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Enhancement of propranolol hydrochloride and diazepam skin absorption in vitro: effect of enhancer lipophilicity.

The enhancement of model hydrophilic (propranolol hydrochloride) and lipophilic (diazepam) drug penetration across rat and hairless mouse skin in vitro has been studied. Preliminary experiments established that most n-alkanes having chain lengths of between 7 and 16 promote the flux of both drugs. For propranolol, enhancement varied parabolically with carbon number; for diazepam, heptane was ineffective and all others were essentially equipotent. Enhancement by n-nonane was then compared with that by n-nonanol. Propranolol flux was increased by both enhancers, whereas diazepam penetration was not affected by the less lipophilic alcohol. The enhancement of propranolol by n-nonane and n-nonanol was examined as a function of adjuvant concentration in the applied formulation. Maximum increases in maximum penetration rates of 6.5-fold (n-nonane) and 8.2-fold (n-nonanol) were determined. As expected, the enhancement was saturable, indicative of a maximally perturbed stratum corneum. Finally, the penetration enhancing abilities of six monoterpenes were assessed. The purely hydrocarbon analogues promoted both propranolol and diazepam transport to an extent similar to that of n-nonane. The terpenes with hydrogen-bonding ability, however, only enhanced propranolol flux (at a level comparable to n-nonanol). While the data reported do not directly reveal mechanistic information on percutaneous penetration enhancement, they do provide a starting point for the rational investigation of interrelationships between drug, enhancer, and skin. Such information is clearly essential for the optimization and exploitation of transdermal drug delivery.

Alkanes↗

Fumigant toxicity of volatile natural products from Korean spices and medicinal plants towards the rice weevil, Sitophilus oryzae (L).

The fumigant toxicity of various volatile constituents of essential oils extracted from sixteen Korean spices and medicinal plants towards the rice weevil, Sitophilus oryzae L (Coleoptera: Curculionidae), was determined. The most potent toxicity was found in the essential oil from Mentha arvensis L. var piperascens (LC50 = 45.5 microliters litre-1 air). GC-MS analysis of essential oil from M arvensis showed it to be rich in menthol (63.2%), menthone (13.1%) and limonene (1.5%), followed in abundance by beta-pinene (0.7%), alpha-pinene (0.6%) and linalool (0.2%). Treatment of S oryzae with each of these terpenes showed menthone to be most active (LC50 = 12.7 microliters litre-1 air) followed by linalool (LC50 = 39.2 microliters litre-1 air) and alpha-pinene (LC50 = 54.9 microliters litre-1 air). Studies on inhibition of acetylcholinesterase activity of S oryzae showed menthone to have a nine-fold lower inhibitory effect than menthol, despite menthone being 8.1-fold more toxic than menthol to the rice weevil. Different modes of toxicity of these monoterpenes towards S oryzae are discussed.

Acetylcholinesterase↗

Phytochemical analysis and biological screening of leaf and twig extracts from Kunzea ericoides.

Kunzea ericoides is a member of the Myrtle group of tea trees. Leaf and twig material of K. ericoides was extracted with different solvents to afford terpene (including the essential oil), flavonoid and lipid classes (but no alkaloid class), which were subsequently screened for antibacterial, antitumour, cytotoxic, antioxidant and antiinflammatory activity. Differences were observed in the biological activity for the chemical classes tested, and in general, the leaf extracts were comparatively more bioactive than the twig extracts. The leaf lipid extract was the most bioactive fraction, exhibiting antibacterial, antitumour and antiinflammatory activity. Thin layer chromatography and gas chromatography-mass spectroscopy analysis of each extract revealed previously identified phytochemicals that may be responsible for the observed bioactivities.

Drug Screening Assays, Antitumor↗

Structural elucidation of monoterpene oxidation products by ion trap fragmentation using on-line atmospheric pressure chemical ionisation mass spectrometry in the negative ion mode.

Based on ion trap mass spectrometry, an on-line method is described which provides valuable information on the molecular composition of structurally complex organic aerosols. The investigated aerosols were generated from the gas-phase ozonolysis of various C(10)H(16)-terpenes (alpha-pinene, beta-pinene, 3-carene, sabinene, limonene), and directly introduced into the ion source of the mass spectrometer. Negative ion chemical ionisation at atmospheric pressure (APCI(-)) enabled the detection of multifunctional carboxylic acid products by combining inherent sensitivity and molecular weight information. Sequential low-energy collision-induced product ion fragmentation experiments (MS(n)) were performed in order to elucidate characteristic decomposition pathways of the compounds. Dicarboxylic acids, oxocarboxylic acids and hydroxyketocarboxylic acid products could be clearly distinguished by multistage on-line MS. Furthermore, sabinonic acid and two C(9)-ether compounds were tentatively identified for the first time by applying on-line APCI(-)-MS(n).

Aerosols↗

Direct analysis of highly oxidised organic aerosol constituents by on-line ion trap mass spectrometry in the negative-ion mode.

On-line ion trap mass spectrometry (ITMS) enables the characterisation of constituents of biogenic secondary organic aerosols in complex organic reaction mixtures. This real-time analysis is achieved by directly introducing the airborne particles into the ion source of the mass spectrometer. Negative-ion chemical ionisation at atmospheric pressure (APCI(-)) was used as the ionisation method of choice. The aerosols were generated from the gas-phase ozonolysis of two C10H16-terpenes (alpha-pinene and limonene), and investigated by performing on-line APCI(-)-ITMS(n). Highly oxidised compounds were tentatively identified as important particle-phase products. Based on recent investigations of low-energy collision-induced dissociation pathways of a wide range of deprotonated multifunctional carboxylic acid species derived from monoterpene precursors (Warscheid B, Hoffmann T. Rapid Commun. Mass Spectrom. 2001; 15: 2259), the formation of structurally different C10H16O5 and C10H16O6 species, such as acidic esters from alpha-pinene and aldo-hydroxycarboxylic acids from limonene, is proposed.

Aerosols↗

Cloning, expression, and characterization of (+)-delta-cadinene synthase: a catalyst for cotton phytoalexin biosynthesis.

In cotton, sesquiterpene phytoalexins are elicited in response to bacterial or fungal infection. A Gossypium arboreum cell suspension culture which produces the sesquiterpene phytoalexin gossypol showed a time-dependent 10-fold increase in a 1.9-kb mRNA in response to a challenge by a preparation from Verticillium dahliae. The mRNA prepared from these elicited cultures was used to isolated two cDNA clones that contain open frames coding for proteins of 554 amino acids with M(r) 64,096 and 64,118. The encoded protein shows a significant degree of sequence identity with the other known plant terpene cyclases. Western blot analyses with a cross-reactive monoclonal antibody from a related sesquiterpene synthase in Nicotiana tabacum showed a time-dependent increase of a 65-kDa protein which reached a maximal level 24 h post elicitor treatment. The encoded protein from the pXC1 cDNA was produced in Escherichia coli and purified by affinity column chromatography. The enzymatic properties of this protein were identified by a radiochemical assay for cyclization of farnesyldiphosphate and a product structure was assigned by GC-MS, chiral phase GC, and NMR analyses as (+)-delta-cadinene. The fungal-elicited production of a (+)-delta-cadinene synthase is consistent with a role for this enzyme as the first committed step in the pathways leading to the related phytoalexins gossypol and lacinilene C in cotton.

Amino Acid Sequence↗

Reductase gene sequences and protein structures: p-cymene methyl hydroxylase.

Oxygenases are critical to cycling carbon in the biosphere and dependent on reductase action, principally from flavoprotein enzymes. Oxygenase diversity among organisms and strains carries a common theme of protein sequence and folding. p-Cymene (para-isopropyl toluene) was chosen as a point of convergence in terpene-aromatic mineralization to characterize a methyl hydroxylase electron transport system with the aerobe Pseudomonas aureofaciens. The cymA hydroxylase reductase gene was isolated and sequenced and the protein primary structure deduced. Optimized amino acid sequence alignments of flavoprotein reductases revealed major similarities over protein length, in the binding domains for NAD(P)H, and the flavine centers of pro- and eukaryote systems.

Amino Acid Sequence↗

Flavor deterioration in yogurt.

Volatile components of flavored yogurt preserved at 5 degrees C in the dark for 0 day, 3 days and 10 days were recovered by simultaneous distillation extraction (SDE) and headspace (HS) procedures. Gas chromatography (GC) and GC-mass spectrometry (GC-MS) analyses of those samples showed remarkable changes in some compounds. Aldehydes which contribute to expressing citrusy notes were reduced to alcohols during fermentation process and storage. As a result, the strength of flavors which expressed well-balanced citrusy notes in yogurt were weakened, and fatty or oily notes mainly caused from alcohols were strengthened reversely. Hydrocarbons were also digested by bacteria during a fermentation process. A small amount of other compounds, such as esters and terpene alcohols changed. Fewer effects of sorption into a package material and chemical reactions, such as hydrolysis esters, hydration or oxidation of hydrocarbons, were observed.

Adsorption↗

Renal elimination of verbenols in man following experimental alpha-pinene inhalation exposure.

The renal elimination of verbenols after experimental exposure to (+) and (-)alpha-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 alpha-pinene was less than 0.001%.

Adult↗

Distribution and strain-dependent formation of volatile metabolites in the genus Ceratocystis.

The accumulation of volatile metabolites in cultures of 34 strains comprising ten species of the genus Ceratocystis (Ascomycetes) has been investigated under defined culture conditions. The identified compounds include short-chain alcohols and esters, lower terpenes, terpenoids, and 2-phenylethyl acetate. Certain species can be recognized by a number of common volatiles traced in all strains, although the quantities of these constituents may vary enormously (up to a factor 1:1000) within one species. The formation of some metabolites is restricted to a few strains.

Acetates↗

Mammary carcinoma regression induced by perillyl alcohol, a hydroxylated analog of limonene.

The monoterpene perillyl alcohol has been shown to induce the regression of 81% of small mammary carcinomas and up to 75% of advanced mammary carcinomas initiated by 7,12-dimethylbenz(a)anthracene (DMBA) in the Wistar-Furth rat. Dietary perillyl alcohol was greater than 5 times more potent than the monoterpene limonene at inducing tumor regression. Perillyl alcohol is rapidly metabolized in the rat, as is limonene. Rats chronically fed perillyl alcohol had the same circulating plasma metabolites as rats fed limonene; however, the levels of these metabolites found in the plasma were higher for perillyl alcohol-fed rats. For example, rats given a 2% perillyl alcohol diet for 10 weeks had plasma levels of terpene metabolites of 0.82 mM whereas those fed a 10% limonene diet for the same period had blood levels of 0.27 mM. It thus appears that the increased potency of perillyl alcohol over limonene in causing tumor regression may be due at least in part to differences in the pharmacokinetics of these two monoterpenes. We feel that perillyl alcohol is a good candidate for clinical testing of anticancer efficacy in humans.

9,10-Dimethyl-1,2-benzanthracene↗

The effect of ascaridole on the in vitro development of Plasmodium falciparum.

Ascaridole is a terpene isolated from the plant Chenopodium ambrosioides (American wormseed); it is one of the few naturally occurring endoperoxidases. Artemisinin, which also belongs to this group, is a potent antimalarial. We therefore undertook a study to determine the effect of ascaridole, a known anthelmintic, on the in vitro development of Plasmodium falciparum. Ascaridole was found to be a potent inhibitor of plasmodial growth; after 3 days, development was arrested by a drug concentration of 0.05 microM, and at 0.1 microM no parasites were visible in the culture. At lower concentrations the effect was observed mainly at the trophozoite stage, whereas the ring stage was marginally affected. However, even at these lower concentrations, the ring culture could not continue normal development and ceased to grow at a later stage. The peroxide group is essential for the antimalarial activity of ascaridole, as judged from the fact that cineol, which bears an epoxide group instead of the peroxide group found in ascaridole, was totally inactive at identical concentrations.

Animals↗

Asymmetric syntheses of pipecolic acid and derivatives.

Results in the field of asymmetric synthesis of pipecolic acid derivatives are reviewed. Three sections describe the asymmetric syntheses of the title compounds (i) from the chiral pool (alpha-amino acids or carbohydrates) (ii) using a chiral auxiliary either derived from terpenes, alpha-amino acids, tartaric acid, an amine or beta-amino alcohols (iii) by means of asymmetric catalysis.

Amino Acids↗

Sawdust-induced inflammatory changes in rat lung: effects on alveolar and interstitial cells in relation to time.

Exposure to sawdust and its contaminants, e.g., terpenes, may cause respiratory tract and lung parenchymal inflammation. To monitor these changes over time. Sprague-Dawley rats were exposed at one occasion to 2.5 mg sawdust or saline by intratracheal instillation. Flow cytometry analyses were done on bronchoalveolar lavage (BAL) cells. Lung tissue specimens were analyzed histologically and immunohistochemically. After one week, the number of BAL polymorphonuclear leukocytes was increased (P < 0.05, N = 8), followed at six weeks by increases of macrophages and lymphocytes (both P < 0.01, N = 8). Enhanced expressions of class II antigens and complement receptors on macrophages after one week were even more pronounced at six weeks, indicating cellular activation. The BAL findings, also including increased (P < 0.001, N = 8) concentrations of hyaluronan with progressing changes over time, confirmed the signs of inflammation, as did the histological analysis of the lung tissue specimens with an accumulation of polymorphonuclears, macrophages, and hyaluronan in the interstitium.

Animals↗

Geraniol interferes with membrane functions in strains of Candida and Saccharomyces.

Geraniol, an olefinic terpene, was found to inhibit growth of Candida albicans and Saccharomyces cerevisiae strains. Geraniol was shown to enhance the rate of potassium leakage out of whole cells and also was shown by fluorescence polarization to increase C. albicans membrane fluidity. Biophysical studies using differential scanning calorimetry, fluorescence polarization and osmotic swelling of phospholipid vesicles demonstrated that geraniol decreased the phase-transition temperature of dipalmitoylphosphatidylcholine vesicles, affected fluidity throughout the bilayer, particularly the central portion of the bilayers, and caused an increase in bilayer permeability to erythritol. Geraniol may have potential use as an antifungal agent.

Acyclic Monoterpenes↗

An overview of the non-mevalonate pathway for terpenoid biosynthesis in plants.

Terpenoids are known to have many important biological and physiological functions. Some of them are also known for their pharmaceutical significance. In the late nineties after the discovery of a novel non-mevalonate (non-MVA) pathway, the whole concept of terpenoid biosynthesis has changed. In higher plants, the conventional acetate-mevalonate (Ac-MVA) pathway operates mainly in the cytoplasm and mitochondria and synthesizes sterols, sesquiterpenes and ubiquinones predominantly. The plastidic non-MVA pathway however synthesizes hemi-, mono-, sesqui- and di-terpenes, along with carotenoids and phytol chain of chlorophyll. In this paper, recent developments on terpenoids biosynthesis are reviewed with respect to the non-MVA pathway.

Acetates↗

A new sesquiterpene lactone from Artemisia rubripes nakai.

The chromatographic separation of a methylene chloride extract of Artemisia rubripes led to the isolation of a new sesquiterpene lactone (3), together with four known compounds, a coumarin (2) and three terpenes (1, 4, and 5). Their structures were characterized to be 1beta,6alpha-dihydroxy-4(15)-eudesmene (1), scopoletin (2), 1alpha,4beta-dihydroxy-8alpha-acetoxy-guaia-2,10(14), 11(13)-triene-6,12-olide (3), 1alpha,4beta-dihydroxy-8alpha-acetoxy-guaia-2,9,11(13)-triene-6,12-olide (4), and beta-sitosterol-3-O-beta-D-glycoside (5) by spectroscopic means.

Artemisia↗