Arabian Journal of Chemistry (2013) xxx, xxxxxx

King Saud University

Arabian Journal of Chemistry

www.ksu.edu.sa
www.sciencedirect.com

ORIGINAL ARTICLE

Fatty acid composition and tocopherol content

in four Tunisian Hypericum species: Hypericum perforatum,
Hypericum tomentosum, Hypericum perfoliatum and
Hypericum ericoides Ssp. Roberti
Karim Hosni

a,*

, Kamel Msaada b, Mouna Ben Taarit b, Brahim Marzouk

a
Laboratoire des Substances Naturelles, Institut National de Recherche et dAnalyse Physico-chimique,
Biotechpole de Sidi Thabet 2020, Tunisia
b
Laboratoire des Substances Bioactives, Centre de Biotechnologie a` la technopole de Borj Cedria 2050, Tunisia

Received 28 October 2012; accepted 21 October 2013

KEYWORDS
Hypericum sp.;
Hypericaceae;
Fatty acids;
Tocopherols;
Chemical variation

Abstract The fatty acid and tocopherol constituents of four Tunisian Hypericum species:
Hypericum perforatum, Hypericum perfoliatum, Hypericum tomentosum and the endemic subspecies
Hypericum ericoides Ssp. Roberti were analyzed in detail. Results revealed that all species have very
low total lipid contents (0.63.5 mg/g dw). The major identied fatty acids were linoleic
(11.2137.62%), oleic (11.223.27%) and palmitic acid (4.0320.67%). Analysis of tocopherols
allowed the identication of three isoforms (a-, c- and d-tocopherols). The d-tocopherol
(2.6922.32 lg/g dw) was found as the prominent tocopherol. Quantitative differences in the fatty
acid and tocopherol proles between Hypericum species were observed. H. perfoliatum and H. ericoides Ssp. Roberti showed signicantly higher content of linoleic acid, whereas signicantly higher
amounts of oleic acid and palmitic acid were detected in H. perforatum and H. tomentosum, respectively. Multivariate analysis (principal components analysis and hierarchical cluster analysis) based
on the fatty acid proles joined H. perfoliatum and H. ericoides in one group, while H. perforatum
and H. tomentosum were joined in a second group at the same linkage distance. With the exception
of H. perforatum, this is the rst report on the fatty acid and tocopherol constituents of H.
perfoliatum, H. tomentosum and H. ericoides Ssp. Roberti.
2013 King Saud University. Production and hosting by Elsevier B.V. All rights reserved.

* Corresponding author. Tel.: +216 71537666; fax: +216 71537677.

E-mail addresses: karim.hosni@inrap.rnrt.tn, hosni_karim@voila.fr
(K. Hosni).
Peer review under responsibility of King Saud University.

Production and hosting by Elsevier

1. Introduction
The genus Hypericum is a member of the Hypericaceae family,
belonging to the large clade of mostly tropical plants known as
Clusioid clade (Meseguer et al., 2013). The Hypericaceae
family encompasses approximately 500 species (Nurk et al.,

1878-5352 2013 King Saud University. Production and hosting by Elsevier B.V. All rights reserved.
http://dx.doi.org/10.1016/j.arabjc.2013.10.019
Please cite this article in press as: Hosni, K. et al., Fatty acid composition and tocopherol content in four Tunisian Hypericum species: Hypericum perforatum, Hypericum
tomentosum, Hypericum perfoliatum and Hypericum ericoides Ssp. Roberti. Arabian Journal of Chemistry (2013), http://dx.doi.org/10.1016/j.arabjc.2013.10.019

2
2013) accommodated in 36 sections (Robson, 2006). Several
Hypericum species, in particular Hypericum perforatum, are
of great economical importance since they have been used as
a consolidated source of natural active pharmaceuticals.
Because of its well established market position, its popularity
and its efcacy, H. perforatum is one of the best selling herbs
for the past two decades (De Smet, 2005). The whole extract
and some dened phytochemicals extracted from some Hypericum species exhibit numerous pharmacological properties,
ranging from wound healing and antiseptics to antiviral,
anti-inammatory, antitumoral and apoptosis-inducing activities (Sanchez-Mateo et al., 2002; Gibbons et al., 2005; Po Shiu
and Gibbons, 2006). Moreover, recent laboratory studies have
conrmed their antioxidants, antifungal, antimicrobial and
cytotoxic activities (Cakir et al., 2005; Housseinzadeh et al.,
2005).
As a consequence of the popularity gained and to sustain
the massive market demand, a great effort has been directed
toward chemical investigation of numerous species from the
genus Hypericum. These investigations have led to the identication and isolation of a wide array of components reputedly
responsible for the aforementioned biological activities
(Smelcerovic et al., 2006). They are mainly phenols, avonoids,
xanthones, phloroglucinols, naphtodianthrones and essential
oils (De Smet, 2005). However, most of these phytochemical
studies were focused on particular secondary metabolites and
comprehensive data in the minor components such as fatty
acids and tocopherols are scarce.
Therefore, the present contribution aimed at identifying the
fatty acid composition and tocopherol content in four
Tunisian Hypericum species: H. perforatum, Hypericum perfoliatum, Hypericum tomentosum and the endemic subspecies
Hypericum ericoides Ssp. Roberti. Our results will add valuable
information to the existing knowledge on the phytochemistry
of the genus Hypericum and to dene the possible application
areas for the rational use of these species.
2. Materials and methods
2.1. Plant material
The aerial parts of H. perforatum, H. perfoliatum, H. tomentosum and H. ericoides Ssp Roberti (top of 2/3 plants) were
collected at the full owering stage, during June 2006 from
wild populations located in El Feidja (North-western
Tunisia; latitude 36290 (N); longitude 8150 (E); altitude
779 m). The site was characterized by annual precipitation
of 1600 mm and mean annual temperature of 16.8 C. The
sampling site was not grazed or mown during the period
when the plants were gathered. The sampling was done by
a randomized collection of 1520 plants. To avoid the
sampling on the same plants, minimum distance of 10 m
was adopted. The plant material was botanically characterized by Prof. Mohammed El Hedi El Ouni (Department
of Biology, Faculty of Sciences, Bizerte, Tunisia) and
according to the morphological description presented in
Tunisian ora (Pottier-Alapetite, 1981). The harvested material was air-dried at room temperature (20 2 C) in the
dark for 1 week and subsequently essayed for their fatty acid
composition and tocopherol content.

K. Hosni et al.
2.2. Extraction and analysis of fatty acids
Samples of ground powder (1 g) in triplicate were weighed and
extracted with chloroform: methanol (2:1, v/v) (LabScan,
Dublin, Ireland) following the modied procedure of Bligh
and Dyer (1959). The mixture was shaken and centrifuged
(Eppendorf 5810R, LePecq, France) at 3000g for 10 min to
allow phase development. The bottom (organic) layer was collected and ltered. The total extracted lipid material was recovered after the solvent was removed in a stream of nitrogen,
weighed and stored at 0 C for further analysis.
Fatty acid methyl esters (FAMEs) were prepared by using
sodium methoxide (SigmaAldrich, Buchs, Switzerland)
according to the method of Cecchi et al. (1985). Methyl nonadecanoate (C19:0) was used as internal standard.
The FAMEs were analyzed on a HP 6890 gas chromatograph (Agilent Palo Alto, CA, USA) equipped with a ame
ionization detector (FID). The esters were separated on a
RT-2560 capillary column (100 m length, 0.25 mm i.d,
0.20 mm lm thickness). The oven temperature was kept at
170 C for 2 min, followed by a 3 C/min ramp to 240 C
and nally held there for an additional 15 min. Nitrogen was
used as carrier gas at a ow rate of 1.2 mL/min. The injector
and detector temperature was maintained at 225 C. Identication of FAMEs was made by comparison of their retention
time with those of reference standards purchased from Fluka
(Steinheim, Germany).
2.3. Determination of tocopherols
Tocopherols were extracted from total lipids with hexane containing 0.01% of butylated hydroxytoluene (BHT P 99%, SigmaAldrich, which was added to inhibit the oxidative
degradation of tocopherols during extraction) (Sivakumar
et al., 2005). This solution (20 lL) was injected into the highperformance liquid chromatography system. The HPLC
system consisted of a Shimadzu liquid chromatograph (Shimadzu Corp, Kyoto, Japan) equipped with a LC-20AT quaternary pump, a DGU-20A3 degasser, an SPD-M20A diode
array detector (DAD) and a manual rheodyne injector with
a 20 mL loop. The analytical column was a C18 reverse phase
Hypersil ODS, 250 mm 4.6 mm with a packing material of
5 mm of particle size. Separation of tocopherols was based
on isocratic elution with methanol: acetonitrile (9/1) at a ow
rate of 0.8 mL/min and the wavelength was set at 292 nm. Tocopherols were identied by comparing their retention times
with those of authentic standards obtained from SigmaAldrich (St Louis, MO, USA) and they were quantied using
the external standard method.
2.4. Statistical analysis
Data on total lipids, fatty acid composition and tocopherols
were reported as mean standard deviation (SD) from triplicate determinations for each sample. Mean comparison was
performed by analysis of variance (ANOVA) followed by
Tukey post hoc test at the signicance level of p 6 0.05. The
multivariate statistical analyses, i.e., the principal component
analysis (PCA) and the hierarchical cluster analysis (HCA)
were applied to examine the inter-relationships between the

Please cite this article in press as: Hosni, K. et al., Fatty acid composition and tocopherol content in four Tunisian Hypericum species: Hypericum perforatum, Hypericum
tomentosum, Hypericum perfoliatum and Hypericum ericoides Ssp. Roberti. Arabian Journal of Chemistry (2013), http://dx.doi.org/10.1016/j.arabjc.2013.10.019

Fatty acid composition and tocopherol content in four Tunisian Hypericum species
investigated species, utilizing the content of all identied fatty
acids. All statistical analyses were carried out using the Statistica v 5.5 software (Statsoft, 1998).
3. Results and discussion
3.1. Total lipids and fatty acid prole
As illustrated in Fig. 1, a statistically signicant (p < 0.05) variation was determined in the total lipid content between the
Hypericum species. H. perfoliatum and H. tomentosum were
outstanding with their markedly higher total lipid content with
their values 3.5 and 3.2 mg/g dw, respectively. For H. ericoides
Ssp. Roberti and H. perforatum, the total lipid content ranged
from 0.6 to 1.2 mg/g dw. The total lipid content in the present
samples was apparently lower than those reported for Hypericum triquetrifolium Turra. (Hosni et al., 2007). Taking into
account that the studied species grow under the same pedoclimatic circumstances and processed under the same conditions,
we can argue that the observed discrepancy among Hypericum
species might be due their genetic makeup (Richards et al.,
2008; Hosni et al., 2010).
The fatty acid composition of the four investigated Hypericum sp. is given in Table 1. The proportional composition of
the analyzed fatty acids displayed a signicant (p < 0.05) variation between species. In fact, oleic (23.27%), palmitic
(17.43%) and linoleic acids (11.21%) were the most abundant
fatty acids in H. perforatum. The same fatty acids were also
found as the major fatty acid compounds in H. perfoliatum
but with different proportions (11.2%, 37.62% and 16.8%
for oleic, palmitic and linoleic acids, respectively). The Fatty
acid prole of H. tomentosum was characterized by the abundance of palmitic (20.67%) followed by oleic (17.33%), stearic
(14.8%) and a-linolenic (13.3%) acids. Linoleic acid (36.47%)
followed by capric (20.74%), oleic (15.1%) and myristic
(10.82%) acids were the most abundant compounds in H.

0,45

0,4

Total lipid content (mg/g dw)

0,35
0,3
0,25
0,2
0,15

0,1

0,05
0
H, perforatum

H, perfoliatum H, tomentosum

H, ericoides

Figure 1 Total lipid content (mg/g dw) in four Hypericum

species. Data are expressed as mean SD (n = 3). Data marked
with different superscript are signicantly different (p < 0.05).

ercoides Ssp. Roberti. The striking differences in the proportion of individual fatty acids were also reected in the ratio
saturated to unsaturated fatty acids (1.54, 0.91, 1.27 and 0.84
for H. perforatum, H. perfoliatum, H. tomentosum and H.
ericoides Ssp. Roberti, respectively).
To understand the relationships between the studied Hypericum species with respect to their fatty acid composition, a
principal component analysis (PCA) was carried out. As
shown in Fig. 2, along the principal component 1 (PC1) which
accounts for 62% of total variance, all species were positively
related. Along PC2 axis, accounting for a further 25.65% of
the total variance, H. perforatum and H. tomentosum were negatively related to H. perfoliatum and H. ericoides. Accordingly,
the PCA distinguished two main groups; the rst group includes H. perfoliatum and H. ericoides Ssp. Roberti (characterized by their relatively higher linoleic and capric acids) while
the second group includes H. perforatum and H. tomentosum
(characterized by their relatively higher palmitic and stearic
acids). Grouping the samples observable from the PCA plot
was in general agreement with the results of hierarchical cluster
analysis HCA (Fig. 3).
To the best of our knowledge, the fatty acid composition of
H. perfoliatum, H. tomentosum and H. ericoides Ssp. Roberti is
reported herein for the rst time. Nevertheless, the fatty acid
composition of some Hypericum species has been previously
reported. For example, palmitic, a-linolenic and oleic acids
were reported as the prominent fatty acids in H. perforatum
(Omarovam and Artamonovam, 1999). Alpha-linolenic and
palmitic acids were reported as the major compound of Turkish Hypericum lysimachioides var. lysimachioides (Ozen et al.,
2004a). The latter authors have also analyzed the fatty acid
proles of H. perforatum and H. Hypericum retusum Aucher
and found that palmitic acid and linolenic acid were the major
components (Ozen et al., 2004b). They also found large
amounts of 3-hydroxy fatty acid mainly 3-hydroxytetradecanoic acid (3-OH-C14:0) and 3-hydroxyoctadecanoic acid (3OH-C18:0) in their oil samples. Report from the same country
had indicated that linolenic and linoleic acids were the most
abundant fatty acids in Hypericum scabrum, while linolenic
and palmitic acids were found as the most plentiful ones in
Hypericum scabroides and Hypericum amblysepalum (Ozen
and Bashan, 2003). In the same year, Stojanovic et al. (2003)
compared the fatty acid prole of H. perforatum, Hypericum
maculatum and Hypericum olympicum and found that linoleic
followed by palmitic and oleic acids were the most abundant
fatty acids in H. maculatum and H. olympicum. In contrast,
palmitic, oleic and lignoceric acids were found as the major
fatty acids in H. perforatum. Linoleic, linolenic and palmitic
acids were also reported as the main fatty acid in the lipidic
fraction of Hypericum androseumum seeds and H. elatum root
bark (Hargreaves et al., 1967). In our previous work on fatty
acid composition of H. triquetrifolium, we have reported the
abundance of a-linolenic, linoleic, aleic and palmitic acids.
Moreover, we have successfully identied the stearidonc acid
(C18:4) which is an unusual fatty acid in the oil of this species
(Hosni et al., 2007). More recently, Shafagat (2011), has reported that omega-3 fatty acid followed by linoleic and palmitic acids were the main components of the hexane extracts
of H. scabrum from Iran. Based on these earlier reports and
the present study, it can be inferred that the fatty acid composition of Hypericum sp. varies depending on the species and the
origin of plant.

Please cite this article in press as: Hosni, K. et al., Fatty acid composition and tocopherol content in four Tunisian Hypericum species: Hypericum perforatum, Hypericum
tomentosum, Hypericum perfoliatum and Hypericum ericoides Ssp. Roberti. Arabian Journal of Chemistry (2013), http://dx.doi.org/10.1016/j.arabjc.2013.10.019

K. Hosni et al.
Table 1

Fatty acid composition (% of total fatty acids) of Hypericum species.

Fatty acid

Hypericum
perforatum

perfoliatum

Caprylic acid (C8:0)

Capric acid (C10:0)
Lauric acid (C12:0)
Myristic acid (C14:0)
Palmitic acid (C16:0)
Palmitoleic acid (C16:1)
Stearic acid (C18:0)
Oleic acid (C18:1)
Linoleic acid (C18:2)
a-linolenic acid (C18:3)
Arachidic acid (C20:0)
Behenic acid (C22:0)
SFA
UFA
SFA/UFA

tomentosum

4.1
2.2b

4.93c
16.8b
2.3b
8.43bc
11.2c
37.62a
1.23c
6.43a
4.76b
47.65b
52.35a
0.91b

0.56
2.62b
4.29a
7.98b
17.43ab
4.63a
10.1b
23.27a
11.21b
0.19d
8.032a
9.69a
60.7a
39.3b
1.54a

ericoides

0.88b
20.74a
1.32b
10.82a
4.03c
0.06d
7.24c
15.1b
36.47a
2.73b
0.16b
0.45d
45.64b
54.36a
0.84b

0.6
1.34b

7.4b
20.67a
1.48c
14.8a
17.33b
12.4b
13.3a
6.58a
4.1c
55.49a
44.51b
1.27ab

Values are means of three determinations. SFA: Saturated fatty acids; UFA: Unsaturated fatty acids.
Data within the same line and marked with different superscript are signicantly different (p < 0.05).

0,8
H. ericoides

0,6

Axe 2 (25.65%)

0,4

H. perfoliatum

0,2
0,0
-0,2
-0,4
-0,6
0,66

H. perforatum
H. tomentosum

0,70

0,74

0,78

0,82

0,86

0,90

Axe 1 (62.01%)

Figure 2

Principal component analysis of four Hypericum species on the basis of their fatty acid composition.

3.2. Tocopherol content

The tocopherol contents of the investigated Hypericum species
are presented in Fig. 4. Three isoforms, a-, c- and d-tocopherols were detected and identied in all samples in signicantly
(p < 0.05) varying degrees. Individual tocopherol contents
exhibited great variations among the studied species. The isoform d-tocopherol had the highest content followed by c- and
a-tocopherol. In terms of variations in different isoforms between species, H. ericoides had the highest content of tocopherols (22.32, 4.28 and 4.89 lg/g dw for d-, c- and a-tocopherol,
respectively), while the lowest content of these isoforms was
observed for H. tomentosum (2.69, 0.61 and 0.54 lg/g dw for
d-, c- and a-tocopherol, respectively). H. perforatum and H.
perfoliatum have showed intermediate values. The tocopherols
are suggested to be synthesized by the action of c-tocopherol

methyl-transferase to either c- or d-tocopherol which can be

further synthesized to a- and b-tocopherol, respectively
(Collakova and DellaPenna, 2003). Our ndings indicate that
the biosynthesis of d-tocopherol is a major activity in the aerial
part of the studied Hypericum species. Published data related
to the tocopherol content in Hypericum species are not available and comparison is not possible. However, the tocopherol
constituents of some species of the closely related family Clusiaceae have previously been reported. In this context, Crane
et al. (2005) have compared the tocopherol content of two
Calophyllum species from Guadeloupe and found that atocopherol was the main isoform in the Calophyllum calaba,
whereas, the isoform c-tocopherol was the main one in
Calophyllum inophyllum. Another report from Vietnam had
revealed that a-tocopherol was the main isoform in the oil of
C. inophyllum (Matthaus et al., 2003). In another Clusiaceae

Please cite this article in press as: Hosni, K. et al., Fatty acid composition and tocopherol content in four Tunisian Hypericum species: Hypericum perforatum, Hypericum
tomentosum, Hypericum perfoliatum and Hypericum ericoides Ssp. Roberti. Arabian Journal of Chemistry (2013), http://dx.doi.org/10.1016/j.arabjc.2013.10.019

Fatty acid composition and tocopherol content in four Tunisian Hypericum species

H. perforatum

H. tomentosum

H. perfoliatum

H. ericoides

20

30

40

50

60

70

80

90

Figure 3

Dendrogram of four Hypericum species obtained by cluster analysis using square Euclidean distance.

Figure 4

Tocopherol content (lg/g dw) in four Hypericum species. Data are expressed as mean SD (n = 3).

species, Caraipa densifolia, only a- and c-tocopherols were detected in its hexane extract (da Silveira et al., 2010).
In general, data regarding the tocopherol content in different species were conicting and variable depending on species,
origin, plant part, plant physiology and environmental factors
(Bruni et al., 2004; Symanska and Kruk, 2008). At this point,
the latter authors have showed that a-tocopherol is the most
abundant isoform in leaves with only some exceptions reported
for lettuce, spinach, dodder shoots, or some seedling where
c-, d-tocopherols were found at the highest amounts. They also
reported that d-tocopherol was the dominant isoform in Cuscuta epithymum and Cuscuta japonica (Symanska and Kruk,
2008). In Brassica napus and Brassica juncea, the tocopherol
content was found to be deeply inuenced by environmental
factors namely the daily temperature and rainfall (Richards
et al., 2008).

From a chemical perspective, it is well recognized that

tocopherols interact with polyunsaturated acyl groups,
protecting the lipids (especially polyunsaturated fatty acids)
from oxidative damage by scavenging lipid peroxy radicals
and quenching or chemically reacting with reactive oxygen
species (DellaPenna and Pogson, 2006). Therefore, it seems
logical to speculate that the higher content of tocopherols in
H. ericoides might have such physiological role since it presents
the higher content of polyunsaturated fatty acids. This species
might be considered as a potential source of natural antioxidant due to its high d-tocopherol content (Fazio et al., 2013).
It is worthy to note that the present tocopherol composition
might be useful for the taxonomical purposes for the infrageneric classication of the genus Hypericum.
In summary, the present contribution provided a new
insight into the chemistry of H. perforatum, H. tomentosum,

Please cite this article in press as: Hosni, K. et al., Fatty acid composition and tocopherol content in four Tunisian Hypericum species: Hypericum perforatum, Hypericum
tomentosum, Hypericum perfoliatum and Hypericum ericoides Ssp. Roberti. Arabian Journal of Chemistry (2013), http://dx.doi.org/10.1016/j.arabjc.2013.10.019

6
H. perfoliatum and H. ericoides Ssp. Roberti. It provides base
line information on the fatty acid composition and tocopherol
content in the aforementioned species.
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Please cite this article in press as: Hosni, K. et al., Fatty acid composition and tocopherol content in four Tunisian Hypericum species: Hypericum perforatum, Hypericum
tomentosum, Hypericum perfoliatum and Hypericum ericoides Ssp. Roberti. Arabian Journal of Chemistry (2013), http://dx.doi.org/10.1016/j.arabjc.2013.10.019