ArticlePDF AvailableLiterature Review

The essential oil of turpentine and its major volatile fraction (α- and β-pinenes): A review

Authors:

Abstract and Figures

This paper provides a summary review of the major biological features concerning the essential oil of turpentine, its origin and use in traditional and modern medicine. More precisely, the safety of this volatile fraction to human health, and the medical, biological and environmental effects of the two major compounds of this fraction (alpha- and beta-pinenes) have been discussed.
Content may be subject to copyright.
IJOMEH 2009;22(4) 331
REVIEW PAPERS
International Journal of Occupational Medicine and Environmental Health 2009;22(4):331 342
DOI 10.2478/v10001-009-0032-5
THE ESSENTIAL OIL OF TURPENTINE
AND ITS MAJOR VOLATILE FRACTION
(α- AND β-PINENES): A REVIEW
BEATRICE MERCIER
1
, JOSIANE PROST
1
, and MICHEL PROST
2
1
Université de Bourgogne, Dijon, France
Faculté des Sciences de la Vie
2
Lara-Spiral SA, Couternon, France
Abstract
This paper provides a summary review of the major biological features concerning the essential oil of turpentine, its origin
and use in traditional and modern medicine. More precisely, the safety of this volatile fraction to human health, and the
medical, biological and environmental effects of the two major compounds of this fraction (α- and β-pinenes) have been
discussed.
Key words:

Received: July 1, 2009. Accepted : September 28, 2009.
Address reprint request to B. Mercier, UPRES EA 4183 “Lipides & Signalisation Cellulaire”, Faculté des Sciences de la Vie, Université de Bourgogne 6, Boulevard
Gabriel, F-21000 Dijon (e-mail: beamercier@laposte.net).
ORIGIN OF TURPENTINE
The term “essential oil of turpentine” designates the ter-
penic oil, obtained by hydrodistillation of the gem pine.
It is also named the “spirits of turpentine”, “pine tree
terpenic”, “pine oleoresin”, “gum turpentine”, “terpenes
oil” or “turpentine from Bordeaux”. Due to its pleasant
fragrance, the terpenic oil is used in the pharmaceuti-
cal industry, perfume industry, food additives and other
chemical industries (household cleaning products, paint-
ings, varnishes, rubber, insecticides, etc.) [1].
TRADITIONAL MEDICINE AND TURPENTINE
The eminent doctors of antiquity, Hippocrates, Dios-
coride or Galien, used the terpenic oil for its properties
against lung diseases and biliary lithiasis. In France, Thil-
lenius, Pitcairn, Récamier and Martinet recommended
it against the blennorrhoea and cystitis. Chaumeton,
Peschiez, Kennedi, Mérat prescribed it against the
neuralgias. It was also used in the treatment of rheuma-
tism, sciatica, nephritis, drop, constipation and mercury
salivation.
Those scientists also recognized that the terpenic oil may
be a booster at an average dose and may have a paralyz-
ing activity at high doses. In Germany, (Rowachol and
Rowatinex), Slovenia (Uroterp) and Poland (Terpichol
and Terpinex), the traditional drugs for renal and hepatic
diseases (especially against cholesterol stones in the gall
bladder and the bile duct) contain α- and β-pinenes [2].
Modern phytotherapy describes the following properties
of the terpenic oil: antiparasitic, analgesic, revulsive, dis-
infectant (external use); balsamic, active on bronchial se-
cretion and pulmonary and genito-urinary tract infections,
haemostatic, dissolving gallstones, diuretic, antispasmodic,
antirheumatic, deworming, being an antidote for poison-
ings caused by phosphorus [3] and improving the ciliary
and secretory activity in patients who present chronic ob-
structive bronchitis (internal use ) [4].
REVIEW PAPERS B. MERCIER ET AL.
IJOMEH 2009;22(4)332
action [8]. They also reduce cough and help cure respiratory
diseases, particularly chronic bronchitis or asthma [23].
Table 1. Summary of the properties of terpene oxides reported
in scientic literature
Oxidized terpenes
Relaxing smooth muscles
Acting as cough preservatives
Relieving congestion
Acting as anti-inammatory agents
Having disinfectant properties (bactericidal)
Increasing HbO2
Increasing O2 arterial partial pressure
Increasing O2 tissue diffusion
Increasing the redox system activity
Being water-soluble
ENVIRONMENTAL IMPACT OF THE VOLATILE
TURPENTINE FRACTION
The most volatile components of turpentine are two ter-
penes: alpha (α) and beta (β) pinenes. They are the domi-
nant odorous compounds emitted by trees, shrubs, owers
and grasses [25].
In the lower troposphere, and depending on the weather
conditions at the top of the trees, these compounds can re-
act with OH° radicals, ozone, NO
3
radical and O
2
. Indeed,
the electric eld in the canopy atmosphere (at the upper-
most level of the pine, r and spruce forests) is sufcient
to produce discharges, particularly in stormy weather, or
more generally, in wet weather, through which ozone (O
3
)
and hydrogen peroxides (H
2
O
2
[26]) are released. Ozone
also forms during sunny weather, particularly in the sum-
mer and autumn [27]. Reactions in both these conditions
result in the generation of aerosols in the ultrane par-
ticle form [28] as well as of peroxides (hydrogen peroxides
and organic peroxides), carbon monoxide (CO), acid rains
(starting from organic acids, of NO
3
and SO
4
2-
), ozone, or
oxidizing radicals, like the OH° radical.
Winterhalter et al. [29] showed that in the presence of
volatile organic compounds, such as NOx or OH° radicals,
At present, the Vidal drugs Compendium lists 14 dif-
ferent drugs containing turpentine as active molecules,
and 4 drugs containing turpentine as an excipient.
OXIDIZED TURPENTINE
Perfumes are, next to nickel, the most common allergic
substances in the world. This property is connected with
the fact that the majority of oils are sensitive to oxida-
tion [5]. However, in some oils, like in the Indian plant
Chaulmoogra [6] as well as in turpentine, the ageing/oxi-
dation contributes to the therapeutic effect of these com-
pounds, although they have the highest peroxide index of
all terpenes [7]. For example, old oxidized terpenes be-
come water-soluble (instead of lipid-soluble) and are able
to capture and deliver oxygen (the property known since
Berthelot’s studies [8]). Thus, they can enhance the satu-
ration rate of HbO
2
[9] or PaO
2
[10], which was conrmed
by Mercier et al. in their study on “Bol d’Air Jacquier
®
”,
a modern device using oxidized turpentine vapour to
combat cellular hypoxia [11,12]. Oxidized turpentine is
considered to be an anti-inammatory agent [13] and its
peroxidized form is thought to exhibit an antiradical ac-
tivity [12,14–18]. It seems to be a general trend that the
essential oils which contain monoterpene hydrocarbons,
oxygenated monoterpenes and/or sesquiterpenes have
a higher antioxidative potential [19].
At high concentrations or when combined with a second-
ary organic aerosol, these oxidized products may be pro-
inammatory [20] and cause weak or moderate irritation
with time [21]. However, acute and chronic toxicities in ex-
perimental animals (rat, rabbit) are low, and they refer to
higher doses than those envisaged for therapeutic purpos-
es [11]. It is interesting to underline that when administered
at low doses, they possess remarkable properties. Speci-
cally, they are used as relaxants of the smooth muscles of
the bronchi (“Ozothin”
®
) [22] as well as disinfectants and
bactericides [23]. They also decrease PpCO
2
in hypercap-
nic patients (in whom the treatment does not generate hy-
perventilation) and improve the redox system activity and
tissue diffusion [23], particularly when this substance is
administered as an aerosol [24] with a broncho-secretolytic
SPIRITS Of TuRPEnTInE: A REVIEW REVIEW PAPERS
IJOMEH 2009;22(4) 333
Alpha-pinenes
The effects of α-pinenes vary depending on the compo-
sition of monoterpenes and sesquiterpenes. Scientic re-
search is generally related to the whole compounds rather
than the molecular level because under natural conditions,
it is always a family of terpenes that the plant generates.
In addition, the biological effect is often due to a synergy
between the compounds [41]. This explains many contra-
dictions in the reported results: for example, α-pinenes are
the major components of the Amazonian plant Cordiaver-
benacea spp. (approximately 27%). This plant possesses
a remarkable effectiveness against Gram-positive bacteria
and yeasts, but not against Gram-negative species [42].
However, other studies report the antibacterial effect of
these terpenes on both Gram-negative and Gram-positive
bacteria as well as a strong antifungal activity [43].
The mechanism through which α- and β-pinenes are ac-
tive against yeast or bacteria lies mainly in their capacity to
induce toxic effects on the membrane structure and func-
tions [44]. We know that the cytoplasmic membranes of
bacteria and the mitochondrial membranes of yeast pro-
vide a barrier to the passage of small ions such as H
+
, K
+
,
Na
+
and Ca
2+
and allow the cells and organelles to control
the entry and exit of different compounds. This role of
the cell membranes as a permeability barrier is integral
to many cellular functions, including the maintenance of
the energy status of the cell, other membrane-coupled
energy transducing processes, solute transport, regulation
of metabolism, and control of turgor pressure [45]. Sik-
kema et al. [46] showed that due to their lipophilic charac-
ter, cyclic monoterpenes will preferentially partition from
an aqueous phase into membrane structures. This results
in membrane expansion, increased membrane uidity and
inhibition of a membrane-embedded enzyme. In yeast
cells and isolated mitochondria, α-pinenes and β-pinenes
destroy cellular integrity, inhibit respiration and ion trans-
port processes and increase membrane permeability [44].
More recently, Helander et al. [47] have described the
effects of different essential components on outer mem-
brane permeability in Gram-negative bacteria.
Thus, terpenes, containing the rst or the second largest
part of α-pinenes, ght against pathogenic bacteria and
α-pinenes undergo an ozonolysis and transform mainly to
acid products (cis-pinic, cis-pinonic and hydroxypinonic
acids). These acids can react with primary pollutants like
cyclohexene, propanol or formaldehyde [30] and, in gen-
eral, photocatalysors like anthracene or zinc oxide [31].
Beta-pinens can also generate organosulfates or nitroxy-
organosulfates [32]. Due to the presence of a double bond
between two atoms of carbon, the volatile monoterpenes
are very reactive. According to the authors cited above,
they could be the origin of secondary pollutants. Following
other researchers, they rather seem to be natural scaven-
gers of hazardous substances such as ozone [33].
Apart from the roles specied above, the volatile parts
of turpentine exhibit several other properties, like an al-
lelopathic activity [25]. Traumatic resinosis (mechanical
wounding, abiotic stress, insect attack, pathogen inva-
sion, elicitor molecules derived from fungal or plant cell
walls [34]) make the volatile fraction of turpentine acquire
insecticidal, acaricidal, “pesticidal” and/or insect repellent
properties, according to the type of predator. This fraction
plays a role in attracting pollinators [35]. The radical scav-he radical scav-
enging properties may contribute to the defense potential
of the plant against pests [36].

Volatile pinenes of turpentine enter the body through in-
halation but also through the skin, with a good correla-good correla-
tion between the level of contamination of particular body
parts and the potential body exposure [37]. The ability of
volatile pinenes to penetrate through the skin, the low ir-
ritancy potential and the inclusion in the list of the sub-
stances that are Generally Recognized as Safe (GRAS),
make it possible to use them as a support to increase the
absorption of various chemicals. They are used, for exam-
ple, for enhanced neuroleptic drug absorption [38]. The
mechanisms responsible for enhancing the percutaneous
activity of terpenes have been explained elsewhere [39].
The turpentine respiratory sessions considerably increase
the capacity of the organism to transform the xenobiotics at
the hepatic level, by increasing the activity of the NADPH
cytochrome C reductase and the 7-ethoxycoumarine
de-ethylase [40].
REVIEW PAPERS B. MERCIER ET AL.
IJOMEH 2009;22(4)334
not on the healthy cells like the red blood cells [12,18] or
whole organisms [12,25]. Mercier [12] demonstrated that
the peroxidizing α- and β-pinenes decrease the antiradi-
cal capacity of abnormal Jurkat cells. For Diaz et al. [56],
the α- and β-pinenes were cytotoxic on several cell lines
(breast cancer and leukemic cell lines). Zhou et al. [57]
reported that α-pinenes are especially involved in the
inhibition of the human monocyte factor NF-α. On the
other hand, Lampronti et al. [58] did not note an anti-
tumor effect of the α- or β-pinenes alone. They did not
exclude a possible synergistic effect with other monot-
erpenes, or sesquiterpenes like caryophyllene. All these
studies provide further insight into the potential use
of terpenes or a mixture of terpenes as the inducers of
apoptosis in cancer cells.
Terpenes are also antioxidants [12], but Grass-
mann et al. [59] postulated that this antioxidant activity
is effective only in a lipophilic environment. These com-
pounds also possess anti-inammatory properties [60]
and exert spasmolytic and myorelaxant activity on the
smooth muscles of the intestine [61]. These effects may
explain their traditional use in the German and Polish
traditional drugs for colic, diarrhea, cough and asthma.
This antispasmodic activity would be due to the inhibi-
tion of the calcium channels. They also exhibit antinoci-
ceptive and antistress activity in rats [62]. However, the
activity of α-pinenes was observed only at low doses. At
higher doses, their activity referred to a number of neu-
rological mechanisms regulating the cardiac function,
which were activated or not, depending on the level of
pinenes in the organism. From these ndings, there de-
rives a hypothesis of a different and pinene dose-depen-
dent neurological response mechanism of the cardiac
function.
As reported by Umezu et al. [63], experiments on mice in-
dicated that the antistress property was reserved for other
monoterpenes. However, they could not exclude a syner-
gistic effect between all the components of the essential oil
of lavender which was tested.
We also observed a regeneration of the β cells of the islets
of Langerhans in the pancreas, resulting in the decrease of
glycaemia, in a study investigating Nigella sativa L., a plant
all kinds of fungi. They are able to eliminate the micro-
organisms or inhibit their growth as well as intervene on
their metabolism (for example, by preventing methane
oxidation in the bacterium Methylobacter luteus [48]).
They form an essential oil which is particularly effective
on Gram-positive bacteria, including Clostridium perfrin-
gens, C. sporogenes, Staphyllococcus aureus [36] and S. epi-
dermis [49].
Alpha-pinenes constitute a large part of the active solu-
tions used against the Gram-negative bacteria, particu-
larly on the strains responsible for jaw infections, paro-
dontitis or periodontitis (Actinobacillus actinomycetem-
comitans, Prevotella intermedia, Porphylomonas gingivalis,
Fusobacterium nucleatum [50], Yersinia enterocolitica [36],
Salmonella typhi [36], Proteus vulgaris [36,43], and Aceto-
bacter spp. [36]. On the other hand, the results obtained for
α-pinenes used to destroy Escherichia coli vary undoubt-
edly, depending on the bacterial strain (there exist the
pathogenic and non-pathogenic strains) or on a possible
synergy with other monoterpens. Pichette et al. [49] dem-
onstrated the inefcacy of α-pinenes; Magwa et al. [36]
and Cha et al. [50] showed otherwise.
Moreover, α-pinenes are used against mushrooms and
yeasts (dermatophytes [44]), especially on Candida albi-
cans [36] and other related species such as Candida tropi-
calis, C. glabrata [60], Aspergillus spp. [36], Cryptococcus
neoformans [43], Penicillium notatum [36], etc.
Finally, α-pinenes also act as insecticides, especially on
mosquitoes like Culex pipiens causing paludism, and Nile
fever vector [34], or on dengue’s vector Aedes aegypti [51].
They act on the eggs of Pediculus humanis capitis, and
against the female cockroaches, even if their effectiveness
is lower than that of β-pinenes [52]. From another point of
view, α-pinenes appear to have an inhibitory effect against
Pityogenes bidentatus, or bark beetle [53].
In addition to their high effectiveness in controlling vectors
of various diseases and parasites of all kinds, α-pinenes
also exhibit certain biological effects: pre-treatment with
α-pinenes decreases the hexobarbital sleep time of fe-
male rats by inducing microsomal enzyme activity [54].
They are inhibitors in breast cancer, and in vitro present
cytotoxic activity against human cancer cells [12,55], but
SPIRITS Of TuRPEnTInE: A REVIEW REVIEW PAPERS
IJOMEH 2009;22(4) 335
Beta-pinenes
According to literature reports, β-pinenes generally ac-
company α-pinenes in low quantities in the volatile ex-
tracts, essential oleoresins and oils, i.e. all the pine extracts
which were tested for their biological properties. Some
specic studies show that β-pinenes, along with α-pinenes
and other terpenes, are cytotoxic on cancer cells [55]. They
represent a great part of essential oils with sedative prop-
erties [66]. When α- and β-pinenes are the major constitu-
ents of an essential oil, they warrant the anti-inammatory
and analgesic activity [67].
The β-pinenes also show antifungal properties [68], es-
pecially on Candida spp. [36]. When acting on yeast,
they were found to inhibit mitochondrial respiration, the
proton pump activity and K+ transport, and to increase
membrane uidity [69]. They also exhibit pest-destroying
properties against the protozoon Plasmodium berghei (ma-
laria vector [70]), insecticidal properties against lice [71]
and the mosquito Aedes aegypti [51] as well as an antiseptic
effect on oral bacterial ora [50]. In general, they exert
a considerable antibacterial effect, especially on a methi-
cilline-resistant S. aureus and other Gram-positive and
Gram-negative bacteria [43].
Without α-pinenes, but with other terpenes, β-pinenes
present antiradical activity (DPPH system [72] and elimi-
nation of the superoxide anion [73]). They belong to the
essential oils used against the osteoclast activity (they thus
play a protective role against osteoporosis [74]).
Beta-pinenes, when administered alone, exhibit moder-
ate antimicrobial activity [68]; they are sometimes inef-
fective on specic strains like Pseudomonas spp. [75].
As the major or important components of essential oils,
they are particularly powerful on fungus, like Tricoder-
ma spp. [76]. Takikawa et al. [77] showed that β-pinenes
acted on a pathogenic strain of Escherichia coli, but this
activity is less pronounced against the non-pathogenic
strains. Besides, β-pinenes show an insecticidal activity
against the third larval stage of the y Musca domes-
tica [78]. In a synergistic activity with other terpenes,
they act against the fruit y, Bemisia argentifolii [79]. In
competition with α-pinenes, they seem more active as
antifungal agents (on Fusarium culmorum, F. solani and
containing α-pinenes [63]. Mercier [12] showed in in vivo
and ex vivo studies a decrease in the rate of glycated hae-
moglobin after inhalation of oxidised turpentine vapours.
Some studies investigating the effect of various terpenes,
including α-pinenes, documented that the level of induced
CYP2B, as measured by immunoassay, increased several
times. Furthermore, CYP2B activity increased when labo-
ratory rats were given an oral dose of α-pinene [64]. There
is no evidence for induction of CYP3A with α-pinene [65].
Several essential oils are used for their memory-enhanc-
ing effects in the European folk medicine. Among the
components, α-pinenes were found to inhibit AChE
in an uncompetitive and reversible manner when they
acted synergistically. They were responsible for the in-
hibitory effect of the essential oil of the Salvia species.
Thus, when in synergy with other compounds, they could
be benecial in the treatment of cognitive impairments,
due to their multifarious activities related to Alzheimer’s
disease [65].
It has also been shown that α-pinenes do not exhibit an
oestrogenic activity [60] or a behavioural effect [63].
Table 2. Summary of the properties of α-pinenes,
alone or in synergy with other pinenes, reported
in scientic litterature
α-pinenes
Lipophilic
Bactericidal
Fungicidal
Insecticidal
Pesticidal
Anticarcinogenic (cytotoxic on cancer cells)
Diuretic
Antioxidant
Immunostimulant
Anti-inammatory
Anti-convulsive
Sedative
Anti-stress
Hypoglycaemic
Capable of expelling xenobiotics
Anticholinesterase activity
REVIEW PAPERS B. MERCIER ET AL.
IJOMEH 2009;22(4)336
turpentine. Likewise, 14 other people were cured of ec-
zema by using turpentine without δ-3-carene (cases ob-
served between 1967 and 1969 in Strasbourg).
In fact, the greatest danger related to turpentine use seem
to be the δ-3-carenes, a variety of terpenes.These chemical
compounds were at the origin of dermatitis and respira-
tory problems as they induced broncho-constriction [87],
and there is a dose-dependent relationship between the
viability of alveolar macrophages and the concentration
of δ-3-carenes. They appear to have provoked a stronger
reaction than did α-pinenes [88].
For the α- and β-pinenes (the main volatiles monoter-
penes), many authors have a moderate opinion regarding
their irritant capacity. First of all, a signicant quantity is
needed for the product to produce adverse health effects:
as reported by Menezes et al. [89], the toxic effect for the
mice starts at 5 g/kg. Kasanen et al. [90] postulated that
it is highly unlikely that monoterpenes alone can cause
irritation under normal conditions (“all pinenes possess
sensory irritation properties and also induced sedation
and sign of anaesthesia but had no pulmonary irritation
effects”). Fransman et al. [91] observed that the respira-
tory problems referring to laminated wood workers were
associated with the presence of formaldehyde among all
the agents that these people inhaled at work (dust, bacte-
rial endotoxins, abietic acid, formaldehyde and terpenes).
Dutkiewicz et al. [92] found out that dermatitis among
Polish workers resembled that characteristic of exposure
to oak and pine wood dusts, and concluded that the pres-
ence of this pathology was due to dust inhalation rather
that the composition of these dusts.
Thus, to paraphrase Paracelse, “Sola dosis facit vene-
num”, which translates as “the dose makes the poison”.
The rate of irritation from terpene exposure correlates
with exposure level. Accordingly, monoterpenes become
pro-oxidants at higher doses [93]. At a low dose, they are
included in the composition of pharmaceuticals used for
the kidney and liver disorders [2]. At high-level exposure,
they are hepato- and nephrotoxic. They can also cause
nervous system disorders (convulsions, disorders of bal-
ance [26]).
F. poae, fungal phytopathogens [80]) and as inhibitors
of Brassica campestris germination (colza), in a dose-
dependant manner [81]. Beta-pinenes showed a better
effectiveness than did α-pinenes in ghting against cock-
roaches [82].
In addition, the compounds are active on the smooth mus-
cles of the ileum part of rat intestine. They act by inhibit-
ing the 5-HT3 receptors of the serotoninergic system of
the murine intestinal cells [83].
In rats, β-pinenes exert an antinoxious effect on the supra
spinal parts, but not on the spinal cord itself [28].
Table 3. Summary of the properties of β-pinenes,
alone or in synergy with other pinenes, reported
in scientic literature
β-pinènes
Lipophilic
Bactericidal
Fungicidal
Insecticidal
Acting against osteoclasts
Anticarcinogenic (cytotoxic on cancer cells)
Pesticidal
Antioxidant
Sedative
Harmlessness of the turpentine vapours
Some turpentine varieties, especially those originating
from the Scandinavian countries, Switzerland, Germany
or Italy, generate various types of allergies. Monoterpenes
are released in the form of gas during the sawing and pro-
cessing of fresh wood. They pose a potential health hazard
for workers at sawmills [84]. They cause irritation to the
skin, eyes and mucous membrane. They may be associated
with the development of contact dermatitis (allergic or
non-allergic) [85].
Turpentine inhalation increased resistance of the upper
airways and induced chronic irritation, but did not gener-
ate acute respiratory problems [86].
Foussereau [85] observed 12 cases of eczema following
the use of the Swedish turpentine instead of the French
SPIRITS Of TuRPEnTInE: A REVIEW REVIEW PAPERS
IJOMEH 2009;22(4) 337
The transformation from a “terpene” form to a “terpin-
eol” form also means new biological properties. The new
molecules exhibit the following biological activities: the
cis-verbenol is an antioxidant [9], it prevents the resorp-
tion of osteoclasts, thus having a positive effect on osteo-
porosis (the α-pinenes do not possess this property [74]),
and it is active against Escherichia coli, Staphylococcus
aureus, and Bacillus subtilis [36].
IN VIVO
Filipsson [97] reported that approximately 66% of
β-pinenes are eliminated in blood (two-hour inhalation of
turpentine solution at the rate of 450 mg/m
3
) and that their
half-life in blood is approximately 25 hours (their rate of
elimination is higher than that of α-pinenes). The evolu-
tion scheme of β-pinenes is displayed in Figure 2 [98]. The
hydroxylated products also exhibit new biological proper-
ties. For example, the α-terpineol exerts an anti-inam-
matory activity by reducing the rate of TNF α, interleukins
IL-1β, IL-8, IL-10 and prostaglandins E2 (α-terpineol is
the major component of the essential oil of the tea tree
Melaleuca alternifolia [100]).
CONCLUSION
The essential oil of turpentine and its two major volatile
compounds are natural products, which pose no hazard
when used in small quantities. They have a number of
properties that are benecial to human health and wellbe-
ing and may be used in the pharmaceutical and cosmetic
industries. The major characteristics of these compounds
are summarized in Figure 3.
IN VIVO
The in vivo oxygenated derivatives of terpenes are ter-
pineols, which have been used for centuries in the tradi-
tional medicine and perfumery. Currently, there are more
than 22 000 terpineols known for their biological proper-
ties such as antioxidative activity, inuence on immune
functions, and anticancer potential [94].
Scientic studies, especially those of the Scandinavian
researchers, made it possible to identify the absorption
pathways of these monoterpenes in the body. As re-
ported by Falk et al. [95], approximately 60% of the
inhaled α-pinenes are eliminated in blood and show
a high afnity with fat tissue. They are also elimi-
nated through the lungs (8%) and to a lesser degree
(0.001%) through the kidneys [96]. Filipsson [97], in
his report on a two-hour inhalation of turpentine so-
lution at the rate of 450 mg/m
3
,
demonstrated that
α-pinenes are eliminated in exhaled air (3% to 5%)
and that their half-life (clearance) in blood is approxi-
mately 32 hours. The remaining part is metabolized by
hydration and hydroxylation (this degradation is uni-
versal, from bacteria to mammals). These reactions
take place at the hepatic cells level, and especially at
the P
450
cytochrome level [98]. The metabolites are ex-
creted in urine [19,20,96,97].
Also known is the transformation of α-pinenes into li-
monene, myrtenol, oxidized α-pinene and pinocarveol
(List of All UM-BBD Biotransformation Rules, Min-
nesota University, USA). The process is widespread in
the entire world, starting from fungus to vegetal cells
or bacteria. In mammals, the most common chemical
evolution of α-pinenes is their hydroxylation to ver-
benol (C10H16O), and, also to myrtenol and myrtenic
acid [98,99] (Fig. 1).
Fig. 1. Alpha-pinene evolution in mammals [98].
Fig. 2. Beta-pinene evolution in mammals [98].
REVIEW PAPERS B. MERCIER ET AL.
IJOMEH 2009;22(4)338
4. Dorow P, Weiss T, Felix R, Schmutzler H. Effect of a secre-
tolytic and a combination of pinene, limonene and cineole
on mucociliary clearance in patients with chronic obstruc-
tive pulmonary disease. Arzneimittelforschung 1987;37(12):
1378–81.
5. Karlberg AT, Bergström MA, Börje A, Luthman K, Nils-
son JL. Allergic contact dermatitis — formation, structural re-
quirements, and reactivity of skin sensitizers. Chem Res Toxi-Chem Res Toxi-
col 2008 Jan;21(1):53–69.
6. Lefèvre R, Baranger P. Peroxides and polyphenol derivatives
in the treatment of cancer. G Ital Chemioter 1956;3(3–4):
397–407 [in French].
7. Chapard C. Chemical and analytical study of some oxidized
terpenic gasolines. Physicochemical control of the drugs which
derive from it [dissertation]. Bordeaux: Universite de Bor-
deaux; 1971 [in French].
8. Kleinschmidt J, Römmelt H, Zuber A. The pharmacokinetics
of the bronchosecretolytic ozothin after intravenous injection.
Int J Clin Pharmacol Ther Toxicol 1985;23(4):200–3.
9. Grimm W, Gries H. Researchers about terpineol allergies.
Berufsdermatosen 1967;15:253–69 [in German].
10. Bohe MG. New studies on the autoxidation of α-pinene. Essenze
Deriv Agrum 1983;53:492–500.
11. Jacquier R. From atom to life — cancers and diseases. Paris:
Ed. Amphora; 1981 [in French].
12. Mercier B. Evaluation of biological and antiradical effects
of peroxidizing terpenes [dissertation] Dijon: Université de
Bourgogne [in French].
13. Stolz E. Investigations of the surface-active lm in the lung
alveoli reaction after the inhalation of ethereal oils. Med
Welt 1976;27:1107–9 [in German].
14. Mercier B., Prost J. Impact of Bol d’Air Jacquier®) on oxygen-
ation of mammals [poster]. Forum des Jeunes Chercheurs
2008, Besançon, France [in French].
15. Mercier B, Prost J. Impact of Bol d’Air Jacquier® on cell
antiradical capacity [poster]. Forum des Jeunes Chercheurs
2006, Besançon, France [in French].
16. Mercier B, Prost J. Antioxidant activity of Bol d’Air Jacqui-
er® Breathing Sessions in Wistar rats [oral communication].
Forum des Jeunes Chercheurs 2007, Dijon, France [in
French].
ACKNOWLEDGEMENTS
Béatrice Mercier’s research has been nanced by the Holiste
Laboratory & Development (Le Port F-71110 Artaix). Several
people at this Laboratory have been instrumental in enabling
this project to be completed. We would like to thank Madame
Marie-Laure Delanef, the General Manager of the Holiste Lab-
oratory, and especially Isaac Masih and Ewa Brejnakowska for
rereading the article.
REFERENCES
1. International Flavors & Fragrances Inc. α and β pinene. Avail-Avail-
able from: URL: http://www.iff.com/Ingredients.nsf/0/9B9B9
B1AD927E71B852569910065EDF1.
2. Sybilska D, Kowalczyk J, Asztemborska M, Ochocka RJ,
Lamparczyk H. Chromatographic studies of the enantio-
meric composition of some therapeutic compositions applied
in the treatment of liver and kidney diseases. J Chromatogr
A 1994;665(1):67–73.
3. Valnet J. Phytotherapy: treatment of diseases by plants. Paris: Le
Livre de Poche; 1983. [in French].
Fig. 3. Origin, impact and elimination of the essential oil of
turpentine and its two main volatile components.
SPIRITS Of TuRPEnTInE: A REVIEW REVIEW PAPERS
IJOMEH 2009;22(4) 339
of Eucalyptus camaldulensis leaves, in rodents. Planta
Med 2007;73(12):1247–54.
29. Winterhalter R, Van Dingenen R, Larsen BR, Jensen NR,
Hjorth J. LC-MS analysis of aerosol particles from the oxida-
tion of α-pinene by ozone and OH-radicals. Atmos Chem Phys
Discuss 2003;3:1–39.
30. Docherty KS, Wu W, Lim YB, Ziemann PJ. Contributions of
organic peroxides to secondary aerosol formed from reactions of
monoterpenes with O3. Environ Sci Technol 39(11):4049–59.
31. Chiron F, Chalchat JC, Garry RP, Pilichowski JF, Lacoste J.
Photochemical hydroperoxidation of terpenes. I. Synthesis and
characterization of α-pinene, α-pinene and limonene hydroper-
oxides. J Photochem Photobiol A: Chem 1997;111(1–3):
75–86.
32. Iinuma Y, Müller C, Berndt T, Böge O, Claeys M, Her-
rmann H. Evidence for the existence of organosulfates from
β-pinene ozonolysis in ambient secondary organic aerosol.
Environ Sci Technol 2007;41(19):6678–83.
33. Keinan E, Alt A, Amir G, Bentur L, Bibi H, Shoseyov D.
Natural ozone scavenger prevents asthma in sensitized rats.
Bioorg Med Chem 2005;13(2):557–62.
34. McKay SA, Hunter WL, Godard KA, Wang SX, Martin DM,
Bohlmann J, et al. Insect attack and wounding induce trau-
matic resin duct development and gene expression of (-)-pinene
synthase in Sitka spruce. Plant Physiol 2003;133(1):368–78.
35. Jaenson TG, Pålsson K, Borg-Karlson AK. Evaluation
of extracts and oils of mosquito (Diptera: Culicidae) repel-
lent plants from Sweden and Guinea-Bissau. J Med Ento-
mol 2006;43(1):113–9.
36. Magwa ML, Gundidza M, Gweru N, Humphrey G. Chemi-
cal composition and biological activities of essential oil from
the leaves of Sesuvium portulacastrum. J Ethnopharma-
col 2006;103(1):85–9.
37. Eriksson K, Wiklund L. Dermal exposure to monoterpenes
during wood work. J Environ Monit 2004;6(6):563–8.
38. Almirall M, Montana J, Escribano E, Obach R, Ber rozpe JD.
Effect of d-limonene, α-pinene and cineole on in vitro transder-
mal human skin penetration of chlorpromazine and haloperi-
dol. Arzneimittelforschung 1996;46(7):676–80.
39. Sapra B, Jain S, Tiwary AK. Percutaneous permeation en-
hancement by terpenes: mechanistic view. AAPS J 2008;10(1):
120–32.
17. Mercier B, Prost J. Evaluation of the antiradical status by
urine analysis of Bol d’Air Jacquier® breathing sessions in
rats [oral communication]. Forum des Jeunes Chercheurs
2008, Besançon, France [in French].
18. Mercier B, Prost J, Prost M. Antioxidant Activity of Bol d’Air
Jacquier® Breathing Sessions in Wistar Rats — First Stud-
ies. Int J Occup Med Environ Health 2008;21(1):31–46.
DOI 10.2478/v10001-008-0003-2
19. Tepe B, Donmez E, Unlu M, Candan F, Daferera D, Vard-
ar-Unlu G, et al. Antibacterial and antioxidative activities of
the essential oils and methanol extracts of Salvia cryptantha
(Montbret et Aucher ex (Benth.) and Salvia multicaulis (Vahl).
Food Chemistry 2004;84:519–25.
20. Jang M, Ghio AJ, Cao G. Exposure of BEAS-2B cells to
secondary organic aerosol coated on magnetic nanoparticles.
Chem Res Toxicol 2006;19(8):1044–50.
21. Rohr AC, Wilkins CK, Clausen PA, Hammer M, Nielsen GD,
Wolkoff P, et al. Upper airway and pulmonary effects of oxida-
tion products of (+)-α-pinene, d-limonene, and isoprene in
BALB/c mice. Inhal Toxicol 2002;14(7):663–84.
22. Bermudez J, Burgess MF, Cassidy F, Clarke GD. Activity of
the oxidation products of oleum terebenthinae “Landes” on
guinea pig airway smooth muscle in vivo and in vitro. Arzneim-
Forrsch (Drug Res) 1987;37(11):1258–62.
23. Bourgine P. Therapeutic effects of oxidised terpenes in respira-
tory pathologies. M.M. 1977;138:59–62 [in French].
24. INRS. Turpentine oil. Fiche toxicologique 132, 1987
et 2000 [in French].
25. Ennifar S, Ferbach S, Kraut C, Rolli H. Physiological and
pharmacological properties of monoterpenes.Strasbourg:
Université Pasteur; 2001 [in French].
26. Borra JP, Roos RA, Renard D, Lazar H, Golman A, Gold-
man M. Electrical and chemical consequences of point dis-
charges in a forest during a mist and a thunderstorm. J Phys D
Appl Phys 1997;30:84–93.
27. Utiyama M, Fukuyama T, Maruo YY, Ichino T, Izumi K,
Hara H, et al. Formation and Deposition of Ozone in a Red
Pine Forest. Water Air Soil Pollut 2004;151(1–4):53–70.
DOI 10.1023/B:WATE.0000009891.12108.b9.
28. Liapi C, Anifantis G, Chinou I, Kourounakis AP, Theo-
dosopoulos S, Galanopoulou P. Antinociceptive proper-
ties of 1,8-Cineole and β-pinene, from the essential oil
REVIEW PAPERS B. MERCIER ET AL.
IJOMEH 2009;22(4)340
40. Jarvisalo J, Vainio H. Enhancement of hepatic drug biotrans-
formation by a short-term intermittent turpentine exposure in
the rat. Acta Pharmacol Toxicol (Copenh) 1980;46(1):32–6.
41. Sonboli A, Babakhani B, Mehrabian AR. Antimicrobial ac-
tivity of six constituents of essential oil from Salvia. Z Natur-
forsch [C] 2006;61(3–4):160–4.
42. de Carvalho PM Jr, Rodrigues RF, Sawaya AC, Marques MO,
Shimizu MT. Chemical composition and antimicrobial activity
of the essential oil of Cordiaverbenacea D.C. J Ethnopharma-
col 2004;95(2–3):297–301.
43. Martins AP, Salgueiro LR, Goncalves MJ, Proenca da
Cunha A, Vila R, Canigueral S. Essential oil composition
and antimicrobial activity of Santiria trimera bark. Planta
Med 2003;69(1):77–9.
44. Andrews RE, Parks LW, Spence KD. Some Effects of Douglas
Fir Terpenes on Certain Microorganisms. Appl Environ Mi-
crobiol 1980;40(2):301–4.
45. Trumpower BL, Gennis RB. Energy transduction by cyto-
chrome complexes in mitochondrial and bacterial respiration:
the enzymology of coupling electron transfer reactions to trans-
membrane proton translocation. Annual Reviews in Biochem-
istry 1994;63:675–716.
46. Sikkema J, de Bont JAM, Poolman B. Interactions of cy-
clic hydrocarbons with biological membranes. J J Biol Chem
1994;269:8022–8.
47. Helander IM, Alakomi HL, Kyosti LK, Mattiala-andholm T,
Pol I, Smid EJ, et al. Characterization of the action of selected
essential oil components on Gram-negative bacteria. J Agric
Food Chem 1998;46:3590–5.
48. Alma MH, Nitz S, Kollmannsberger H, Digrak M, Efe FT,
Yilmaz N. Chemical composition and antimicrobial activity of
the essential oils from the gum of Turkish pistachio (Pistacia
vera L.). J Agric Food Chem 2004;52(12):3911–4.
49. Pichette A, Larouche PL, Lebrun M, Legault J. Composition
and antibacterial activity of Abies balsamea essential oil. Phy-
tother Res 2006;20(5):371–3.
50. Cha JD, Jeong MR, Jeong SI, Moon SE, Kil BS, Yun SI, et al.
Chemical composition and antimicrobial activity of the essen-
tial oil of Cryptomeria japonica. Phytother Res 2007;21(3):
295–9.
51. Lucia A, Gonzalez Audino P, Seccacini E, Licastro S, Zerba E,
Masuh H. Larvicidal effect of Eucalyptus grandis essential oil
and turpentine and their major components on Aedes aegypti
larvae. J Am Mosq Control Assoc 2007;23(3):299–303.
52. Jung WC, Jang YS, Hieu TT, Lee CK, Ahn YJ. Toxicity of
Myristica fagrans seed compounds against Blattella germani-
ca (Dictyoptera: Blattellidae). J Med Entomol 2007;44(3):
524–9.
53. Byers JA, Zhang QH, Birgersson G. Strategies of a bark bee-
tle, Pityogenes bidentatus, in an olfactory landscape. Naturwis-
senschaften 2000;87:503–7.
54. Pap A, Szarvas F. Effect of α-pinene on the mixed function
of microsomal oxidase system in the rat. Acta Med Acad Sci
Hung 1976;33(4):379–85.
55. Setzer WN, Setzer MC, Moriarity DM, Bates RB, Ha-
ber WA. Biological activity of the essential oil of Myrcian-
thes sp. nov. „black fruit“ from Monteverde, Costa Rica. Planta
Med 1999;65(5):468–9.
56. Díaz C, Quesada S, Brenes O, Aguilar G, Cicció JF. Chemi-
cal composition of Schinus molle essential oil and its cyto-
toxic activity on tumour cell lines. Nat Prod Res 2008;22(17):
1521–34.
57. Zhou J Y, Tang FD, Mao GG, Bian RL. Effect of α-pinene
on nuclear translocation of NF-kappa B in THP-1 cells. Acta
Pharmacol Sin 2004;25(4):480–4.
58. Lampronti I, Saab AM, Gambari R. Antiproliferative activity
of essential oils derived from plants belonging to the Magnolio-
phyta division. Int J Oncol 2006;29(4):989–95.
59. Grassmann J, Hippeli S, Vollmann R, Elstner EF. Antioxi-
dative properties of the essential oil from Pinus mugo. J Agric
Food Chem 2003;51(26):7576–82.
60. Perry NS, Houghton PJ, Sampson J, Theobald AE, Hart S,
Lis-Balchin M, et al. In-vitro activity of S. lavandulaefolia
(Spanish sage) relevant to treatment of Alzheimer’s disease.
J Pharm Pharmacol 2001;53(10):1347–56.
61. Camara CC, Nascimento NR, Macedo-Filho CL, Almei-
da FB, Fonteles MC. Antispasmodic Effect of the Essential
Oil of Plectranthus barbatus and some Major Constituents on
the Guinea-Pig Ileum. Planta Med 2003;69(12):1080–5.
62. González-Trujano ME, Peña EI, Martínez AL, Moreno J,
Guevara-Fefer P, Déciga-Campos M, et al. Evaluation of the
antinociceptive effect of Rosmarinus ofcinalis L. using three
different experimental models in rodents. J Ethnopharma-
col 2007;111(3):476–82.
SPIRITS Of TuRPEnTInE: A REVIEW REVIEW PAPERS
IJOMEH 2009;22(4) 341
74. Mühlbauer RC, Lozano A, Palacio S, Reinli A, Felix R. Com-
mon herbs, essential oils, and monoterpenes potently modulate
bone metabolism. Bone 2003;32(4):372–80.
75. Iacobellis NS, Lo Cantore P, Capasso F, Senatore F. Antibac-
terial activity of Cuminum cyminum L. and Carum carvi L.
essential oils. J Agric Food Chem 2005;53(1):57–61.
76. Joy B, Rajan A, Abraham E. Antimicrobial activity and chem-
ical composition of essential oil from Hedychium coronarium.
Phytother Res 2007;21(5):439–43.
77. Takikawa A, Abe K, Yamamoto M, Ishimaru S, Yasui M,
Okubo Y, et al. Antimicrobial activity of nutmeg against Es-
cherichia coli O157. J Biosci Bioeng 2002;94(4):315–20.
78. Abdel-Hady NM, Abdei-Halim AS, Al-Ghadban AM.
Chemical composition and insecticidal activity of the volatile
oils of leaves and owers of Lantana camara L. cultivated in
Egypt. J Egypt Soc Parasitol 2005;35(2):687–98.
79. De Andrade IL, Bezerra JN, Lima MA, de Faria RA,
Lima MA, Andrade-Neto M, et al. Chemical composition
and insecticidal activity of essential oils from Vanillosmop-
sis pohlii baker against Bemisia argentifolii. J Agric Food
Chem 2004;52(19):5879–81.
80. Krauze-Baranowska M, Mardarowicz M, Wiwart M,
Pobłocka L, Dynowska M. Antifungal activity of the essen-
tial oils from some species of the genus Pinus. Z Naturfor-
sch [C] 2002;57(5–6):478–82.
81. Nishida N, Tamotsu S, Nagata N, Saito C, Sakai A. Allelo-
pathic effects of volatile monoterpenoids produced by Salvia
leucophylla: Inhibition of cell proliferation and DNA synthesis
in the root apical meristem of Brassica campestris seedlings.
J Chem Ecol 2005;31(5):1187–203.
82. Russin WA, Hoesly JD, Elson CE, Tanner MA, Gould MN.
Inhibition of rat mammary carcinogenesis by monoterpenoids.
Carcinogenesis 1989:10(11):2161–4.
83. Riyazi A, Hensel A, Bauer K, Geissler N, Schaaf S, Ver-
spohl EJ. The effect of the volatile oil from ginger rhizomes
(Zingiber ofcinale), its fractions and isolated compounds on
the 5-HT3 receptor complex and the serotoninergic system of
the rat ileum. Planta Med 2007;73(4):355–62.
84. Hedenstierna G, Alexandersson R, Wimander K, Rosén G.
Exposure to terpenes: effects on pulmonary function. Int Arch
Occup Environ Health 1983;51(3):191–8.
63. Umezu T, Nagano K, Ito H, Kosakai K, Sakaniwa M,
Morita M. Anticonict effects of lavender oil and identi-
cation of its active constituents. Pharmacol Biochem Be-
hav 2006;85(4):713–21.
64. Lamb JG, Marick P, Sorensen J, Haley S, Dearing MD.
Liver biotransforming enzymes in woodrats Neotoma stephensi
(Muridae). Comp Biochem Physiol C Toxicol Pharma-
col 2004;138(2):195–201.
65. Orhan I, Senol FS, Kartal M, Dvorská M, Zemlička M, Sme-
jkal K, et al. Cholinesterase inhibitory effects of the extracts
and compounds of Maclura pomifera (Ran.) Schneider.
Food Chem Toxicol 2009;47(8):1747–51. DOI 10.1016/j.
fct.2009.04.023.
66. Sayyah M, Nadjafnia L, Kamalinejad M. Anticonvulsant ac-
tivity and chemical composition of Artemisia dracunculus L.
essential oil. J Ethnopharmacol 2004;94(2–3):283–7.
67. Erazo S, Delporte C, Negrete R, García R, Zaldívar M, Itur-
ra G, et al. Constituents and biological activities of Schinus
polygamus.J Ethnopharmacol 2006;107(3):395–400.
68. Hammer KA, Carson CF, Riley TV. Antifungal activity of
the components of Melaleuca alternifolia (tea tree) oil. J Appl
Microbiol 2003;95(4):853–60.
69. Uribe S, Ramirez T, Pena A. Effects of β-pinene on yeast
membrane functions. J Bacteriol 1985;161:1195–200.
70. Tchoumbougnang F, Zollo PH, Dagne E, Mekonnen Y.
In vivo antimalarial activity of essential oils from Cymbopogon
citratus and Ocimum gratissimum on mice infected with Plas-
modium berghei. Planta Med 2005;71(1):20–3.
71. Yang YC, Choi HY, Choi WS, Clark JM, Ahn YJ. Ovicidal
and adulticidal activity of Eucalyptus globulus leaf oil terpe-
noids against Pediculus humanus capitis (Anoplura: Pediculi-
dae). J Agric Food Chem 2004;52(9):2507–11.
72. Kelen M, Tepe B. Chemical composition, antioxidant and anti-
microbial properties of the essential oils of three Salvia species
from Turkish ora. Bioresour Technol 2008;99(10):4096–104.
DOI 10.1016/j.biortech.2007.09.002.
73. Karioti A, Hadjipavlou-Litina D, Mensah ML, Fleischer TC,
Skaltsa H. Composition and antioxidant activity of the essen-
tial oils of Xylopia aethiopica (Dun) A. Rich. (Annonaceae)
leaves, stem bark, root bark, and fresh and dried fruits, growing
in Ghana. J Agric Food Chem 2004;52(26):8094–8.
REVIEW PAPERS B. MERCIER ET AL.
IJOMEH 2009;22(4)342
workers to work-related airborne allergens. Ann Agric Envi-
ron Med 2001;8(1):81–90.
93. Estévez M, Ventanas S, Ramírez R, Cava R. Inuence of the
addition of rosemary essential oil on the volatile pattern of por-
cine frankfurters. J Agric Food Chem 2005;53(21):8317–24.
94. Grassmann J. Terpenoids as plant antioxidants. Vitam
Horm 2005;72:505–35.
95. Falk AA, Hagberg MT, Lof AE, Wigaeus-Hjelm EM, Wang ZP.
Uptake, distribution and elimination of α-pinene in man after
exposure by inhalation. Scan J Work Environ Health 1990;16:
372–8.
96. Levin JO, Eriksson K, Falk A, Lof A. Renal elimination of
verbenols in man following experimental α-pinene inhalation
exposure. Int Arch Occup Environ Health 1992;63(8):571–3.
97. Filipsson AF. Short term inhalation exposure to turpentine:
toxicokinetics and acute effects in men. Occup Environ
Med 1996;53(2):100–5.
98. Ishida T, Asakawa Y, Takemoto T, Aratani T. Terpenoids
biotransformation in mammals II: Biotransformation of
α-pinene, β-pinene, pinane, 3-carene, carane, myrcene, and
p-cymene in rabbit. J Pharm Sci 1981;70(4):406–15.
99. Lindmark-Henriksson M, Isaksson D, Vanek T, Valterova I,
Hogberg HE, Sjodin K. Transformation of α-pinene using Pi-
cea abies suspension culture. Nat Prod 2003;66(3):337–43.
100. Hart PH, Brand C, Carson CF, Riley TV, Prager RH, Finlay-
Jones JJ. Terpinen-4-ol, the main component of the essential
oil of Melaleuca alternifolia (tea tree oil), suppresses inam-
matory mediator production by activated human monocytes.
Inamm Res 2000;49(11):619–26.
85. Foussereau J. Allergic eczema to turpentine. Fiche d’aller-Fiche d’aller-d’aller-
gologie dermatologie professionnelle 15, 1978, INRS [in
French].
86. Eriksson KA, Levin JO, Sandström T, Lindström-Espeling K,
Lindén G, Stjernberg NL. Terpene exposure and respiratory ef-
fects among workers in Swedish joinery shops. Scand J Work
Environ Health 1997;23(2):114–20.
87. Låstbom L, Falk-Filipsson A, Boyer S, Moldéus P, Ryr-
feldt A. Mechanisms of 3-carene-induced bronchoconstriction
in the isolated guinea pig lung. Respiration 1995;62(3):130–5.
88. Mølhave L, Kjaergaard SK, Hempel-Jørgensen A, Juto JE,
Andersson K, Stridh G, et al. The eye irritation and odor
potencies of four terpenes which are major constituents of
the emissions of VOCs from Nordic soft woods. Indoor
Air 2000;10(4):315–8.
89. Menezes IA, Marques MS, Santos TC, Dias KS, Silva AB,
Mello IC, et al. Antinociceptive effect and acute toxic-
ity of the essential oil of Hyptis fruticosa in mice. Fitotera-
pia 2007;78(3):192–5.
90. Kasanen JP, Pasanen AL, Pasanen P, Liesivuori J, Kosma VM,
Alarie Y. Stereospecicity of the sensory irritation receptor for
nonreactive chemicals illustrated by pinene enantiomers. Arch
Toxicol 1998;72(8):514–23.
91. Fransman W, McLean D, Douwes J, Demers PA, Le-
ung V, Pearce N. Respiratory symptoms and occupational
exposures in New Zealand plywood mill workers. Ann Occup
Hyg 2003;47(4):287–95.
92. Dutkiewicz J, Skórska C, Dutkiewicz E, Matuszyk A,
Sitkowska J, Krysińska-Traczyk E. Response of sawmill
... vaseyana; the concentration of this monoterpene in the oils of the other Artemisia species did not vary significantly within a species (Table 2). Alpha-pinene, an alkene (C10H16), is a major constituent in orange peel EO, but also in the EO of many other species ranging from Cannabis sativa, Rosemarinus officinalis to Pinus ssp [27][28][29]. Mercier et al. (2009) [28] have reviewed the many biological effects of α-and β-pinenes (in turpentine and its fractions). Table 3 shows the square root of Mean Squares Error (MSE) of the studied variables that estimates the common standard deviation ( ). ...
... Alpha-pinene, an alkene (C10H16), is a major constituent in orange peel EO, but also in the EO of many other species ranging from Cannabis sativa, Rosemarinus officinalis to Pinus ssp [27][28][29]. Mercier et al. (2009) [28] have reviewed the many biological effects of α-and β-pinenes (in turpentine and its fractions). Table 3 shows the square root of Mean Squares Error (MSE) of the studied variables that estimates the common standard deviation ( ). ...
... Alpha-pinene, an alkene (C10H16), is a major constituent in orange peel EO, but also in the EO of many other species ranging from Cannabis sativa, Rosemarinus officinalis to Pinus ssp [27][28][29]. Mercier et al. (2009) [28] have reviewed the many biological effects of α-and β-pinenes (in turpentine and its fractions). Table 3 shows the square root of Mean Squares Error (MSE) of the studied variables that estimates the common standard deviation ( ). ...
Article
Full-text available
Sagebrush (Artemisia spp.) are dominant wild plants in large areas of the U.S., Canada and Mexico, and they include several species and subspecies. The aim was to determine if there are significant differences in essential oil (EO) yield, composition, and biological activity of sagebrush within the Bighorn Mountains, U.S. The EO yield in fresh herbage varied from 0.15 to 1.69% for all species, including 0.25–1.69% in A. tridentata var. vaseyana, 0.64–1.44% in A. tridentata var. tridentata, 1% in A. tridentata var. wyomingensis, 0.8–1.2% in A. longifolia, 0.8–1% in A. cana, and 0.16% in A. ludoviciana. There was significant variability in the EO profile between species, and subspecies. Some EO constituents, such as α-pinene (0–35.5%), camphene (0–21.5%), eucalyptol (0–30.8%), and camphor (0–45.5%), were found in most species and varied with species and subspecies. The antioxidant capacity of the EOs varied between the species and subspecies. None of the sagebrush EOs had significant antimicrobial, antimalarial, antileishmanial activity, or contained podophyllotoxin. Some accessions yielded EO with significant concentrations of compounds including camphor, eucalyptol, cis-thujone, α-pinene, α-necrodol-acetate, fragranol, grandisol, para-cymene, and arthole. Therefore, chemotypes can be selected and possibly introduced into culture and be grown for commercial production of these compounds to meet specific industry needs.
... [9,13] Essential oils containing α-pinene have been used to treat several diseases. [14] It has been reported that alpha-pinene exerts its neuroprotective effect through the restoration of antioxidant capacity and reduction of inflammation in the ischemic rat brain. [15] The antioxidant and protective potential of the monoterpenes α-pinene have been confirmed in H 2 O 2 -induced oxidative stress in rat pheochromocytoma cells. ...
... [23] However, several studies have reported the biological effects of alpha-pinene-containing extract. [14,[24][25][26] Alpha-pinene enhances GABAA receptor function and increases postsynaptic GABA-dependent chloride flow in GABAA receptors. [27] In addition, it has been reported that oral use of alpha-pinene, through binding with the GABA receptor benzodiazepine, produces a beneficial hypnotic agent. ...
... Large amounts of pinenes are used in the flavor and fragrance industry [24]. However, due to their strong odor, they cannot be extensively used as additives in flavors or fragrances; pinenes are chemically converted to more valuable products, such as verbenone, a monoterpene that exhibits an ecological role as an anti-aggregating pheromone (tree protection) [25][26][27][28][29][30]. Besides this, pinenes might also be used in the production of pharmaceuticals, plasticizers, repellents, insecticides, solvents, perfumery, cosmetics, and antiviral and antimicrobial compounds [26][27][28][29][30][31][32]. ...
... However, due to their strong odor, they cannot be extensively used as additives in flavors or fragrances; pinenes are chemically converted to more valuable products, such as verbenone, a monoterpene that exhibits an ecological role as an anti-aggregating pheromone (tree protection) [25][26][27][28][29][30]. Besides this, pinenes might also be used in the production of pharmaceuticals, plasticizers, repellents, insecticides, solvents, perfumery, cosmetics, and antiviral and antimicrobial compounds [26][27][28][29][30][31][32]. Some investigations have been carried out with the aim of assessing the economic viability of performing resin-tapping operations [21,[33][34][35]. ...
Article
Full-text available
Tree resin is a macroergic component that has not yet been used for energy purposes. The main goal of this work is to determine the energy content of the resin of spruce, pine, and larch and of wood components—pulp and turpentine. The combustion heat of resin from each timber was determined calorimetrically. Approximately 1.0 g of liquid samples was applied in an adiabatic calorimeter. The energy values of the tree resin (>38.0 MJ·kg−1) were 2.2 and 2.4 times higher than that of bleached and unbleached cellulose, and the highest value was recorded for turpentine (>39.0 MJ·kg−1). Due to the high heating values of the resin, it is necessary to develop approaches to the technological processing of the resin for energy use. The best method of resin tapping is the American method, providing 5 kg of resin ha−1 yr−1. The tapped resin quantity can be raised by least 3 times by applying a stimulant. Its production cost compared to other feedstocks was the lowest. Tree resin can be applied as a means of mitigating global warming and consequently dampening climate change by reducing the CO2 content in the atmosphere. One tonne of tree resin burned instead of coal spares the atmosphere 5.0 Mt CO2.
... The 1,8-cineole performs essential ecological functions, such as repelling insects and deterring herbivores [53,54]. The bicyclic monoterpenes α-pinene and β-pinene, among the frequently occurring volatiles in bay leaves, are lipophilic, insecticidal, sedative, fungicidal, and anticarcinogenic effects [55]. The phenylpropene derivatives eugenol, methyl eugenol, and elemicin are also reported in the bay leaf, and these are responsible for the spicy aroma of the leaves and are significant factors determining its sensory quality. ...
Article
Full-text available
Laurus nobilis L. is an aromatic medicinal plant widely cultivated in many world regions. L. nobilis has been increasingly acknowledged over the years as it provides an essential contribution to the food and pharmaceutical industries and cultural integrity. The commercial value of this species derives from its essential oil, whose application might be extended to various industries. The chemical composition of the essential oil depends on environmental conditions, location, and season during which the plants are collected, drying methods, extraction, and analytical conditions. The characterization and chemotyping of L. nobilis essential oil are extremely important because the changes in composition can affect biological activities. Several aspects of the plant’s secondary metabolism, particularly volatile production in L. nobilis, are still unknown. However, understanding the molecular basis of flavor and aroma production is not an easy task to accomplish. Nevertheless, the time-limited efforts for conservation and the unavailability of knowledge about genetic diversity are probably the major reasons for the lack of breeding programs in L. nobilis. The present review gathers the scientific evidence on the research carried out on Laurus nobilis L., considering its cultivation, volatile composition, biochemical and molecular aspects, and antioxidant and antimicrobial activities.
... Turpentine oil has also been reported to exhibit pharmacological activities such as diuretic, hypoglycemic, anticholinergic, antioxidant, immunomodulatory, and xenobiotic expelling effects. Certain neurological activities, such as antistress and anticonvulsant, are also attributed to turpentine oil [102]. It has been reported to be an effective penetration enhancement effect when incorporated into topical formulations [25,103,104]. ...
Article
Full-text available
Oils, including essential oils and their constituents, are widely reported to have penetration enhancement activity and have been incorporated into a wide range of pharmaceutical formulations. This study sought to determine if there is an evidence base for the selection of appropriate oils for particular applications and compare their effectiveness across different formulation types. A systematic review of the data sources, consisting of Google Scholar, EMBASE, PubMed, Medline, and Scopus, was carried out and, following screening and quality assessment, 112 articles were included within the analysis. The research was classified according to the active pharmaceutical ingredient, dosage form, in vitro/in vivo study, carrier material(s), penetration enhancers as essential oils, and other chemical enhancers. The review identified four groups of oils used in the formulation of skin preparations; in order of popularity, these are terpene-type essential oils (63%), fatty acid-containing essential oils (29%) and, finally, 8% of essential oils comprising Vitamin E derivatives and miscellaneous essential oils. It was concluded that terpene essential oils may have benefits over the fatty acid-containing oils, and their incorporation into advanced pharmaceutical formulations such as nanoemulsions, microemulsions, vesicular systems, and transdermal patches makes them an attractive proposition to enhance drug permeation through the skin.
Article
Understanding the mechanism of insect resistance to toxic effects of phytochemicals can provide an insight into plant–herbivore interactions. Monochamus alternatus Hope, a main vector of pine wood nematode (Bursaphelenchus xylophilus), prefers to infest masson pine (Pinus massoniana Lamb) and causes huge economic and environmental losses. α‐Pinene is the primary component of resin produced by masson pine and plays a crucial role in defending against herbivorous insects, but its defensive effects on M. alternatus larvae are barely known. Here, we explored the physiological metabolism in M. alternatus larvae that were fumigated with (+)‐α‐pinene, (‐)‐α‐pinene, β‐pinene, (R)‐(+)‐limonene, myrcene and (‐)‐α‐phellandrene. (+)‐α‐Pinene showed the highest fumigant toxicity to M. alternatus larvae among these monoterpenes, and the fourth instar larvae possessed the highest resistance to this compound at the larval stage. Comparative transcriptome analysis detected 423 up‐regulated and 311 down‐regulated genes in the larvae fumigated with (+)‐α‐pinene, which were mainly related to detoxification, energy and protein metabolism. Among the differentially expressed genes encoding for detoxification enzymes, 14 P450s, 13 UGTs, 1GSTs and 3ABCs were dramatically up‐regulated in the larvae fumigated with (+)‐α‐pinene. Silencing of P450s via RNA interference led to an increased mortality in the larval fumigated with (+)‐α‐pinene. Piperonyl butoxide exposure significantly increased the mortality and inhibited the expressions of P450s, UGTs and ABCs in the larvae fumigated with (+)‐α‐pinene. These results suggested an important role of P450s in the resistance of M. alternatus larvae to (+)‐α‐pinene fumigation, which may facilitate the understanding of terpenoid detoxification in M. alternatus larvae.
Article
Turpentine essential oil (TEO) is a commercially available product having application as food additive, due to its ethno-botanical and ethnopharmacological properties. In the present study, we performed chemical composition of TEO by Gas Chromatography-Mass Spectrometry (GC-MS). Further, TEO was nanoemulsified, encapsulated and characterized by droplet size, PDI, Zeta potential and transmittance. The obtained turpentine nanoemulsion (TNE) was investigated for its antibacterial and antibiofilm potentiality against methicillin-resistant Staphylococcus aureus (MRSA), a model biofilm-forming microorganism. Small micellar TEO nanoparticles were succesfully formed with a mean droplet size ranging from 22.52 to 26.54 nm. Thermodynamic stability studies revealed homogeneous dispersion of the droplets size confirming the stability of TNEs. The developed nano-emulsions displayed two fold enhanced antagonistic activity against S. aureus in comparison with TEOs, with minimum inhibitory concentration (MIC) values at 0.039% (v/v) against MRSA. Additionally, TNEs displayed potent antibiofilm activity against MRSA strains with percent biofilm disruption of around 70.83%. Findings from this study validates the phytomedicinal significance of turpentine nanoemulsions and envisage its exploration as a natural and cost-effective strategy against bacterial biofilms in medical and industrial sectors.
Article
Full-text available
Oleoresin samples collected directly from living-trees by three different tapping methods, and from four geographical origins were analyzed using two gas chromatography (GC) methods. The GC was coupled to a flame ionization detector (GC-FID) for quantification, and to a mass spectrometer (GC-MS) for identifying the chemical composition. Twenty-eight chemical components were detected and quantified. The proportions of each chemical component varied exceedingly between different samples, and other associated factors. The specific sample traits, including Pinus species, tapping method and geographical origin differentiated the sample batches. Notwithstanding, the main chemical components present in all the characterized samples are α-pinene and β-pinene. Statistical analysis demonstrated that the majority of molecules are of significant importance to sample traits. Moreover, the statistical analysis allows for the identification of the biomarkers associated with the sample traits. Additionally, Linear Discriminant Analysis models have shown very good performance in classifying samples based on the sample traits. Furthermore, the biomarkers allowing the establishment of differences between geographical origins are sativene, camphene, limonene, isopimaric acid and pimarinal, whereas the differentiation between tapping methods is established by sativene, pimaric acid, β-phellandrene, isopimaric acid, retinol and camphene, and lastly biomarkers allowing the differentiation between Pinus species are palustric acid, limonene, β-pinene and sativene.
Article
This research aims to identify the volatile compounds from rhizomes and leaves of Newmania sontraensis. The constituents of essential oil from the rhizomes and leaves of N. sontraensis were analyzed by Gas Chromatography-Mass Spectrometry (GC/MS). Thirty-one compounds were identified in the rhizomes compared to the leaves which showed thirty-two volatile compounds corresponding to 83.28 % and 76.41 % of the oil content, respectively. The chemical composition of the rhizome oil was characterized by hydrocarbon monoterpenes accounting for 36.26 %. The major compounds found in the rhizome oil included β-pinene (22.41%), 1,8-cineole (8.32 %), bicyclogermacrene (6.94 %), α-terpinyl acetate (5.74 %), α-pinene (5.71 %), and camphene (5.58 %). Meanwhile, sesquiterpene hydrocarbons were the main compounds found in the leaf oil accounting for 54.18 %. Bicyclogermacrene (14.60 %), δ-elemene (9.89 %), β-elemene (7.26 %), and α-terpinyl acetate (4.27 %) were determined to be the main components found in leaf oil. This was the first report on the chemical constituents of essential oils from rhizomes and leaves of N. sontraensis.
Article
Full-text available
The first part of this paper is devoted to the electrical characteristics of the air below the canopy of a pine and spruce forest. In fair weather conditions, the site influence, i.e. the filtering effect of the trees on air conductivity and electric field, is evidenced. Under disturbed weather conditions, the meteorological influence is depicted to show: (i) that electric fields sufficiently high to produce `point discharges' occur not only during thunderstorms but also during mist; (ii) that, by taking into account the gaseous ions produced by the point discharges, it becomes possible to understand on the one hand the field divergence with height observed in the mist, and on the other hand the detection of alternatively positive and negative gaseous clouds of charges during the thunderstorm. The second part presents the results of chemical analysis performed below and just above the canopy on the same site and for the same period. Increased ozone and hydrogen peroxide concentrations were measured during the thunderstorm. It is shown that these chemical species were not only locally produced by photochemistry and/or transported from different (industrial and traffic) sources, but also arose from transient electrical point discharges in the forest under high electric field conditions. Their local concentration is shown to be influenced by the electrical discharge current density on the one hand, and by the local conditions of atmospheric stability and of water content, determining the evolution of the chemical products, on the other hand. Actually, after their production, the initially gaseous chemical products were shown to be involved in the local droplet chemistry. Under specific weather conditions, ionic densities as well as chemical by-products of a forest therefore depend both on the electrodynamical characteristics of the lower atmosphere and on the local environmental conditions (liquid water content of the air and atmospheric stability) associated with the two different situations investigated, a mist and a thunderstorm.
Article
Full-text available
Objective and Design: To evaluate potential anti-inflammatory properties of tea tree oil, the essential oil steam distilled from the Australian native plant, Melaleuca alternifolia.¶Material and Methods: The ability of tea tree oil to reduce the production in vitro of tumour necrosis factor-α (TNFα), interleukin (IL)-1β, IL-8, IL-10 and prostaglandin E2 (PGE2) by lipopolysaccharide (LPS)-activated human peripheral blood monocytes was examined.¶Results: Tea tree oil emulsified by sonication in a glass tube into culture medium containing 10% fetal calf serum (FCS) was toxic for monocytes at a concentration of 0.016% v/v. However, the water soluble components of tea tree oil at concentrations equivalent to 0.125% significantly suppressed LPS-induced production of TNFα, IL-1β and IL-10 (by approximately 50%) and PGE2 (by approximately 30%) after 40 h. Gas chromatography/ mass spectrometry identified terpinen-4-ol (42%), α-terpineol (3%) and 1,8-cineole (2%, respectively, of tea tree oil) as the water soluble components of tea tree oil. When these components were examined individually, only terpinen-4-ol suppressed the production after 40 h of TNFα, IL-1β, IL-8, IL-10 and PGE2 by LPS-activated monocytes. Conclusion: The water-soluble components of tea tree oil can suppress pro-inflammatory mediator production by activated human monocytes.
Article
Full-text available
Concentrations of ozone and nitrogen oxides, together with air temperature and solar radiation intensity, were measured at several heights on a tower standing through the canopy of a red pine forest in summer and in autumn. In the summer observation, the diurnal variation patterns of ozone concentration both above and below the canopy were all similar and parallel to the solar radiation intensity. Using the data collected immediately above the canopy, deviation from the Leighton relationship and variations of concentration sums [O3] + [NO] and [NO2] + [NO] were examined, and as a result, it was supposedthat ozone was photochemically formed there in the daytime, probably because hydrocarbons emitted from pine trees broke the photostationary state among ozone and nitrogen oxides. The vertical temperature profile exhibited an inversion at the leaf-layer, which must have hindered vertical mixing of the air and made the trunk space more or less isolated from the upper atmosphere. These observations led to an idea that the similarity of the ozone variation pattern at every height was caused by the photochemical formation that proceeded simultaneously above and below the canopy rather than by vertical transport. Such situations of ozone formation were supported by observation of two maximums in the ozone vertical profile, one immediately above the canopy and another in the trunk space. Another feature of the ozone profile was a deep minimum in the leaf layer, which indicated ozone deposition onto leaf surfaces. This study thus revealed concurrence of ozone formation and deposition, and left two potentially important implications worthy of further investigation: (1) a forest is not always a sink but can be a source of ozone in sunlit conditions, and (2) deposition of ozone to trees can take place not only from outside but also from inside of a forest. In the autumn observation, however, the ozone formation was barely recognizable above the canopy and no longer found in the trunk space; in addition, the ozone concentration minimum in the leaf layer disappeared, suggesting that the deposition or removal was dependent on temperature.
Article
Full-text available
 Volatiles from leaves or bark of nonhost birch (Betula pendula) and Norway spruce (Picea abies) dramatically reduced the attraction of the bark beetle, Pityogenes bidentatus (Coleoptera: Scolytidae), to their aggregation pheromone components (cis-verbenol and grandisol) in the field. In addition, odors from both the needles and bark of the host Scots pine (Pinus sylvestris) similarly inhibited attraction. Monoterpenes of pine and spruce (α-pinene, β-pinene, terpinolene, and 3-carene) as well as ethanol, chalcogran and some nonhost green leaf alcohols [(Z)-3-hexen-1-ol, (E)-2-hexen-1-ol, and 1-hexanol], also reduced catches. Collections of volatiles from the field-tested plant tissues indicated they released monoterpenes in amounts similar to the synthetics that inhibited responses. The various plant and insect sources of these inhibitory compounds indicate that P. bidentatus bark beetles have evolved several strategies to increase their fitness by avoiding nonhost and unsuitable host trees in a complex olfactory landscape.
Article
Studies demonstrating the elimination of radioactive particles during a 7-day course of therapy with 3 x 30 mg ambroxol or 4 x 1 capsule. Gelomyrtol forte® (1 capsule = 0.3 g Myrtol, standardised to at least 20 mg of alpha-pinene, 75 mg of limonene and 75 mg of cineole (eucalyptol)) yield improved mucociliary clearance in both groups. No change of lung function was observed.
Article
Eye goggles were used to estimate human thresholds for sensory eye irritation from four monoterpenes: (+)3-carene, (-)limonene and (+)α-pinene and (rac)α-terpineol all known as air pollutants emitted from wood. Only a ranking of the irritation thresholds relative to that of n-butanol is given. The measurements showed that the thresholds for eye irritation of the terpenes ranged from subthreshold to below 1,250 mg/m3. It appears that the irritation of 3-carene and limonene in contrast to the expectations was of the same size as or less than that of n-butanol. Too few subjects reported eye-irritation for α-pinene and α-terpineol to allow estimates of thresholds of these compounds which therefore have much less irritative potency than n-butanol, 3-carene, and limonene. The measurements of one terpene alcohol do not support the hypothesis that monoterpene alcohols, would have lower eye irritation threshold than monoterpene hydrocarbons. The sequence from strongest odorant to weakest was α-terpineol, 3-carene, n-butanol, limonene and α-pinene. In conclusion, the tested terpenes can probably be ruled out as cause of acute eye irritation indoors. The measured odor thresholds did not deviate from the few values reported in the literature.
Article
Salvia lavandulaefolia Vahl. (Spanish sage) essential oil and individual monoterpenoid constituents have been shown to inhibit the enzyme acetylcholinesterase in-vitro and in-vivo. This activity is relevant to the treatment of Alzheimer's disease, since anticholinesterase drugs are currently the only drugs available to treat Alzheimer's disease. Other activities relevant to Alzheimer's disease include antioxidant, anti-inflammatory and estrogenic effects. Results of in-vitro tests for these activities are reported here for S. lavandulaefolia extracts, the essential oil and its major constituents. Antioxidant activity (inhibition of bovine brain liposome peroxidation) was found in the EtOH extract of the dried herb (5 mg mL−1) and the monoterpenoids (0.1 M) α- and β-pinene and 1,8-cineole. Thujone and geraniol had lower antioxidant effects, while camphor had no antioxidant effects. Possible anti-inflammatory activity (eicosanoid inhibition in rat leucocytes) was found in the EtOH extract (50 μg mL−1) and was shown by the monoterpenoids α-pinene and geraniol (0.2 mM), but not 1,8-cineole, thujone or camphor. Possible estrogenic activity (via induction of β-galactosidase activity in yeast cells) was found in the essential oil (0.01 mg mL−1) and the monoterpenoid geraniol (0.1–2 mM). 1,8-Cineole, α- and β-pinene and thujone did not exhibit estrogenic activity in this analysis. These results demonstrate that S. lavandulaefolia, its essential oil and some chemical constituents have properties relevant to the treatment of Alzheimer's disease and provide further data supporting the value of carrying out clinical studies in patients with Alzheimer's disease using this plant species.
Article
To clarify the existence of a receptor protein for sensory irritants in trigeminal nerve endings, d- [i.e. (+)] and l- [i.e. (−)] enantiomers of α- and β-pinene as models of nonreactive chemicals were evaluated for their potency in outbred OF1 and NIH/S mice using ASTM E981-84 bioassay. All pinenes possess sensory irritation properties and also induced sedation and signs of anaesthesia but had no pulmonary irritation effects. According to the ratio of RD50 (i.e. concentration which causes a 50% decrease in respiratory rate, f ) and vapour pressure (Po), all pinenes are nonreactive chemicals. For nonreactive chemicals, P° and olive oil-gas partition (LOil) can be used to estimate their potency as sensory irritant. Thus, for enantiomers with identical physicochemical properties, the estimated RD50 values are the same. In addition, although α- and β-pinene do not have identical Po and LOil values, their estimated potencies are quite close. However, the experimental results showed that d-enantiomers of pinenes were the most potent as sensory irritants and a difference in potency also exists between α- and β-pinene. RD50 for d-enantiomers of α- and β-pinene were almost equal, 1053 ppm and 1279 ppm in OF1 strain and 1107 ppm and 1419 ppm in NIH/S strain, respectively. Values differed by a factor of ∼4 to 5 from l-β-pinene for which the RD50 was 4663 ppm in OF1 and 5811 ppm in NIH/S mice. RD50 could not be determined for l-α-pinene; this pinene was almost inactive. d-α-pinene seems to best fit the receptor because its experimental RD50 was one-half of the estimated value while for d-β-pinene those values were equal. On the contrary, l-β-pinene was about 3 to 4␣times less potent than estimated. l-α-pinene was only slightly active although it was estimated to be as potent as d-α-pinene. The remarkable difference in potency between l-enantiometers is most likely due to a structural difference between α- and β-pinene: the more flexible β-pinene can bend to fit into the receptor better than the rigid α-pinene. The results showed that the commonly used physicochemical descriptors cannot fully explain the potency of these chemicals; their three-dimensional structure should also be considered. Because of the stereospecificity of pinenes, a target site for nonreactive sensory irritants is most likely a receptor protein containing a chiral lipophilic pocket.
Article
The renal elimination of verbenols after experimental exposure to (+) and (–)-pinene was studied in humans following exposure to 10, 225, and 450 mg m–3 terpene in an exposure chamber. The pulmonary uptake was about 60%. About 8% was eliminated unchanged in exhaled air. Depending on the exposure level, about 1%–4% of the total uptake was eliminated as cis and trans-verbenol. Most of the verbenols were eliminated within 20 h after a 2-h exposure. The renal excretion of unchanged -pinene was less than 0.001%.