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GC-MS analysis and antimicrobial activity of alkaloid extract from Genista

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DOI: 10.1080/13880200802448674

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 Pharmaceutical Biology, 2009; 47(1): 81–85

Original Article

GC-MS analysis and antimicrobial activity of alkaloid

extract from Genista vuralii
Nurgun Erdemoglu1, Semiha Ozkan2, Ahmet Duran3, and Fatma Tosun1
1
Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Ankara, Turkey, 2Department of
Pharmaceutical Microbiology, Faculty of Pharmacy, Gazi University, Ankara, Turkey, and 3Department of Biology,
Faculty of Education, Selcuk University, Konya, Turkey
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Abstract
In the present study, the alkaloid composition of the aerial parts of Genista vuralii A. Duran & H. Dural
(Fabaceae) was investigated by capillary GC-MS. Ten quinolizidine alkaloids were identified by capillary
GC-MS, namely, N-methylcytisine, cytisine, tetrahydrorhombifoline, 17-oxosparteine, 5,6-dehydrolupanine,
lupanine, 17-oxolupanine, anagyrine, baptifoline, and 13α-tigloyloxylupanine. Among them, anagyrine
(93.04%) was the most abundant alkaloid. Furthermore, antibacterial and antifungal activities of the alka-
loid extract of G. vuralii were tested against standard strains of bacteria (Escherichia coli, Pseudomonas aeru-
ginosa, Bacillus subtilis, Staphylococcus aureus) as well as fungi (Candida albicans, Candida krusei). The alka-
loid extract of G. vuralii presented good activity against S. aureus, B. subtilis, and C. krusei, with minimum
For personal use only.

inhibitory concentrations (MIC) of 62.5 µg/mL. The remaining MIC values were found to range between 125
and 500 µg/mL. To the best of our knowledge, the current work is the first to report the alkaloid profile and
antimicrobial activity of G. vuralii L. growing in Turkey.
Keywords:  Alkaloids; antimicrobial activity; Fabaceae; GC-MS; Genista; Genista vuralii

Introduction pure QA or mixtures of QA (Kinghorn & Balandrin, 1984;

The genus Genista L. (Fabaceae) includes chiefly decidu-
ous shrubs or small trees in the Mediterranean area and
Western Asia. There are 14 Genista (Fabaceae) species in
the flora of Turkey and the East Aegean Islands; among
these species, G. aucheri, G. burdurensis, G. sandrasica,
G. involucrate, and G. vuralii are endemic (Gibbs, 1970;
Davis et  al., 1988; Duran & Dural, 2003). G. vuralii A.
Duran & H. Dural, a procumbent or ascending small
shrublet, grows in the transition territory of Central and
North Anatolia, Euro-Siberian element. G. vuralii grows
in rocky areas, steppes, and forest clearings, flowering in
June–July (Duran & Dural, 2003).
Quinolizidine alkaloids (QA) are characteristic sec-
ondary metabolites of the Fabaceae family and are
especially abundant in the tribes Genisteae, Sophoreae,
and Thermopsideae (Kinghorn & Balandrin, 1984; Wink,
1993). A wide range of biological activities is attributed to
Wink, 1984; Wippich & Wink, 1985; Ohmiya et al., 1995;
Erdemoglu et al., 2007). In addition, QA play a chemical
defensive role in plants against herbivores, and inhibit
the growth of bacteria and pathogen microorganisms
(Wink, 1984, 1988, 1992; Wippich & Wink, 1985).
In our previous studies on Genista species, we isolated
alkaloids from 11 Genista species growing in Turkey, as
well as flavonoids from G. aucheri and G. involucrata
(Tosun et al., 1986, 1987a,b,c, 1988, 1994; Nasution et al.,
1991; Tosun & Akyuz, 1998, 2000). In our other studies,
the aerial parts of 11 Genista species were analyzed for
their total and free genistein and daidzein contents
by use of LC-MS (Tosun et  al., 2003; Erdemoglu et  al.,
2006). Both the alkaloids and the flavonoids are sig-
nificant chemotaxonomic markers of the genus Genista
(Harborne, 1994). In the present work, the alkaloid com-
position and antimicrobial activity of the alkaloid extract
of the aerial parts of G. vuralii were investigated.

Address for Correspondence: Nurgun Erdemoglu, Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Etiler 06330, Ankara, Turkey.
Tel: +90-312-2023177. Fax: +90-312-2235018. E-mail: nurgun@gazi.edu.tr
(Received 22 April 2008; revised 9 June 2008; accepted 11 July 2008)
ISSN 1388-0209 print/ISSN 1744-5116 online © 2009 Informa UK Ltd
DOI: 10.1080/13880200802448674 http://www.informapharmascience.com/phb
 82   N. Erdemoglu et al.
Materials and methods
Plant material
The aerial parts of G. vuralii A. Duran & H. Dural
(Fabaceae) were collected at the flowering stage from
Çankırı, Ilgaz Mountain, Derbent facility, at an altitude
of 1800 m in July 2004 in Turkey. Plant material was
identified by one of us (Associate Professor Dr Ahmet
Duran). Voucher specimens (A. Duran 6735) are kept at
the herbarium in Selcuk University, Faculty of Education,
Department of Biology, in Konya, Turkey.
Extraction of alkaloids
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Alkaloid extraction was carried out as described in Wink
(1993): 2 g plant material were homogenized in 30 mL
of 0.5 N HCl. After 30 min at room temperature, the
homogenate was centrifuged for 10 min at 5000g. For
quantitative work, the pellet was re-suspended in 0.5 N
HCl and centrifuged again. Both supernatants were then
pooled and adjusted to pH 12–14 with NH4OH (25%).
Alkaloids were extracted by solid-phase extraction using
an Extrelut column (Merck, Darmstadt, Germany).
For personal use only.
Total alkaloids were eluted with CH2Cl2 and the solvent
evaporated in vacuo.
Analysis of alkaloids
The alkaloid extract was dissolved in CH2Cl2 and
injected into a GC-MS apparatus (Hewlett Packard
model 6890 series) equipped with a mass selective
detector. Experimental conditions for capillary GC-MS
analysis were developed under the following condi-
tions. Capillary column HP-5 (crosslinked 5% phenyl-
methylsiloxane, 50 m×0.32 mm (i.d.), with 0.17 m
film thickness, model no. HP 19091J-015), detector
temperature 280ºC, injector temperature 250ºC, carrier
gas He (1 mL/min), split ratio 1/20, injection volume
0.2 L, and mass range (m/z) 20–440. GC oven tem-
perature was kept at 120ºC for 2 min, programmed to
300ºC at a rate of 6ºC/min, and kept constant at 300ºC
for 10 min.
Antimicrobial activity
Microorganisms
Standard strains of four bacteria, namely, Escherichia
coli (ATCC 25922), Pseudomonas aeruginosa
(ATCC 27853), Bacillus subtilis (ATCC 6633), and
Staphylococcus aureus (ATCC 25923), were used for
determination of antibacterial activity, along with
standard strains of Candida albicans (ATCC 10231)
and Candida krusei (ATCC 14243) used for determina-
tion of antifungal activity.
Antibacterial and antifungal tests
The minimum inhibitory concentrations (MIC) of the
extracts and references (ciprofloxacin and flucanozole)
were determined by broth microdilution techniques
according to the Clinical Laboratory Standards Institute
(CLSI, 1996, 2002). Mueller–Hinton broth (Merck) and
Mueller–Hinton agar (Oxoid Ltd, Basingstoke, UK)
were applied for growing and diluting of the bacteria.
Sabouraud liquid medium (Oxoid Ltd) and Sabouraud
dextrose agar (Oxoid Ltd) were applied for growing and
diluting of the fungi. The medium RPMI-1640 (Sigma
Chemical Co., St. Louis, MO, USA) with l-glutamine was
buffered at pH 7 with MOPS. The extracts were dissolved
in DMSO. Extract concentrations ranging from 1.000 to
3.75 µg/mL were prepared. Microorganism inoculums
were standardized to a turbidity equivalent to that of a
0.5 McFarland standard (106 yeasts or 108 bacterial cells),
and diluted for the broth microdilution procedure. Final
concentrations were approximately 1–5×103 cells/mL
for yeasts and 1–5×104 for bacteria. Microtiter plates
were incubated under normal atmospheric conditions
at 37°C for 24 h for bacteria and at 30°C for 48 h for yeast.
The microorganisms and pure media (positive and neg-
ative controls) were placed in the wells of a microtiter
plate. The MIC was defined as the lowest concentration
of extracts that produced an 80% reduction in visible
growth compared with control. The bacterial growth was
indicated by the presence of a white ‘pellet’ on the well
bottom. Each extract was tested in triplicate.
The in vitro antimicrobial results of the extracts were
classified as follows: the antibacterial activity was con-
sidered as significant when the MIC was 100 µg/mL
or less; moderate, when the MIC was 100–500 µg/mL;
weak, when the MIC was 500–1000 µg/mL; and inactive,
when the MIC was above 1000 µg/mL.
Results and discussion
In the present study, we aimed to investigate the alka-
loid profile of G. vuralii by capillary GC-MS analysis and
the antimicrobial activity of its alkaloid extract. Ten alka-
loids were identified in the alkaloid extract of the aerial
parts of G. vuralii. The structures of the alkaloids were
identified based on comparison of their Kovats retention
indices and mass spectral fragmentation with those of
reference data in the literature (Wink, 1993; Wink et al.,
1995) as well as by a library search (Wiley GC-MS library
databank) and comparison with authentic alkaloids
such as anagyrine and cytisine. Relative contents of %
alkaloids were determined via areas under the peaks
from total ion chromatography using Hewlett Packard
software. The quantitative pattern of the minor alkaloids
is given in Table 1. Anagyrine (93.04%) was determined
as the major alkaloid in the aerial parts of G. vuralii. In
 GC-MS analysis and antimicrobial activity of Genista vuralii   83
Table 1.  Alkaloid composition and alkaloid content of the aerial parts of Genista vuralii.
No. Alkaloid
1 N-Methylcytisine
2 Cytisine
3 Tetrahydrorhombifoline
4 17-Oxosparteine
5 5,6-Dehydrolupanine
6 Lupanine
7 17-Oxolupanine
8 Anagyrine
9 Baptifoline
10 13-Tigloyloxylupanine
KI, Kovats retention index; Mt, Molecular ion.
addition, N-methylcytisine, cytisine, tetrahydrorhombi-
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foline, 17-oxosparteine, 5,6-dehydrolupanine, lupanine,
17-oxolupanine, baptifoline, and 13-tigloyloxylupanine
were detected as the minor alkaloids in the plant.
There are a number of reports on the alkaloid patterns
of Genista species by capillary GC-MS (Montllor et al.,
1990; Greinwald et al., 1992; Wink & Witte; 1993; Kirch
et al., 1995; Pistelli et al., 2001; Martins et al., 2005). In
the Montllor et al. (1990) study, dehydroaphyllidine and
N-methylcytisine were detected as the major alkaloids
For personal use only.
in G. monspessulana, together accounting for 74% of
the total alkaloids. Greinwald et al. (1992) investigated
the alkaloid pattern of G. cinerea subsp. ausetana, G.
cinerascens, and G. majorica, and detected cytisine
and anagyrine as the main alkaloids in these plants. In
Wink and Witte’s study (1993), 12 QA were identified
in G. acanthoclada, with sparteine, cytisine, retamine,
and 17-oxosparteine found to be the main compounds.
In another study, the alkaloid profiles of G. lobelia and
G. salzmannii were studied by GC-MS, and sparteine,
lupanine, 5,6-dehydrolupanine, anagyrine, cytisine,
N-methylcytisine, and ammodendrine were identified
as the major alkaloids (Kirch et al., 1995). In the study of
Pistelli et al. (2001) on QA patterns of Genista species,
anagyrine, lupanine, retamine, 17-oxoretamine, and
12-hydroxylupanine were found in the aerial parts of
G. ephedroides. Martins et al. (2005) reported ten alka-
loids, anagyrine, lupanine, cytisine, N-methylcytisine,
and N-formylcytisine as the major components, and
dehydrocytisine, 5,6-dehydrolupanine, rhombifoline,
aphylline, and thermopsine in only trace amounts, in
the aerial parts of G. tenera. Comparing the present
results with the above-mentioned literature findings,
the alkaloid compositions were similar in these spe-
cies, but the relative amounts of the alkaloids showed a
higher diversity. For example, while anagyrine (93.04%)
was the most abundant alkaloid in the present study,
sparteine (46.1%) was the main alkaloid and anagyrine
(0.7%) was a minor amount in G. acanthoclada (Wink &
Witte, 1993). Moreover, in G. tenera, anagyrine (34.5%)
was the major compound (Martins et al., 2005).
KI M+ % of total alkaloid content
1955 204 0.35
1990 190 1.02
2050 248 0.38
2070 248 0.70
2132 246 0.42
2165 248 0.75
2350 262 0.71
2390 244 93.04
2650 260 2.18
2753 346 0.45
In our previous research on Turkish Genista spe-
cies, including G. acanthoclada, G. anatolica, G.
sessilifolia, G. aucheri, G. carinalis, G. involucrata,
G. albida, G. tinctoria, G. burdurensis, G. lydia var.
lydia, G. lydia var. antiochia, and G. libanotica, 21
QA, calycotomine (tetrahydroisoquinoleine), and
N-methylamodendrine (dipiperidine) were isolated.
In these studies, lupanine, anagyrine, cytisine, and
N-methylcytisine were found in almost all of the above-
mentioned Genista species. Besides, for the first time,
genisteine, pusilline, 13-hydroxysparteine, 13-epimeth-
oxylupanine, N-acetylcytisine, N-formylcytisine,
N-methylammodendrine, calycotomine, oxymatrine,
and 10-hydroxymethylsparteine were obtained
from Genista species in addition to other known QA
compounds (Tosun et  al., 1986, 1987a,b,c, 1988, 1994;
Nasution et al., 1991). In agreement with our previous
findings in Turkish Genista species, N-methylcytisine,
cytisine, tetrahydrorhombifoline, 17-oxosparteine, 5,6-
dehydrolupanine, lupanine, 17-oxolupanine, anagyrine,
and baptifoline were found in the alkaloid profile of the
aerial parts of G. vuralii in the present study. Although
the esters of hydroxylupanine are not usual components
encountered in Genista genus (Wink, 1993; Ohmiya
et  al., 1995), 13-tigloyloxylupanine was determined
for the first time from a Turkish Genista species. 13-
Tigloyloxylupanine was previously detected in G. cin-
erea subsp. ausetana, G. cinerascens, and G. majorica
(Greinwald et al., 1992).
In addition, the antibacterial and antifungal activi-
ties of G. vuralii alkaloid extract against standard
strains of bacteria (E. coli, P. aeruginosa, B. subtilis, S.
aureus) as well as fungi (C. albicans, C. krusei) were
also investigated in the present work. Results of the
antibacterial and antifungal activities are given in
Table 2. The alkaloid extract of G. vuralii presented
significant activity against the Gram-positive bacteria
S. aureus and B. subtilis (MIC=62.5 µg/mL), moderate
activity against the Gram-negative bacterium P. aeru-
ginosa (MIC=125 µg/mL), and weak activity against the
Gram-negative bacterium E. coli (MIC=500 µg/mL). In
 84   N. Erdemoglu et al.
Table  2.  Antimicrobial activity of Genista vuralii alkaloid extract.
MIC (g/mL)
Microorganism Alkaloid extract Standard
Bacteria Ciprofloxacin
Staphylococcus aureus 62.5 0.08
Bacillus subtilis 62.5 0.02
Escherichia coli 500 0.02
Pseudomonas aeruginosa 125 0.04
Fungi Flucanozole
Candida albicans 250 1.75
Candida krusei 62.5 1.75
MIC, minimum inhibitory concentration.
the anti-yeast assay, the extract displayed significant
activity against C. krusei (MIC=62.5 µg/mL), but this
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extract had only moderate activity against C. albicans
(MIC=250 µg/mL).
A number of biological activities of QA such as
hypoglycemic activity, inhibition of edema, nicotine-
like activity, inhibition of -glucuronidase, inhibition
of acetylcholinesterase, nematocidal, and antimi-
crobial activities have been reported (Wink, 1984;
Wippich & Wink, 1985; Tyski et  al., 1988; Matsuda
et  al., 1989; Ohmiya et  al., 1995; Erdemoglu et  al.,
For personal use only.
2007). In addition, QA have a deterrent activity by way
of repel feeding of herbivores, or a directly toxic or
mutagenic effect (Wink, 1988, 1992). In Wink’s study
(1984), sparteine was reported to possess antimicro-
bial activity against bacteria and phytopathogenic
fungi. In addition, Wippich and Wink (1985) reported
that sparteine, lupanine, and 13-tigloyloxylupanine
inhibited the germination of conidia Erysiphe graminis
f. sp. hordei. Tyski et al. (1988) reported that pure QA,
namely, lupanine, 13-hydroxylupanine, angustifo-
line, and sparteine, showed bacteriostatic effects on S.
aureus, B. subtilis, E. coli, P. aeruginosa, and Bacillus
thuringiensis. In addition, various biological effects of
anagyrine such as nematocidal and acetylcholineste-
rase inhibitory activity as well as teratogenic effect have
been reported in the literature (Matsuda et  al., 1989;
Ohmiya et al., 1995). Our antimicrobial results support
the idea that QA may be involved in the antimicrobial
defense system of plants (Wink, 1984; Wippich & Wink,
1985). Also, our GC-MS analysis demonstrated that
the alkaloid extract of G. vuralii contained anagyrine
as the main alkaloid. Although no antimicrobial activ-
ity for anagyrine has been reported to date, anagyrine
might be responsible for the antimicrobial activity of
the alkaloid extract of G. vuralii which has been found
herein to have significant antimicrobial activity against
S. aureus, B. subtilis, and C. krusei.
Declaration of interest: The authors report no conflicts
of interest. The authors alone are responsible for the
content and writing of the paper.
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