1, R4: H; R2: -O-glucose-glucose; R3: OH).
Brazil G. Ferguson 9. Kaempferol 7-glucoside (Rt: glucose; R2: OH; R3, R4: H).
Ecuador I. Padilla
10. Quercetin 7-glucoside (RI: glucose; R2, R3: OH; R4: H).
FIG. 1. FLAVONOID COMPOUNDS ISOLATED FROM LEAVES AND
(Received 24 December 1980) FLOWERS OF LUFFA SPECIES.

263
264 EDWARD E. SCHILLING AND CHARLES B HEISER, J R

tABLE 2. DISTRIBU FION OF LEAF AND FLOWER FLAVONOIDS IN LUFFA SPECIES Compounds numbered lollowing Fi{..; !
teat Flowers*
Species Compound 1 1 2 3 4 5 6 7 8 1 2 5 (i Z 8 9 10
L aoutangu/a vat acutangula t ¢ t
L aoutangu/a var. amara
L aegyptlaca
L ech/nata
L forskalli/ ! {
L graveofens i
L operculata T 4 !
*Compounds 3 and 4 are not present
t See Fig 1.

identical to those from leaves or simpler, except
in L. aegyptiaca (Table 2).
Leaf flavonoids in a given species usually
consist of either flavones or fiavonols (Table 2).
Luffa acutangu/a, L. aegyptiaca, L. echinata and
L. forskalii contain fiavone 7-glucosides, whereas
L. graveolens and L. operculata contain only
flavonol 3-glucosides. One species, L. aegyptiaca,
has both flavones and ftavonols in flower
material, but the floral flavonols were in the form
of 7-glucosides (Table 2).
Discussion
A scheme illustrating evolutionary relationships
among Luffa species based on flavonoid chem-
istry is shown in Fig. 2. Three trends appear
to characterize changes in flavonoid chemistry in
the genus: loss of either flavones or flavonols;
reduction in number of compounds; modification
of compounds by glycosylation or methylation.
These trends have been observed commonly in
flavonoid evolution of other angiosperm groups
[4, 5].
The genus may be divided into two groups of
species based on the type of leaf flavonoids (Fig.
2). Flavone 7-glucosides characterize L.
aegkptiaca, L. acutangu/a, L. echinata and L.
forskalii. The other group consists of L. graveolens
and L. operculata, and contains only flavonol 3-
glucosides.
Within the groups characterized by leaf
flavones, several modifications of flavonoids have
occurred (Fig. 2). The chemistry of L acutangula
and L. aegyptiaca is very similar, with luteolin and
apigenin 7-glucosides present. There is a
tendency toward the loss of apigenin 7-glucoside
in some samples of L. acutangu/a var. acutangula.
Complete loss of flavonoids is observed in L.
acutangula var. amara (Table 2; Fig. 2). The
derived nature of the fiavonoid chemistry of this

Hypothetical ancestor
Flavones and flavonols

LOSS of leaf fiavonols Loss of flovones

/ J

L oegyf/oco / / ~
opercu/oto
/ Loss of all
Gain of / f ,ovo~,s
3' - methox}; Loss of B - ring
dihydroxy
L ocutongulo
vor ocutongulo

J \Loss of all
I
L gfavoo/ons
Gain of
L ech/noto 4 ' - glucosylotion flavonoids
/ \
L forskolu L ocutongu/o v q r omora

FIG 2 PROPOSED EVOLUTIONARY REt.ATIONSHtPS AMONG LL/FFA SPECIES BASED ON F[AVONOIDCHEMISFRY

FLAVONOIDSAND THE SYSTEMATICSOFLUFFA
spontaneously occurring variety indicates that it
probably represents an escaped descendant of
the domesticated var. acutangu/a, rather than
being its progenitor. The flavonoids of L. forskalii
are based on the same aglycones as those of L.
acutangula and L. aegyptiaca, but have been
modified by 4'-glucosylation (Fig. 2). Finally, in L.
echinata, the loss of luteolin-type compounds by
modification of the B-ring to produce compounds
of the chrysoeriol-type has occurred (Fig. 2).
Both species of the group characterized by
flavonols contain unique compounds (quercetin
3-diglucoside in L. graveolens; kaempferol 3-
glucoside in L. operculata), making it impossible
to assign phyletic relationships within this group.
It is likely that both species are descended from a
common ancestor which found its way to the
New World to give rise to L. opercu/ata.
The distinct flavonoid chemistry of Luffa
species is in accord with their distinct nature, and
correlates well with other evidence on species
relationships in most cases. Flavonoid chemistry
supports the close relationship between L.
acutangula and l_. forskalii (Fig. 2) suggested by
morphology and by the fertility of their interspeci-
fic hybrid. Morphological data are also in support
of flavonoid evidence in suggesting a close
relationship between L. graveolens and L.
operculata. The unique occurrence of chrysoeriol
7-glucoside in L. ech/nata (Table 2) is in accord
with the distinctive nature of this species. Luffa
ech/nata differs from all other species in having
white corollas (others are yellow) and being
dioecious (other species are monoecious).
Flavonoid chemistry also appears to be in
agreement with the suggestion of Roy and Dutt
[6] that the domestic species, L. acutangula and
L. aegypt/aca, are genetically close, on the basis
of securing fertile hybrids between the two.
However, Pathak and Singh [7] and Heiser [8]
265
report considerable reduction of fertility in this
interspecific hybrid, and the two species differ in
a number of prominent morphological traits. It
may be that although these species share a
common origin, they are not particularly closely
related.
Experimental
Flavonoids were isolated from 10-20 g of dried leaf material
of each species. Extraction of plant material and chromato-
graphic and spectral proceduresfollowed those of Mabry et
al. [9]. Floral fiavonoids were identified by comparison of Rf
values and color characteristics and by co-chromatography.
Voucher specimens are deposited at the Indiana University
herbarium.
Acknowledgements-This study was supported by a
University of Tennesseefaculty research award (to E.E.S.)
and by a grant from the National Science Foundation (to
C.B.H.). The authors thank those who provided seed
samples (Table 1) and L. Johnson for collecting plant
material.
References
1. Chakravarty, H. L. (1959) Rec. Bot. Survey India 17, 72.
2. Cogniaux, A. and Harms, H. (1924) Engler Pf/anzereich
88 (IV.275, II), 61.
3. Heiser,C. B. (t980) GourdlO, 6.
4. Gornall, R. H. and Bohm, B. A. (1978) Syst. Botany 3,
353.
5. Harborne,J. B. (1977)Biochem. Syst. Ecol. 5, 7.
6. Roy, R. P. and Dutt, B. (1980) Program and abstracts,
Conferenceon the Biology and Chemistry of the Cucur-
bitaceae. Cornell University, Ithaca, NY.
7. Pathak, G. N. and Singh, S. N. (1949)lndianJ. Genet. 9,
18.
8. Heiser, C. B. (1979) The Gourd Book. University of
Oklahoma PressNorman.
9. Mabry, T. J., Markham, K. R. and Thomas, M. B. (1970)
The Systematic Identification of Flavonoids. Springer,
Berlin.