C. IRAK, J. RADUIEN, V. JANULIS, L. IVANAUSKAS, N. AMA, A. K.

AYAN
Turk J Biol
35 (2011) 449-456
TBTAK
doi:10.3906/biy-1002-36

Phenolic constituents of Hypericum triquetrifolium

Turra (Guttiferae) growing in Turkey:
variation among populations and plant parts
Cneyt IRAK1,*, Jolita RADUIEN2, Valdimaras JANULIS3, Liudas IVANAUSKAS3, Necdet AMA1,
Ali Kemal AYAN
1

Ondokuz Mays University, Bafra Vocational High School, 55040 Samsun - TURKEY
2

Institute of Botany, Zaliuju ezeru 49, Vilnius LT-08406 - LITHUANIA

Kaunas University of Medicine, Mickeviciaus 9, LT-44307 - LITHUANIA

Received: 19.02.2010

Abstract: Hypericum triquetrifolium Turra (Guttiferae) has received considerable scientific interest in recent years, as
it is a source of a variety of biologically active compounds including phenolics. The present study was conducted to
determine the variation in the content of several phenolics, namely phenylpropane chlorogenic acid and flavonoids
such as rutin, hyperoside, apigenin-7-O-glucoside, kaempferol, quercitrin, quercetin and amentoflavone among four
H. triquetrifolium populations from the Central Black Sea Region of Turkey. The aerial parts representing a total of
30 shoots were collected at full flowering in each population. After drying at room temperature, they were dissected
into floral, leaf and stem tissues and subsequently assayed for phenolic compounds by HPLC. The populations varied
significantly in phenolic content. Among different plant parts, the flowers were found to be the principle organ for
chlorogenic acid, hyperoside, apigenin-7-O-glucoside, kaempferol, quercetin and amentoflavone accumulations, while
rutin and quercitrin were accumulated mainly in the leaves. The presence of apigenin-7-O-glucoside and amentoflavone
in H. triquetrifolium is reported by us for the first time. The chemical variation among the populations and plant parts is
discussed as being possibly the result of different genetic, environmental and morphological factors.
Key words: Chlorogenic acid, flavonoids, HPLC, Hypericum triquetrifolium, population variability

Trkiyede yetien Hypericum triquetrifolium Turra (Guttiferae) un fenolik

bileenleri: poplasyon ve bitki ksmlar arasndaki varyasyon
zet: Hypericum triquetrifolium Turra (Guttiferae) son yllarda bilimsel dikkatleri zerine eken bir bitki olup,
fenoliklerin de dahil olduu ok sayda biyoaktif bileen iermektedir. Bu alma, lkemizin Orta Karadeniz blgesinde
bulunan drt H. triquetrifolium populasyonunda baz fenolik bileenlerin (srasyla fenilpropan bileii olan klorojenik
asit, ve flavonoid bileikleri rutin, hiperozit, apigenin-7-O-glukozit, kemferol, kersitrin, kersetin ve amentoflavon)
varyasyonunu belirlemek amacyla yrtlmtr. Tam ieklenme dneminde her poplasyon iin toplam 30 bitki
toplanmtr. Materyal oda scaklnda kurutulduktan sonra iek, yaprak ve sap ksmlarna ayrlm; fenolik ierikleri
belirlenmek zere HPLC analizlerine tabi tutulmulardr. Poplasyonlarn fenolik ierikleri nemli seviyede farkl
bulunmutur. Farkl bitki ksmlar ierisinde klorojenik asit, hiperozit, apigenin-7-O-glukozit, kemferol, kersetin ve

449

Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts

amentoflavonun esas olarak ieklerde, rutin ve kersitrinin ise yapraklarda biriktii belirlenmitir. H. triquetrifoliumun
apigenin-7-O-glukozit ve amentoflavon ierdii ilk olarak bu almada rapor edilmitir. Poplasyonlar ve bitki ksmlar
arasnda gzlenen kimyasal varyasyon farkl genetik, evresel ve morfolojik faktrlerin muhtemel bir sonucu olduu
balamnda tartlmtr.
Anahtar szckler: Klorojenik asit, flavonoidler, HPLC, Hypericum triquetrifolium, poplasyon deikenlikleri

Introduction
Hypericum triquetrifolium Turra (Guttiferae),
native to Eastern Europe and the Mediterranean
area, is a herbaceous perennial plant that grows in
open dry stony/sandy ground and cultivated fields
in Turkey (1). It has traditionally been used in the
treatment of burns and gastrointestinal diseases in
Turkish folk medicine (2). Results from recent studies
reporting the antinociceptive (3), anti-inflammatory
(4), antioxidant (5), antibacterial (6), antifungal
(7), and cytotoxic (8) activities of H. triquetrifolium
demonstrate the great potential of this species for use
as a medicinal plant.
The methanolic extract of the aerial parts
of Hypericum species has been reported to
contain many bioactive compounds, namely the
naphthodianthrones hypericin and pseudohypericin
(9), the phloroglucinol derivatives hyperforin and
adhyperforin, flavonoids (10), essential oils (11),
xanthones (12), tannins (13), procyanidins, and
other water-soluble components (14) that possess a
wide array of biological properties.
Phenolic compounds are well-known antioxidant
agents, some of which exert therapeutic antiviral,
anti-allergic, anti-platelet, and anti-inflammatory
activities (15-18). Flavonoids have attracted
considerable interest as dietary constituents and the
results of clinical studies have indicated their possible
role in preventing cardiovascular diseases and several
kinds of cancer (19). Although hypericins and
hyperforin have been reported to mainly contribute
to the pharmacological effects of Hypericum extracts,
flavonoids have also made an important contribution
to antidepressant activity (20,21). For these reasons,
many individual or groups of Hypericum species
have been investigated for the presence of phenolics
(22-31). H. triquetrifolium was reported previously
to contain chlorogenic acid, rutin, hyperoside,
quercitrin, quercetin (6), kaempferol (5), and
phenolic and flavonoid compounds (32). However, no
450

study has been done on the variation in the phenolic

constituents in H. triquetrifolium. Thus, the present
study was conducted to determine the variation in the
content of the phenylpropane chlorogenic acid and
flavonoids, namely rutin, hyperoside, apigenin-7O-glucoside, kaempferol, quercitrin, quercetin, and
amentoflavone among H. triquetrifolium populations
from Turkey. So far, apigenin-7-O-glucoside and
amentoflavone have not yet been detected in H.
triquetrifolium. This article also describes the first
occurrence of these compounds in this species.
Materials and methods
Brief description of plant materials
The plant materials have been described in our
previous studies (33). The species were identified
by Dr. Hasan Korkmaz, Faculty of Science and Art,
Department of Biology, 19 Mays University, Samsun,
Turkey.
Experimental procedures
The aerial parts of H. triquetrifolium plants
representing a total of 30 shoots were collected at
full flowering from 4 sites in northern Turkey (Table
1). The sampling sites were not grazed or mown
during the plant-gathering period. The top 2/3 of the
plants were harvested between 1100 and 1300 hours.
Conditions on the day of collection were clear and
sunny at all the sites. Temperatures ranged from 24
to 35 C. After collection, 10 individuals were kept as
whole plants and the rest were dissected into floral,
leaf and stem tissues. The plant materials were dried
at room temperature (20 2 C), and subsequently
assayed for their chemical contents by HPLC.
Preparation of plant extracts
Samples of 0.5-1.0 g of air-dried plant material
with a moisture content of 10.0% were mechanically
ground with a laboratory mill to obtain a homogeneous
drug powder and extracted with 96% EtOH (50 mL)

C. IRAK, J. RADUIEN, V. JANULIS, L. IVANAUSKAS, N. AMA, A. K. AYAN

Table 1. Geographical data and seasonal climatic conditions of Hypericum triquetrifolium growing localities from northern Turkey.
Sites

Mean

Collection date

Voucher no.

Latitude (N)

Longitude (E)

Elevation (m)

Precipitation (mm)

ahinler

20 July 2007

BMYO # 1/1

4041

3623

640

11.3

653

Rocky and open slopes

Taova

18 July 2007

BMYO # 1/2

4043

3624

272

10.6

578

Arid pasturelands

temperature (C)

Habitat

Niksar

19 July 2007

BMYO # 1/3

4027

3644

713

11.7

450

Arid pasturelands

Erbaa

14 July 2007

BMYO # 1/4

4039

3637

264

13.2

350

Sides of cultivated area

min 55% A, 45% B; 50-55 min 55%-95% A, 45%5% B. Flow rate: 0.4 mL/min. Injection volume: 10
L. The column temperature was 20 C. The elution
was monitored at 360 nm and the data obtained were
compared with authentic samples of the respective
compounds (35).

for 72 h, at room temperature. The prepared extracts

were kept in the dark in a refrigerator until used (34).
Before HPLC separation, the extracts were filtered
through a membrane filter with a pore size of 0.22
m (Carl Roth GmbH, Karlsruhe, Germany).
HPLC analysis

The quantity of compounds was calculated from

an external standard calibration in the concentration
range of 0.5-100.0 g/mL (r2 = 0.9999). Each sample
was analyzed twice and the mean value was used
for calculation. A typical HPLC chromatogram of
a flower extract is shown in Figure 1. All solvents
and standards of reference substances were of HPLC
grade and purchased from Roth Chemical Company
(Karlsruhe, Germany).

HPLC analysis of phenolic acid and flavonoids

was performed using a Waters model 2690 gradient
pump with Waters 2487 UV-detector and XTerra
RP18 column (150 3.9 mm, 3.5 m). Compounds
on the column were separated with 5% water
including 0.1% trifluoracetic acid (solvent A) and
95% acetonitrile containing 0.1% trifluoracetic acid
(solvent B), using the following gradient elution
program: 0-45 min 95%-55% A, 5-45% B; 45-50
3

0.140
0.130
0.120
0.110
0.100
0.090
AU

0.080

0.070
0.060
0.050

0.040
0.030
0.020
0.010

4
2

0.000
200 400 600 800 1000 1200 1400 1600 1800 2000 2200 2400 2600 2800 3000 32003400 3600 3800 4000 4200 4400 4600 4800 5000 5200 5400

Minutes

Figure 1. Typical chromatograms of Hypericum triquetrifolium flower extracts obtained by HPLC

separation. Peak identified: 1-chlorogenic acid, 2-rutin, 3-hyperoside, 4-apigenin-7-Oglucoside, 5-quercitrin, 6-quercetin, 7-kaempferol, and 8-amentoflavone.

451

Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts

Data analysis
Data for the chlorogenic acid, rutin, hyperoside,
apigenin-7-O-glucoside, kaempferol, quercitrin,
quercetin, and amentoflavone contents of the plant
material including whole plant, stem, leaf, and flower
were subjected to ANOVA and significant differences
among mean values were tested with the Duncans
multiple range test (P < 0.01) using MSTAT statistical
software. The mean values of the chemical contents
were normalized using x = x + 1 transformation
before conducting ANOVA, when necessary, because
some chemicals were not detected in several cases.
Results and discussion
The content levels of chlorogenic acid, rutin,
hyperoside, quercitrin, quercetin, kaempferol,
apigenin-7-O-glucoside, and amentoflavone in the
plant materials including whole shoots, stem, leaf,
and flower tissues varied significantly among the
populations (P < 0.01). The chlorogenic acid, rutin,
quercitrin, and apigenin-7-O-glucoside contents of
the whole shoots were similar among the populations
and plants, while plants from the Taova population
produced the highest amount of corresponding
compounds (4.04, 5.22, 2.87, and 0.27 mg/g DW for
chlorogenic acid, rutin, quercitrin, and apigenin-7-Oglucoside, respectively). The hyperoside, quercetin,
and kaempferol contents of the whole shoots reached
the highest level in the ahinler population (15.97,
2.08, and 0.02 mg/g DW for hyperoside, quercetin,
and kaempferol, respectively). Generally, lower
accumulation levels were observed in the Niksar and
Erbaa populations for all examined compounds with
the exception of amentoflavone, the highest level

of which was produced by plants from the Niksar

population (0.02 mg/g DW) (Table 2).
The stems, leaves and reproductive tissues
differed significantly with regard to the accumulation
of phenolics (Figures 2 and 3). The highest levels of
chlorogenic acid, hyperoside, quercetin, apigenin7-O-glucoside, and amentoflavone were detected in
the flowers of all populations. Similarly, kaempferol
was accumulated mainly in the flowers of plants
from the Taova, Niksar, and Erbaa populations,
while the highest level of this compound was found
in the leaves of plants from the ahinler population.
Of note was that the leaves were found to be superior
to the flowers in terms of rutin and quercitrin
accumulations. Leaves produced the highest level
of these compounds at all sites. As for the stems,
significantly lower accumulation levels of the
secondary metabolites were observed in the organs
and they did not produce amentoflavone.
Variations in the levels of bioactive secondary
metabolites in populations of Hypericum plants have
an important impact on the pharmacological activity
of the tested extracts (36). Hence, investigations of
population variability in the content of secondary
metabolites from different species of Hypericum
have been performed over several decades. In the
present study, significant differences were detected
in phenolic accumulation among wild populations
of H. triquetrifolium. The populations were located in
different parts of northern Turkey and their growing
sites differed from each other in terms of climatic
and geographic factors (Table 1). As a result of these
environmental differences, each populations growing
site has specific ecological conditions and habitat.

Table 2. Chlorogenic acid, rutin, hyperoside, quercitrin, quercetin, kaempferol, apigenin-7-O-glucoside, and amentoflavone contents
of Hypericum triquetrifolium whole shoots from wild populations located in northern Turkey (mg/g DW).
Populations

Chlorogenic acid

Rutin

Hyperoside

Quercitrin

Quercetin

Kaempferol

Apigenin-7-O-glucoside

Amentoflavone

ahinler

1.77 ba

2.39 b

15.97 a

1.32 b

2.08 a

0.02 a

0.12 b

0.007 b

Taova

4.04 a

5.22 a

5.46 c

2.87 a

1.76 b

0.005 b

0.27 a

0.006 b

Niksar

2.11 b

2.53 b

3.88 d

2.74 a

0.20 c

0.01 a

0.10 b

0.04 a

Erbaa

0.54 c

2.01 b

8.68 b

1.22 b

1.13 b

0.01 a

0.10 b

0.02 a

Values followed by different small letters in each column are significantly different (P < 0.01) according to Duncans multiple range test.

452

7
6
5
4
3
2
1
0

(A)
b

ahinle

Rutin (mg/g DW)

Chlorogenic acid (mg/g DW)

C. IRAK, J. RADUIEN, V. JANULIS, L. IVANAUSKAS, N. AMA, A. K. AYAN

a a

7.5

(B)

4.5

3
1.5

Niksar

ahinle

Erbaa

Taova

Qercitrin (mg/g DW)

a
a
b

b b

Niksar

Erbaa

Sites

Sites
Hyperoside (mg/g DW)

0
Taova

a
21 (C)
18
15
b
12
9
6
c
3
0
ahinle

Taova

a
b

Niksar

(D)

5
a

3
2

Erbaa

a a

ahinle

Taova

Sites

b
Niksar

Erbaa

Sites
Stem

Leaf

Flower

(A)

3
2

b
a a

0
ahinle

Apigenin-7-O-glucoside (mg/g DW)

Kaempferol (mg/g DW)

b
Taova

Niksar

0.04

(B)

0.03

0.4

(C)

0.01

ahinle

0
ahinle

Taova

Erbaa

0.3

0.1

Taova

Niksar

Erbaa

Sites

0.2

0.02

Sites
Amentoflavone (mg/g DW)

Qercetin (mg/g DW)

Figure 2. Chlorogenic acid (A), rutin (B), hyperoside (C), and apigenin-7-O-glucoside (D) contents in stem, leaf, and flower of
Hypericum triquetrifolium plants from wild populations located in northern Turkey (values with different small lettersa,
b, cwithin columns for each site differ significantly at the level of P < 0.01; Bars are s.e.).

Niksar

Erbaa

0.06

(D)

0.05

0.04
0.03

0.02
0.01

b
b

0
ahinle

Sites

Taova

Niksar

Erbaa

Sites

Stem

Leaf

Flower

Figure 3. Kaempferol (A), quercitrin (B), quercetin (C), and amentoflavone (D) contents in stem, leaf and flower of H. triquetrifolium
plants from wild populations located in northern Turkey (values with different small lettersa, b, cwithin columns for each
site differ significantly at the level of P < 0.01; Bars are s.e.).

453

Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts

The chemical variability in the content of phenolics

evaluated among the populations may be attributed
to the different environmental conditions of the
sampling sites. However, the present findings also
indicate a significant genetic difference/similarity
among the populations. For example, the ahinler and
Niksar populations are separated by a distance of 170
km and have a substantially different environment
(mean temperature, precipitation, elevation etc.).
Hence, they should represent distinct populations.
However, both populations produced similar
amounts of chlorogenic acid, rutin, kaempferol,
and apigenin-7-O-glucoside. In contrast, although
the ahinler and Taova populations are separated
by only 8 km and have very similar environmental
conditions, 3- and 4-fold differences were detected
between the populations in terms of hyperoside and
kaempferol contents, respectively.
Hypericum plants are characterized by the
presence of secretory structures, including light
glands, dark glands, and secretory canals, in which
biologically active substances are synthesized and/
or accumulated (37). The localization of the various
types of secretory structures varies among the plant
tissues, and the levels of phytomedicinal compounds
present in a particular Hypericum tissue depend on
the relative abundance of these secretory structures
on the harvested material. In the present study, the
flowers were found to be the main organs for the
accumulation of the phenolics tested, except for rutin
and quercitrin.

The differences in chemical composition between

the leaves and flowers for H. triquetrifolium did not
correspond to those described for other Hypericum
species. The floral parts had the highest level of
quercitrin, quercetin, and apigenin-7-O-glucoside,
whereas the leaves were superior to generative tissues
with respect to chlorogenic acid and hyperoside
accumulation in H. origanifolium and H. perfoliatum
(29,30). The flowers of H. montbretii accumulated
the highest level of apigenin-7-O-glucoside and the
highest content of quercitrin was found in stems
of flowering plants, while leaves were superior to
the other tissues with respect to chlorogenic acid
and hyperoside accumulation (31). In the case of
H. perforatum, the flowers accumulated higher
amounts of hypericin, quercetin, and quercitrin,
while the leaves had the highest levels of hyperoside
and rutin (10,24). The differences in the phenolic
content of plant tissues among Hypericum plants
may be attributed to the genotypic differences of the
corresponding species.
Results from the present study indicate that H.
triquetrifolium accumulates lower concentrations
of rutin and quercetin; comparable concentrations
of chlorogenic acid, apigenin-7-O-glucoside,
and quercitrin; and higher concentrations of
hyperoside and amentoflavone when compared to H.
perforatum, a well known and commercial source of
the compounds examined (Table 3). The results also
indicate that both species contain a similar array of
phenolic constituents.

Table 3. Comparison of the content (mg/g DW) of chlorogenic acid, rutin, hyperoside, quercitrin, quercetin, kaempferol, apigenin-7O-glucoside, and amentoflavone in Hypericum triquetrifolium and H. perforatum.
Compounds
Chlorogenic acid

H. triquetrifolium
0.54-4.04

H. perforatum

References

1.11-2.19

Maggi et al. (38)

Rutin

2.01-5.22

0.19-34.71

Radusiene et al. (10);

Martonfi and Repak (22)

Hyperoside

3.88-15.97

2.07-7.69

Maggi et al. (38)

Apigenin-7-O-glucoside

0.10-0.27

0.05-0.2

Quercitrin

1.22-2.87

0.05-4.77

Quercetin

0.2-2.08

0.05-24.12

Kaempferol

0.005-0.02

rak et al. (30)

Radusiene et al. (10)
Martonfi and Repak (22)
Radusiene et al. (10)
Martonfi and Repak (22)
No previous report

Amentoflavone

0.006-0.02

0.001-0.005

Greeson et al. (14)

The values are the lowest and highest level of the corresponding phenolics in the whole shoots of plants from different populations.

454

C. IRAK, J. RADUIEN, V. JANULIS, L. IVANAUSKAS, N. AMA, A. K. AYAN

The main issue in medicinal plant standardization

is the huge variability in the secondary metabolite
profile of a given plant material. Screening the
wild plant populations to obtain the improved
phytochemical profiles seems to be first step in
identifying superior germplasm. The results of the
present study indicate a significant variation in the
phenolic constituent content of H. triquetrifolium
among Turkish populations. The regional distribution
of this medicinal plant may be an important source
of chemical variability and should be considered
while optimizing the processing methodology
of wild-harvested plant material. In the present
study, the presence of apigenin-7-O-glucoside and
amentoflavone in H. triquetrifolium was reported
by us for the first time. Such data could also be
useful for the elucidation of the chemotaxonomic

significance of the corresponding compounds and

the phytochemical evaluation of H. triquetrifolium.
Acknowledgment
The chemical evaluation was supported by
the Scientific Foundation of Kaunas University of
Medicine.
Corresponding author:
Cney IRAK
Ondokuz Mays University,
Bafra Vocational High School,
55040 Samsun - TURKEY
E-mail: cuneytc@omu.edu.tr

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