Chapter 74
Rockroses (Cistus sp.) Oils
Enrique Barrajón-Catalán1, Laura Tomás-Menor1, Aranzazu Morales-Soto2, Nuria Martí BruÅ„á1,
Domingo Saura López1, Antonio Segura-Carretero2, Vicente Micol1
1
Universidad Miguel Hernández, Instituto de Biología Molecular y Celular (IBMC), Avenida de la Universidad s/n, Alicante, Spain; 2Research and
Development of Functional Food Centre (CIDAF), Health Science Technological Park, Avda. del Conocimiento s/n, Granada, Spain
INTRODUCTION
Cistus plants, also known as rockroses, are a Mediterranean native genus of shrubs included in the Cistaceae family,
which is formed by a total of eight genera. The Cistus genus (25 different species according NCBI Taxomony Browser;
http://www.ncbi.nlm.nih.gov/taxonomy) is the most numerous, common, and well known, but Helianthemum and Hali-
mium genera are also important for their number of species, relevance, and phytochemical composition. Cistus species
are disseminated over different areas of the Mediterranean area Portugal, Spain, Canary Islands, north-west Africa, Italy,
Greece, and Turkey (Barrajon-Catalan et al., 2011), following a particular distribution pattern for each species, depend-
ing on climatological and soil conditions. Some of the Cistus species are endemic and other species are widespread in the
Mediterranean area. Some Cistus plants such as Cistus ladanifer adapt easily to wildfires, as their seeds resist them and raise
rapidly forest biomass increasing the risk of wildfires in some areas of Spain (Barrajon-Catalan et al., 2011).
Most Cistus species are very fragrant and sweet-smelling, and are much appreciated in the perfume industry and for
ornamental purposes. Volatile compounds are found not only in essential oils, but also in aqueous and hydroalcoholic
extracts (Greche et al., 2009). All Cistus species secrete essential oils in different amounts (Kintziou et al., 2001). Moreover,
in some species (C. ladanifer), the leaves are coated with a highly aromatic resin called labdanum, which is sometimes mis-
takenly considered as an essential oil in the literature. Labdanum also shows a high content of volatile compounds which
have been deeply studied (Weyerstahl et al., 1998; Greche et al., 2009). As is often the case for plants, Cistus essential oils
are normally obtained by steam distillation, but in the case of C. ladanifer, supercritical CO2 extraction has also been used
(Rincón et al., 2000), yielding an essential oil with higher quality and purity.
BOTANICAL ASPECTS
Cistus plants are perennial shrubs with evergreen, opposite, simple, usually slightly rough-surfaced, 2 8 cm long leaves.
Their flowers are hermaphroditic, actinomorphic, and hypogynous, with three or five sepals (usually with the outer sepals
smaller than the inner ones) opposite to petals. They present five petals with colors ranging from white to purple and dark
pink depending on the subgenus, with a conspicuous dark red spot at the base of each petal in a few species. Figure 1 shows
pictures corresponding to diverse colored flowers of representative members of the Cistus genus. The androecium has
numerous fertile stamens and the gynoecium is formed by a three or five carpellate ovary (although C. ladanifer displays 6
to 12 carpels) and a solitary style with a single capitate or discoid stigma. From an ecological point of view, Cistus plants
present insect-dependent pollination, flower-dependent reproduction, and spring-dependent phenology, and characteristics
that demonstrate their adaptation to Mediterranean ecosystems (Guzmán and Vargas, 2005). Cistus plants grow in different
ways, from a woodland understory, to be the dominant species in evergreen scrub. Co-occurring species of Cistus are also
very frequent, particularly in mountain ranges (Guzmán and Vargas, 2005).
Taxonomical and phylogenic relationships among these species have been based primarily on vegetative and reproduc-
tive characters. At the present, these taxonomic data have been significantly improved using genetic approaches (Guzmán
and Vargas, 2005). The polyphenolic composition has been also utilized to establish different chemotypes, therefore permit-
ting classification of the members of Cistus genus, which confirms taxonomic and evolutionary studies (Barrajon-Catalan
et al., 2011). As shown in Figure 2, the Cistus genus is divided into three subgenera: Cistus, Leucocistus, and Halimioides.
The first includes purple flowered plants and the last two comprise species showing white flowers. Whereas the Cistus
Essential Oils in Food Preservation, Flavor and Safety. http://dx.doi.org/10.1016/B978-0-12-416641-7.00074-2
Copyright © 2016 Elsevier Inc. All rights reserved. 649
650 PART | II Named Essential Oils
(A) (B) (C)
FIGURE 1 Flowers from representative Cistus plants. Three species of Cistus flowers are shown as an example of white (Cistus salviifolius, Leucocistus
subgenus, A); purple (Cistus incanus, Cistus subgenus, B); and dark red spotted white flowers (Cistus ladanifer, Leucocistus subgenus, C). The intensity
and exact color vary between species, especially for Cistus subgenera, which present different tones of purple on each species. The presence of a red spot
in Cistus ladanifer is not always observed, as occurs in Cistus ladanifer var. albiflorus. (Unpublished figure).
FIGURE 2 Taxonomic relationships
between Cistus species with character-
ized essential oils. Taxonomic relationships
between the different Cistus species (grouped
in subgenus) with reported data on their
essential oils. A photographic detail of the
flowers is shown close to the name of each
species. (Unpublished figure).
subgenus is almost devoid of ellagitannins and contain mostly flavonoids, Leucocistus and Halimioides subgenera are
enriched in ellagitannins and contain smaller amounts of flavonoids. Previously reported phylogenetic and taxonomic stud-
ies (Guzmán and Vargas, 2005) pointed out the relationship between the members of these subgenera. These are summa-
rized in Figure 2, showing the most representative species with characterized essential oils of each subgenus. Essential
oils and resins in plants have several vital functions, they contribute to pollination, act as insect repellent agents, protect
against fungal or bacterial attack, and prevent against water evaporation and ultraviolet (UV) damage. It has been proposed
that morphological leaf traits and labdanum secretion in white-flowered Cistus linage have been influenced by UV radia-
tion, therefore determining their successful adaptation to different Mediterranean habitats (Guzmán et al., 2009).
USAGE AND APPLICATIONS
Traditional folk medicine has used Cistus species, their extracts, and/or essential oils for a large variety of purposes such as
antiinflammatory, antiulcerogenic, wound healing, antimicrobial, cytotoxic, or vasodilator remedies. They have also been
used as an antidiarrheic, antacid, and antispasmodic by simple decoction of their leaves (Zidane et al., 2013). Studies have
revealed information on the possible candidate compounds for all these effects, but new activities are being discovered and
attributed to various Cistus-derived products. These include antimicrobial, antioxidant, antitumor, antinociceptive, analge-
sic, and neuroprotective effects (De Andres et al., 1999; Kupeli and Yesilada, 2007; Barrajon-Catalan et al., 2010; Loizzo
et al., 2013).
The compounds in essential oils and exudates may have also allelopathic effects by inhibiting the growth of
another species and reducing their germination, due to phytotoxicity over plants and soil (Verdeguer et al., 2012).
Rockroses (Cistus sp.) Oils Chapter | 74 651
That is the case for some flavonoids found in C. ladanifer leafs and in soils where this plant was grown (Chaves et al.,
2001). Although labdanum cannot be considered an essential oil, it contains a high percentage of volatile compounds,
most of them shared with the corresponding essential oil. Both labdanum and essential oil, especially obtained from
C. ladanifer, are very much appreciated in the perfume industry being an essential component in about 30% of mod-
ern perfumes. Its fragrance is reminiscent of gray amber and it combines perfectly with the fragrance families of
amber, chypre, and fern due to its excellent fixative properties. Labdanum from C. ladanifer is also used as an additive
to aromatize some types of tobacco.
Undoubtedly, the major potential of Cistus essential oil is related to its antimicrobial capacity. Several studies have
reported the potential antimicrobial activity of essential oils and extracts derived from Cistus plants, especially those
from C. ladanifer (Greche et al., 2009; Zohra and Atik, 2011; Tomás-Menor et al., 2013), but also those derived from
other species such as Cistus incanus (Demetzos et al., 1995, 1997), Cistus albidus (Tomás-Menor et al., 2013), Cistus
monspeliensis (Bouamama et al., 1999), Cistus salviifolius (Demetzos et al., 2002; Tomás-Menor et al., 2013), Cistus
laurifolius (Kintziou et al., 2001), and Cistus parviflorus (Demetzos et al., 1990; Güvenç et al., 2005). Nevertheless, still
much research must be done in order to use these materials for food preservation purposes or as ingredients for cosmet-
ics and toiletries.
USAGE AND APPLICATIONS IN FOOD SCIENCE
Cistus essential oils and resins have not been used in food science and industry regularly, only marginal use as a flavoring
agent for food or active ingredient for food supplements is reported. Labdanum oleoresin from Cistus spp. was included by
the Council of Europe in the list of substances granted approval (COE No. 134). The United States Food and Drug Admin-
istration (FDA, 2014) also approved it for use as a food additive or flavoring agent (FDA Code of Federal Regulations,
title 21, vol 3; 21CFR172.510) in low quantities (2 14 ppm). Cistus incanus extract is also used as an ingredient in food
supplements with immune boosting properties. No further reports on an established use of Cistus-derived products in food
purposes are available. Nevertheless, two new potential uses for Cistus oils and other Cistus-derived products are emerging
from the literature that can be exploited in the future:
1. Antioxidant or radical scavenging activity: Not only the essential oils, but also all Cistus-derived products (labda-
num, aqueous, alcoholic and hydroalcoholic extracts) possess significant antioxidant activity (Amensour et al., 2010;
Barrajon-Catalan et al., 2010; Guimarćes et al., 2010; Zidane et al., 2013), which may have a potential use to prepare
ingredients focused to preserve foods from oxidation or to inhibit lipid peroxidation (Jerónimo et al., 2012). In fact,
some novel cosmetic products already include Cistus ingredients as antioxidants in their formulations. Table 2 shows
values of reported antioxidant activity of Cistus derived products, that is, leaf extracts and essential oils.
2. Antimicrobial activity: Cistus essential oils and extracts have a proven antimicrobial activity which has been reported
against several Gram-positive and Gram-negative bacteria and also against some fungal infections (Demetzos et al.,
1997; Bouamama et al., 1999; Kintziou et al., 2001; Greche et al., 2009; Barrajon-Catalan et al., 2010; Rauwald et al.,
2010; Zohra and Atik, 2011; Tomás-Menor et al., 2013). This reported activity would allow the use of Cistus essential
oils as preservative agents in the food industry, but first, adequate dosage and toxicity assessments must be established
before food safety authorities approve their use.
Nowadays, the use of green chemistry is encouraged as an alternative to conventional chemicals in order to reduce
health and environmental risks. The use of Cistus spp. ingredients as preservative or antimicrobial agents may suppose an
option to reduce the use of chemicals in food or cosmetic sectors (Anastas and Eghbali, 2010).
In addition to their proven antioxidant and antimicrobial activities, the composition of the most representative Cistus
essential oils and extracts is described, and their potential use in food science and industry is discussed.
Cistus ladanifer L
Cistus ladanifer (Figure 1(C)) essential oil is the most deeply characterized one among all Cistus essential oils and its
chemical composition has been thoroughly studied (Pascual et al., 1982; Mariotti et al., 1997; Robles et al., 2003; Gomes
et al., 2005; Oller-López et al., 2005; Costa et al., 2009). Although there are differences between the reported data probably
due to the plant origin, variety, or seasonal variations, the most abundant compounds include Ä…-pinene, viridiflorol, borneol,
trimethyl cyclohexanone, and camphene (Figure 3, Table 1). As mentioned, C. ladanifer is the only essential oil which has
been obtained by supercritical CO2 extraction with small differences in composition when compared with traditional stem
distillation (Rincón et al., 2000).
652 PART | II Named Essential Oils
TABLE 1 Main Terpene Compounds of the Essential Oils Derived from Different Cistus Species. References for Each
Species Have Been Included
Species Main Compounds References
Cistus ladanifer Ä…-Pinene, viridiflorol, trimethyl Pascual et al. (1982), Mariotti et al. (1997), Robles
ciclohexanone, borneol and camphene et al. (2003), Gomes et al. (2005), Oller-López et al.
(2005), Costa et al. (2009), Zidane et al. (2013)
Cistus incanus Manoyl oxide, viridiflorol, carvacrol, Demetzos et al. (1995), Paolini et al. (2009), Loizzo
and cadinene et al. (2013)
Cistus albidus Ä…-Zingiberene, Ä…-curcumene, Ä…-cadinol, Robles and Garzino (1998), Maccioni et al. (2006),
and Ä…-bisabolol Paolini et al. (2008)
Cistus salviifolius Camphor, viridiflorol, longiborneol, phylloclad- Demetzos et al. (2002)
ene, abietatriene, and cis-feruginol
Cistus monspeliensis Manoyl oxide, bisabolol, 1,8-cineole, Robles and Garzino (2000), Angelopoulou et al.
bornyl acetate, and ą-pinene (2001a), Angelopoulou et al. (2002), Oller-López
et al. (2005), Viuda-Martos et al. (2011)
Cistus laurifolius Borneol and nonacosane Öç
ütveren and Tetik (2004a)
Cistus libanotis Camphene, Ä…-pinene, ²-pinene, sabinene, Loizzo et al. (2013), Zidane et al. (2013)
Å‚-terpinene, bornyl acetate, terpineol,
and borneol
Cistus parviflorus Carvacrol, caryophyllene oxide, Angelopoulou et al. (2001b), Öç
ütveren and
abietatriene, 4-epi-dehydroabietol, Tetik (2004b)
dehydro abietol, cis-ferruginol, 8-Ä…-13-
oxy-14-ene-epilabdane, and manoyl oxide
Labdanum has also been well characterized (Weyerstahl et al., 1998; Greche et al., 2009) but its oral ingestion is very
limited due to reported neurotoxic, hepatotoxic, and nephrotoxic effects. However, it has been traditionally used at low
doses as an ingredient in sedative tea, coffee, and other infusions to prevent insomnia and anxiety.
Cistus ladanifer essential oil and other derivatives have shown significant antioxidant and antimicrobial properties. Prob-
ably, C. ladanifer materials are the most deeply characterized among all of the Cistus species in relation with these activities
(Table 2). The antimicrobial activity of the essential oil has been proven against various bacterial and fungal strains, whereas
labdanum resinoid showed poor activity (Greche et al., 2009). A remarkable activity of C. ladanifer essential oil against
pathogenic bacteria such as Listeria monocytogenes was reported (Zohra and Atik, 2011). The highest antimicrobial activity
against a variety of Gram-positive and Gram-negative clinical pathogens was observed for the most polar fraction of the
essential oil, primarily containing mono- and sesquiterpene alcohols, which even inhibited multidrug-resistant Enterobacter
aerogenes (Guinoiseau et al., 2011). A modest capacity of this essential oil has also been reported to inhibit the growth of
Helicobacter pylori, which may allow its use as food additive to improve present therapies (Bergonzelli et al., 2003). Cistus
ladanifer leaves have also been used as an additive for feeding to improve lamb meat quality. A deceased level of meat
deterioration induced by lipid oxidation (Jerónimo et al., 2012) and increased content of unsaturated fatty acids in muscle
were observed (Jerónimo et al., 2010), without affecting meat color or sensory properties. Because in these studies com-
plete leaves and stems were utilized, it must be presumed that the terpene fraction from oil together with polyphenols are
the responsible for such effect. However, other studies showed that C. ladanifer leaves exudates may impair mouth skeletal
muscle relaxation through inhibition of the sarcoplasmic reticulum Ca2+ ATPase (Sosa et al., 2004), therefore these effects
and the potential responsible compounds must be further carefully studied.
Cistus incanus L
Cistus incanus (also known as Cistus creticus, Cistus villosus, or pink or hairy rockrose) (Figure 1(B)) essential oil is
probably the second most characterized one among all Cistus essential oils. All the C. incanus-derived products are deeply
characterized in their composition by high pressure liquid chromatography and gas chromatography mass spectrometry
(GC MS), as occurred with C. ladanifer. Several studies have reported the characterization of materials obtained from this
plant: extracts derived from leaves using different solvents (Barrajon-Catalan et al., 2011; Skorić et al., 2012), labdanum
Rockroses (Cistus sp.) Oils Chapter | 74 653
TABLE 2 Antioxidant Activity of Different Cistus-Derived Products Obtained from the Bibliography
Product Assay Value (Units) References
Aqueous extract of Cistus ladanifer leaves TEAC 35.85 Ä… 1.25 mmol TE/100 g DW Barrajon-Catalan et al.
(2010)
FRAP 117.72 Ä… 4.38 mmol Fe2+/100 g DW
ORAC 3329.0 Ä… 182.1 µmol TE/g
TBARS 73.13 Ä… 8.12% of inhibition (0.375 mg/mL)
Aqueous extract of Cistus salviifolius leaves TEAC 365.85 Ä… 5.28 mmol TE/100 g DW Tomás-Menor et al.
(2013)
FRAP 435.77 Ä… 5.87 mmol Fe2+/100 g DW
ORAC 5459.00 Ä… 66.53 µmol TE/g
TBARS 0.007 Ä… 0.003 mg/mL (50% inhibition)
Essential oil of Cistus ladanifer DPPH scavenging 36.28 Ä… 0.36 mg/mL Guimaraes et al. (2010)
Essential oil of Cistus incanus DPPH scavenging 828.1 Ä… 3.6 µg/mL (IC50) Loizzo et al. (2013)
TEAC 395.1 Ä… 3.5 µg/mL (IC50)
FRAP 0.4 Ä… 0.09 µM Fe (II)/g
Essential oil of Cistus salviifolius DPPH scavenging 814.7 Ä… 3.4 µg/mL (IC50) Loizzo et al. (2013)
TEAC 394.7 Ä… 3.8 µg/mL (IC50)
FRAP 5.2 Ä… 0.8 µM Fe (II)/g
Essential oil of Cistus libanotis DPPH scavenging 499.9 Ä… 3.1 µg/mL (IC50) Loizzo et al. (2013)
TEAC 272.5 Ä… 2.7 µg/mL (IC50)
FRAP 19.4 Ä… 1.6 µM Fe (II)/g
Essential oil of Cistus monspeliensis DPPH scavenging 991.9 Ä… 4.4 µg/mL (IC50) Loizzo et al. (2013)
TEAC 4.5% at 396 µg/mL (IC50)
NA
Each row shows the name of the Cistus species, the kind of sample (solvent used or essential oil), the result for different antioxidant assays, and the biblio-
graphic source. DW: dry weight; TE: Trolox equivalents; DPPH: 2,2-diphenyl-1-picrylhydrazyl radical; NA: not assayed; TEAC: Trolox equivalent antioxidant
capacity; TBARS: thiobarbituric acid-reactive substances assay; ORAC: oxygen radical absorbance capacity; FRAP: Ferric reducing ability power. A detailed
description for each antioxidant assay can be obtained from Barrajon-Catalan et al. (2010).
oleoresin (Demetzos et al., 1994), and essential oil (Demetzos et al., 1995; Paolini et al., 2009; Loizzo et al., 2013).
Although the reports on essential oil composition are slightly different, diterpenes such as manoyl oxide, bicyclic sesquiter-
penes such as cadinene, oxygenated sesquiterpenes such as viridiflorol, and burnesol and oxygenated monoterpenes such
as carvacrol are the most abundant compounds in almost all the analysis (Figure 3, Table 1).
The essential oil of C. incanus is not used as a food additive at industrial level, but their infusions and teas are very popu-
lar and have been traditionally used to treat respiratory infections and colds. Studies have reported their antiviral capacity
against avian influenza A virus in cellular and animal models (Droebner et al., 2007; Ehrhardt et al., 2007) and in a ran-
domized, placebo controlled human trial (Kalus et al., 2009). There are some commercial teas and nutraceutical products
containing C. incanus extracts or their leaves. As this product was not used as food ingredient in the European Union before
May 1997, a safety assessment, and probably its consideration under Novel Food Regulation, would be required before
being authorized for food use (European-Commission, 2014).
The antimicrobial activity of C. incanus essential oil is well documented against a panel of Gram-positive and Gram-
negative bacteria (Demetzos et al., 1995, 1997). A more detailed study has reported that volatile compounds from essen-
tial oil showed stronger growth inhibitory effect than leaf extracts against Borrelia burgdorferi (Rauwald et al., 2010).
Moreover, diterpenes isolated from labdanum of C. incanus showed potential antileishmania activity, which has allowed
designing of semisynthetic potent diterpenes with selective leishmanicidal activity (Fokialakis et al., 2006). The antimicro-
bial activity of extracts derived from C. incanus leaves is also well documented. Extracts obtained with different solvents
654 PART | II Named Essential Oils
FIGURE 3 Chemical structures of the main terpene compounds in Cistus essential oils. Chemical structures of the main terpenes in Cistus essential
oils: Ä…-pinene (A); borneol (B); camphene (C); viridiflorol (D); zingiberene (E); carvacrol (F); bisabolol (G); curcumene (H); and longiborneol
(I). (Unpublished figure).
Rockroses (Cistus sp.) Oils Chapter | 74 655
exhibited growth inhibitory activity against Gram-positive bacteria (Staphylococcus aureus, Streptococcus faecalis, Bacil-
lus subtilis, Bacillus cereus) and Gram-negative bacteria (Escherichia coli) (Güvenç et al., 2005), and also antifungal activ-
ity (Bouamama et al., 1999).
A study demonstrated that essential oils of various Cistus species, including C. incanus, possess acetylcholinesterase
and/or butyrylcholinesterase inhibitory activity, which can be useful for prevention and treatment of Alzheimer s disease.
This promising discovery opens new alternatives to the development of pharmaceutical and nutraceutical formulations
focused to increase the therapeutic arsenal for Alzheimer s patients (Loizzo et al., 2013).
Cistus albidus L
Cistus albidus (white rockrose) essential oil has also been well characterized by different studies (Robles and Garzino,
1998; Maccioni et al., 2006; Paolini et al., 2008). This oil mostly contains sesquiterpenes, being Ä…-zingiberene the most
abundant oil followed by other such as Ä…-curcumene, Ä…-cadinol, and Ä…-bisabolol (Figure 3, Table 1), which reach a signifi-
cant abundance. The percentages of these compounds vary depending on their seasonal and geographical origin. There are
no current food applications for C. albidus products beyond its potential antimicrobial and antioxidant activities. However,
some studies have reported their potential use in ethnomedicine (Tomás-Menor et al., 2013) and ethnoveterinary (Benítez
et al., 2012).
Cistus salviifolius L
Little work has been done on the composition of C. salviifolius (Figure 1(A)) essential oil. However, a complete GC MS
analysis of the composition of essential oils derived from several populations of this plant has been reported (Demetzos
et al., 2002). These essential oils were characterized by the presence of high percentages of oxygenated sesquiterpenes,
such as viridiflorol and longiborneol (Figure 3, Table 1). The oxygenated monoterpene camphor was also detected as the
major compound in most samples analyzed. Finally, among the diterpenes, phyllocladene, abietatriene, and cis-feruginol
were the most abundant ones (Demetzos et al., 2002).
No special application has been described for C. salviifolius in the food industry. Like other Cistus species, the anti-
microbial activity of C. salviifolius is well documented both for extracts deriving from leaves (Tomás-Menor et al., 2013)
and the essential oil (Demetzos et al., 2002). Leaf extracts are more potent against Gram-positive microorganisms than
against Gram-negative ones. Accordingly, Gram-positive bacteria (Staphylococcus epidermidis and S. aureus) were more
susceptible to different chemotypes of essential oils derived from C. salviifolius than Gram-negative bacteria (E. coli and
Pseudomonas aeruginosa). Among three different chemotypes identified in Crete (Greece), the Gram-positive antimicro-
bial capacity seems to be related to the chemotype bearing high camphor content. Cistus salviifolius essential oil has also
exhibited neuroprotective activity by inhibiting acetylcholinesterase and, to a lesser degree, butyrylcholinesterase (Loizzo
et al., 2013). Therefore, it could be a potential ingredient to prevent neurodegenerative disorders.
Cistus monspeliensis L
Cistus monspeliensis, also known as black-rockrose, is probably much less known than other species, but its essential oil
has been deeply analyzed in numerous studies (Robles and Garzino, 2000; Angelopoulou et al., 2001a, 2002; Oller-López
et al., 2005; Viuda-Martos et al., 2011). Once again, there are differences between the different reports probably due to soil,
climate, and origin factors. Diterpenes such as manoyl oxide are the main constituents in all the samples. Other compounds
such as the sesquiterperne Ä…-bisabolol, and monoterpenes such as 1,8-cineole (eucalyptol), bornyl acetate, and Ä…-pinene are
also abundant in this essential oil (Figure 3, Table 1).
Essential oils from Cistus monspeliensis present moderate cytotoxic activity against leukemia cell lines (Angelopoulou
et al., 2001a). They also show potential neuroprotective activity, but to a lesser degree than other Cistus species (Loizzo
et al., 2013). In contrast, no antimicrobial activity was found for C. monspelliensis essential oil compared with C. parvi-
florus (Demetzos et al., 1990). The antiparasitary activity against leishmania of a triterpene isolated from C. monspeliensis
has also been reported (Fokialakis et al., 2006).
Cistus laurifolius L
The essential oil of C. laurifolius, also known as mountain rockrose, is also poorly characterized compared with other
Cistus species. The main components include terpenes such as borneol and other compounds such as the paraffin with
656 PART | II Named Essential Oils
pheromone activity nonacosane (Figure 3, Table 1) (Öç
ütveren and Tetik, 2004a). Although the antiinflammatory and anti-
nociceptive activities have been described for C. laurifolius-derived products (Kupeli and Yesilada, 2007), only a potential
antimicrobial activity has been reported for its essential oil (Kintziou et al., 2001).
Cistus libanotis L
Also known as Lebanon rockrose, C. libanotis essential oil has been well characterized in several studies (Loizzo et al.,
2013; Zidane et al., 2013). Monoterpenes represent the main family of compounds with camphene, Ä…-pinene, ²-pinene,
sabinene, and Å‚-terpinene as the major compounds. Oxygenated monoterpenes such as bornyl acetate, terpineol, and bor-
neol are the most representative (Figure 3, Table 1). There are no references on the food potential application of C. libanotis
essential oil. The essential oil of C. libanotis has shown stronger butyrylcholinesterase inhibitory activity than other Cistus
essential oils, which could be explained through the synergic interaction among the terpene compounds in the oil. This may
support its functional role in the prevention of neurodegenerative diseases (Loizzo et al., 2013). Cistus libanotis essential
oil also exhibited stronger antioxidant capacity when compared to C. creticus, C. salviifolius or C. monspeliensis essential
oils, as compared by using different radical scavenging tests (Table 2) (Loizzo et al., 2013).
Cistus parviflorus
This Cistus species is a particular one, their flowers are purple, but their botanical characteristics are closer to the white
flowered Cistus, suggesting that it could have originated as a hybrid species in the past (Guzmán and Vargas, 2005, 2009).
Its essential oil is well characterized by GC MS (Angelopoulou et al., 2001b; Öç
ütveren and Tetik, 2004b). Monoterpenes
and bicyclic sesquiterpenes such as carvacrol and caryophyllene oxide, respectively, as well as diterpenes such as abietatri-
ene, 4-epi-dehydroabietol, dehydro abietol, and cis-ferruginol were found in high percentage composition. Labdane-type
diterpenes such as 8-Ä…-13-oxy-14-ene-epilabdane and manoyl oxide mixture of isomers were also found (Angelopoulou
et al., 2001b; Öç
ütveren and Tetik, 2004b) (Figure 3, Table 1). The antimicrobial activity for C. parviflorus essential oil has
been documented (Demetzos et al., 1990), but no reference to other activities has been published so far.
SUMMARY POINTS
l All Cistus species secrete essential oils in different amounts, which are mostly composed of monoterpenes, sesquiterpenes,
and diterpenes.
l Labdanum, the exudate secreted by leaves and stems, is not an essential oil; however, it shares volatile compounds and
activities.
l Depending on the species, pinene, borneol, camphor, and carvacrol (monoterpenes), viridiflorol and zingiberene (oxygen-
ated sesquiterpenes), and manoyl oxide and abietatriene (diterpenes) are the most abundant and common compounds of
Cistus essential oils.
l Antimicrobial and antioxidant activities are the most characterized and well documented for most Cistus essential oils.
Nevertheless, still further research into safety must be done in order to use these materials for food preservation purposes.
ACKNOWLEDGMENTS
Some of the concepts expressed in this review chapter have been supported by competitive public grants from different institutions: AGL2011-
29857-C03-03, IDI-20120741, IDI-20120888 (Spanish Ministry of Science and Innovation), PROMETEO/2012/007, and ACOMP/2013/093
from Generalitat Valenciana (GV), and CIBER (CB12/03/30038, Fisiopatología de la Obesidad y la Nutrición, CIBERobn, Instituto de Salud
Carlos III).
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