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Biological properties and resistance reversal effect of Helichrysum italicum (Roth) G. Don


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Helichrysum italicum, which belongs to the family Asteraceae, is an evergreen plant native to the Mediterranean area. Since older times, extracts and essential oils (EOs) from the aerial parts (leaves, flowering tops) of the plant are used in traditional medicine for herbal remedies. They are known to possess several biological properties, including antimicrobial, anti-inflammatory, antioxidant and anti-viral activities, as well as preventive effects against insects. The chemical variability exhibited by H. italicum extracts and EOs could explain all these health promoting activities. This review summaries the present state of knowledge on chemical constituents of H. italicum and its biological properties.
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Biological properties and resistance reversal effect of Helichrysum
italicum (Roth) G. Don
E. Guinoiseau1, V. Lorenzi1,*, A. Luciani1, A. Muselli2, J. Costa2, J. Casanova3 and L. Berti1
Université de Corse, UMR CNRS 6134, Laboratoire Biochimie et Biologie Moléculaire du Végétal, Campus Grimaldi,
BP 52, 20250 Corte, France
Université de Corse, UMR CNRS 6134, Laboratoire Chimie des Produits Naturels, Campus Grimaldi, BP 52, 20250
Corte, France
Université de Corse, UMR CNRS 6134, Laboratoire de Chimie et Biomasse, Route des Sanguinaires, 20000 Ajaccio,
*E-mail address of corresponding author:
Helichrysum italicum, which belongs to the family Asteraceae, is an evergreen plant native to the Mediterranean area.
Since older times, extracts and essential oils (EOs) from the aerial parts (leaves, flowering tops) of the plant are used in
traditional medicine for herbal remedies. They are known to possess several biological properties, including antimicrobial,
anti-inflammatory, antioxidant and anti-viral activities, as well as preventive effects against insects. The chemical
variability exhibited by H. italicum extracts and EOs could explain all these health promoting activities. This review
summaries the present state of knowledge on chemical constituents of H. italicum and its biological properties.
Keywords Helichrysum italicum sp; biological activities; chemical constituents; essential oils; extracts.
1. Introduction
The genus Helichrysum (Miller) belongs to the Asteraceae family and is a very large genus including approximately
600 species widespread all over the world. Helichrysum species are distributed from the lower-meso-Mediterranean to
the lower-sub-humid bioclimatic environments, growing at a wide range of altitudes from the sea level up to 1700 m,
preferably on sandy or loamy soils [1]. Almost 25 species are native of Mediterranean area and the most widespread
species is Helichrysum italicum (Roth) G. Don (syn. H. augustifolium DC). It is a small aromatic shrub, up to 40-50 cm
high, with yellow flowers growing on dry cliffs and sandy soil (Figure 1).
Fig. 1 photography of the yellow flowering tops of the plant.
H. italicum subsp. italicum and H. italicum subsp. microphyllum (Willd.) Nyman are the most investigated
subspecies [2].
H. italicum has some fairly unusual and very useful properties. In Europe, the plant is used over the years to refresh
the air, repel insects and for medicinal purposes [3]. For instance, dried inflorescences of this plant are used as a moth
antifeedant whereas flowering tops find application in folk medicine for their anti-inflammatory and anti-allergic
properties and in cosmetics for treatment of skin sunburn and erythema [4-5]. Decoctions of flowering tops are also
used for fumigations in the treatment of asthma [6].
Besides its ornamental value, the success of this plant is also due to several activities related to the essential oils
(EOs) produced by the glandular hairs present on their leaves and flower heads. Only the EO extracted from the plants
belonging to H. italicum species is used in aromatherapy practice. Its cicatrizant properties suggest that the EO can be
used to aid skin regeneration and help with wound healing. Voinchet and Giraud-Robert [7] investigated the therapeutic
effects and potential clinical applications of H. italicum EO and a macerated oil of musk rose (Rosa rubiginosa) after
cosmetic and reconstructive surgery. The objectives of reducing inflammation, oedema and bruising were well
Microbial pathogens and strategies for combating them: science, technology and education (A. Méndez-Vilas, Ed.)
achieved. The authors highlighted that neryl acetate, a main component of the EO, contributed to pain relief. -They also
attributed the observed effects to the occurrence of italidiones in H. italicum EO. This class of molecules is also reputed
to have anti-haematomal properties so that H. italicum EO is often called the ‘super arnica of aromatherapy’. That is
why this useful phlebotonic is indicated for couperose skin (red veins), haematoma (even old haematomas), thrombosis
and the prevention of bruises [8]. When H. italicum EO is mixed with some other specific EOs, the mixtures are thought
to be anti-allergenic. So, these aromatherapy prescriptions could be helpful in cases of asthma, hay fever or eczema
(Table 1).
Table 1 H. italicum essential oil in aromatherapy prescriptions
System H. italicum in mixture with
Integumentary (eczema, inflammation, wound
Lavender, Roman chamomile, geranium, yarrow, vetiver,
patchouli, sandalwood, cypress, rose
Can be used neat or diluted (10-50%)
Immune (allergic responses) Rose, sandalwood, German chamomile
Due to its skin regenerative properties, H. italicum EO is known to prevent skin aging. That is why it is widely used
in the formulation of anti-aging creams and cosmetics based on H. italicum EO that are now flooding the market.
The EO of H. italicum is obtained by steam distillation of flowering tops. The flowering tops are cut by hand, in wild
places, and the cut is from mid-June to mid-July, early flowering. The flowering tops are processed after harvesting.
The yield of production is about 0.9 to 1.5: ie a ton of flowering tops produces about 900 g to 1.5 kg of EO. This EO is
increasingly sought after, but unfortunately many sites are endangered (fires, advanced buildings...) and its price
becomes higher due to its rarity.
2. Components of H. Italicum Extracts and Essential Oils
Since the end of the fifties, phytochemicals belonging to different families of compounds have been identified in
solvent extracts of H. italicum and when necessary their structure elucidated. Representative components are listed
- acids: acetic acid, caprilic acid [9], fatty acids [10];
- angeloylated glycerides, constituting an unusual class of lipids named santinols [11];
- phenolic compounds: caffeic, p-coumaric, ferulic and chlorogenic acids [9, 12] as well as phenolics that includes
coumarates, benzofurans, pyrones [11] and 7-hydroxy-5-methoxyphthalide and 12-hydroxytremetone (bitalin A) [12];
- triterpenes: β- sitosterol and ursolic acid [10], α-amyrin, uvaol and ursolic acid lactone [13]
- flavonoids : apigenin, glycosyl-apigenin, luteolin, gnafalin, naringenin, glycosyl-naringenin [4], kaempferol-3-
glucoside and naringenin-glycoside [5], B-ring deoxyflavonoids [14];
- chalcones: glycosyl-chalcone [4] 4,2',4',6'-tetrahydroxychalcone-2'-glucoside [14];
- acetophenone glucosides and a benzo-γ-pyrone glucoside [15];
- arzanol, a prenylated heterodimeric phloroglucinyl α-pyrone and helipyrone, a dimeric pyrone [15,16,17].
Identification of individual components of H. italicum EO has been investigated since a long time. However, our
attention will be focused on papers that report on chemical analyses carried out with modern analytical techniques. H.
italicum EO exhibited various compositions depending of the sub-species, the location of harvest, the physiological
stage of the plant, etc. They are summarized on the table 2.
In short, H. italicum EOs contained numerous monoterpenes and sesquiterpenes usually found in EOs. The structure
of new compounds has been elucidated, various acyclic 1,3-diones [18, 19], italicene and isoitalicene, helifolene and
iso-helifolene, various bisabolane diols [32] eudesm-5-en-11-ol [20].
H. italicum of the Adriatic coast (sub-species not specified) produces EO with α-pinene, α- and γ-curcumene as
major components [33, 34, 35]. EO (subsp italicum) from Tuscany contained mainly α-pinene and neryl acetate [25]
while an oil sample from Southern Italy was dominated by iso-italicene epoxide [26]. Other Italian EOs contained
mainly γ-curcumene, β-selinene and α-selinene [27].
H. italicum EOs from Mediterranean islands exhibited various compositions. For instance, oil from the Greek island
of Amorgos (ssp italicum) was dominated by geraniol [28] while plants from Crete (ssp microphyllum) produced oil
containing mainly sequiterpene hydrocarbons [21]. H. italicum ssp microphyllum from Corsica and Sardinia is rich in
neryl acetate [1, 22, 23] while some samples contained appreciable amounts of eudesm-5-en-11-ol [24]. Some Sardinian
oil samples contained rosifoliol and γ-curcumene as main components [22].
The composition of H. italicum ssp italicum EO from Corsica and Tuscan Archipelago Islands was dominated by
neryl acetate [25, 29, 30]. Correlations between the EO composition and various parameters were shown: texture and
acidity of soils, inorganic composition of plant and soil, vegetative stage of development [37]. Some oil samples from
Microbial pathogens and strategies for combating them: science, technology and education (A. Méndez-Vilas, Ed.)
Tuscan Archipelago Islands contained unusually high amounts of β-diketones [30]. Oils from Elba Island (Italy) were
characterized by a high content of oxygenated monoterpenes while monoterpene hydrocarbons and sesquiterpene
hydrocarbons reached appreciable in some samples [31, 35, 36].
Table 2 Components of H. italicum essential oils.
origin Major components Other components Ref
Helichrysum italicum ssp microphyllum
-selinene (17.1/16.7%),
γ-curcumene (13.7/6.6%)
α-selinene (3.8/5.4%),
Italicene (5.1/1.4%). [21]
neryl acetate (28.9%),
neryl propionate (11.4%)
-curcumene (11.4%),
nerol (10.7%) [22]
Sardinia rosifoliol (20.2%),
γ-curcumene (18.2%) linalool (14.9%) [22]
Sardinia neryl acetate (21.4/16.9%),
dihydro-occidentalol (12.2/7.6%)
nerol (7.3/5.4%),
neryl propionate (5.6/4.6%) [23]
Sardinia neryl acetate (17.6-56.1%), eudesmen-
5-en-11-ol (3.7-23.5%) nerol (3.7-14.4%) [24]
Corsica neryl acetate (55.7/41.5%) neryl propionate (12.7/5.6%) [1]
Helichrysum italicum ssp italicum
(Italy) α-pinene (4.1-53.5%),
neryl acetate (0.3-22.0%)
-selinene (7.2-12.5%),
β-caryophyllene (5.7-11.0%) [25]
(Italy) iso-italicene epoxide (16.8%) hexadecene (9.8%),
β-costol (7.5%) [26]
-curcumene (0-41.0%),
β-selinene (0-38.0%),
α-selinene (0-26.5%),
γ-eudesmol (0-20.4%)
nerol (0.4-18.8%),
(E)-β-caryophyllene (0-18.6%),
neryl acetate (0.4-15.1%)
(Greece) geraniol (35.6%) geranyl acetate (14.7 %),
(E)-nerolidol (11.9%). [28]
neryl acetate (15.8-42.5%)
γ-curcumene (0.8-13.6%)
limonene (1.9-7.3%),
neryl propionate (1.5-6.7%),
neryl acetate (32.0%),
ar-curcumene (6.4%)
4,6,9-trimethyldec-8-en-3,5-dione (11.0%) [27]
neryl acetate (14.9–44.5%),
neryl propionate (3.0–16.4%)
γ-curcumene (5.4-13.7%),
nerol (1.4-7.6%),
eudesm-5-en-11-ol (1.1-7.6%)
Elba Island
neryl acetate (5.6-45.9%),
α-pinene (0.8 –32.9%),
1,8-cineole (up to 18.2%)
eudesm-5-en-11-ol (1.8-17.2%),
nerol (up to 12.8%),
limonene (up to 12.9%)
Elba Island
neryl acetate (11.4%),
γ−eudesmol (8.5%)
caryophyllene (7.8%),
γ-curcumene (7.7%) [27]
Sub-species not specified
Ex-Yugoslavia α-pinene (21.7%),
γ-curcumene (10.4%)
neryl acetate (6.1%),
β-selinene (6.0%), [32]
Croatian Adriatic
coast α-pinene (0.1-29.9%),
α-curcumene (1.0-28.6%),
γ-curcumene (0-22.0%)
α-cedrene (0.2-16.7%),
neryl acetate (4.1-13.5%),
spathulenol (up to 13.2%)
Croatia α-pinene (10.2%),
neryl acetate (11.5%) α-cedrene (9.6%) [34]
Elba island
neryl acetate (25.3% ± 2.9),
α-pinene (14.5% ± 2.1)
limonene (12.3% ± 2.8),
γ-curcumene (8.7% ± 1.4).
It is likely that the variability of components present in H. italicum extracts and EOs has a strong influence on their
biological activity.
Microbial pathogens and strategies for combating them: science, technology and education (A. Méndez-Vilas, Ed.)
3. Biological Activities of H. Italicum Essential Oil and Extracts
Metabolites isolated from H. italicum, and especially its volatile fraction, have been found to display many biological
properties, such as antimicrobial, anti-inflammatory, anti-viral antioxidant activities. The insecticidal effects of the EO
have also been described. Until now, no reports on the possible phytotoxic activity of the secondary metabolites of the
plant have been reported.
3.1. Antimicrobial activity
Of all the properties claimed for H. italicum, the antibacterial effect of extracts, EOs and their constituents has received
a main attention. Several data report the effectiveness of H. italicum extracts against Gram positive bacteria. Nostro and
coworkers [38] demonstrated that diethyl ether extracts of H. italicum has inhibitory effect on Staphylococcus aureus
strains reducing both their growth and some of the enzymes considered as virulence factors. With minimum inhibitory
concentration (MIC) values ranging from 125 to 500 mg/L, this extract is so effective on methicillin sensitive S. aureus
strains (MSSA) as on methicillin resistant S. aureus isolates (MRSA). It also inhibits the enzymatic activity of these
strains with a more pronounced effect on the coagulase than on the DNAse, lipase and thermonuclease. Other works
have been done to evaluate the effects of H. italicum extracts on different bacterial virulence factors, such as toxins
production or cell aggregation. It has been shown that low concentrations of H. italicum diethyl ether extract reduce the
enterotoxins B and C production by S. aureus [39]. In the same way, it was highlighted that subminimum inhibitory
concentrations (7.81 to 31.25 µg/mL) of H. italicum ethanolic extracts inhibit in vitro adherence and cellular
aggregation of the cariogenic Streptococcus mutans bacterium [40] extracts seem to be able to interfere with bacterial
virulence and thereby show considerable interest to control undesirable and pathogenic bacteria.
Two main studies carried out in our laboratories report the antibacterial properties of H. italicum EO and its related
constituents. Rossi and coworkers [41] demonstrated that the EO, obtained from endemic plants of Corsica, is more
effective on the Gram positive bacterium S. aureus than on the Gram negative strains Escherichia coli, Enterobacter
aerogenes, Pseudomonas aeruginosa. It is commonly known that Gram negative bacteria are less susceptible to EOs
than Gram positive bacteria, and this is directly connected to the bacterial cell wall structure. In Gram negative bacteria,
the cell wall is a complex envelope constituted by the cytoplasmic membrane, the periplasm and the outer membrane.
The latter one restricts diffusion of hydrophobic molecules through its lipopolysaccharide covering, thus acting as a
strong permeability barrier [42].
So, these bacteria are particularly difficult to eradicate, especially as they have also developed effective mechanisms
of resistance such as efflux pumps overexpression. Efflux pumps play a key role in the bacterial resistance to antibiotics
and contribute to the spread of multidrug resistant pathogens (MDR phenotype). These protein carriers are able to expel
from the cells structurally diverse drugs, including antibiotics, rendering them therapeutically ineffective. By blocking
this mechanism with efflux pump inhibitors (EPIs), it is possible to restore the effectiveness of antibiotics. Lorenzi and
coworkers [43] have shown that H. italicum EO significantly reduces the MDR resistance of several Gram negative
strains of Enterobacter aerogenes, Escherichia coli, Pseudomonas aeruginosa, and Acinetobacter baumannii. The
highest activity was obtained for the MDR clinical isolate of E. aerogenes EA27, which overexpresses the AcrAB-TolC
efflux pump and are thus resistant against the last resort antibiotic used in intensive care units, i.e chloramphenicol. At a
concentration of 2.5%, H. italicum EO reduces eightfold the MIC (from 1,024 to 128 mg/L) of chloramphenicol for
EA27 strain. Moreover, H. italicum EO restores the chloramphenicol susceptibility of EA27 to a level that is close to
that of the control phenylalanine arginine ß-naphthylamide (PAßN), i.e MIC of 64 mg/mL. It is clear from these data
that H. italicum EO contains one or more compounds that have EPI activity. Therefore, a chromatographic fractionation
assay was made to isolate that or these agents. Then, the EPI’s activity of the main fractions recovered was evaluated
against the derivative mutant of E. aerogenes EA27, i.e EAEP289 strain. It has been shown that combinations of the
two most active fractions (italidiones, F2 and alcohols, F3) can reduce chloramphenicol resistance from an initial MIC
of 1,024 to 128 mg/L. Reduction of resistance was also achieved when either the F2 or F3 fraction was combined with
PAßN. Combination of the latter produced the strongest effect comparable to a complete reversal of chloramphenicol
resistance (MIC of less than 0.25 mg/L). Due to the high activity of the F3 fraction, several chloramphenicol
susceptibility assays were performed with commercially available constituents of this fraction. Among the compounds
tested, geraniol produces significant restoration of susceptibility of the MDR strain EAEP289 to chloramphenicol by as
much as 16-fold. When combined with PAßN, it rendered the bacterium fully susceptible to chloramphenicol, i.e., it
completely reversed initial resistance. Geraniol (3,7-dimethylocta-2(E),6-dien-1-ol) is an acyclic monoterpenic
compound which presents a stereochemistry (E). Its hydrocarbon backbone is constituted of two isoprene units and
functionalized with an hydroxyl group (Figure 2).
Microbial pathogens and strategies for combating them: science, technology and education (A. Méndez-Vilas, Ed.)
Fig. 2 Chemical structure of geraniol
Geraniol is soluble in dimethylsulfoxide (DMSO) and methanol. These solvents complicate experiments and cause reproducibility
difficulties, related to the lack of homogeneity of the solutions. So, complementary tests were carried out with several derivatives
compounds of geraniol in order to improve its solubility while retaining its efficiency. It was found that hydrochloride geranyl amine
salt (Figure 3), a water soluble compound, is as effective as geraniol since it reduces the MIC of chloramphenicol to the same extent
as PAßN.
Fig. 3 Chemical structure of hydrochloride geranyl amine
It was thus concluded that the replacement of the primary alcohol group of geraniol by an amino-hydrochloride
function has improved the solubility of the molecule.
If the antibacterial properties of H. italicum are widely described in the literature, less is known about its effect
against yeasts and fungi. However, it has been reported that the EO of H. italicum from Croatia and, more precisely, its
oxygenated fraction are active against Candida albicans. The terpenoid components of this fraction inhibit the growth
of the yeast by producing an inhibition zone of 10 mm and a MIC of 5 µg/mL [37].
3.2. Anti-inflammatory activity
H. italicum is known to contain ketones that contribute to reduce the inflammation process. Arzanol, a prenylated
heterodimeric phloroglucinyl α-pyrone (Figure 4), was identified as the major anti-inflammatory component [44].
Fig. 4 Chemical structure of arzanol
Inflammation is a complex biological response that involves several enzymatic reactions. The prostanoids and
leukotrienes (LTs) formed from arachidonic acid via the cyclooxygenase (COX)-1/2 and 5-lipoxygenase (5-LO)
pathway, respectively mediate inflammation, chronic tissue modeling, cancer, asthma and autoimmune disorders. The
non-steroidal anti-inflammatory drugs administered for therapeutic purposes act by blocking formation of all the
prostanoids but their clinical use is hampered by severe side effects including gastrointestinal injuries, renal irritations
and cardiovascular risks [19]. It has been shown that arzanol potently inhibits the nuclear transcription factor NFκβ
activation in T cells as well as the release of pro-inflammatory mediators such as interleukin (IL)-1β, Il-6, Il-8, tumor
necrosis factor (TNF)α and in lipopolysaccharide stimulated monocytes [18]. More recently, Bauer and coworkers [44]
have investigated the effects of arzanol on the biosynthesis of prostanoids and LTs and have evaluted its anti-
inflammatory efficacy in vitro and in vivo. They have shown that this molecule potently inhibits the inducible
microsomal prostaglandin (PG)E2 synthase (EC, COX-1(EC 1.14.99) and 5-LO (EC in vitro with
IC50 values ranging from 0.4 to 9 µM. In vivo, arzaanol suppresses the inflammatory response of the carrageenan-
induced pleurisy in rats (3.6 mg/kg, intraperitoneal) with significantly reduced levels of PGE2 (2.27 ng/rat) in the
pleural exudates. Taken together, all these findings show that arzanol act as potent dual-inhibitor of pro-inflammatory
mediators and inflammatory enzymes, providing a mechanistic rationale for the well-known anti-inflammatory activity
of H. italicum. Moreover, this compound displays a large spectrum of properties including anti-oxidant and anti-viral
activities (see sections 3.3 and 3.4).
Microbial pathogens and strategies for combating them: science, technology and education (A. Méndez-Vilas, Ed.)
3.3. Anti-viral activity
A few studies of the anti-viral properties of H. italicum extracts and their constituents have been published. It has been
pointed out that a diethyl ether extract, obtained from the flowering tops of H. italicum, possesses significant activity
against the herpes simplex virus type 1 (HSV-1) at concentrations ranging from 100 to 400 µg/mL. Moreover, this
extract has no genotoxic effect since it does not provoke DNA damages at concentrations up to 200 µg per disk [45]. In
a more recent study, Appendino and coworkers [18] have shown that arzanol inhibits the HIV-1 replication in T cells.
This anti-HIV activity was further investigate by infecting Jurkat cells with the pNL4-3 HIV-1 clone pseudotyped with
the VSV envelope, which can supports a robust HIV-1 replication. Upon integration into host chromosomes, this
recombinant virus expresses the firefly luciferase gene, and therefore, luciferase activity in infected cells correlates with
the rate of viral replication. A pretreatment of Jurkat cells 30 min prior to infection with increasing doses of arzanol
resulted in a dose-dependent inhibition of luciferase activity.
3.4. Antioxidant activity
Some flavonoids constituents of H. italicum exhibit antioxidant activities, which are closely related to their anti-
inflammatory effects. In a study investigated by Sala and coworkers [46], whose purpose was to assess the antioxidant
properties of three flavonoids (gnaphaliin, pinocembrin and tiliroside) isolated from the aerial parts of H. italicum, the
tiliroside was identified as the most active compound. More precisely, the scavenger properties of these flavonoids were
tested first in vitro and then in vivo by means of different models of inflammation. Tiliroside shows significant
inhibition of enzymatic and non-enzymatic lipid peroxidation (IC50 values: 12.6 and 28 µM respectively). It has
scavenger properties (IC50 = 21.3 µM) and very potent antioxidant activity in the reduction of stable radical 1,1-
diphenyl-2-pycryl-hydrazyl (DPPH) test (IC50 = 6 µM). In vivo, it significantly reduces the mouse paw oedema induced
by phospholipase A2 (ID50 = 35.6 mg/kg) and the mouse ear inflammation induced by TPA (ID50 =
0.357 mg/ear).
Recently, the protective effect in lipid peroxidation of azarnol was highlighted. Its antioxidant activity was assessed
against the oxidative modification of lipid components induced by Cu2+ ions in human low density lipoprotein (LDL)
and by tert-butyl hydroperoxide (TBH) in cell membranes. In vitro, LDL pretreatment with azarnol significantly
preserves lipoproteins from oxidative damage at 2 h of oxidation and exerts a remarkable reduction of polyunsaturated
fatty acids and cholesterol levels. At non-cytotoxic concentrations, it also protects VERO cells against TBH induced
oxidative stress [47]. So, azarnol can be qualified as a potent natural antioxidant with a protective effect against lipid
oxidation in biological systems.
3.5. Anti-larvicidal activity
Only a few reports describe the effects of H. italicum against insects. It has been recently shown that the EO isolated
from the leaves of H. italicum, growing on Elba Island, induces larval mortality of the Culicidae mosquito Aedes
albopictus at 300 ppm with mortality rates ranging from 98.3% to 100% [38]. Use of botanical derivatives in mosquito
control, instead of synthetic insecticides, is thought to be harmless to humans and other nontarget organisms. So, further
investigations are needed to identify natural mosquitocidal compounds, which could be utilized in commercial
4. Conclusion
In conclusion, this survey of the literature showed that H. italicum sp exhibits interesting biological activities that seem
to be due to the large diversity of its chemical contents. These remarkable properties explain the enthusiasm that exists
around H. italicum sp essential oil and extracts. However, care should be taken to the species or species derivatives,
maturation state, part of the plant used, and to the extraction procedures that are undertaken to produce bio-active
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Microbial pathogens and strategies for combating them: science, technology and education (A. Méndez-Vilas, Ed.)
... G. Don is a perennial aromatic shrub that belongs to the Helichrysum genus (family Asteraceae), which includes approximately 600 species widespread all over the world. It is the most widespread of the 25 species from the Helichrysum genus, native to the Mediterranean area (Guinoiseau et al., 2013). Due to the fact that it is a xerophyte plant, H. italicum can grow in dry, sandy, and stony areas at a wide range of altitudes, up to 2200 m (Viegas et al, 2013). ...
... Yellow flowers that blossom between May and June give the H. italicum its ornamental value. Besides ornamental, it also has medicinal value due to its anti-inflammatory, anti-allergic, antiviral, anti-microbial, insecticidal and repellent properties (Dimitrova, Nacheva, 2018;Guinoiseau et al., 2013;Ninčević et al., 2019). Its flowers and leaves are traditionally used in the treatment of a variety of health disorders such as allergies, colds, coughs, skin, liver, and gallbladder disorders, inflammation, infections, and sleeplessness (Viegas et al, 2013). ...
Helichrysum italicum (Roth.) G. Don is an aromatic perennial shrub widespread across the Mediterranean Basin. Plants from this species show a high degree of morphological variability. This research examines morphological variation inside the H. italicum population growing in natural conditions and the correlation between observed morphological traits. Morphometric characteristics of shrub and synflorescence were measured on H. italicum plants from the wild population on the northwestern coast of Istria, at eight locations a short distance apart. Results showed significant variation in the plants’ height and diameter. Pearson’s correlation analysis showed a strong positive correlation between the diameter and height of the shrubs. Hierarchical cluster analysis (HCA) indicates that the observed plants are divided into two clades, based on characteristics measured. Principal component analysis (PCA) showed clear separation of the plants into two groups. Observed characteristics accounted for nearly 76% of the total variance.
... The widespread usage of immortelle oil in folk medicine has encouraged extensive studies of its bioactive potential in the last 20-30 years. It has been shown that the oil has antimicrobial, antioxidant, antiinflammatory, insecticidal, phytotoxic, cytotoxic, and antigenotoxic properties (Antunes Viegas et al., 2014;Guinoiseau et al., 2013;Maksimović et al., 2017). The antimicrobial activity of immortelle oil has been most profoundly studied and it was found that the tested immortelle oils could exhibit a wide range of activities, e.g. from being completely inactive to very prominent activity (Antunes Viegas et al., 2014). ...
... On the other hand, only three papers are dealing with the antiinflammatory properties of immortelle oil available in the literature (Aćimović et al., 2021;Djihane and Mihoub, 2016;Voinchet and Giraud Robert, 2007). This is somewhat surprising bearing in mind that one of the most documented applications of this oil in folk medicine is for wound healing and skin regeneration (Guinoiseau et al., 2013). This ethnopharmacological use of immortelle oil has been partially confirmed by Voinchet and Giraud Robert (2007) in their clinical trial during which they developed an effective protocol, based on the local application of immortelle oil, which reduced local tissue inflammation and accelerated the disappearance of edema, bruising and hematoma in patients after plastic and reconstructive chest surgery. ...
Immortelle (Helichrysum italicum, Asteraceae) essential oil has been widely used in alternative medicine to accelerate wound healing, as well as in cosmetic products to stimulate skin regeneration and to reduce the appearance of wrinkles. It is also considered a natural and safe culinary spice that could also be applied in the food industry as a preservative in the future. The therapeutic efficacy of this oil changes with the natural variability of the composition. Herein we tested and mutually compared the antimicrobial and anti-inflammatory activities of four commercial immortelle oils differing in the relative amounts of marker compounds, i.e. neryl esters, α-pinene, γ- and ar-curcumenes, and β-diketones. The anti-inflammatory effect of selected chromatographic fractions, enriched in the aforementioned constituents, was evaluated by studying toxicity toward rat peritoneal macrophages, their nitric oxide production, myeloperoxidase, and arginase activities. Subsequently, the compositional and activity data were subjected to a multivariate statistical treatment to reveal the possible correlation(s) between the percentage of essential-oil constituents and the observed activities. The obtained results imply that immortelle oil efficiency as an antimicrobial and/or anti-inflammatory agent is most plausibly a result of a synergistic action between its constituents, and/or, rather unexpectedly, the presence of some minor constituents.
... The genus Helichrysum Mill. belongs to the Asteraceae family and includes over six hundred species and subspecies globally widespread [1,2]. In the Mediterranean area, there are currently about 25 species [3] some of which have very similar genetic traits despite the fact that they may show different morphological characteristics. ...
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Two wild populations of Helichrysum (Mill.) located at Elba Island (Tuscan Archipelago, Central Italy) were morphologically and phytochemically analyzed to taxonomically identify H. litoreum (population A) and H. italicum subsp. italicum (population B). Micromorphological and histochemical analyses were performed on the indumentum using Scanning Electron Microscope (SEM) and Light Microscope (LM). Morphometric analyses on vegetative and reproductive traits were also conducted. Finally, a chemotaxonomic analysis was carried out on the terpene profile of flowers, leaves and bark tissues using gas chromatography (GC-MS). Results suggested that morphological discriminant traits were mainly in leaves and cypselae glandular tissues. Phytochemical analysis indicated that a high relative content of α-pinene and β-caryophyllene were the main markers for population A, while a high relative content of neryl-acetate, α-curcumene, isoitalicene and italicene, especially in the terpene profile of bark tissue, were the main compounds for discriminating population B. The analysis suggested that the wild population A could be mainly ascribed to H. litoreum, whilst population B is defined by H. italicum.
... It is worth noting that many world-leading cosmetic companies have developed product lines with the H. italicum essential oil, due to its anti-aging effect, which is most likely related to antioxidant properties. So far, the mixture of H. italicum essential oil and macerated oil of musk rose was tested on the skin after reconstructive surgery [7,22,56]. According to Andjić et al. [57], H. italicum essential oil in formulations such as gel and ointment exhibited a significant wound repairing effect in the incision wound model. ...
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Helichrysum italicum (Roth) G. Don. is one of the most important cosmetic and medicinal plants originating from the Mediterranean region of Europe. The aim of this study was to assess the chemical profile as well as antioxidant and antibacterial potential of the species cultivated in the temperate climate of Central Europe. The analyses were carried out using herbs and inflorescences. The content of essential oil ranged from 0.25 g × 100 g-1 in the herb to 0.31 g × 100 g-1 in the inflorescences. Neryl acetate, accompanied by α-pinene in the herb (10.42%), and nerol in inflorescences (15.73%) were the dominants here. Rutoside, as well as rosmarinic, chlorogenic, neochlorogenic, isochlorogenic b and cichoric acids, were detected in both raw materials using HPLC-DAD. Within this group, cichoric acid was the dominant (2647.90 mg × 100 g-1 in the herb, 1381.06 mg × 100 g-1 in the inflorescences). The herb appeared to be more abundant in phenolics in comparison with the inflorescences. When given antioxidant activity (determined using DPPH and ABTS assays), both methanolic extract and essential oil obtained from the herb indicated higher potential than those originating from the inflorescences (74.72, 61.38 and 63.81, 58.59% in the case of DPPH, respectively). In turn, regarding antimicrobial activity, the essential oil from inflorescences was distinguished by stronger bacteriostatic power than the herb essential oil. Gram-positive bacteria were more sensitive to both essential oils in comparison with Gram-negative ones, with S. aureus ATCC 25923 as the most susceptible (MIC 1; MBC 16 mg × mL-1) among tested strains.
... Triterpenes and sterols are bioactive substances that have been shown to possess anti-inflammatory, antimicrobial, antiallergic, antiviral, hepatoprotective, cytotoxic and other important biological activities (Holanda et al. 2008;Sultana and Ata 2008;Vázquez et al. 2012). The presence of triterpenes in H. italicum has already been reported in the literature (Mezzetti et al. 1970;Nostro et al. 2000;Guinoiseau et al. 2013). The occurrence of triterpene acids in significant amounts in the extracts from by-products after steam and water distillation was found in the present study. ...
... Triterpenes and sterols are bioactive substances that have been shown to possess anti-inflammatory, antimicrobial, antiallergic, antiviral, hepatoprotective, cytotoxic and other important biological activities (Holanda et al. 2008;Sultana and Ata 2008;Vázquez et al. 2012). The presence of triterpenes in H. italicum has already been reported in the literature (Mezzetti et al. 1970;Nostro et al. 2000;Guinoiseau et al. 2013). The occurrence of triterpene acids in significant amounts in the extracts from by-products after steam and water distillation was found in the present study. ...
Distillation wastewater, by-products from steam and water distillation as well as raw material used as control of flower heads of Helichrysum italicum were comparative analyzed for content of the biologically active compounds by GC/MS. Acetone exudates, methanol extracts and ethyl acetate fractions obtained after alkaline hydrolyze of the studied materials were received. The three types of extraction products as well as the distillation wastewater were examined for free radical scavenging activity by DPPH assay. Phenol, fatty- and organic acids, sterols, triterpenes, sugars and sugar alcohols were identified. Succinic acid and myo-inositol were identified as main components of distillation wastewater. Hydroxycinnamic acid, caffeic acid and 4(p)-hydroxybenzoic acid were dominant compounds of the ethyl acetate fractions. Triterpenes and fatty acids, sterols and flavonoids are among the main biologically active substances in the methanolic extracts and acetone exudates. The ethyl acetate fractions were found to possess the highest free radical scavenging activity (IC50 < 50 µg/mL). Significant differences in the activity between wastes and raw materials were not found. The results showed that the waste products after distillation of H. italicum contain important biologically active substances and the extracts with high antioxidant activity can be obtained from them.
... The activity of arzanol, a prenylated phloroglucinol a-pyrone compound from H. italicum has been identified as an inhibitor of PGE 2 production. The presence of these types of compounds has been identified in H. odoratissimum and could, therefore, be responsible for the observed COX-II activity (Lourens et al., 2008;Guinoiseau et al., 2013). The presence of benzothiazole was identified as one of the major constituents in the extract using GC-MS. ...
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The Gram-positive bacterium Cutibacterium acnes (previously Propionibacterium acnes), plays an important role in the pathogenesis and progression of the dermatological skin disorder acne vulgaris. The methanolic extract of Helichrysum odoratissimum (L.) Sweet (HO-MeOH) was investigated for its ability to target bacterial growth and pathogenic virulence factors associated with acne progression. The gas chromatography–mass spectrometry (GC-MS) analysis of HO-MeOH identified α-humulene (3.94%), α-curcumene (3.74%), and caryophyllene (8.12%) as major constituents, which correlated with previous reports of other Helichrysum species. The HO-MeOH extract exhibited potent antimicrobial activity against C. acnes (ATCC 6919) with a minimum inhibitory concentration (MIC) of 7.81 µg/ml. It enhanced the antimicrobial activity of benzoyl peroxide (BPO). The extract showed high specificity against C. acnes cell aggregation at sub-inhibitory concentrations, preventing biofilm formation. Mature C. acnes biofilms were disrupted at a sub-inhibitory concentration of 3.91 µg/ml. At 100 µg/ml, HO-MeOH reduced interleukin-1α (IL-1α) cytokine levels in C. acnes-induced human keratinocytes (HaCaT) by 11.08%, highlighting its potential as a comedolytic agent for the treatment of comedonal acne. The extract exhibited a 50% inhibitory concentration (IC50) of 157.50 µg/ml against lipase enzyme activity, an enzyme responsible for sebum degradation, ultimately causing inflammation. The extract’s anti-inflammatory activity was tested against various targets associated with inflammatory activation by the bacterium. The extract inhibited pro-inflammatory cytokine levels of IL-8 by 48.31% when compared to C. acnes-induced HaCaT cells at 7.81 µg/ml. It exhibited cyclooxygenase-II (COX-II) enzyme inhibition with an IC50 of 22.87 µg/ml. Intracellular nitric oxide (NO) was inhibited by 40.39% at 7.81 µg/ml when compared with NO production in lipopolysaccharide (LPS)-induced RAW264.7 cells. The intracellular NO inhibition was potentially due to the 2.14 fold reduction of inducible nitric oxide synthase (iNOS) gene expression. The HO-MeOH extract exhibited an IC50 of 145.45 µg/ml against virulent hyaluronidase enzyme activity, which is responsible for hyaluronan degradation and scar formation. This study provides scientific validation for the traditional use of H. odoratissimum as an ointment for pimples, not only due to its ability to control C. acnes proliferation but also due to its inhibitory activity on various targets associated with bacterial virulence leading to acne progression.
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Immortelle (Helichrysum italicum (Roth) G. Don; Asteraceae) is a perennial plant species native to the Mediterranean region, known for many properties with wide application mainly in perfume and cosmetic industry. A total of 18 wild H. italicum populations systematically sampled along the eastern Adriatic environmental gradient were studied using AFLP markers to determine genetic diversity and structure and to identify loci potentially responsible for adaptive divergence. Results showed higher levels of intrapopulation diversity than interpopulation diversity. Genetic differentiation among populations was significant but low, indicating extensive gene flow between populations. Bayesian analysis of population structure revealed the existence of two genetic clusters. Combining the results of FST - outlier analysis (Mcheza and BayeScan) and genome-environment association analysis (Samβada, LFMM) four AFLP loci strongly associated with the bioclimatic variables Bio03 Isothermality, Bio08 Mean temperature of the wettest quarter, Bio15 Precipitation seasonality, and Bio17 Precipitation of driest quarter were found to be the main variables driving potential adaptive genetic variation in H. italicum along the eastern Adriatic environmental gradient. Redundancy analysis revealed that the partitioning of genetic variation was mainly associated with the adaptation to temperature oscillations. The results of the research may contribute to a clearer understanding of the importance of local adaptations for the genetic differentiation of Mediterranean plants and allow the planning of appropriate conservation strategies. However, considering that the identified outlier loci may be linked to genes under selection rather than being the target of natural selection, future studies must aim at their additional analysis.
Helichrysum italicum (Roth) G. Don fil., Asteraceae, possesses numerous secondary plant metabolites with a wide range of biological activities. Yet, data on the potential of supercritical fluid extraction (SFE) in their isolation are scarce. This study provides analyses of the chemical profiles of extracts obtained by SFE with or without ethanol as a cosolvent using GC-FID, GC-MS, HPLC, and UHPLC-MS techniques. Among the compounds with proven biological activity identified, the presence of arzanol was confirmed. In the next step, the integrated process of supercritical fluid extraction and impregnation was applied to deliver active compounds to cotton gauze and polypropylene fabric for possible topical applications. The analytical procedures results showed a considerable affinity of both textile materials for incorporating active components present in the H. italicum. The study indicated the high-pressure techniques applied as very efficient in the isolation of bioactive components from H. italicum and their adsorption on selected carriers.
Immortelle (Helichrysum italicum (Roth) G. Don), also known as curry plant, is a herbaceous perennial plant with documented biological properties that contribute to its attractiveness and use in the cosmetic, pharmaceutical, and food industry. Availability of DNA markers can significantly improve the knowledge of complex genetics and biochemistry of this aromatic plant. To improve in-depth genetic studies, high-throughput sequencing of a genomic DNA has been performed and a set of 24 SSR markers was developed. In total, 17,025,076 high quality reads were assembled in contigs with the cumulative length of 258.6 Mbp. Genome-wide microsatellite sequences were identified in 8.19% (36,882) contigs, among which dinucleotide (71.2%) and trinucleotide (24.4%) repeats were the most abundant. Twenty-four finally selected microsatellite loci (including di- and tri-nucleotides) which exhibited polymorphism with unambiguous and reproducible amplification products, were used for detailed genetic diversity analysis on a set of 28 H. italicum samples. The Unweighted Pair Group Method with Arithmetic Mean (UPGMA) method based on the Jaccard index differentiated 27 genotypes into two main clusters according to their geographical origin (Northern and Southern Adriatic region), whereas the commercially available plant did not cluster with other H. italicum individuals and morphological evaluation confirmed that it belongs to Helichrysum angustifolium (Lam.) DC. The great diversity of H. italicum samples from the Adriatic observed by new microsatellites will serve for selection of most promising genotypes for propagation and their implementation in agricultural production. The first set of microsatellites developed in the present study provides a valuable resource of DNA markers for further breeding programs, germplasm characterization, and cross-species transferability studies.
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Immortelle was collected at nine different locations along the Adriatic coast. One location was chosen to study variations in oil yields and composition in different vegetative stages (six samples). The oil yield of the samples collected from different locations ranged from 0.08% to 0.32%, and for samples in different stages of development it ranged from 0.06% to 0.35%. The composition of the oils was analyzed by GC and GC/MS.
Helichrysum italicum ssp. microphyllum extract was isolated by supercritical CO2 extraction with a fractional separation technique. Operative conditions were: extractor, 90 bar and 50°C for 240 min; first separator, 90 bar and -10°C; second separator, 15 bar and 15°C. GC/MS analysis of the leaf volatile concentrate revealed that it mainly consisted of neryl acetate (26.0%), nerol (9.1%), neryl propionate (6.7%), γ-curcumene (10.8%) and cis-dihydro-occidentalol (4.3%). The differences observed between the composition of the SFE volatile concentrate and the hydrodistilled oil were minor.
Three new acetophenone glucosides (4-6), three known aglycons (1-3), and a benzo-gamma -pyrone glucoside (7) were isolated from the CH2Cl2, EtOAc, and BuOH extracts from the aerial parts of Helichrysum italicum. All the compounds tested showed antiinflammatory activity in a 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced mouse ear edema test, and the ID50 value of compound 2, the most active compound, was determined.
The components of essential oils of Helichrysum italicum subsp. italicum growing in Corsica were investigated by the combination of GC and GC–MS. In a first part, nine commercial and laboratories-prepared samples were analysed and Corsican oils were found to contain neryl acetate as predominant compound, with amounts from 15.8% (from plants in stage of early shoots) to 42.5% (in full flowering period). In a second part, we sampled Helichrysum italicum subsp. italicum from three locations over the growth cycle of the plant. Significant variations were observed in the concentration of the main constituents, pointing out a chemical composition of oils produced from plants in early shoots (higher amounts of ketones and β-diketones) different from that obtained from samples harvested in the stages of flowering (higher contents of neryl acetate). Copyright © 2001 John Wiley & Sons, Ltd.