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PubMed2001

Permeation of oxygen, water vapor, and limonene through printed and unprinted biaxially oriented polypropylene films.

Oriented polypropylene (OPP) and coated OPP (acrylic/OPP/PVDC) films were printed with two commercially available inks to investigate the influence of inks on water vapor and oxygen transmission rates. The permeation of an aroma compound (d-limonene) through coated OPP film printed with these inks was also evaluated at 35 degrees C and 100% relative humidity. The water vapor transmission rate increased significantly through OPP film printed with nitrocellulose-based ink. The oxygen transmission rate was significantly lower through both OPP and coated OPP films printed with the nitrocellulose ink. The effect of inks on limonene permeation was minor compared to the marked increase in permeation measured when the PVDC side of the coated film was exposed to the aroma, compared to the acrylic side. Scanning electron micrographs of coated film cross sections revealed changes in film structure upon exposure to limonene vapors, which were most pronounced when the PVDC side was exposed to limonene.

Biofilms↗
PubMed2006

Induction of apoptosis by d-limonene is mediated by a caspase-dependent mitochondrial death pathway in human leukemia cells.

Using K562 and HL60 cell lines, we have investigated the anti-tumoral activity of d-limonene, a monocyclic monoterpene, in human leukemia cells. Apoptosis was evaluated by Hoechst staining and by the annexin V/propidium iodide binding assay. d-Limonene induced apoptosis in a dose- and time-dependent manner in both cell lines. Our findings and data, demonstrating an increase in Bax protein expression, the release of cytochrome c from mitochondria, and an increase in caspase-9 and cleaved caspase-3, but not caspase-8, after the treatment of d-limonene, all suggest that the mitochondrial death pathway is primarily involved in the development of d-limonene-induced apoptosis.

Anticarcinogenic Agents↗
PubMed2002

Upper airway and pulmonary effects of oxidation products of (+)-alpha-pinene, d-limonene, and isoprene in BALB/c mice.

The oxidation products (OPs) of ozone and the unsaturated hydrocarbons d-limonene, (+)-alpha-pinene, and isoprene have previously been shown to cause upper airway irritation in mice during 30-min acute exposures. This study evaluated the effects of OPs and the hydrocarbons themselves on the upper airways, the conducting airways, and the lungs over a longer exposure period. The time course of development of effects and the reversibility of effects were investigated; in addition, we assessed possible exacerbation of sensory responses of the airways to the unreacted hydrocarbons. Respiratory parameters in male BALB/c mice were monitored via head-out plethysmography. Exposures to OPs or hydrocarbons were for 60 min, followed by a 30-min challenge period with air or hydrocarbon, and a 15-min recovery period with air only. Experiments were also performed where limonene/ozone exposures were separated 6 h from the challenge period. Ozone concentration in the reaction mixture was 3.4 ppm, and concentrations of hydrocarbons were 47 ppm (alpha-pinene), 51 ppm (d-limonene), and 465 ppm (isoprene). Due to reaction, the ozone concentration at the point of exposure was less than 0.35 ppm; exposure to 0.30 ppm ozone for 60 min did not produce effects different from air-exposed control animals. As previously established, upper airway irritation was a prominent effect of OP exposure. In addition, over the longer exposure period we observed the development of airflow limitation that persisted for at least 45 min postexposure. All effects from limonene/ozone exposures were reversible within 6 h. Exposures to OPs did not cause enhanced upper airway irritation during challenge with the hydrocarbons, indicating that a 1-h exposure to OPs did not increase the sensitivity of the upper respiratory system. However, airflow limitation was exacerbated in animals exposed to d-limonene alone immediately following exposure to limonene OPs. These findings suggest that terpene/ozone reaction products may have moderate-lasting adverse effects on both the upper airways and pulmonary regions. This may be important in the context of the etiology or exacerbation of lower airway symptoms in office workers, or of occupational asthma in workers involved in industrial cleaning operations.

Administration, Inhalation↗
PubMed1986

Mouse skin tumor promoting activity of orange peel oil and d-limonene: a re-evaluation.

Orange peel oil has previously been shown to be a promoter of mouse skin tumors. It has been assumed that this activity is due to its major (95%) constituent, d-limonene. We have tested both orange peel oil and purified d-limonene as skin tumor promoters in a two-stage skin carcinogenesis model in which tumors were initiated with 7,12-dimethylbenz[a]-anthracene. We confirmed that topically applied orange peel oil is a very weak promoter of both skin papillomas and carcinomas. However, this promotional activity could not be accounted for by topically applied d-limonene. We thus feel that one or more minor components of orange peel oil has promotional activity. Neither orange peel oil nor d-limonene had promotional activity when given via the diet.

9,10-Dimethyl-1,2-benzanthracene↗
PubMed2003

Determination of limonene oxidation products using SPME and GC-MS.

Limonene is a common component found in consumer goods ranging from beverages to cleaning compounds. Limonene oxidation products, however, have a less desirable flavor and fragrance. Early detection of limonene oxide formation would aid quality control. A method is developed to determine the concentration of limonene oxide in essential oils and beverages using solid-phase microextraction (SPME). A headspace sampling technique is used to reduce or eliminate the presence of less volatile components. Several different SPME fibers are tested, varying in polymer thickness, polymer cross-linking and bonding, and polarity of the polymer. For each fiber tested, the sampling time is optimized for reproducible results. The 7-microm-thick bonded poly(dimethylsiloxane) fiber provides the best results. External standards are used for quantitation.

Chromatography, Liquid↗
PubMed2006

Influence of ozone-limonene reactions on perceived air quality.

UNLABELLED: This study conducted short-term assessments of perceived air quality (PAQ) for six different realistic concentrations of ozone and limonene, separately or together, in room air. The impact of filtration and the influence of the ozone generation method were also examined. The evaluations were made in four identical 40 m3 low-polluting test offices ventilated at 1.4 h(-1) or in two identical 30 m3 stainless-steel chambers ventilated at 1.9 h(-1). Concentrations of ozone, total volatile organic compounds and size-fractionated particles were continuously monitored in each experiment. The results indicate that, for each of the six conditions, the PAQ was poorer when ozone and limonene were present together compared with when only ozone or only limonene was present. In the test offices a correlation was observed between the number of secondary organic aerosols produced by a given ozone/limonene condition and the sensory pollution load for that condition. The particles themselves do not appear to be the primary causative agents, but instead are co-varying surrogates for sensory offending gas-phase species. PRACTICAL IMPLICATIONS: Although the health consequences of long-term exposures to the products of ozone-initiated indoor chemistry remain to be determined, we judge that the sensory offending nature of selected products provides an additional reason to limit indoor ozone levels. Devices that emit ozone at significant rates should not be used indoors. Ozone-filtration of make-up air should also be beneficial in mechanically ventilated buildings located in regions that repeatedly violate outdoor ozone standards. Additionally, the use of limonene containing products should be curtailed during periods when indoor ozone levels are elevated.

Aerosols↗
PubMedDate not supplied

Effect of limonene and sobrerol on monocrotaline-induced lung alterations and pulmonary hypertension.

The effects of two monocyclic monoterpenes, limonene and sobrerol, known as inhibitors of farnesyltransferase activity, were studied on monocrotaline (MCT)-induced lung injury, pulmonary hypertension and right ventricular hypertrophy in male Wistar rats. After 14 days, pulmonary arterial pressure values and the right ventricle to left ventricle plus septum weight ratios, RV/(LV + S), were markedly increased in rats subcutaneously injected with MCT (60 mg/kg). Limonene and sobrerol, administered daily at the oral dose of 400 mg/rat, markedly decreased the MCT-induced alterations. After treatment for 21 days, limonene still prevented pulmonary hypertension and the increase in RV/(LV + S). Both monoterpenes also reduced the increase in pulmonary arterial media thickness, the development of interstitial fibrosis and the increase in the number of macrophages in intra-alveolar spaces and of lymphocytes around the pulmonary veins. The present data indicate that treatment of rats with inhibitors of farnesyltransferase, like limonene and sobrerol, regulate the development of pulmonary hypertension.

Alkyl and Aryl Transferases↗
PubMed1995

Combined effect of d-limonene pretreatment and temperature on the rat skin permeation of lipophilic and hydrophilic drugs.

The combined effect of d-limonene and temperature on the skin permeation of lipophilic and hydrophilic penetrants has been investigated in rats in vitro. Prednisolone was used as a lipophilic penetrant, and glucose and isoniazid were used as hydrophilic ones, respectively. When the skin was pretreated with 30% ethanol without d-limonene, the steady state permeability coefficient (P) of every penetrant through the skin was difficult to calculate because of very low permeability. On the other hand, the cumulative amount of each penetrant increased with an increase in temperature when the skin was pretreated with 1.5% d-limonene in 30% ethanol. The Arrhenius plots of P values for glucose and isoniazid showed a linear relationship, and the activation energies of skin permeation were estimated to be 87.6 and 66.5 kJ/mol, respectively. When prednisolone was used as penetrant, however, the Arrhenius plot of P values exhibited a convex curvature. This may suggest that the combined use of d-limonene and temperature effectively changes the barrier structure of the non-polar pathway in the stratum corneum, while no synergistic effect was observed on the polar pathway.

Administration, Cutaneous↗
PubMed2000

Ozone and limonene in indoor air: a source of submicron particle exposure.

Little information currently exists regarding the occurrence of secondary organic aerosol formation in indoor air. Smog chamber studies have demonstrated that high aerosol yields result from the reaction of ozone with terpenes, both of which commonly occur in indoor air. However, smog chambers are typically static systems, whereas indoor environments are dynamic. We conducted a series of experiments to investigate the potential for secondary aerosol in indoor air as a result of the reaction of ozone with d-limonene, a compound commonly used in air fresheners. A dynamic chamber design was used in which a smaller chamber was nested inside a larger one, with air exchange occurring between the two. The inner chamber was used to represent a model indoor environment and was operated at an air exchange rate below 1 exchange/hr, while the outer chamber was operated at a high air exchange rate of approximately 45 exchanges/hr. Limonene was introduced into the inner chamber either by the evaporation of reagent-grade d-limonene or by inserting a lemon-scented, solid air freshener. A series of ozone injections were made into the inner chamber during the course of each experiment, and an optical particle counter was used to measure the particle concentration. Measurable particle formation and growth occurred almost exclusively in the 0.1-0.2 microm and 0.2-0.3 microm size fractions in all of the experiments. Particle formation in the 0.1-0.2 microm size range occurred as soon as ozone was introduced, but the formation of particles in the 0.2-0.3 microm size range did not occur until at least the second ozone injection occurred. The results of this study show a clear potential for significant particle concentrations to be produced in indoor environments as a result of secondary particle formation via the ozone-limonene reaction. Because people spend the majority of their time indoors, secondary particles formed in indoor environments may make a significant contribution to overall particle exposure. This study provides data for assessing the impact of outdoor ozone on indoor particles. This is important to determine the efficacy of the mass-based particulate matter standards in protecting public health because the indoor secondary particles can vary coincidently with the variations of outdoor fine particles in summer.

Aerosols↗
PubMedDate not supplied

Regio- and stereoselective fungal oxyfunctionalisation of limonenes.

Selective transformations of limonene by asco- and basidiomycetes were investigated. On the shake flask scale, Penicillium citrinum hydrated R-(+)-limonene to a-terpineol [83% regioselectivity (rs), more than 80 mg l(-1) product yield], and Gongronella butleri catalysed the terminal oxidation to yield perillyl alcohol (60% rs, 16 mg l(-1)). On the laboratory bioreactor scale, Penicillium digitatum produced a peak concentration of 506 mg a-terpineol l(-1) in the fed-batch mode, equivalent to a theoretical yield of 67%, and no volatile by-products were found. Fusarium proliferatum transformed R-(+)-limonene enantiospecifically to cis-(+)-carveol (98.6% ee, more than 35 mg l(-1) product yield) and S-(-)-limonene predominantly to trans-(-)-carveol (96.3% ee). Pleurotus sapidus selectively dehydrogenised the accumulating trans-(-)-carveol to the corresponding enantiopure R-(-)-carvone. The results show that a careful selection of strain and bioprocess parameters may improve both the yield and the optical purity of a desired product.

Ascomycota↗
PubMedDate not supplied

d-limonene chemoprevention of hepatocarcinogenesis in AKR mice: inhibition of c-jun and c-myc.

We have studied the chemopreventive effect of d-limonene, a monoterpene monocyclic compound, against N-nitrosodiethylamine (NDEA) alone and along with phenobarbital (PB) induced hepatocarcinogenesis in AKR mice. Histopathological analysis clearly indicates the maintenance of normal features when the mice were given limonene 15 days prior to carcinogen treatment. The immunohistochemical analysis of c-jun and c-myc oncoprotein shows an increased protein expression (2-3 fold) in NDEA and NDEA-PB mediated hepatocarcinogenesis after 60 days of NDEA treatment. Our earlier work by northern blot analysis has already indicated an increased transcription of c-jun and c-myc in NDEA mediated hepatocarcinogenesis. However, such overexpression of c-myc and c-jun both at mRNA and oncoprotein levels has been completely inhibited when d-limonene was used along with NDEA or NDEA-PB. Thus, the present investigation explains the anti-tumour effect of d-limonene for the first time on the level of oncogene expression in NDEA and NDEA-PB mediated hepatocarcinogenesis.

Animals↗
PubMed1998

[Effect of d-limonene, Salvia miltiorrhiza and turmeric derivatives on membrane association of Ras gene product and gap junction intercellular communication].

Gap junction intercellular communication (GJIC), H-ras oncogene expression and Ras oncogene product(P21ras protein) expression were studied in four human solid tumor cell lines, W1-38, CACO2, A549 and PaCa (with the different Ras gene mutation rate), and the effects of four compounds, Salvia miltiorrhiza derivative (SMD), d-limonene, turmeric derivative I(TD-I) and turmeric derivative II(TD-II), on them. The abilities of the four solid tumor cell lines to transfer dye to adjacent cells were examined using the scrape-loading/dye transfer technique, and the H-ras oncogene expression by Northern blotting and P21ras protein expression by Western blotting. The results showed the loss of intercellular coupling in PaCa cells, slight GJIC in A549 and CACO2 cells, and good GJIC in W1-38 cells. The four compounds used was shown to improve the GJIC of PaCa to different extents. The amount of total and membrane associated P21ras in PaCa cells were decreased after treatment with SMD, d-limonene and TD-I(2.5 micrograms.ml-1) for 48 h. Concomitantly, the growth of PaCa cells decreased in soft agar and GJIC was enhanced. The relative potency was found to be: d-limonene > SMD > TD-I = TD-II. No significant effect of the four compounds on H-ras oncogene expression was observed. These results suggest that 1. there was an excellent correlation between loss of Lucifer Yellow dye transfer and ras gene mutation rate in the four solid tumor cell lines used (ras gene mutation rate inversely correlated with average cell number couplied, r = 0.98) i.e., showing that high ras gene mutation is closely correlated with loss of GJIC in these malignant human tumor cells; 2. the antitumor effect of the monoterpene d-limonene and the phenol compound, SMD, might be related to the inhibition of P21ras membrane association and enhancement of GJIC, whilst that of the others may be by a different mechanism; 3. the inhibition of P21ras membrane association is directly related to the enhancement of gap junction intercellular communication.

Antineoplastic Agents, Phytogenic↗
PubMed2003

[D-limonene induces apoptosis of gastric cancer cells].

OBJECTIVE: To investigate the apoptosis effect induced by D-limonene on BGC-823 gastric cancer cells. METHODS: The expression of p53, bc1-2 in BGC-823 cells and qualitative, quantitative index of cell apoptosis were detected with MTT, electron microscopy, flow cytometry and immunohistochemical method. RESULTS: D-limonene could induce the formation of apoptotic bodies in a dose- and time-dependent manner. The expression of bcl-2 protein decreased and p53 protein increased in BGC-823 cells treated with D-limonene, compared with the control cells. CONCLUSION: D-limonene exerts its cytotoxic effect on BGC-823 gastric cancer cells by inducing apoptosis.

Adenocarcinoma↗
PubMed2003

Effect of naturally occurring monoterpenes carvone, limonene and perillic acid in the inhibition of experimental lung metastasis induced by B16F-10 melanoma cells.

The effects of naturally occurring monoterpenes on lung metastasis induced by B16F-10 melanoma cells were studied in C57BL/6 mice. Administration of monoterpenes such as limonene (100 micromoles/kg body wt. 10 doses i.p.) and perillic acid (50 micromoles/kg body wt 10 doses i.p.) remarkably reduced the metastatic tumour nodule formation by 65% and 67%, respectively. These results correlated with the biochemical parameters such as serum sialic acid, lung collagen hydroxyproline and uronic acid contents. Serum sialic acid level in control group was 126.8 microg/ml serum which was significantly lowered in limonene (49.3 microg/ml serum) and perillic acid treated animals (53.6 microg/ml serum). Uronic acid level was also inhibited to 56% and 39.7% in limonene and perillic acid treated animals, respectively. Histopathological studies also correlated with these above results. Administration of Carvone even at 100 micromoles/kg body wt. did not have any significant effect on the metastatic tumour growth. These results indicate that limonene and perillic acid could inhibit the metastatic progression of B16F-10 melanoma cells in mice.

Animals↗
PubMed1991

The presence of alpha 2u-globulin is necessary for d-limonene promotion of male rat kidney tumors.

In a 2-year carcinogenesis bioassay, d-limonene (dL) induced kidney tumors in male F344 rats, but not in female F344 rats or either sex of mice, d-Limonene-1,2-oxide, a metabolite of dL, has been shown to bind reversibly the male rat-specific urinary protein, alpha2u-globulin (alpha 2u-G), lysosomal degradation than alpha 2u-G alone. This reduced degradation of alpha 2u-G-chemical complex leads to an accumulation of this protein in the proximal convoluted tubules of the male rat kidney and to the morphological changes characteristic for alpha 2u-globulin nephropathy. The only male rat strain known to be resistant to this renal disease is the alpha 2u-G deficient NCI-Black-Reiter (NBR) rat. The objectives of this study were to determine whether or not dL causes sustained increases in cell proliferation and has promoting activity for renal adenomas in male rats and if the male rat-specific urinary protein, alpha 2u-G, is required. In a 32-week initiation-promotion assay, male F344 and NBR rats were treated with either 0 or 500 ppm N-ethyl-N-hydroxyethylnitrosamine (EHEN) in the drinking water for 2 weeks. Experimental groups of 31 to 38 rats then received 0 or 150 mg d-limonene/kg/day in corn oil for 30 weeks by p.o. gavage 5 days/week. Cell proliferation in the proximal tubules was assessed via 5-bromo-2'-deoxyuridine-filled osmotic mini-pumps and immunohistochemistry after 7 weeks (2 weeks EHEN + 5 weeks dL) and at the end of the study (2 weeks EHEN + 30 weeks dL). Preneoplastic and neoplastic lesions were quantified in perfusion-fixed kidneys. A 5-fold increase in the labeling index of P2-cells was found after 5 weeks and 30 weeks of promotion in all dL-treated F344 rats, whereas no difference between treatment groups was detected in NBR rats. No increase in tumors or preneoplastic lesions was detected in dL-treated NBR rats, whereas a 10-fold increase in renal adenomas and atypical hyperplasias was found in the EHEN-dL-treated F344 rats compared with F344 rats treated with EHEN-corn oil. d-Limonene treatment alone caused a significant increase in the number of atypical tubules and atypical hyperplasias in F344 rats when compared with the F344 vehicle control. On the other hand, a significantly lower incidence of liver tumors was found in EHEN-dL-treated F344 rats compared with F344 rats treated with EHEN-corn oil, suggesting a chemopreventative effect of dL on EHEN-induced liver carcinogenesis in F344 rats.(ABSTRACT TRUNCATED AT 400 WORDS)

Adenoma↗
PubMed1986

Regression of rat primary mammary tumors following dietary d-limonene.

The effects of d-limonene on rat mammary tumors were investigated. Following the appearance of mammary tumors induced by 7,12-dimethylbenz[a]anthracene in female (W/Fu X F344)F2 rats, animals were assigned to pairs in which 1 rat was fed a diet containing 10% d-limonene and the other was pair fed an isocaloric diet containing 10% cellulose. There was a highly significant increase in the regression of the first tumors in the rats fed d-limonene. In addition, d-limonene given at this time inhibited the formation of subsequent multiple tumors in these rats.

9,10-Dimethyl-1,2-benzanthracene↗
PubMed1983

The influence of limonene on induced delayed hypersensitivity to citral in guinea pigs. II. Label distribution in the skin of 14C-labelled citral.

14C-labelled citral was applied on four groups of guinea pigs: (a) one sensitized to citral alone; (b) one sensitized to a citral-d-limonene 1 : 1 molar mixture; (c) FCA-treated controls; (d) controls. The most important results concern the amount of labelled material in soluble compared with insoluble skin protein extracts (SPE). In citral-sensitized animals, more label was found in the soluble SPE when citral + limonene was applied to the skin; in citral + limonene sensitized animals, the same trend (i.e. more label in soluble SPE) was found. The possible role of limonene in alleviating the allergic reaction to citral is discussed.

Acyclic Monoterpenes↗
PubMed1996

Effect of d-limonene, alpha-pinene and cineole on in vitro transdermal human skin penetration of chlorpromazine and haloperidol.

The aim of this research is to carry out a comparative study of the ability to cross human skin of two neuroleptic drugs: chlorpromazine (CAS 50-53-3) and haloperidol (CAS 52-86-8), in the absence and in the presence of three terpenes (cineole, d-limonene and alpha-pinene) with the purpose of considering the possibility of improving their transdermal penetration profile. Franz diffusion cells were used, in conjunction with human skin as permeation membrane. The permeation parameters calculated were permeability constant (Kp), flux (J) and lag time (Tl) in the presence and in the absence of enhancers. None of the three enhancers assayed improved the penetration profile of chlorpromazine, and d-limonene even reduced the transdermal permeability (enhancement index, EI = 0.67) since its coefficient of relative activity was reduced, (Xr = 0.73). Cineole and d-limonene increased the permeation profile of haloperidol, giving EI values of 1.95 and 4.21, respectively, and leading to a fourfold increase in the flux value for both enhancers. alpha-Pinene did not modify the permeation profile of haloperidol. None of the three terpenes assayed had a significant effect on the lag time of chlorpromazine or haloperidol. In these experimental conditions the concentration values predicted at steady state of chlorpromazine formulated without enhancers are within the therapeutic range. In contrast, therapeutic levels of haloperidol cannot be predicted in the absence of enhancers such as d-limonene or cineole.

Antipsychotic Agents↗