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ORIGINAL ARTICLE

Fatty acid composition and tocopherol content

in four TunisianHypericumspecies:Hypericum perforatum,

Hypericum tomentosum, Hypericum perfoliatumand

Hypericum ericoides Ssp. Roberti

Karim Hosni a,*, Kamel Msaa da b, Mouna Ben Taa rit b, Brahim Marzouk b

a Laboratoire des Substances Naturelles, Institut National de Recherche et dAnalyse Physico-chimique,

Biotechpole de Sidi Thabet 2020, Tunisiab 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 tomentosumand the endemic subspecies

Hypericum ericoidesSsp. Robertiwere analyzed in detail. Results revealed that all species have very

low total lipid contents (0.63.5 mg/g dw). The major identified fatty acids were linoleic

(11.2137.62%), oleic (11.223.27%) and palmitic acid (4.0320.67%). Analysis of tocopherols

allowed the identification 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 profiles between Hypericumspecies were observed. H. perfoliatumandH. erico-

ides Ssp. Robertishowed significantly higher content of linoleic acid, whereas significantly higher

amounts of oleic acid and palmitic acid were detected in H. perforatumand H. tomentosum, respec-

tively. Multivariate analysis (principal components analysis and hierarchical cluster analysis) based

on the fatty acid profiles joined H. perfoliatum and H. ericoides in one group, while H. perforatum

andH. tomentosumwere joined in a second group at the same linkage distance. With the exception

of H. perforatum, this is the first 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.

1. Introduction

The genusHypericumis 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 (Nu rk et al.,

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

E-mail addresses: [email protected], [email protected]

(K. Hosni).

Peer review under responsibility of King Saud University.

Production and hosting by Elsevier

Arabian Journal of Chemistry (2013) xxx, xxxxxx

King Saud University

Arabian Journal of Chemistry

www.ksu.edu.sawww.sciencedirect.com

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 Hypericumspecies:Hypericum perforatum, Hypericum

tomentosum, Hypericum perfoliatum and Hypericum ericoidesSsp. Roberti. Arabian Journal of Chemistry (2013), http://dx.doi.org/10.1016/j.arabjc.2013.10.019
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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 efficacy, H. perforatum is one of the best selling herbs

for the past two decades (De Smet, 2005). The whole extract

and some defined phytochemicals extracted from some Hyper-

icum species exhibit numerous pharmacological properties,ranging from wound healing and antiseptics to antiviral,

anti-inflammatory, antitumoral and apoptosis-inducing activi-

ties (Sanchez-Mateo et al., 2002; Gibbons et al., 2005; Po Shiu

and Gibbons, 2006). Moreover, recent laboratory studies have

confirmed 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

genusHypericum. These investigations have led to the identifi-

cation and isolation of a wide array of components reputedly

responsible for the aforementioned biological activities

(Smelcerovic et al., 2006). They are mainly phenols, flavonoids,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

TunisianHypericum species: H. perforatum, Hypericum perfo-

liatum, Hypericum tomentosum and the endemic subspecies

Hypericum ericoidesSsp.Roberti.Our results will add valuable

information to the existing knowledge on the phytochemistry

of the genus Hypericum and to define the possible application

areas for the rational use of these species.

2. Materials and methods

2.1. Plant material

The aerial parts ofH. perforatum, H. perfoliatum, H. tomen-

tosum and H. ericoides Ssp Roberti (top of 2/3 plants) were

collected at the full flowering 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 16.8C. The

sampling site was not grazed or mown during the periodwhen 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 character-

ized by Prof. Mohammed El Hedi El Ouni (Department

of Biology, Faculty of Sciences, Bizerte, Tunisia) and

according to the morphological description presented in

Tunisian flora (Pottier-Alapetite, 1981). The harvested mate-

rial was air-dried at room temperature (20 2C) in the

dark for 1 week and subsequently essayed for their fatty acid

composition and tocopherol content.

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 modified 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 col-

lected and filtered. The total extracted lipid material was recov-ered 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 ofCecchi et al. (1985). Methyl non-

adecanoate (C19:0) was used as internal standard.

The FAMEs were analyzed on a HP 6890 gas chromato-

graph (Agilent Palo Alto, CA, USA) equipped with a flame

ionization detector (FID). The esters were separated on a

RT-2560 capillary column (100 m length, 0.25 mm i.d,

0.20 mm film thickness). The oven temperature was kept at

170C for 2 min, followed by a 3 C/min ramp to 240C

and finally held there for an additional 15 min. Nitrogen was

used as carrier gas at a flow rate of 1.2 mL/min. The injector

and detector temperature was maintained at 225 C. Identifica-

tion 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 con-

taining 0.01% of butylated hydroxytoluene (BHTP 99%, Sig-

maAldrich, which was added to inhibit the oxidative

degradation of tocopherols during extraction) (Sivakumar

et al., 2005). This solution (20lL) was injected into the high-

performance liquid chromatography system. The HPLCsystem consisted of a Shimadzu liquid chromatograph (Shima-

dzu Corp, Kyoto, Japan) equipped with a LC-20AT quater-

nary 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 flow

rate of 0.8 mL/min and the wavelength was set at 292 nm. Toc-

opherols were identified by comparing their retention times

with those of authentic standards obtained from SigmaAl-

drich (St Louis, MO, USA) and they were quantified 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 tripli-

cate determinations for each sample. Mean comparison was

performed by analysis of variance (ANOVA) followed by

Tukey post hoc test at the significance 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

2 K. Hosni et al.

Please cite this article in press as: Hosni, K. et al., Fatty acid composition and tocopherol content in four Tunisian Hypericumspecies: Hypericum perforatum, Hypericum

http://dx.doi.org/10.1016/j.arabjc.2013.10.019http://dx.doi.org/10.1016/j.arabjc.2013.10.019


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investigated species, utilizing the content of all identified fatty

acids. All statistical analyses were carried out using the Statis-

tica v 5.5 software (Statsoft, 1998).

3. Results and discussion

3.1. Total lipids and fatty acid profile

As illustrated inFig. 1, a statistically significant (p< 0.05) var-iation 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.Robertiand 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 Hyper-

icum triquetrifolium Turra. (Hosni et al., 2007). Taking into

account that the studied species grow under the same pedocli-

matic 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 Hyper-

icum sp. is given inTable 1. The proportional composition of

the analyzed fatty acids displayed a significant (p< 0.05) var-

iation 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 profile of H. tomentosum was characterized by the abun-

dance 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.

ercoides Ssp. Roberti. The striking differences in the propor-

tion of individual fatty acids were also reflected 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 Hyper-

icum species with respect to their fatty acid composition, a

principal component analysis (PCA) was carried out. As

shown inFig. 2, along the principal component 1 (PC1) whichaccounts for 62% of total variance, all species were positively

related. Along PC2 axis, accounting for a further 25.65% of

the total variance,H. perforatumandH. tomentosumwere neg-

atively related toH. perfoliatumandH. ericoides. Accordingly,

the PCA distinguished two main groups; the first group in-

cludes H. perfoliatum and H. ericoides Ssp.Roberti(character-

ized 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. ericoidesSsp.Robertiisreported herein for the first 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 Turk-

ish Hypericum lysimachioides var. lysimachioides (Ozen et al.,

2004a). The latter authors have also analyzed the fatty acid

profiles ofH. 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-hydroxytetradeca-

noic acid (3-OH-C14:0) and 3-hydroxyoctadecanoic acid (3-OH-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 profile ofH. perforatum, Hypericum

maculatumand 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 ofHypericum androseumum seeds and H. elatum rootbark (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 identified 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 re-

ported that omega-3 fatty acid followed by linoleic and pal-

mitic 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 compo-

sition ofHypericumsp. varies depending on the species and the

origin of plant.

0

0,05

0,1

0,15

0,2

0,25

0,3

0,35

0,4

0,45

H, perforatum H, perfoliatum H, ericoidesH, tomentosum

Totallipidco

ntent(mg/gdw)

aa

b

c

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 significantly different (p< 0.05).

Fatty acid composition and tocopherol content in four Tunisian Hypericum species 3




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3.2. Tocopherol content

The tocopherol contents of the investigated Hypericumspecies

are presented inFig. 4. Three isoforms, a-, c- and d-tocophe-rols were detected and identified in all samples in significantly

(p< 0.05) varying degrees. Individual tocopherol contents

exhibited great variations among the studied species. The iso-

formd-tocopherol had the highest content followed by c- and

a-tocopherol. In terms of variations in different isoforms be-

tween species,H. ericoideshad the highest content of tocophe-

rols (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 0.54lg/g dw for

d-, c- and a-tocopherol, respectively). H. perforatum and H.

perfoliatumhave showed intermediate values. The tocopherols

are suggested to be synthesized by the action ofc-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 findings indicate that

the biosynthesis ofd-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 avail-

able and comparison is not possible. However, the tocopherol

constituents of some species of the closely related family Clusi-

aceae 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 a-

tocopherol 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

Table 1 Fatty acid composition (% of total fatty acids) ofHypericum species.

Fatty acid Hypericum

perforatum perfoliatum tomentosum ericoides

Caprylic acid (C8:0) 0.56b 4.1a 0.6b 0.88b

Capric acid (C10:0) 2.62b 2.2b 1.34b 20.74a

Lauric acid (C12:0) 4.29a 1.32b

Myristic acid (C14:0) 7.98b 4.93c 7.4b 10.82a

Palmitic acid (C16:0) 17.43ab

16.8b

20.67a

4.03c

Palmitoleic acid (C16:1) 4.63a 2.3b 1.48c 0.06d

Stearic acid (C18:0) 10.1b 8.43bc 14.8a 7.24c

Oleic acid (C18:1) 23.27a 11.2c 17.33b 15.1b

Linoleic acid (C18:2) 11.21b 37.62a 12.4b 36.47a

a-linolenic acid (C18:3) 0.19d 1.23c 13.3a 2.73b

Arachidic acid (C20:0) 8.032a 6.43a 6.58a 0.16b

Behenic acid (C22:0) 9.69a 4.76b 4.1c 0.45d

SFA 60.7a 47.65b 55.49a 45.64b

UFA 39.3b 52.35a 44.51b 54.36a

SFA/UFA 1.54a 0.91b 1.27ab 0.84b

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 significantly different (p< 0.05).

Axe 1 (62.01%)

Axe2(25.6

5%)

H. perforatum

H. perfoliatum

H. tomentosum

H. ericoides

-0,6

-0,4

-0,2

0,0

0,2

0,4

0,6

0,8

0,66 0,70 0,74 0,78 0,82 0,86 0,90

Figure 2 Principal component analysis of fourHypericum species on the basis of their fatty acid composition.

4 K. Hosni et al.




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species,Caraipa densifolia, onlya- andc-tocopherols were de-

tected in its hexane extract (da Silveira et al., 2010).

In general, data regarding the tocopherol content in differ-

ent species were conflicting and variable depending on species,origin, plant part, plant physiology and environmental factors

(Bruni et al., 2004; Syman ska 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 Cus-

cuta epithymum and Cuscuta japonica (Syman ska and Kruk,

2008). In Brassica napus and Brassica juncea, the tocopherol

content was found to be deeply influenced 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 radicalsand 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. ericoidesmight 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 antioxi-

dant 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 infragen-

eric classification of the genus Hypericum.

In summary, the present contribution provided a new

insight into the chemistry of H. perforatum, H. tomentosum,

H. ericoides

H. perfoliatum

H. tomentosum

H. perforatum

20 30 40 50 60 70 80 90

Figure 3 Dendrogram of fourHypericum 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).

Fatty acid composition and tocopherol content in four Tunisian Hypericum species 5




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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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tomentosum Hypericum perfoliatum and Hypericum ericoides Ssp Roberti Arabian Journal of Chemistry (2013) http://dx doi org/10 1016/j arabjc 2013 10 019
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