Phyrochemir~ry,Vol. 22, No.
Printed in Gnat Britain.
6, pp. 1417- 1420, 1983.
@ISi-9422/83/061417-04$03.00/O
Q 1983Pergamon Press Ltd.
COMPARATIVE STUDY OF THE FLAVONOIDS OF SOME LOCAL MEMBERS
OF THE UMBELLIFERAE
NABIEL A. M. SALEH, SABRY I. EL-NEGOUMY, MOHAMED N. EL-HADIDI* and HASNAA A. HOSNI*
National Research Centre, El-Dokki, Cairo, Egypt; *Department of Botany, Faculty of Science, Cairo University, Egypt zyxwvutsrqp
(Revisedreceioed 13 September 1982)
Key
Word
Index-Umb4iferae;
Apioideae; flavonoid glycosides; chemosystematics.
Abstract-Thirty-six
species belonging to 27 genera of the sub-family Apioideae, family Umbelliferae, were investigated for their leaf and stem flavonoids. Fourteen flavonoid glycosides of the aglycones kaempferol, quercetin,
isorhamnetin,
apigenin
and luteolin
were identified.
Chemosystematic
In the Umbelliferae, flavonoids, phenylpropanoids, acetylenes, terpenoids and coumarins are characteristic chemical constituents [l, 21. Kaempferol, quercetin, apigenin
and luteolin are the most common flavonoid aglycones.
Isorhamnetin, chrysoeriol, diosmetin and acacetin occur
less frequently and flavanones rarely [3]. Glycosylation is
common in position 3 for flavonols and position 7 for
flavones [3]. Sulphated flavonoids have also been reported in the family [4].
On the basis of fruit morphology, taxa with spines on
both the primary and secondary ridges of the fruits, are
grouped in the Caucalideae by Bentham and Hooker [S]
and Boissier [6]. But Drude [7] divided these species
between two tribes: the Scandiceae (sub-tribe Caucalinae)
and the Dauceae. The largest genus in the Caucalinae is
Torilis and in Dauceae is Daucus. At the tribal level,
Harborne [3] from the flavonoid evidence, divided the
family into two broad groups: the first group of nine tribes
in which flavones are rare or absent; and the second group
of four tribes in which flavones are common or predominant (Apieae, Dauceae, Laserpitieae and Scandiceae sensu
Drude). Similar patterns were observed in the present
study of 36 species belonging to the sub-family Apioideae
(Table 1).
Harborne [3] carried out a detailed study of the
flavonoid constituents of the tribe Caucalideae sensu
Boissier. The study concentrated on the fruit flavonoids
and to a lesser extent on those in leaf and flowers. A
correlation between flavonoids and evolutionary progression within the Caucalideae was based on the presence or
absence of flavones versus flavonols. It has been suggested
that flavones represent advancement by loss mutation
over the corresponding flavonols [8]. This correlates with
advanced and primitive characters in the Umbelliferae [3]
and the Oleaceae [9].
The data reported in the present study correlate with
the results previously reported in the fruits by Harborne
[3] as well as the survey of aglycones by Crowden et al.
[lo]. The most common flavonol glycoside is the 3glucoside followed by the 3-rutinoside, while the most
common flavone glycoside is the 7-glucoside (Table 1).
Although the chromosomal data [l l] do not correlate
with the tentative grouping of the tribes of the Apioideae
based on the presence or absence of flavones and flavonols
relationships
are discussed.
[lo], a close similarity between the distribution of
numbers in the Scandiceae and Dauceae support their
close relationship based on chemical evidence [3, lo].
Furthermore,
serological data confirm that in the
Scandiceae and Dauceae greater changes in protein
chemistry have occurred [12]. Also, both tribes have
evolved stomata1 characters [13]. The serological evidence, however, did not support Bentham and Hooker’s
[S] treatment of placing Torilis and Daucus in the tribe
Caucalideae. Both species contain flavone 5-glycosides,
which indicate a rather specialized character (Table 1 and
results in ref. [3]) It is interesting to note that all Torilis
species examined
only contained
flavone glycosides, while
species proved to contain both flavone and
flavonol glycosides (see Table 1 and ref. [3]).
Serological data indicated a great protein similarity
between tribes Coriandreae and Ammineae, as well as a
close correspondence
among
both
tribes
and
Peucedaneae [12]. All three tribes contain mainly flavonols as their major glycosides, with the exception of
Pimpinella etbacia, Cuminum cyminum and Ammoides
Daucus
pusilla which contain
grain characters
flairone glycosides (Table 1). Pollen
indicated that Bupleurum species (tribe
Ammineae) showed primitive characters [ 141. All species
investigated in the present study only contained flavonol
glycosides, and similar results are also reported in the
literature for other Bupleurum species [lo].
It is interesting to note that in the case of Bupleurum
semicompositum two chemical races exist, one with the 3rutinosides of quercetin and isorhamnetin as the major
glycosides and the second with the 3-glucosides as well as
the 3-rutinosides. Similarly, Foeniculum uulgare also
proved to have two chemical races [15].
EXPERIMENTAL
Plant material.
Fresh material was
used whenever possible.
Herbarium samples of all investigated taxa are deposited at the
Herbarium, Department of Botany, Cairo University.
Isolationand identification
ofjavonoid constituents. The plant
material (leaf and stem) was extracted with 707; EtOH.
Flavonoid glycosides were isolated using elution techniques, and
identified according to standard methods [16, 171.
1417
z
E
Table 1. Distribution of flavonols and Savones in the sul+family Apioideae
Flavones?
Flavonols*
Sub-family Apioideae (sensu Drude)
No.
of
samples
Kaempferol
3Glc
3Glur
Quercetin
3Glc
3Gal
3Glur
3Rut
3Poly
3Glc
3Rut
Tribe I : Echinophoreae zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIHGFEDCBA
_
Py concy cla tomentosa Decne
1
+++
Tribe II : Scandiceae
Subtribe 1: Scandicinae
L.
(Sol.) Thell.
var. hirsutum (C. Koch.) Thell.
Subtribe 2: Caucalinae
Torilis nodosa (L.) Gaertner
Torilis radiata Moench
Torilis bracteosa Bianca ex Nym.
Torilis arvensis (Hudson) Link
Caucalis tenella Del.
Pseudorlaya pumila (L.) Grande
Tribe III: Coriandreae
Coriandrum satioum L.
Scandix pecten- ueneris
Apigenin
Isorhamnetin
Luteolin
7Glc
7Glur
7Glc
7Glur
5Glc
-
-
-
-
-
_
1
-
-
-
-
-
-
_
_
-
+
-
+++
-
1
-
-
_
-
-
-
-
-
-
+
-
+++
_
1
2
2
1
1
1
_
-
_
_
-
_
-
-
-
-
-
_
-
_
-
-
_
+
+
+
+
+
+
+
+
-
+++
+++
+++
+
++
+++
+
+
+
?
+
-
+++
+++
1
-
+
+
++
+++
++
-
-
-
-
-
1
-
-
-
-
-
+++
_
-
+++
-
-
-
-
-
1
1
4
{4
-
-
++
+++
+++
+++
_
+
+
+++
++
t++
t++
+++
-
-
-
-
-
+
+
+
+++
-
-
-
-
1
3
1
1
1
1
-
_
-
-
-
?
-
+++
+
++
-
_
-
-
-
t+t
_
-
-
-
-
+++
+
-
+++
+++
+++
-
-
5
2
1
1
++
++
++
+++
+++
++t
-
+++
-
-
-
-
+
-
Scandicium stellatum
Tribe IV: Ammineae
Subtribe 1: Carinae
Bupleurum lancifolium Homem.
Bupleurum
falcatumL.
var.
(Boiss.) Tackh.
Poir.
lineargolium
Bupleurum nanum
Bupleurum semicompositum
Pituranthos tortuosus
L.
(Desf.) Benth.
& Hook. f.
L.
Ammi oisnaga (L.) Lam.
Berula erecta (Hudson) Coville
Pimpinella etbacia Schweinf.
Rido&a segetum (L.) Moris
Apium leptophy llum (Pers.) F. Muell.
ex Benth.
Apium graveolens L.
Helosciadium nodz@ orum (L.) Koch
Carum carvi L.
Ammi majus
+++
-
-
+
+
+
-
-
t+t
-
-
5Glur
L.
(Brot.) Breistr.
Subtribe 2: Seselinae
Foeniculum vulgare (L.) Mill. sub.
piper&urn (Ucria) Coutinho
Foeniculum uulgare (L.) Mill. sub.
Cuminum cy minum
Ammoides pusilla
vulgare
L.
L.
Crithmum maritimum
Anethum graveolens
Tribe V : Peucedaneae
Subtribe 1: Ferulinae
Ferula marmarica Asch. & Taub.
Ducrosia ismaelis Asch.
Subtribe 2: Tordylinae
M alabaila suaveolens Coss.
Zosima orientalis
Hoffm.
_
+$
-
-
+++$
+++
-
-
-
-
_
-
-
_
-
-
++
++
-
-
-
5
1
1
-
-
-
_
+
-
-
2
_
++
+
-
+++
-
-
1
1
1
-
++
-
+
+
-
-
+++
+++
-
+
-
1
1
-
-
+++
+++
-
-
-
1
1
-
-
-
-
-
-
+ll
1
-
-
1
-
+II
_
-
-
-
-
-
+++
-
-
-
-
-
-
-
_
-
-
-
-
_
-
-
-
_
-
+**
-
-
-
-
-
-
-
-
-
Tribe VI: Dauceae
Daucus littoralis Sibth.
& Sm.
Tribe VII: Smyrnieae
Astoma seselifolium DC.
+++
-
-
-
-
-
-
-
-
-
-
-
*3 Glc, 3-glucoside; 3 Gal, 3galactoside; 3Glur. 3glucuronide; 3 Rut, 3-rutinoside; 3 Poly, 3polyglycoside.
t 7 Glc,
zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIHGFEDCBA
7-glucoside; 7 Glur, 7-glucuronide; 5 Glc, 5glucoside; 5 Glur, 5-glucuronide.
$7-Polyglycosides also present.
§Isorhamnetin is the major aglycone.
11
Quercetin Fglucoside.
T[Quercetin 3,7diglucoside.
**Traces of a C-glycoside were detected.
+++
co
k
s
8.
B
1420
N.
A. M.
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