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α-Bisabolol is a naturally occurring sesquiterpene alcohol which was first isolated from Matricaria chamomilla (Asteraceae) in the twentieth century and has since been identified in other aromatic plants such as Eremanthus erythropappus, Smyrniopsis aucheri and Vanillosmopsis species. Recently, α-bisabolol was identified as a major constituent of Salvia runcinata essential oil, a plant indigenous to South Africa. The use of α-bisabolol or bisabolol-rich oil as an anti-inflammatory agent is ubiquitous. This compound also exhibits several other pharmacological properties such as analgesic, antibiotic and anticancer activities. Mutagenicity and genotoxicity of bisabolol have also been investigated. Due to the low toxicity associated with bisabolol the Food and Drug Administration (FDA) has granted this constituent with Generally Regarded as Safe (GRAS) status which has promoted its use as an active ingredient in several commercial products. This review aims to summarise the role of α-bisabolol in pharmacological and/or physiological processes and to discuss some of the possible mechanisms of action of this commercially important molecule.
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REVIEW
A Review of the Application and Pharmacological Properties
of a-Bisabolol and a-Bisabolol-Rich Oils
Guy P. P. Kamatou
Alvaro M. Viljoen
Received: 11 July 2009 / Revised: 15 August 2009 / Accepted: 1 October 2009 / Published online: 29 October 2009
Ó AOCS 2009
Abstract a-Bisabolol is a naturally occurring sesquiterpene
alcohol which was first isolated from Matricaria chamomilla
(Asteraceae) in the twentieth century and has since been
identified in other aromatic plants such as Eremanthus ery-
thropappus, Smyrniopsis aucheri and Vanillosmopsis species.
Recently, a-bisabolol was identified as a major constituent of
Salvia runcinata essential oil, a plant indigenous to South
Africa. The use of a-bisabolol or bisabolol-rich oil as an anti-
inflammatory agent is ubiquitous. This compound also
exhibits several other pharmacological properties such as
analgesic, antibiotic and anticancer activities. Mutagenicity
and genotoxicity of bisabolol have also been investigated.
Due to the low toxicity associated with bisabolol the Food and
Drug Administration (FDA) has granted this constituent with
Generally Regarded as Safe (GRAS) status which has pro-
moted its use as an active ingredient in several commercial
products. This review aims to summarise the role of a-bi-
sabolol in pharmacological and/or physiological processes
and to discuss some of the possible mechanisms of action of
this commercially important molecule.
Keywords a-Bisabolol Biological properties
Matricaria chamomilla Toxicity
Introduction
Terpenoids constitute a class of lipophilic secondary
metabolites derived from mevalonate and isopentenyl
pyrophosphate which occur widely in nature [1, 2]. These
phytochemicals are diverse in structure and collectively,
they comprise a major component of the volatile fraction of
various aromatic plants. Monoterpenes and sesquiterpenes
are compounds generally found in the essential oils of
several aromatic plants. Sesquiterpenes (C
15
), are formed
biosynthetically from three five-carbon isoprene units or are
synthesised industrially from monoterpenoid feedstocks [3].
Sesquiterpenes have been identified as the active constitu-
ents present in several medicinal plants used in traditional
medicine, with a wide range of biological properties
including anti-infective, anti-oxidant, anti-inflammatory,
anticancer and anticholinesterase activities. Furthermore,
sesquiterpenes are also associated with important biological
and physiological functions such as pheromone interac-
tions, antifeedants, phyto-alexins, etc. [4].
a-(-)-Bisabolol, is a monocyclic sesquiterpene alcohol
which was first isolated in 1951 by Isaac and collaborators
from the blossoms of chamomile (Matricaria chamomilla;
Asteraceae) and it has since been established that a-(-)-bi-
sabolol may exist in four possible stereoisomers (Fig. 1)[5].
a-(-)-Bisabolol has been widely used as an ingredient
in dermatological and cosmetic formulations such as after-
shave creams, hand- and body-lotions, deodorants, lip-
sticks, sun-care and after-sun products, baby care products
and sport creams [6]. It is a preferred active ingredient for
protection against the recurring stresses of the environment
on the skin. The most important biological activities of
bisabolol are the anti-inflammatory, anti-irritant, antibac-
terial and non-allergenic properties.
Natural Origin of Bisabolol
Generally, when referring to bisabolol, a-(-)-bisabolol is
implied. a-(-)-Bisabolol (also known as levomenol) is
G. P. P. Kamatou A. M. Viljoen (&)
Department of Pharmaceutical Sciences,
Faculty of Science, Tshwane University of Technology,
Private Bag X680, Pretoria 0001, South Africa
e-mail: viljoenam@tut.ac.za
123
J Am Oil Chem Soc (2010) 87:1–7
DOI 10.1007/s11746-009-1483-3
present in various plants and can be obtained by hydrodi-
stillation of German chamomile (Matricaria chamomilla),
sage (Salvia runcinata and certain chemotypes of the closely
related S. stenophylla), Vanillosmopsis sp. (e.g. V. pohlii, V.
arborea)andMyoporum grassifolium. Matricaria chamom-
illa and S. runcinata contain up to 50 and 90% a-(-)-
bisabolol, respectively [7, 8]. Another less explored source of
a-bisabolol is the wood of Candeia (Eremanthus erythro-
pappus) which may contain up to 85% of a-bisabolol [9].
Uses
a-(-)-Bisabolol is used in decorative cosmetics, fine
fragrances, shampoos and other toiletries as well as in
non-cosmetic products such as household cleaners and
detergents and also in pharmaceutical formulations [10, 11].
The main application of a-bisabolol in the pharmaceutical
sector is related to its anti-inflammatory, antispasmodic,
anti-allergic, drug permeation and vermifuge properties
[9, 12].
Chemical and Physical Properties
Bisabolol, also known as alpha,4-dimethyl-alpha-(4-
methyl-3-pentenyl)-3-cyclohexene-1-methanol, is a ses-
quiterpene alcohol with the chemical formula C
15
H
26
O.
Bisabolol has a weak sweet flora aroma. It is a colourless
liquid with a relatively low density (0.93) and a boiling point
of 153 °C at 12 Torr [13]. Bisabolol is a very lipophilic
substance, with a propensity to oxidise. It is almost insoluble
in water, nevertheless, soluble in ethanol. The oxidation
products are mainly bisabolol-oxide A and B [14]. The
enantiomer a-(?)-bisabolol is rare in nature and the syn-
thetic equivalent is generally a mixture of a-(±)-bisabolol.
Biological Properties of Bisabolol and Bisabolol-rich Oil
In many parts of the world, German chamomile (confus-
ingly referred to as ‘European ginseng’’) is considered to
have panacea-like properties (universal drug) and it used to
treat a diversity of conditions [15]. The high level of
a-bisabolol present in chamomile oil is credited for
providing the several biological properties ranging from
anti-infective activity to anticancer, anti-inflammatory,
anticholinesterase properties, and also for its ability to
enhance transdermal drug permeation [1620].
Anti-infective Properties of Bisabolol
Several aromatic plants (chamomile and sage) are used as
traditional remedies to treat various ailments. Many studies
have described the composition of essential oils and
reported the biological activity of the major constituents
[21]. Although the antimicrobial activity of certain com-
pounds such as carvacrol, 1,8-cineole and camphor is well
established [22, 23], the antimicrobial activity of many
sesquiterpenes such as bisabolol has only been reported for
a limited number of pathogens. For instance, a-bisabolol
tested active against Gram-positive bacteria, fungi and
Candida albicans [24]. The antimicrobial activity of 20
essential oil constituents including a-bisabolol was inves-
tigated using the microdilution method. Although, a-bisa-
bolol exhibited poor activity against Staphylococcus
aureus, Bacillus cereus and Escherichia coli, the activity
against C. albicans was promising and comparable to
linalool (MIC values: 36 and 39 mM, respectively) [18].
The antifungal activity of sesquiterpenes including
bisabolol against Botrytis cinerea was examined using the
fungal growth inhibition assay. Bisabolol showed mycelial
growth inhibition from 50 ppm, retaining an inhibition
percentage of 49 and 64% at 100 and 200 ppm, respec-
tively, after 6 days [25]. Salvia runcinata (&60% bisabo-
lol) also exhibited in vitro antibacterial activity against
S. aureus, S. epidermidis, B. cereus and B. subtilis with the
MIC values ranging from 1.6 to 3.1 mg/ml [26
].
The antimicrobial activity of chamomile oil varies in the
literature according to the method used and the test organ-
ism implicated. While promising antimicrobial activity of
the oil was recorded against Aspergillus ochraceus and
S. aureus [27], in other studies, chamomile oil showed no
zone of inhibition against Corynebacterium amycolatum,
S. aureus, E. coli, C. amycolatum and C. albicans [28].
The effect of three oils (anise oil, dwarf-pine oil and
chamomile oil) was investigated in vitro against acyclovir-
sensitive and acyclovir-resistant herpes simplex virus type
1 (HSV-1) using a plaque reduction assay. All three oils
exhibited antiviral activity against the acyclovir-sensitive
H
HO
8
4
OH
H
8
44
8
H
OH
4
8
HO
H
(–)-α-Bisabolol (–)-epi-α-Bisabolol (+)-α-Bisabolol (+)-epi-α-Bisabolol
Fig. 1 Stereoisomers of
a-(-)-bisabolol
2 J Am Oil Chem Soc (2010) 87:1–7
123
HSV strain KOS and acyclovir-resistant clinical HSV
isolates as well as acyclovir-resistant Angelotti with
chamomile oil exhibiting the highest activity against the
clinical acyclovir-resistant HSV-1 strains [29]. Plaque
formation was reduced by 97–99.9% when the viruses were
pre-incubated with acyclovir before attachment to the host
cell [29]. The essential oil of chamomile also demonstrated
dose-dependent virucidal activity against the HSV-2 with
an IC
50
value of 0.003%. The possible mechanism of action
was further investigated and the results showed that the
essential oils affected the virus by interrupting adsorption
of herpes viruses in a different manner compared to the
acyclovir which is effective after attachment inside the
infected cells [29, 30].
Four sesquiterpenes; nerolidol, farnesol, bisabolol and
apritone were investigated for their ability to increase the
susceptibility of S. aureus to some conventional antibiotics
(ciprofloxacin, clindamycin, erythromycin, gentamicin,
tetracycline and vancomycin). The results showed that low
concentrations (0.5–2 mM) of nerolidol, bisabolol or
apritone enhanced the susceptibility of S. aureus to the
antibiotic tested [31]. Furthermore, it was suggested that
the sesquiterpenoid compounds may act by disrupting the
normal barrier function of the bacterial cell membrane,
allowing the permeation into the cell of exogenous solutes
such as antibiotics. This effect was found to be more pro-
nounced for Gram-positive bacteria, probably due to the
lack of additional permeability barriers, particularly the
outer membrane of Gram-negative bacteria. A possible
structural resemblance of sesquiterpenes to membrane
lipids (e.g., linear molecules with internal lipophilic char-
acter and a more polar terminus) may also account for the
effectiveness of sesquiterpenes as enhancers of membrane
permeability. For instance, nerolidol and farnesol (with
longer hydrocarbon tails) were found to be more effective
as skin penetration enhancers than bisabolol [32].
Antiplasmodial Activity
German chamomile oil (with bisabolol as the major com-
pound) is used to treat conditions such as dizziness, neu-
ralgia, muscle cramping, headache, malaria and fever.
Various essential oils containing bisabolol have shown
antiplasmodial activity. For instance, the antiplasmodial
activity of S. runcinata (&60% of a-bisabolol) tested
against the chloroquine-resistant strain FCR-3 using the
3
H-hypoxanthine assay exhibited good activity (IC
50
value:
1.2 lg/mL) [26]. However, when a-bisabolol was evalu-
ated as a single component, poor activity was recorded in
comparison to the positive control quinine (IC
50
value: 307
and 0.29 lM, respectively). This result implies other
compounds (either minor or major) are important in the
biological activity of the oil and suggest that the activity of
the crude oil is not always derived from its major constit-
uent as generally speculated.
Anti-oxidant, Anti-inflammatory Activity
and the Effect of Bisabolol on the Skin
Anti-oxidant and Anti-inflammatory Activity
Increasing evidence has suggested that many degenerative
diseases such as brain dysfunction, cancer, heart disease
and immune system decline could be the result of cellular
damage caused by free radicals and that anti-oxidants may
play an important role in disease prevention [33]. The
commonly used anti-oxidants, butylated hydroxyanisol and
butylated hydroxytoluene are synthetic chemicals and the
possible toxicity of these anti-oxidants has resulted in
their reduced use [34]. In recent years, several natural anti-
oxidants have appeared on the market and are generally
regarded as safe [35]. The anti-oxidant activity has been
determined by investigating the effects of a-bisabolol to
interfere with reactive oxygen species (ROS) on chemilu-
minescence of human neutrophil bursts (C. albicans and
N-formyl-methionyl-leucyl-phenylalanine) and cell-free
systems (SIN-1 and H
2
O
2
/HOCl
-
). The results indicated
that a-bisabolol significantly inhibits the luminol-amplified
chemiluminescence at concentrations ranging from 7.7 to
31 lg/mL for C. albicans and N-formyl-methionyl-leucyl-
phenylalanine, respectively. A similar effect was observed
in the SIN-1 and H
2
O
2
/HOCl
-
systems suggesting bisab-
olol as a means of improving the antioxidant capacity
[36]. Although bisabolol has been claimed to exhibit anti-
oxidant activity on chemical and/or biological tests, an
in vitro study showed that a-bisabolol exhibited poor
antioxidant activity against the DPPH radical (IC
50
value [ 450 lg/mL) [18].
Chamomile essential oil is well known and has been used
for centuries as an anti-inflammatory agent and for allevi-
ating the symptoms associated with eczema, dermatitis
and other pronounced irritation. Volatile constituents of
the essential oil of chamomile, notably chamazulene and
a-bisabolol, exert anti-inflammatory activity partly due
to the inhibition of leukotriene synthesis [15, 37]. The
sesquiterpenes such as a-bisabolol appear to be good
5-lipoxygenase (5-LOX) inhibitors and have been widely
reported to have a skin soothing action which strongly
inhibits 5-LOX in vitro. The IC
50
value of this compound on
5-LOX ranged between 10 and 30 lg/mL [17]. As a-bisa-
bolol exhibited activity against the 5-LOX assay, the
essential oils containing higher levels of this sesquiterpene
alcohol are thus expected to inhibit the enzyme. Studies
have demonstrated that S. runcinata oil is good 5-LOX
inhibitor with the IC
50
value of 22.5 lg/mL. However, the
activity of the oil against the COX-2 enzyme was poor [26].
J Am Oil Chem Soc (2010) 87:1–7 3
123
Effect of Bisabolol on the Skin
Hyperpigmentation is the darkening of an area of skin
generally due to the increase of melanin. Several factors
such as inflammatory skin disorders, allergic contact and
irritant contact dermatitis are the main cause of hyperpig-
mentation. The increase of melanogenic enzyme activity or
number of melanocytes may be associated with epidermal
and dermal hyperpigmentation [38]. It is known that the
cAMP response element (CRE) is involved in the
a-melanocyte-stimulating hormone (a-MSH) production.
A study was conducted in order to determine the depig-
mentation effect of a-bisabolol using two different assays:
a cAMP response element luciferase reporter assay and
melanin assay. The results indicated that a-bisabolol
inhibited the CRE activation induced by a-MSH. Similarly,
the compound reduced the melanin content induced by
a-MSH.
Tyrosinase is an enzyme that catalyses the production of
melanin. Studies have demonstrated that a-MSH induces
tyrosinase gene expression via the activation of MITF
(Microphthalmia-associated transcription factor) gene
expression. An investigation was conducted to determine
the effect of a-bisabolol on the a-MSH-induced expression
of MITF and tyrosinase genes and results indicated that
a-bisabolol inhibited the gene expression of MITF and
tyrosinase implying that a-bisabolol inhibits melanogenesis
by lowering intra cellular cAMP levels [38].
Bisabolol as Permeation Enhancers
The percutaneous route of drug delivery is advantageous
over intravenous and oral administration. Nevertheless, the
architecture of the stratum corneum makes it a formidable
barrier to the topical and transdermal administration of
therapeutic agents [39, 40]. The most common approach to
alleviate stratum corneum permeability is the concomitant
use of penetration enhancers [41]. There are several classes
of penetration enhancers and terpenes obtained by distil-
lation from aromatic plants are very efficient for several
reasons. They are natural substances, non toxic, extensively
used in transdermal delivery as permeation enhancers and
Generally Regarded as Safe (GRAS) [42].
Dapiprazole, a known a-blocking drug, is used in topical
eye therapy for the treatment of chronic simple glaucoma,
for induction of pre-operative miosis and for reversion of
pharmacologically induced mydriasis. Many scientists
have suggested that transdermal administration might
present some advantages over the oral route in subjects
suffering from the conditions described above by lower
doses, provide sustained and constant plasma levels, and
improve the patients’ compliance [43]. The in vitro per-
meation rate of dapiprazole base through hairless mouse
skin was investigated in a series of liquid and semisolid
vehicles, both in the absence and in the presence of dif-
ferent penetration enhancers. It was found that the per-
meability coefficient of dapiprazole was significantly
promoted (up to 73 times) by some terpenes such as
I-limonene, a-bisabolol and terpinolene [43]. Furthermore,
the natural occurring (-)-a-bisabolol was twice as active as
enhancer for dapiprazole penetration than racemic (±)-a-
bisabolol [43]. The variation in the activity of bisabolol
demonstrated the role of functional groups in the pharma-
cological properties of certain compounds.
In Vitro and in Vivo Toxicity of Bisabolol
and Bisabolol-Rich Oil
Several studies have been conducted to determine the
toxicity of a-bisabolol. Twenty essential oil constituents
from various classes (ketones, aldehydes, alcohols, phenols
and terpene hydrocarbons) were tested on human epithelial
cells using the MTT assay. a-Bisabolol and nerolidol were
the most toxic compounds (IC
50
value of 41.8 and 5.5 lM,
respectively) [18]. Salvia runcinata (&60% of the oil) was
also found to be toxic on human epithelial cells (IC
50
value: 2.5 lg/ml). However, this toxicity was not corre-
lated to the level of a-bisabolol since toxic compounds
such as nerolidol and camphor were also identified in the
oil [26]. The effect of a-bisabolol on the gastrotoxicity of
acetylsalicylic acid was examined and it was found that
when a-bisabolol is administered orally (dose 0.8–80 mg/
kg) with acetylsalicylic acid (dose 200 mg/kg), a signifi-
cant protective effect is observed (P \ 0.05) [44]. It is
important to mention that the results of any bioassay
depend on the method and the organisms implicated in the
experiment and extrapolating the results of an in vitro
experiment to animal models is not always correct.
Numerous studies have confirmed the safety of chamomile
essential oil which contains a high level of bisabolol [42].
Mutagenicity, Genotoxic Effects and Anticancer
Activity of a-Bisabolol and Bisabolol-rich Oil
and Possible Mechanism of Action
Cancer is a genetic disease and a possible solution to fight the
disease is to reduce exposure to mutagens, chemicals capa-
ble of inducing genomic mutations and disrupting cellular
functions potentially leading to cancer. The ability of
a-bisabolol to induce or increase the frequency of mutation
in TA100, TA98, TA97a and TA1535 Salmonella
typhimurium strains, using the microsome assay with and
without addition of S9 mixture was evaluated. No increase in
the number of his
?
revertant colonies over the negative
control values was observed with any of the four tested
strains at concentrations ranging from 0 to 5000 lg/plate [6].
4 J Am Oil Chem Soc (2010) 87:1–7
123
The capacity of a-bisabolol in chamomile essential oil to
reduce the frequency of micronucleated polychromatic
erythrocytes (MNPE) induced by daunorubicin in mice was
studied by flow cytometry before the administration of the
compounds and at interval periods of 24 h for 72-h post-
administration. Results showed no capacity of a-bisabolol
to significantly increase the rate of micronuclei. However,
a significant dose-dependent inhibitory effect of the mol-
ecule was noted. After 48-h exposure, the percentage
inhibition with 120 and 1200 mg/kg of a-bisabolol was 52
and 65%, respectively [45]. The study also suggested that
a-bisabolol was the molecule responsible of the biological
activities of the volatile fractions of the plant [45].
An experiment was conducted in order to investigate the
effects of a-bisabolol on human and rat glioma cells. It was
found that a-bisabolol has a strong time- and dose-depen-
dent cytotoxic effect on highly malignant human and rat
glioma cell lines (EC
50
= 2 lM). At a lower concentra-
tions (2.5–3.5 lM), the viability of these cells was reduced
after 24 h by 50% with respect to untreated cells [46].
Glioma cells treated with a high concentration of a-bisab-
olol (10.0 lM) resulted in a 100% cell death. The study
also revealed that the viability of normal rat glial cells
(non-neuronial cells) was not affected by treatment with
a-bisabolol at the same concentrations as above. Sugges-
tions were made that a-bisabolol-induced cytotoxicity in
glioma cells may result from the induction of apoptosis
through the mitochondrial pathway [46]. Recent research
has demonstrated that a-bisabolol exerts a rapid and effi-
cient apoptosis-inducing action selectively towards human
and murine malignant glioblastoma cell lines through
mitochondrial damage. Studies have also established that
a-bisabolol can initiate the apoptosis-inducing action
towards highly malignant human pancreatic carcinoma cell
lines without affecting human fibroblast viability [47].
Effect of Bisabolol on Animal Reproduction
and Development
The effects of a-bisabolol was investigated on pregnant rats
dosed daily via gavage on days 6–15 of gestation, at con-
centrations ranging from 250 to 3000 mg/kg body weight.
There was no toxic effect on pre-natal development at
doses up to 1000 mg/kg body weight. However, at con-
centrations higher than 1000 mg/kg body weight, a sig-
nificant reduction in fetal number and subsequent increase
in resorption rate was observed. In addition, slight sedation,
reduced feed intake and reduction of body weight gain
were observed at high dose [48].
The chemoprotection of fertility by chamomile essential
oil (rich in a-bisabolol) was investigated by administration
of 500 mg/kg of essential oil and 5 mg/kg of daunorubicin
(a free radical inductor) to mice and the sperm concen-
tration, motility, viability and fertilisation capacity were
examined. Sperm viability was over 90%, while no effect
on motility and sperm concentration could be observed.
The fertilisation capacity decreased considerably in the
group of animals treated with daunorubicin, while the
fertilisation capacity in the groups receiving chamomile
essential oil was maintained [48] indicating that the
essential oil exhibited a chemopreventive capacity.
Insecticidal Activity and Insect Repellent Capacity
of Bisabolol
Many studies have been undertaken to find new insecticidal
compounds of plant origin. The insecticidal activity of the
heartwood essential oil (Vanillosmopsis pohlii) (which
contains a-bisabolol in high levels) and the pure sesqui-
terpene a-bisabolol have been investigated. The oil and
a-bisabolol exhibited insecticidal activity against Bemisia
argentifolii, the white fly fruit plague. In the search for
alternative chemical control against Aedes aegypti, the
larvicidal effect based on the percentage mortality after
24 h of ten essential oils was tested against the yellow
fever mosquito Aedes aegypti. Among the oils tested, the
essential oil of Vanillosmopsis arborea (rich in a-bisabolol)
displayed the highest larvicidal activity, with CL
50
of
15.9 mg/mL and CL
90
of 28.5 mg/mL [49].
Other Points Not Discussed
The oil obtained from Matricaria chamomilla was inves-
tigated for attention-deficit hyperactivity disorder (ADHD).
The observational study was carried out on three (14–
16 year old) male psychiatric out patients, diagnosed with
ADHD. Using comparisons of Conners’ parent ratings, an
improvement in ADHD symptoms rated by a clinician,
who did not have any information about the Matricaria
chamomilla medication, was observed [50]. The bisabolol
(applied at 50, 200 and 1000 mg/kg body weight/day)
a NOAEL of 200 mg/kg body weight/day was found in a
28-day study on rats. At 1000 mg/kg body eight/day, body
weight gain was slightly reduced.
Chamomile was found to exhibit antispasmodic activity
with a-bisabolol and flavonoids identified as compounds
responsible for the activity [24]. Furthermore, a-bisabolol
exhibited capacity protection against gastric effects of
aspirin (PH
2
). The antipeptic action and proteolytic
capacity of a-bisabolol was examined and results showed
that bisabolol exhibited antipeptic action in a dose depen-
dent manner. It was also found that the proteolytic activity
of pepsin is reduced by 50% through addition of bisabolol
J Am Oil Chem Soc (2010) 87:1–7 5
123
[51]. Essential oil obtained from chamomile is also known
to display no irritant properties. Studies conducted on hen’s
eggs chorioallantoic membrane revealed no irritating
effects of the oil [29]. In vitro studies found that a-bisab-
olol and a-terpineol exhibited wound-healing properties
with EC
50
of 228 and 240 lg/g mouse, respectively [52].
Concluding Comments
Bisabolol is a naturally occurring constituent accumulated
in the essential oil of various species with a vast range of
uses (cosmetics, fine fragrances, pharmaceutical). This
compound although identified in various aromatic plants
is present in substantial amounts in Matricaria chamom-
illa, Salvia runcinata, Myoporum grassifolium and Er-
emanthus erythropappus essential oils. The in vitro and in
vivo investigation of bisabolol and bisabolol-rich oil has
demonstrated several pharmacological properties ranging
from anti-inflammatory to anticancer activities. Although
the antimicrobial activity of bisabolol is known, it is
imperative that this molecule be tested on a broader range
of pathogens to establish the spectrum of antimicrobial
activity. Bisabolol and bisabolol rich-oil have also dem-
onstrated the capacity to enhance the percutaneous
absorption of certain molecules and may prove to be an
important ingredient in future cosmetic and skin care
products. Taking into account the low toxicity of bisab-
olol, it is important to determine other pharmacological
properties such as the potential use of this compound in
alleviating conditions related to the central nervous sys-
tem. The action of essential components in the cytoplas-
mic membrane and on membrane-bound phospholipids is
not yet fully understood and this could prove to be a
rewarding topic in future investigations. Elucidation of the
various mechanisms of action ascribed to bisabolol may
be useful to provide a firm scientific basis for the inclu-
sion of this bioactive molecule in various consumer
products.
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... NIST library-based identification has revealed bisabolol as the prime bioactive metabolites along with long chain alcohols, phenols and organic acids. Bisabolol is an all-square component with antibacterial, antioxidative, anti-irritant, leshmenicidal activity etc. [18]. This study for the first time reports the bisabolol production from any Lycopodium clavatum derived endophytic source. ...
... The EI mass spectrum of LCS1 derived bisabolol and standard bisabolol is compared to confirm its occurrence (S4 Fig). It produces an essential oil bisabolol (a monocyclic sesquiterpene alcohol) which is of immense industrial importance due to its multipurpose use in food industry as flavour enhancer, in pharmaceutical industry as ingredients of aroma therapies and as anti-irritant, anti-inflammatory, antimicrobial compound combined with skin healing properties [18]. Alpha bisabolol not only inhibits bacterial growth but also increases the penetrance of other antimicrobial agents through the cell wall (cause leakage of DNA and protein contents) and increases the antibacterial effect synergistically acting with other bioactive secondary metabolites [36]. ...
... It has also been characterized as anti-Leishmania amazonensis and a potent agent to cope up with leishmaniasis [38]. Earlier bisabolol has been reported from Myoporum grassifolium, Matricaria chamomilla, Vanillosmopsis arborea, Eremanthus erythropappus, Salvia runcinata, Smyrniopsis aucheri [18,19,39]. It is the first time an endophytic fungi Colletotrichum alatae Antimicrobial activity against phytopathogens [40] LCS1 isolated from Lycopodium clavatum collected from an unpopular uncommon geographical place produced this essential oil in a good amount. ...
Article
Full-text available
Endophytes are silent microbial partners of green plants that ensure hosts' survival in odd conditions. They are known as the factories of multipotent metabolites with diverse bioactivities beneficial to modern pharmaceuticals industry. Endophytic fungi have been screened from a variety of plants and it is the first-time endophytes of club moss is being studied for production of antibacterial and antioxidative compounds. The present study reveals that Lycopodium clavatum L. harbors a potent niche of bioactive endophytic fungi and Colletotrichum alatae LCS1 was the prime producer of antibacterial and antioxidative compounds among them. The minimum inhibitory and bactericidal concentrations of ethyl- acetate culture extract ranged from 15.62 to 250 μg/mL against four Gram negative and three Gram positive microorganisms including methicillin resistant Staphylococcus aureus (ATCC-33591). Bio-autogram based screening followed by Gas chromatographic analysis confirmed the occurrence of 17 bioactive compounds and α-bisabolol is known to be the prime one. Alfa bisabolol is a unique and versatile bioactive essential oil and facilitates variety of functions. Killing kinetics data along with leakage of macromolecules into extracellular environment supports the cidal activity of the antibacterial principles at MBC values. Isolate C. alatae LCS1 was optimized by one variable at a time system coupled with response surface methodology for broad spectrum antibacterial production. The organism yielded maximum response (22.66±0.894 mm of zone of inhibition against MRSA) in 250 mL Erlenmeyer flask containing 50 mL potato dextrose broth supplemented with (g/L) glucose, 7.53; yeast extract concentration, 0.47; NaCl, 0.10 with medium pH 6.46; after 134 hours of incubation at 26°C. Optimized fermentation parameters enhanced antibacterial activity up-to more than 50% than the pre-optimized one (10.33±0.57 mm). Endophytic LCS1 was also efficient in free radical scavenging tested by DPPH, ABTS, H2O2 and FRAP assay with an IC50 values of 23.38±5.32 to 82.873±6.479 μg/mL.
... Essential oils with high potential free radical scavenging might be useful in the prevention of diseases like brain dysfunction, cancer, heart disease as well as immune system decline. Actually, the free radicals may induce a cellular attack, resulting in various disorders (Kamatou and Viljoen 2010). ...
... Essential oils with the crucial scavenging potential of free radicals can also additionally play a crucial position in a few disease prevention, inclusive of mind dysfunction, cancer, coronary heart disorder, and immune system decline. In fact, those sicknesses can also be an end result of cell harm resulting from free radicals (Kamatou and Viljoen 2010). It is generally known that phenols plus secondary metabolites containing conjugated double bonds normally have considerable antioxidant activity (Dhifi et al. 2016). ...
Article
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Purpose: Essential oils (EOs) obtained from spices, herbs and medicinal plants are well known in traditional medicine and are an area of interest due to their various biological activities. Therefore, present study investigate the chemical composition, phytochemical properties as well as the biological activity of EOs recovered from un-irradiated and irradiated (2.5, 5, and 10 kGy) caraway seeds. Materials and methods: Carum carvi L. seeds were irradiated with gamma irradiation at dose levels 2.5, 5, and 10 kGy, then EOs were recovered from all the samples. The chemical composition, phenols and flavonoids content were evaluated. As well as, antimicrobial and antitumor activities against the two cell lines [colorectal adenocarcinoma (Caco-2) and liver cancer (HepG-2)] were invistigated. Results: The results indicated the percentage of oil increased by radiation, especially at dose of 10 kGy, which gave the highest percentage (3.50%) compared to the control. Also, the Gas Chromatography/Mass Spectrometry (GC-MS) analysis revealed the presence of twenty six compounds in the essential oil extracts . The main constituent of caraway seeds EOs was Carvone followed by Limonene. According to the results, there was an increase in the content of phenols and flavonoids by using gamma rays compared with control, the maximum increase was observed at dose level 10 kGy (13.70 and 7.38 mg/g oil, respectively) followed by 5 kGy (11.20 and 5.86 mg/g oil, respectively). The antioxidant properties of the caraway essential oils were increased by increasing irradiation dose level (2.5 to 10 kGy) analyzed by DPPH radical and metal chelating activity. Caraway essential oils have an antimicrobial action against Gram positive and Gram negative bacteria as well as fungi. The antimicrobial activity was increased as irradiation dose raised and the10 kGy dose was more effective in suppressing the growth of bacteria and fungi. Aditionally, the caraway essential oils have anticancer activity against the two cell lines studied; colorectal adenocarcinoma (Caco-2) and liver cancer cell line (HepG-2) as reduced the cell viability and density. Conclusion: The 10 kGy dose was more effective for oil yield, phenols, flavonoids and antioxidant activity as well as antibacterial and antifungal activities. Furthermore, the caraway essential oils indicated anticancer activity against the two cell lines studied; colorectal adenocarcinoma (Caco-2) and liver cancer cell line (HepG-2) as reduced the cell viability and density. So caraway could be considered an important herb with multiple therapeutic uses.
... [30] reported that BIS suppressed inflammatory reactions and extracellular matrix degeneration in chondrocytes, as well as attenuating radiological and histopathological changes in the destabilization of the medial meniscus mouse osteoarthritis model, indicating the potential of BIS in arthritis therapy. In addition, BIS is already found in the formulation of various pharmaceutical products, including dermatological and cosmetic formulations [31,32], being classified by the US Food and Drug Administration as a substance that is Generally Regarded as Safe (GRAS) due to its low toxicity [32]. ...
... [30] reported that BIS suppressed inflammatory reactions and extracellular matrix degeneration in chondrocytes, as well as attenuating radiological and histopathological changes in the destabilization of the medial meniscus mouse osteoarthritis model, indicating the potential of BIS in arthritis therapy. In addition, BIS is already found in the formulation of various pharmaceutical products, including dermatological and cosmetic formulations [31,32], being classified by the US Food and Drug Administration as a substance that is Generally Regarded as Safe (GRAS) due to its low toxicity [32]. ...
Article
Inflammatory arthritis is the most prevalent chronic inflammatory disease worldwide. The pathology of the disease is characterized by increased inflammation and oxidative stress, which leads to chronic pain and functional loss in the joints. Conventional anti-arthritic drugs used to relieve pain and other arthritic symptoms often cause severe side effects. α-bisabolol (BIS) is a sesquiterpene that exhibits high anti-inflammatory potential and a significant antinociceptive effect. This study evaluates the anti-arthritic, anti-inflammatory and antihyperalgesic effects of BIS alone and in a β-cyclodextrin (βCD/BIS) inclusion complex in a CFA-induced arthritis model. Following the intra-articular administration of CFA, male mice were treated with vehicle, BIS and βCD/BIS (50 mg/kg, p.o.) or a positive control and pain-related behaviors, knee edema and inflammatory and oxidative parameters were evaluated on days 4, 11, 18 and/or 25. Ours findings shows that the oral administration of BIS and βCD/BIS significantly attenuated spontaneous pain-like behaviors, mechanical hyperalgesia, grip strength deficit and knee edema induced by repeated injections of CFA, reducing the joint pain and functional disability associated with arthritis. BIS and βCD/BIS also inhibited the generation of inflammatory and oxidative markers in the knee and blocked MAPK in the spinal cord. In addition, ours results also showed that the incorporation of BIS in cyclodextrin as a drug delivery system improved the pharmacological profile of this substance. Therefore, these results contribute to the pharmacological knowledge of BIS and demonstrated that this terpene appears to be able to mitigate deleterious symptoms of arthritis.
... It was reported that α-bisabolol increased the permeability coefficient of triamcinolone acetonide by 73-fold in human skin samples with respect to untreated skin [77]. This is likely due to its effect of increasing the lipid fluidity of SC, permitting the increase in diffusion rate across the skin barrier [77,78]. Dermocosmetics containing α-bisabolol have shown soothing effects and eczema associated-inflammation reduction as observed through reduced TEWL and improvement in SCORAD, TESS, ESS, and VAS scores [79][80][81][82][83][84]. ...
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Full-text available
Atopic dermatitis, the most common form of eczema, is a chronic, relapsing inflammatory skin condition that occurs with dry skin, persistent itching, and scaly lesions. This debilitating condition significantly compromises the patient’s quality of life due to the intractable itching and other associated factors such as disfigurement, sleeping disturbances, and social stigmatization from the visible lesions. The treatment mainstay of atopic dermatitis involves applying topical glucocorticosteroids and calcineurin inhibitors, combined with regular use of moisturizers. However, conventional treatments possess a certain degree of adverse effects, which raised concerns among the patients resulting in non-adherence to treatment. Hence, the modern use of moisturizers to improve barrier repair and function is of great value. One of the approaches includes incorporating bioactive ingredients with clinically proven therapeutic benefits into dermocosmetics emollient. The current evidence suggests that these dermocosmetics emollients aid in the improvement of the skin barrier and alleviate inflammation, pruritus and xerosis. We carried out a critical and comprehensive narrative review of the literature. Studies and trials focusing on moisturizers that include phytochemicals, natural moisturizing factors, essential fatty acids, endocannabinoids, and antioxidants were identified by searching electronic databases (PubMed and MEDLINE). We introduce the current knowledge on the roles of moisturizers in alleviating symptoms of atopic dermatitis. We then further summarize the science and rationale of the active ingredients in dermocosmetics and medical device emollients for treating atopic dermatitis. Finally, we highlight the limitations of the current evidence and future perspectives of cosmeceutical research on atopic dermatitis.
... When α-bisabolol was evaluated as a single component against a resistant strain of malaria, poor antiplasmodial activity was recorded. This result showed other compounds (either minor or major) are important in the biological activity of the oil and suggested that the activity of the crude oil is not always derived from its major constituent as generally speculated (Kamatou and Viljoen, 2010).While some researchers report 1,8-cineole, β-pinene, α-pinene, α-bisabolol, terpinen-4-ol and (Z)en-yne-dicycloether as dominant compounds of M. recutita (Raal et al., 2011;Farhoudi, 2012), they were found in a minor degree or not found in this research. On the other side, although an appreciable amount of EO was allocated to e-β-farnesene, it has been not reported as the main constitute by another one. ...
Chapter
Full-text available
Variations in the essential oil compositions of three species in Anthemidae from Iran under cultivated condition were studied. The oil yields ranged from 0.6 up to 0.805% using the GC-MS method. Significant qualitative and quantitative differences were observed among the studied species. The dominant constituents of the essential oils of the studied species were as follows, Anthemis tinctoria: α-eudesmol (13.6%), β-eudesmol (5.9%), camphor (5.2%), β-caryophyllene (5.1%) and 1,8-cineole (4.8%); Achille amillefolium: camphor (26.72%), borneol (18.88%), myrtenol (8.12%), E-nerolidol (7.25%) and 1,8-cineole (5.96%); Matricariarecutita: α-bisabolol oxide A (37.17%), e-β-farnesene (22.82%), chamazulene (13.77%), α-bisabolol oxide B (6.17%) and α-bisabolone oxide A (3.16%). The species just contained 5 common compounds (β-pinene, 1,8-cineole, camphor, borneol and spathulenol). The essential oil of A. tinctoria contained all of the valuable pharmaceutical compounds in a balanced quantity. So, it is expected that biological activity of A. tinctoriawill be ina normal range. In addition to, moderate tolerance of A. tinctoria to drought makes it a suitable candidate for cultivation in arid and semi-arid areas. Key words: Anthemis tinctoria, Achille amillefolium, Matricaria recutita, Essential oil and Therapeutic properties.
Chapter
This book provides an update on heterocyclic compounds that serve as key components of anti-cancer agents administered in pre-clinical settings. Many of the compounds highlighted in the book are being actively investigated for the bioactive properties against a range of cancer cell lines. There is potential for heterocyclic compounds to design agents that can target specific molecules to treat different types of cancers. Chapters are contributed by experts in pharmaceutical chemistry and are written to give a general overview of the topic to readers involved in all levels of research and decision-making in pharmaceutical chemistry and anti-cancer drug design. Part 1 of the book set covers these topics: - Heterocyclic anticancer compounds derived from natural sources with their mechanism of action - The role of terpenoids as anticancer compounds: an insight into prevention and treatment - Recent advances in synthesis and anticancer activity of benzothiazole hybrids as anticancer agents - Structure-activity relationship studies of novel hybrid quinoline and quinolone derivatives as anticancer agents - Tetrazoles: structure and activity relationship as anticancer agents - Progress in nitrogen and oxygen-based heterocyclic compounds for their anticancer activity: an update (2017-2020)
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The Red Sea is a rich ecosystem with thousands of species containing a variety of bioactive compounds that have potential pharmacological applications. This study will highlight the potential importance of sea urchins and jellyfish extracts. The gas chromatography-mass spectrometry (GC–MS) revealed many phenolic compounds in the extracts of the sea urchin (Diadema savignyi) and jellyfish (Aurelia aurita). The extracts were also tested for their potential radical scavenging activity as well as their safety and toxicity in vitro and in vivo. Both extracts showed significant total antioxidant capacity (P-value < 0.0001), and free radical scavenging activity (DPPH) compared to ascorbic acid and butylated hydroxyanisole (BHA, P-value < 0.0001). They were found to be safe in vitro and enhanced cell proliferation of fibroblast cells (L929) (P-value < 0.0001), and neuronal cell lines (neuroblastoma SH-SY5Y) (P-value < 0.0001). Intraperitoneal administration of both extracts did not show any significant morbidity within tested concentrations. Liver enzymes (ALT and AST) and renal functions showed no significant changes compared to control. No significant histological changes in the liver or kidney tissues were observed. The current study proved the safety of both sea urchins and jellyfish extracts in vitro and in vivo, which paves the way for further studies on the biomedical application of both extracts in areas of neuroprotection and cancer treatment.
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With these growing and evolving years, antimicrobial resistance has become a great subject of interest. The idea of using natural productive ways can be an effective measure against antimicrobial resistance. The growing prevalence of antimicrobial resistance indicates that advanced natural approaches are a topic of concern for fighting the resistance. Many natural products including essential oils, flavonoids, alkaloids and botanicals have been demonstrated as effective bactericidal agents. In this review, we will discuss in detail about the relevance of such natural products to tackle the problem of antimicrobial resistance, antibiotic adjuvants that aim towards non-essential bacterial targets to reduce the prevalence of resistant bacterial infections, latest bioinformatics approach towards antibacterial drug discovery along with an understanding of biogenic nanoparticles in antimicrobial activity.
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Essential oils and solvent extracts of E. brevifolia F.M and E. strickalndii M. were screened for their chemical composition, and biological activities. 39 compounds were identified in, E. brevifolia F. M. EOs, whereas 41 volatile compounds were identified in E. stricklandii M. EOs. The organic extracts were rich on polyphenols and tannins. The IC50 of the ME of E. stricklandii M. using DPPH· assay was 4.4 ± 0.2 μg/mL. Concerning AChE, the aqueous extract of E. brevifolia F.M. exhibited the highest IC50 value 10.0 ± 0.0 μg/mL. Regarding the anti-inflammatory capacity, E. brevifolia F.M. EOs and E. stricklandii M. ME showed the best IC50 (7.3 μg/mL and 9.7 μg/mL) against the inhibition of 15-LOX. Both plants exhibited a good activity against gram-negative bacteria. Finally, E. stricklandii M. ME was the best cytotoxic extract against HCT116 and K562 with IC50s of 18.0 ± 0.1 μg/mL and 1.8 ± 0.0 μg/mL.
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Twenty nature identical essential oil constituents from seven structural groups were tested for antimalarial, antimicrobial, antioxidant and toxicity properties. The compounds displayed antimalarial activity (IC50 values ranging from 0.9 to 1528.8 μM) with varying toxicity (IC50 values ranging from 5.5 to 1358.4 μM). The data indicates that (-)-pulegone, (E- & Z-)-(±)-nerolidol, linalyl acetate and (+)-α-pinene have the most potent antimalaial activity. Carvacrol (MIC values ranging from <1.66 to 13.3 mM) followed by geraniol (MIC values: 19.5-51.9 mM) displayed the broadest spectrum of antimicrobial activity. The least toxic of the tested compounds, eugenol, was the only compound with antioxidant activity comparable to ascorbic acid. The results demonstrate that the 20 compounds individually display variable biological activity, although further research is required to determine how they may interact when combined.
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In the search for alternative chemical control against Aedes aegypti L., many researches are developed and encouraged in order to find new insecticidal plant substances. In this work, the larvicidal effect of ten essential oils was tested on A. aegypti. The oils were extracted by steam distillation and their chemical composition determined by GL-chromatography coupled with mass spectroscopy. The essential oils were diluted in aqueous solutions of dimethyl sulfoxide with concentrations of: 100, 50, 10, and 1 mg/ml. The larvicidal activity, based on the percentage of larval mortality, was evaluated after 24h exposure to the treatments. The essential oil of Vanillosmopsis arborea Baker presented the highest larvicidal activity, with CL50 of 15.9 mg/ml and CL90 of 28.5 mg/ml. On the other hand the essential oil of O.gratissimum L. showed the lower activity with CL50 de 95,80 mg/ml and CL90 de 102,86 mg/ml.The results indicate that the tested essential oils, and particularly the V. arborea, are composed by substances with larvicidal properties for A. aegypti.
Book
Still considered the definitive work on medicinal herbs and their uses after two decades, the Handbook of Medicinal Herbs has undergone a long-anticipated revision. In the second edition, world-renowned ethnobotanist James A. Duke provides up-to-date data on over 800 of the world's most important medicinal plant species. The book contains more species, phytochemicals, proven indications, folk indications, and dosage data than the first edition in a new easier to use format. The in-depth content, the addition of color plates and over 200 black and white illustrations makes this book the most comprehensive resource on medicinal herbs available. NEW IN THE SECOND EDITION: • Over 100 color plates, 4 color maps • Over 200 black and white illustrations • Over 800 medicinal plants? more than twice as many as the previous edition organized alphabetically by common name • More herbs from the African, Ayurvedic, Chinese, and Jamu traditions EASY ACCESS TO INFORMATION YOU NEED Designed to give you fast access to the information you need on a regular basis, this new edition is organized more systematically than any other medicinal herb publication. The entries are now arranged alphabetically by common name with the scientific name in parenthesis. Major synonyms are also provided. • It has become increasingly clear that there are hundreds of biologically active compounds, often additive or synergistic, in all our plants, foods, spices, herbs, medicinal, and poisonous plants. The debate continues on how these plants work and how they should be used. Blending scientific fact with folk uses and the author's personal experience, Handbook of Medicinal Herbs, Second Edition provides the most well rounded discussions of safety, efficacy, toxicity, and rational use found in any herbal reference.
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There are two distinct types of chamomile, Roman and German. This article explains the differences between the two and looks at the medicinal uses of the plant.
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Aromatherapy utilises a number of essential oils in the treatment of certain inflammatory disorders. The mechanisms of inflammation involve complex cascades of events in which the metabolism of arachidonic acid, which begins by its oxidation by the enzyme 5-lipoxygenase, plays an important role. The prime objective of this study was to assess in vitro, the potential of essential oils, absolutes and natural or nature-identical chemicals to inhibit this enzyme. Thirty-two essential oils, 10 absolutes and 26 chemicals were screened. The results are reported and discussed.