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PubMed1980

Action of douglas fir tussock moth larvae and their microflora on dietary terpenes.

A single type of bacterium, tentatively identified as a member of the genus Bacillus, was isolated from 2 of 20 midguts of Douglas fir tussock moth larvae being fed a diet of fir needles. No bacteria could be isolated from most midguts. Although spherically shaped bodies were present in the food bolus, these bodies, if microorganisms, could not be distinguished from spherical bodies associated with the plant tissue. The Douglas fir tussock moth dietary terpenes were altered during their passage through the insects, with two new terpenes being detected in the feces. One of these was identified as isoborneol. The relative significance of the insect and gut microflora with respect to terpene modification is unresolved. The well-established toxicity of terpenes may account for the near absence of common gut microflora in the insects.

Journal Article↗

PubMed2000

Seasonal patterns of terpene content and emission from seven Mediterranean woody species in field conditions.

The seasonal pattern of terpene content and emission by seven Mediterranean woody species was studied under field conditions. Emission rates were normalized at 30°C and 1000 μmol·m·s PFD (photosynthetic photon flux density). Bupleurum fruticosum, Pinus halepensis, and Cistus albidus stored large amounts of terpenes (0.01-1.77% [dry matter]) with maximum values in autumn and minimum values in spring. They emitted large amounts of terpenes (2-40 μg·g DM·h), but with no clear seasonal trend except for Cistus albidus, which had maximum values in spring and minimum values in autumn. The nonstoring species Arbutus unedo, Erica arborea, Quercus coccifera and Quercus ilex also emitted large amounts of terpenes (0-40 μg·g DM·h) and also tended to present maximum emission rates in spring, although this trend was significant only for A. unedo. At the seasonal scale, emission rates did not follow changes in photosynthetic rates; instead, they mostly followed changes in temperature. From autumn to spring, the least volatile monoterpenes such as limonene were emitted at highest rates, whereas the most volatile monoterpenes such as α-pinene and β-pinene were the most emitted in summer. The monoterpene emission rates represented a greater percentage of the photosynthetic carbon fixation in summer (from 0.51% in Arbutus unedo to 5.64% in Quercus coccifera) than in the rest of the seasons. All these seasonality trends must be considered when inventorying and modeling annual emission rates in Mediterranean ecosystems.

Journal Article↗

PubMed2004

[Studies on the cell growth, differentiation and terpene lactone accumulation in Ginkgo biloba cell suspension cultures].

To provide supports for Ginkgo biloba cell engineering for production of Terpene lactones (Ginkgolides and bilobalide), the cell suspension were established from calli induced from zygote embryos and stems of 30-day-old seedlings respectively. The relationship between cell growth, differentiation and the terpene lactone accumulation in these suspension cultures were investigated. HPLC determination indicated that, the ginkgolide B was found in the embryo derived cell suspension cultures at 0.044% of cell dry weight, and this result was the first time reported in this study. The accumulation of terpene lactone in the suspension cultures derived from both the embryo and seedling stems are effected by the level of the cell differentiation. The ginkgolide B was only found in small cell aggregates in the size smaller than 2mm, and the highest level of ginkgolide B was accumulated in cell aggregates in the size smaller than 1mm; however, the cell aggregates in the size bigger than 3mm could only produced bilobalide and ginkgolide A. In the same size aggregates of the suspension cultures the terpene lactone accumulation is strongly effected by the source of the explant. When the size of cell aggregates was in less than 1mm, the concentration of bilobalide, ginkgolide A and B in the cell suspension cultures derived from the embryos was 2, 1.4 and 0.56-fold, respectively, higher than that of cell cultures derived from seedling stems.

Bilobalides↗

PubMed2004

Chemistry and biology of terpene trilactones from Ginkgo biloba.

Ginkgo biloba, the ginkgo tree, is the oldest living tree, with a long history of use in traditional Chinese medicine. In recent years, the leaf extracts have been widely sold as phytomedicine in Europe and as a dietary supplement worldwide. Effects of Ginkgo biloba extracts have been postulated to include improvement of memory, increased blood circulation, as well as beneficial effects to sufferers of Alzheimer's disease. The most unique components of the extracts are the terpene trilactones, that is, ginkgolides and bilobalide. These structurally complex molecules have been attractive targets for total synthesis. Terpene trilactones are believed to be partly responsible for the neuromodulatory properties of Ginkgo biloba extracts, and several biological effects of the terpene trilactones have been discovered in recent years, making them attractive pharmacological tools that could provide insight into the effects of Ginkgo biloba extracts.

Biology↗

PubMed2005

Adsorption separation of terpene lactones from Ginkgo biloba L. extract using glass fiber membranes modified with octadecyltrichlorosilane.

In this study porous glass fiber membranes were modified by reaction with octadecyl-trichlorosilane to form C18 hydrophobic membranes. The contact angle and the CH2 vibration bands at 2855 and 2920 cm(-1) found by FTIR measurements verified the successful immobilization of C18 groups on the glass fiber membranes. The resulting C18 hydrophobic membranes were used to adsorb terpene lactones from crude Ginkgo biloba L. extracts. In batch adsorption processes, the modified C18 membranes exhibited a better adsorption performance than commercial C18 solid phase extraction adsorbents. Different desorption solvents were tested and ethyl acetate was found to preferentially desorb terpene lactones from the modified C18 membranes. In flow adsorption experiments at 1 mL/min, terpene lactone contents higher than 6 wt% (the standardized content) could be achieved in the elution step using ethyl acetate.

Adsorption↗

PubMed1983

Exposure to terpenes: effects on pulmonary function.

Forty-eight subjects exposed to terpenes (mean air concentration 258 mg m-3) and 47 unexposed subjects, all employed at sawmills, were studied with regard to symptoms and pulmonary function. Dyspnoea and chest oppression were significantly increased in the exposed subjects compared to the unexposed controls. A reduced FEV1, on spirometry and an increased CV% and slope of the alveolar plateau (phase III) on single breath nitrogen washout were seen on Monday morning before exposure to terpenes. There was no correlation between exposure time (duration of employment) and lung function impairment. A day of industrial exposure to terpenes caused no further change in any lung function variable. The unexposed controls showed normal spirometry and nitrogen washouts. The findings indicate a slight stable lung function impairment of an obstructive nature which does not necessarily undergo further deterioration with increased duration of exposure.

Adult↗

PubMed1993

Terpenes enhance metabolic activity and alter expression of adhesion molecules (Mac-1 and L-selectin) on human granulocytes.

Granulocytes from healthy blood donors were exposed to terpenes dissolved in ethanol. Flow cytometry was used to measure the expression of the cell surface receptors Mac-1 L-selectin, and CR1, which were detected by monoclonal antibodies. The phagocytic activity was determined by using C3b-coated yeast particles as prey. The metabolic activity was measured by determining the intracellular hydrogen peroxide production using dichlorofluorescein diacetate. After terpene exposure the expression of Mac-1 and CR1 increased (P < 0.001 and P < 0.01, respectively) and the expression of L-selectin decreased (P < 0.001). There was also an increased metabolic activity (P < 0.001). The cell viability, the cell count, and the phagocytic activity remained unchanged. These findings suggest that terpene exposure triggers the granulocytes to a higher degree of activation in terms of an altered expression of the adhesion molecules and an increased metabolic activity.

Cell Adhesion↗

PubMed1985

[Aroma of the papaya fruit (Carica papaya, L.): indication of volatile precursors of terpene compounds].

In fruit pulp of papaya (Carica papaya, L.) the enzymes were inhibited by Hg2+. These sample were compared with others, in which the enzymes had not been inhibited. After separation and prefractionation of volatiles by means of high vacuum distillation/solvent extraction and subsequent adsorption chromatography on silicagel, capillary gas chromatography-mass spectrometry showed that in the experiment with Hg2+ the formation of terpene alcohols and hydrocarbons as well as benzylisothiocyanate was totally inhibited. The formation of linalooloxides and related compounds was inhibited to about 60%. From these results the occurrence of bound terpene precursors in papaya fruit may be postulated, from which the free volatile terpenes are enzymatically liberated after decompartmentalization of tissue during fruit pulp preparation.

Chromatography, Affinity↗

PubMed2005

Estimation of transdermal permeation parameters in non-stationary diffusion experiments. Application to pre-treatment studies with terpenes.

PURPOSE: To estimate the applicability of transdermal drug permeation parameters in a finite-dose model for skin pre-treated with terpenes and to evaluate the enhancing effect of some terpene formulations on alprazolam permeation. METHODS: In vitro enhancement of alprazolam human skin permeation was investigated using a pretreatment with different terpene solutions. Vertical diffusion, Franz-type cells were used. Intrinsic drug permeation was also investigated. Transdermal permeation parameters were estimated from the permeation tabulates using different theoretical approaches for their calculation. Two groups of permeation parameters were calculated: modelistic (diffusion of a finite-dose of drug model) and parameters nondependent of a diffusional model. RESULTS: In control experiments, all approaches of data treatment satisfactorily described the experimental permeation profiles. When skin pre-treatment was investigated, the fitting of a mathematical sigmoid function was much better than the diffusional approach. Pre-treatment of the skin with Limonene dissolved in ethanol / propylene glycol and Menthol dissolved in propylene glycol increased 15 and 10 times respectively the permeation parameters of alprazolam. CONCLUSIONS: Using enhancers that are rapidly cleared from the skin, skin permeability does not remain constant during the permeation experiment and therefore it is not possible to calculate parameters that are usually true coefficients or definite values. In this case, non-modelistic parameters can be used to estimate an enhancing effect.

Administration, Cutaneous↗

PubMed1992

Porphyrogenic properties of the terpenes camphor, pinene, and thujone (with a note on historic implications for absinthe and the illness of Vincent van Gogh).

Camphor, alpha-pinene (the major component of turpentine), and thujone (a constituent in the liqueur called absinthe) produced an increase in porphyrin production in primary cultures of chick embryo liver cells. In the presence of desferrioxamine (an iron chelator which inhibits heme synthesis and thereby mimics the effect of the block associated with acute porphyria), the terpenes enhanced porphyrin accumulation 5- to 20-fold. They also induced synthesis of the rate-controlling enzyme for the pathway, 5-aminolevulinic acid synthase, which was monitored both spectrophotometrically and immunochemically. These effects are shared by well-known porphyrogenic chemicals such as phenobarbital and glutethimide. Camphor and glutethimide alone led to the accumulation of mostly uro- and heptacarboxylporphyrins, whereas alpha-pinene and thujone resulted in lesser accumulations of porphyrins which were predominantly copro- and protoporphyrins. In the presence of desferrioxamine, plus any of the three terpenes, the major product that accumulated was protoporphyrin. The present results indicate that the terpenes tested are porphyrogenic and hazardous to patients with underlying defects in hepatic heme synthesis. There are also implications for the illness of Vincent van Gogh and the once popular, but now banned liqueur, called absinthe.

5-Aminolevulinate Synthetase↗

PubMed1994

Safety evaluations of food chemicals by "COMPACT". 1. A study of some acyclic terpenes.

A group of 19 acyclic terpenes have been evaluated for potential toxicity/carcinogenicity by molecular orbital determinations of their spatial and electronic parameters, and hence prediction of their metabolic activation or detoxication by the cytochrome P-450 (CYP) superfamily of mixed-function oxidase enzymes. Previous studies have characterized the spatial dimensions of the CYP1A1, 1A2 and 2E1 enzymes, which are known to activate mutagens and carcinogens and to be involved in other mechanisms of toxicity. None of the terpenes was found to have shape or electronic parameters appropriate for metabolic activation by CYP1A1 or 1A2, and hence they are unlikely to be carcinogenic or mutagenic. Furthermore, none of these chemicals had spatial parameters critical for substrates of CYP2E, and they are therefore unlikely to induce the formation of reactive oxygen species (ROS) or to initiate or promote malignancy or toxicity by mechanisms involving ROS. However, citral, and others of these terpenes, are known to undergo metabolism to carboxylic acids that may induce CYP4, and are therefore possible inducers of hepatic peroxisomal proliferation at high dosage, which may have implications for possible hepatotoxicity.

Animals↗

PubMed2005

Biotransformation of terpenes.

The main application of terpenes as fragrances and flavors depends on the absolute configuration of the compounds because enantiomers present different organoleptic properties. Biotransformations allow the production of regio- and stereoselective compounds under mild conditions. These products may be labeled as "natural". Commercially useful chemical building-blocks and pharmaceutical stereo isomers can also be produced by bioconversion of terpenes. Enzymes and extracts from bacteria, cyanobacteria, yeasts, microalgae, fungi, plants, and animal cells have been used for the production and/or bioconversion of terpenes. In addition, whole cell catalysis has also been used. A variety of media and reactors have been assessed for these biotransformations and have produced encouraging results, as discussed in this review.

Bacteria↗

PubMed2006

Determination of terpenes in tequila by solid phase microextraction-gas chromatography-mass spectrometry.

Solid phase microextraction and capillary gas chromatography-mass spectrometry were used for the determination of seven terpenes in tequila. The method was selected based on the following parameters: coating selection (PA, PDMS, CW/DVB, and PDMS/DVB), extraction temperature, addition of salt, and extraction time profile. The extraction conditions were: PDMS/DVB fiber, Headspace, 100% NaCl, 25 degrees C extraction temperature, 30 min extraction time and stirring at 1200 rpm. The calibration curves (50-1000 ng/ml) for the terpenes followed linear relationships with correlation coefficients (r) greater than 0.99, except for trans,trans-farnesol (r = 0.98). RSD values were smaller than 10% confirmed that the technique was precise. Samples from 18 different trade brands of "Aged" tequila analyzed with the developed method showed the same terpenes in different concentrations. The analytical procedure used is selective, robust (more than 100 analyses with the same fiber), fast and of low-cost.

Alcoholic Beverages↗

PubMed2006

Effect of DC/mDC iontophoresis and terpenes on transdermal permeation of methotrexate: in vitro study.

The systemic toxicity caused by methotrexate limits its use and transdermal delivery would be a possible alternative. Transdermal permeation of methotrexate loaded into polyacrylamide-based hydrogel patch, across mice skin was studied in vitro after pretreatment with terpenes and ethanol, alone or in combination with iontophoresis (DC/mDC). Polyacrylamide patches gave the maximum flux as compared to the copolymers of acrylamide and acrylic acid. Of the terpenes used, pure menthol showed maximum enhancement (38%), whereas pure limonene elicited a minimum of 9.9% enhancement. Binary combination of menthol and ethanol increased the permeation to 54.9%, which was further enhanced to 93.69% and 117% when used in combination with DC and square wave (mDC) iontophoresis, respectively. ATR-FTIR of the stratum corneum treated with terpenes showed a split in the asymmetric C-H stretching vibrations along with decrease in peak heights and areas of asymmetric, symmetric C-H stretching, C=O stretching and amide bands. A split in amide II band was observed with iontophoresis. ATR-FTIR studies suggest conformational changes in the lipid-protein domains thereby increasing permeation. Histopathological studies on treated skin samples, gave an insight about the anatomical changes brought by the application of various enhancers. Binary mixture of menthol and ethanol in combination with square wave gave best results.

Acrylic Resins↗

PubMed2005

Atmospheric fate of OH initiated oxidation of terpenes. Reaction mechanism of alpha-pinene degradation and secondary organic aerosol formation.

This paper studies the reaction products of alpha-pinene, beta-pinene, sabinene, 3-carene and limonene with OH radicals and of alpha-pinene with ozone using FT-IR spectroscopy for measuring gas phase products and HPLC-MS-MS to measure products in the aerosol phase. These techniques were used to investigate the secondary organic aerosol (SOA) formation from the terpenes. The gas phase reaction products were all quantified using reference compounds. At low terpene concentrations (0.9-2.1 ppm), the molar yields of gas phase reaction products were: HCHO 16-92%, HCOOH 10-54% (OH source: H2O2, 6-25 ppm); HCHO 127-148%, HCOOH 4-6% (OH source: CH3ONO, 5-8 ppm). At high terpene concentrations (4.1-13.2 ppm) the results were: HCHO 9-27%, HCOOH 15-23%, CH3(CO)CH3 0-14%, CH3COOH 0-5%, nopinone 24% (only from beta-pinene oxidation), limona ketone 61% (only from limonene oxidation), pinonaldehyde was identified during alpha-pinene degradation (OH source H2O2, 23-30 ppm); HCHO 76-183%, HCOOH 12-15%, CH3(CO)CH3 0-12%, nopinone 17% (from beta-pinene oxidation), limona ketone 48% (from limonene oxidation), pinonaldehyde was identified during alpha-pinene degradation (OH source CH3ONO, 14-16 ppm). Pinic acid, pinonic acid, limonic acid, limoninic acid, 3-caric acid, 3-caronic acid and sabinic acid were identified in the aerosol phase. On the basis of these results, we propose a formation mechanism for pinonic and pinic acid in the aerosol phase explaining how degradation products could influence SOA formation and growth in the troposphere.

Aerosols↗

PubMed2026

High-level terpene production via a novel Actinomycetota-derived MVA pathway in E. coli.

The heterologous production of terpene in microbial hosts is often limited by inefficient and unstable pathway expression, creating a major bottleneck for industrial-scale synthesis. While E. coli as a chassis offers significant advantages, such as rapid growth, ease of cultivation, and genetic tractability. Its endogenous supply of terpenoid precursors remains a critical constraint, fundamentally restricting high-yield production. To address this challenge, we developed a genomically integrated Mevalonate (MVA) pathway from Actinomycetota in E. coli BL21(DE3) to enhance terpene precursor supply. Our approach began with an in silico multi-layer global genome mining analysis of 25,261 Actinomycetota genomes to identify a series of MVA pathway enzymes with potentially high catalytic efficiency, created a high-efficiency chassis E. coli MVA platform (ecMVA-1 and ecMVA-2) for terpene precursor synthesis. Its functionality was validated by testing eight distinct TSs. Among them, the fermentation of artemisinin precursor amorphadiene using a 5-liter bioreactor yielded 947.80 mg/L. These results indicated that E. coli (MVA) is well-suited for TS studies in the laboratory as well as holding significant promise for industrial applications. In addition, this in silico approach offers a new perspective for metabolic engineering and provides potential reservoir of diverse chassis for the industrial production of terpenoid-derived compounds.

Actinomycetota↗

PubMed2001

Artificial neural network modeling of Kováts retention indices for noncyclic and monocyclic terpenes.

A quantitative structure-property relationship study based on multiple linear regression (MLR) and artificial neural network (ANN) techniques was carried out to investigate the retention behavior of some terpenes on the polar stationary phase (Carbowax 20 M). A collection of 53 noncyclic and monocyclic terpenes was chosen as data set that was randomly divided into two groups, a training set and a prediction set consist of 41 and 12 molecules, respectively. A total of six descriptors appearing in the MLR model consist of one electronic, two geometric, two topological and one physicochemical descriptors. Except for the geometric parameters the remaining descriptors have a pronounced effect on the retention behavior of the terpenes. A 6-5-1 ANN was generated by using the six descriptors appearing in the MLR model as inputs. The mean of relative errors between the ANN calculated and the experimental values of the Kováts retention indexs for the prediction set was 1.88%. This is in aggreement with the relative error obtained by experiment.

Neural Networks, Computer↗

PubMed2001

The effect of terpenes on the biodegradation of polychlorinated biphenyls by Pseudomonas stutzeri.

The effect of two terpenes, carvone and limonene, on the biodegradation of DELOR 103, a commercial mixture of polychlorinated biphenyls (PCBs), by Pseudomonas stutzeri, an isolate from long-term PCB-contaminated soil, was studied in detail. The addition of both carvone and limonene as potential inducers of the dioxygenase metabolic pathway exerted an enhancing effect on PCB biodegradation when glycerol and xylose were used as carbon sources, whereas no such effect could be determined with biphenyl and glucose as substrates. Promising biodegradation values were determined with xylose as carbon source and carvone as terpene inducer. In this system, 30-70% of the congeners were degraded in the presence of 10 mg l(-1) and 20 mg l(-1) carvone, respectively, irrespective of the used concentration, whereas only 7-37% of individual PCB congeners were eliminated from the system without terpene addition.

Antineoplastic Agents, Phytogenic↗