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PubMed2005

How does the type of vehicle influence the in vitro skin absorption and elimination kinetics of terpenes?

Terpenes are widely used in the topical dermal preparations, cosmetics and toiletries and also in the experimental dermopharmacy, as penetration enhancers. Terpenes do not need to penetrate into viable skin tissue and this event is not even desired. The aim of this study was to investigate skin absorption and elimination kinetics of two terpenes, namely linalool and terpinen-4-ol, incorporated in three different dermatological vehicles: oily solution, hydrogel and o/w emulsion. The preparations were applied onto the human skin in vitro, and after 1-4 h the content of terpenes in the stratum corneum layers and in the epidermis/dermis was determined using GC. Similarly, the amounts of terpenes in the skin were analysed during 4 h elimination process following 1 h absorption. The highest skin absorption was observed when terpenes were applied in hydrogel--their total content in the skin after 4 h was 385 and 705 microg/cm2 for linalool and terpinen-4-ol, respectively. After 1 h of the elimination process about 10-20% drop of the total content of both terpenes in the skin was noted for all formulations. The skin penetration of both terpenes from the vehicles is increasing in the following order: emulsion < oily solution < hydrogel, while the elimination phase is relatively slower for terpenes applied in hydrogel.

Acyclic Monoterpenes↗
PubMed2006

Changes in terpene content in milk from pasture-fed cows.

Changes of terpene content in milk from cows grazing natural diversified upland pasture were examined in this observational trial. A homogeneous plot divided into 2 subplots was used from May 31 to July 1, 2003 (first growth) and again from October 1 to October 7, 2003 (vegetative regrowth). Each subplot was grazed by 6 dairy cows in 2 ways: strip grazing (SG), with new allocations of pasture strips at 2-d intervals, and paddock grazing (PG). The PG subplot was divided into 3 paddocks and the cows were moved to a new paddock on June 13 and June 24, 2003. Milk from the 6 cows was collected twice a week, pooled, and used for terpene analyses by dynamic headspace gas chromatography-mass spectrometry system. Twenty mono- and 23 sesquiterpenes desorbing from the milk fat were separated. The most abundant monoterpenes were beta-pinene, alpha-pinene, gamma-terpinene, limonene, alpha-tujene, terpinolene, and alpha-phellandrene. The most abundant sesquiterpenes were beta-caryophyllene, alpha-copaene, beta-cedrene, transmuurola-4-(14)-5-diene, beta-bisabolene, and delta-cadinene. Both mono- and sesquiterpenes in SG milk increased across time with an 8-fold increase in total terpenes in milk from the beginning to the end of June. In parallel, dicotyledons, including the main terpene-rich plants, increased from 17 to 31% of total biomass of the vegetation and the development of Dactylis glomerata progressed from boot to ripening stage. The terpenes in PG milk were equivalent to those in SG milk for the first paddock at the beginning of June and remained constant or doubled for the sum of mono- and sesquiterpenes, respectively. The lower variability of the PG milk terpene content could be related to the opportunity that PG cows had to choose ingested herbage, whereas the SG cows had limited choice within the smaller allocated pasture strips. Milk from cows grazing regrowth pastures in October contained low levels of terpenes, and values were similar for PG and SG milks. Change in the sum of monoterpenes is representative of changes for most monoterpenes (except for limonene) and, conversely, the change in the sum of sesquiterpenes mainly reflected changes in beta-caryophyllene and alpha-copaene. In addition to effects of botanical composition of pasture, it appears that terpene content in milk may vary according to factors linked to grazing management that need more intensive study. Nevertheless, current results raise questions about the precision of terpenes as feed tracers.

Animal Feed↗
PubMed1984

Evidence for a terpene-based food chain in the gulf of alaska.

A mixture of C-terpenes was prepared from conifer seedlings and introduced into fresh seawater samples taken near Seward, Alaska. Initial rates of oxidation by the indigenous bacteria were linear and faster than the rates of toluene oxidation. Turnover times were 4 to 19 days. Autoradiographic measurements with H-terpenes indicated that at least 10% of the 0.6 x 10 to 2.7 x 10 bacteria per liter present could catabolize terpenes. The rate of terpene oxidation, 24 mug of terpenes per g of cells per h with 3 mug of terpenes added per liter, was a constant function of bacterial biomass. The specific affinity of the process was estimated to be between 8.1 and 81 liters/g of cells per h, indicating a high state of induction and the probable presence of terpenes. Terpene-oxidizing bacteria were grown on [C]alanine and added to fresh seawater samples. Transfer of the bacterial radioactivity into larger particles at a rate of 146 pg/liter per h from the 2.3 x 10 organisms added indicated that any terpenes present would participate in the food chain.

Journal Article↗
PubMed2006

Terpene degradation and extraction from basil and oregano leaves using subcritical water.

In the first part of this study, the stability of five terpenes (alpha-pinene, limonene, camphor, citronellol, and carvacrol) under subcritical water conditions was investigated. The stability studies were carried out at four different temperatures (100, 150, 200, and 250 degrees C) with two different heating times (30 and 300 min). When water temperature was increased, the degradation of terpenes became more serious. Prolonged exposure time to each heating temperature also caused decreased terpene stability. The terpene recoveries were determined by conducting subcritical water extraction of sand spiked with terpenes. The recoveries are typically around 70 to 80% for extractions at 100 degrees C. Terpene recoveries were decreased with increasing water temperature due to poorer stability of terpenes. After the degradation and recovery studies, basil and oregano leaves were extracted using water at both 100 and 150 degrees C. The concentrations of each individual terpene in the water extract generally ranged from trace quantity to 65 microg terpene/g herb. However, the concentration of carvacrol in the oregano-water extract at 150 degrees C was found to be as high as 4270 microg carvacrol/g oregano.

Analytic Sample Preparation Methods↗
PubMed2006

The effect of terpene concentrations on the skin penetration of diclofenac sodium.

Terpenes and sesquiterpenes have been suggested as promising non-toxic, non-irritating transdermal penetration enhancers. This investigation aimed to study the effect of terpene concentration on the transdermal absorption of diclofenac sodium from ethanol:glycerin:phosphate buffer solution (60:10:30). Therefore, enhancing effects of various terpenes (menthone, limonenoxide, carvone, nerolidol and farnsol) with different concentrations (0.25, 0.5, 1, 1.5 and 2.5%, v/v) on the permeation of diclofenac sodium were evaluated using Franz diffusion cells fitted with rat skin. Furthermore, solubility of diclofenac sodium in the vehicle in presence of different concentrations of terpenes was determined. The results showed that despite the negligible effect of terpenes on the drug solubility, there was a profound skin penetration enhancement effect, although the terpene enhancers varied in their ability to enhance the flux of diclofenac sodium. The results showed that at the highest concentration of terpene (2.5%, v/v) the rank order of enhancement effect for diclofenac sodium was nerolidol>farnesol>carvone>methone>limonenoxide, whereas at the low concentration of 0.25% the rank order was farnesol>carvone>nerolidol>menthone>limonenoxide. No direct relationship existed between terpene concentration and the permeation rate. The most outstanding penetration enhancer was nerolidol, providing an almost 198-fold increase in permeability coefficient of diclofenac sodium, followed by farnesol with a 78-fold increase.

Administration, Cutaneous↗
PubMed2000

The effect of terpene enhancer lipophilicity on the percutaneous permeation of hydrocortisone formulated in HPMC gel systems.

The percutaneous permeation of hydrocortisone (HC) was investigated in hairless mouse skin after application of an alcoholic hydrogel using a diffusion cell technique. The formulations contained one of 12 terpenes, the selection of which was based on an increase in their lipophilicity (log P 1.06-5.36). Flux, cumulative receptor concentrations, skin content, and lag time of HC were measured over 24 h and compared with control gels (containing no terpene). Furthermore, HC skin content and the solubility of HC in the alcoholic hydrogel solvent mixture in the presence of terpene were determined, and correlated to the enhancing activity of terpenes. The in vitro permeation experiments with hairless mouse skin revealed that the terpene enhancers varied in their ability to enhance the flux of HC. Nerolidol which possessed the highest lipophilicity (log P = 5.36+/-0.38) provided the greatest enhancement for HC flux (35.3-fold over control). Fenchone (log P = 2.13+/-0.30) exhibited the lowest enhancement of HC flux (10.1-fold over control). In addition, a linear relationship was established between the log P of terpenes and the cumulative amount of HC in the receptor after 24 h (Q(24)). Nerolidol, provided the highest Q(24) (1733+/-93 microg/cm(2)), whereas verbenone produced the lowest Q(24) (653+/-105 microg/cm(2)). Thymol provided the lowest HC skin content (1151+/-293 microg/g), while cineole produced the highest HC skin content (18999+/-5666 microg/g). No correlation was established between the log P of enhancers and HC skin content. A correlation however, existed between the log P of terpenes and the lag time. As log P increased, a linear decrease in lag time was observed. Cymene yielded the shortest HC lag time, while fenchone produced the longest lag time. Also, the increase in the log P of terpenes resulted in a proportional increase in HC solubility in the formulation solvent mixture.

Animals↗
PubMed2003

Induction of volatile terpene biosynthesis and diurnal emission by methyl jasmonate in foliage of Norway spruce.

Terpenoids are characteristic constitutive and inducible defense chemicals of conifers. The biochemical regulation of terpene formation, accumulation, and release from conifer needles was studied in Norway spruce [Picea abies L. (Karst)] saplings using methyl jasmonate (MeJA) to induce defensive responses without inflicting physical damage to terpene storage structures. MeJA treatment caused a 2-fold increase in monoterpene and sesquiterpene accumulation in needles without changes in terpene composition, much less than the 10- and 40-fold increases in monoterpenes and diterpenes, respectively, observed in wood tissue after MeJA treatment (D. Martin, D. Tholl, J. Gershenzon, J. Bohlmann [2002] Plant Physiol 129: 1003-1018). At the same time, MeJA triggered a 5-fold increase in total terpene emission from foliage, with a shift in composition to a blend dominated by oxygenated monoterpenes (e.g. linalool) and sesquiterpenes [e.g. (E)-beta-farnesene] that also included methyl salicylate. The rate of linalool emission increased more than 100-fold and that of sesquiterpenes increased more than 30-fold. Emission of these compounds followed a pronounced diurnal rhythm with the maximum amount released during the light period. The major MeJA-induced volatile terpenes appear to be synthesized de novo after treatment, rather than being released from stored terpene pools, because they are almost completely absent from needle oleoresin and are the major products of terpene synthase activity measured after MeJA treatment. Based on precedents in other species, the induced emission of terpenes from Norway spruce foliage may have ecological and physiological significance.

Acetates↗
PubMed2005

Seasonal changes in foliar terpenes indicate suitability of Douglas-fir buds for western spruce budworm.

The terpene composition of current-year buds of Douglas-fir, Pseudotsuga menziesii (Mirb.) Franco, was analyzed from before budburst to after buds were fully flushed. Terpene composition was measured at weekly intervals for several seasons at eight different locations in the southern interior of British Columbia, Canada. Discriminant functions relating terpene composition to suitability of buds for newly emerged western spruce budworm, Choristoneura occidentalis Freeman, were developed based on terpene profiles of the buds and bioassays measuring the suitability to budworms of a sister group of buds. Changes in percent composition of bud terpenes before and during budburst were closely associated with changes in the suitability of the buds to utilization by budworms at both the tree and site by date levels. Use of a degree-day scale for bud suitability removed much of the year-to-year variation, but remaining differences among sites suggest additional sources of variation influencing the insect host plant relationship. The success of correctly classifying bud suitability using terpene profiles demonstrates the value of foliar terpenes as indicators of seasonal changes in suitability of Douglas-fir foliage during the critical spring emergence period of western spruce budworm. This indicator could be used to screen individual trees susceptible to budworm damage and identify sites at high risk of damaging defoliation.

Animals↗
PubMed2000

Characterisation of tolbutamide hydroxylase activity in the common brushtail possum, (Trichosurus vulpecula) and koala (Phascolarctos cinereus): inhibition by the eucalyptus terpene 1,8-cineole.

Plant constituents such as terpenes are major constituents of the essential oil in Eucalyptus sp. 1,8-Cineole and p-cymene (Terpenes present in high amounts in Eucalyptus leaves) are potential substrates for the CYP family of enzymes. We have investigated tolbutamide hydroxylase as a probe substrate reaction in both koala and terpene pretreated and control brushtail possum liver microsomes and examined inhibition of this reaction by Eucalyptus terpenes. The specific activity determined for tolbutamide hydroxylase in the terpene treated brushtails was significantly higher than that for the control animals (1865+/-334 nmol/mg microsomal protein per min versus 895+/-27 nmol/mg microsomal protein per min). The activity determined in koala microsomes was 8159+/-370 nmol/mg microsomal protein per min. Vmax values and Km values for the terpene treated possum, control, possum and koala were 1932-2225 nmol/mg microsomal protein per min and 0.80 0.81 mM; 1406-1484 nmol/mg microsomal protein per min and 0.87-0.92 mM and 5895-6403 nmol/mg microsomal protein per min and 0.067-0.071 mM, respectively. Terpenes were examined as potential inhibitors of tolbutamide hydroxylase activity. 1,8-Cineole was found to be a competitive inhibitor for the enzyme responsible for tolbutamide hydroxylation (Ki 15 microM) in the possum. In koala liver microsomes stimulation of tolbutamide hydroxylase activity was observed when concentrations of cineole were increased. Therefore, although inhibition was observed, the type of inhibition could not be determined.

Animals↗
PubMed1991

Terpenes and the lipid-protein-partitioning theory of skin penetration enhancement.

A series of terpenes has been assessed as skin penetration enhancers towards the model polar penetrant 5-fluorouracil (5-FU). Cyclic terpenes were selected from the chemical classes of hydrocarbons (e.g., alpha-pinene), alcohols (e.g., alpha-terpineol), ketones (e.g., carvone), and oxides (e.g., 1.8-cineole, ascaridole). Permeation experiments were performed on excised human epidermal membranes and the terpenes varied in their activities; alpha-pinene only doubled the permeability coefficient of aqueous 5-FU, whereas 1.8-cineole caused a near 95-fold increase. Essential oils, e.g., chenopodium (70% ascaridole), were less effective than the corresponding isolated terpenes, 5-FU is less soluble in the terpenes than in water, and the terpenes did not exert their action by increasing partitioning of the drug into the membranes as illustrated by stratum corneum:water partitioning studies. The penetration enhancers increased drug diffusivity through the membranes, an effect which correlated empirically with the enhancer activities. The principal mode of action of these accelerants may be described by the lipid-protein-partitioning theory: the terpenes interacted with intercellular stratum corneum lipids to increase diffusivity, and the accelerant effects were not due to partitioning phenomena. Keratin interaction was assumed negligible.

Adult↗
PubMed2003

Oxide terpenes as human skin penetration enhancers of haloperidol from ethanol and propylene glycol and their modes of action on stratum corneum.

In this study, two terpenes with the same functional group; limonene oxide and pinene oxide were used at 5% w/v concentration in 50% v/v ethanol and 100% v/v propylene glycol (PG) to enhance the in vitro permeation of haloperidol (HP) through the human epidermis (or stratum corneum, SC). The enhancement mechanism of terpenes from both solvents was elucidated with HP-SC binding studies, Fourier transform infrared spectroscopy and differential scanning calorimetry. The enhancement activity of these terpenes was higher in 50% v/v ethanol than in 100% v/v PG. These terpenes in 50% v/v ethanol were predicted to provide the required therapeutic plasma concentration and daily-permeated amounts of the drug. Limonene oxide showed higher enhancement in both solvents, which was attributed to its less bulky structure. The terpenes in both solvents did not increase the partition of HP. Instrumental studies showed that these terpenes in 50% v/v ethanol extracted the SC lipids, disrupted the bilayer packing and partially fluidised the lipids. Limonene oxide in 100% v/v PG possibly disrupted the lipid bilayer, whilst leaving the overall bilayer structure intact and pinene oxide in the same vehicle fluidised the lipids within the ordered environment. This study showed that the mode of interactions of terpenes with SC were different in two solvent systems.

Epidermis↗
PubMed2004

[Studies on analysis of terpene resin in imported chewing gums].

We have developed an analytical method for terpene resins in chewing gum. The fraction including terpene resins was prepared by means of hexane extraction and two silica gel column chromatography treatments (hexane and ethyl acetate) from chewing gum. The terpene resin fraction was analyzed with LC/MS and IR. The terpene resins are mixtures of polymeric pinene and/or limonene, which have a monomer molecular weight of 136. The MS spectrum of the terpene resin peak on the LC/MS total ion chromatogram showed protonated molecular ion (M + H)+ peaks at intervals of m/z 136, characteristic of a complex mixture of polyterpenes. IR spectroscopy is a suitable technique to identify the terpene resin type, ie., pinene or limonene. When the method was applied to imported chewing gum sold in Japan, terpene resins were clearly detected.

Chewing Gum↗
PubMed2001

Genomic organization of plant terpene synthases and molecular evolutionary implications.

Terpenoids are the largest, most diverse class of plant natural products and they play numerous functional roles in primary metabolism and in ecological interactions. The first committed step in the formation of the various terpenoid classes is the transformation of the prenyl diphosphate precursors, geranyl diphosphate, farnesyl diphosphate, and geranylgeranyl diphosphate, to the parent structures of each type catalyzed by the respective monoterpene (C(10)), sesquiterpene (C(15)), and diterpene synthases (C(20)). Over 30 cDNAs encoding plant terpenoid synthases involved in primary and secondary metabolism have been cloned and characterized. Here we describe the isolation and analysis of six genomic clones encoding terpene synthases of conifers, [(-)-pinene (C(10)), (-)-limonene (C(10)), (E)-alpha-bisabolene (C(15)), delta-selinene (C(15)), and abietadiene synthase (C(20)) from Abies grandis and taxadiene synthase (C(20)) from Taxus brevifolia], all of which are involved in natural products biosynthesis. Genome organization (intron number, size, placement and phase, and exon size) of these gymnosperm terpene synthases was compared to eight previously characterized angiosperm terpene synthase genes and to six putative terpene synthase genomic sequences from Arabidopsis thaliana. Three distinct classes of terpene synthase genes were discerned, from which assumed patterns of sequential intron loss and the loss of an unusual internal sequence element suggest that the ancestral terpenoid synthase gene resembled a contemporary conifer diterpene synthase gene in containing at least 12 introns and 13 exons of conserved size. A model presented for the evolutionary history of plant terpene synthases suggests that this superfamily of genes responsible for natural products biosynthesis derived from terpene synthase genes involved in primary metabolism by duplication and divergence in structural and functional specialization. This novel molecular evolutionary approach focused on genes of secondary metabolism may have broad implications for the origins of natural products and for plant phylogenetics in general.

Alkyl and Aryl Transferases↗
PubMed2005

Preparative isolation of terpene trilactones from Ginkgo biloba leaves.

This study investigated and compared some techniques for the preparative isolation of terpene trilactones, including ginkgolides (GA and GB, etc.) and bilobalide (BB), from Ginkgo biloba leaves. The crude Ginkgo biloba L. extracts (GBE) were prepared using an extractor with solvent refluxing operated under an optimal extraction condition. The extraction yield was 20-23% and the purity of terpene trilactones was about 1.0-1.4 wt%. Before the isolation operations, the extracts were dissolved in de-ionized water. The isolation procedures included the method of liquid-liquid extraction and the method of column chromatography. For the method of liquid-liquid extraction using ethyl acetate as the organic solvent operated under the optimal extraction conditions, the purity, concentration ratio, and yield of terpene trilactones were 13.5-18.0%, 15-16, and >99%. For the method of column chromatography, XAD-7HP, XAD-4, and C-18 adsorbents with different polarities were used as the packing materials. Only for the XAD-7HP column, a part of more polar impurities was efficiently separated with the majority of terpene trilactones by a proper step-gradient elution, which resulted in an efficient isolation: the purity, concentration ratio, and yield of terpene trilactones were approximately 20, approximately 15, and approximately 80%. In comparison, the XAD-7HP column achieved the highest purity, but at the expense of the yield of terpene trilactones; on the contrary, the liquid-liquid extraction method, achieving the highest yield but with a slightly lower purity, was proved to be superior to the method of column chromatography in the current isolation stage.

Adsorption↗
PubMed2004

The effect of pretreatment with terpenes on transdermal iontophoretic delivery of arginine vasopressin.

This study investigates the effects of terpenes and iontophoresis on the in vitro permeation of arginine vasopressin (AVP) through rat skin and the biophysical changes induced by the chemical enhancers in the stratum corneum (SC) lipids by FT-IR spectroscopy. Pretreatment with terpenes (e.g. 5% w/v, carvone, pulegone, cineole and menthol in EtOH:W (2:1) system) increased (P < 0.05) the flux of AVP in comparison to control (not pretreated with enhancer) but was not significantly different (P > 0.05) in comparison to iontophoresis. Amongst different terpenes studied maximum enhancement ratio was observed with cineole. In combination, iontophoresis did not further increase (P > 0.05) the permeation of AVP through the enhancer pretreated epidermis in comparison to pretreatment with enhancer or iontophoresis alone. Hence it was concluded that although the combination was effective in flux enhancement compared to control, there was no synergism in action between terpenes and iontophoresis. FT-IR spectroscopic studies revealed that EtOH:W (2:1) system is not effective in lipid extraction. The area under the symmetric and asymmetric stretching peaks at 2850 and 2920 cm(-1) revealed that at the concentration used terpenes did not extract any lipids from the epidermis. The mode of action of terpenes is attributed to the breaking of hydrogen bonds between the ceramide head groups of lipids in the SC leading to greater fluidization of the SC lipids.

Administration, Cutaneous↗
PubMed2006

Induction of terpene biosynthesis in dinoflagellate symbionts of Caribbean gorgonians.

This report describes a series of experiments designed to determine if terpene biosynthesis is inducible in two families of marine terpenes, pseudopterosins from the gorgonian coral Pseudopterogorgia elisabethae and fuscol from Eunicea fusca. Since we have recently shown that terpene biosynthesis is not under the control of the invertebrate host, but rather occurs within a dinoflagellate preparation, we examined the terpene content of the dinoflagellate symbiont following a decrease in UV/vis radiation as well as in response to the addition of methyl jasmonate, salicylic acid and gibberellic acid. We demonstrated that pseudopterosin and fuscol biosynthesis can be markedly increased through the addition of the plant bioactive substances. We also demonstrated that, while the terpene content of P. elisabethae increases in response to decreased UV/vis light, this is due primarily to an increase in the concentration of the dinoflagellate rather than simply an induction of terpene biosynthesis.

Acetates↗
PubMed2002

Transdermal drug delivery of imipramine hydrochloride. I. Effect of terpenes.

The objective of this investigation was to study the effect of different terpenes on IMH permeation in EtOH:W (2:1) system. Permeation studies of IMH were carried out with unjacketed Franz diffusion cells through rat skin. The flux of IMH with terpenes was found to be significantly higher than that in control (EtOH:W, 2:1) (P<0.05). Amongst all studied terpenes, menthol, terpineol, cineole and menthone were found to be effective permeation enhancers for IMH. It was found that the contribution of diffusivity in enhanced permeation of IMH was much higher in comparison to partitioning of IMH in skin with terpene treatment. Results of this study were explained with the help of H-bond breaking potential and self-association of terpenes. In order to elucidate the effect of terpenes on stratum corneum barrier FT-IR was used.

Administration, Cutaneous↗
PubMed2001

Microsomal metabolism of the terpene 1,8-cineole in the common brushtail possum (Trichosurus vulpecula), koala (Phascolarctos cinereus), rat and human.

1. This study reports on the pathways of metabolism and enzyme kinetics of the Eucalyptus terpene, 1,8-cineole, by liver microsomes from the brushtail possum (Trichosurus vulpecula) and koala (Phascolarctos cinereus) (animals that normally include this terpene in their diet), rat and human. 2. The rank order of the ability to metabolize 1,8-cineole with respect to overall 1,8-cineole intrinsic clearance (CL'int = Vmax/Kmax in microl mg protein(-1) min(-1)) was koala (188) > possum (181)>> rat (28) > human (12). This order supports the hypothesis that adaptation to a Eucalyptus diet involves enhanced metabolism of terpenes. 3. The metabolism of 1,8-cineole was also studied in the liver from brushtail possum pretreated with a mixture of terpenes, which have previously been shown to induce cytochrome P450 enzymes. Rats were pretreated with the same mixture of terpenes or phenobarbitone. 4. Terpene pretreatment more than doubled the CL'int of 1,8-cineole by brushtail possum liver microsomes (from 180 to 394 microl mg protein(-1) min(-1)) and increased rat CL'int by nearly 10-fold (from 28 to 259 microl mg protein(-1) min(-1)), but still less than the induced possum value. However, phenobarbitone had the greatest inducing effect, increasing the rat CL'int to 1,825 microl mg protein(-1) min(-1). 5. A regioselective preference of oxidation was evident between adapted and non-adapted species. In rat and human oxidation was preferred at the aliphatic ring carbons over methyl substituents. In possum, many of the available carbons were utilized, however metabolism at methyl substituents was preferred. In the koala, oxidation occurred primarily at the methyl substituents.

Adult↗