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PubMed1989

Protein engineering by cDNA recombination in yeasts: shuffling of mammalian cytochrome P-450 functions.

We have constructed, in the yeast Saccharomyces cerevisiae, a mosaic assembly of genes by in vivo recombination of partially homologous sequences. The approach was tested on cDNAs encoding functionally distinct mammalian cytochromes P-450 (P-450). The selection for recombinant cDNAs used the transformation of yeast cells, which required the recircularization of a linearized plasmid by recombination of two partially homologous cDNAs. Libraries of mosaic genes with bipartite or tripartite structures were generated by intramolecular and intermolecular recombination events. The presence of yeast promoter and terminator sequences on the flanking sides of the recombined cDNAs has allowed the synthesis of encoded mosaic proteins. A library of yeast clones producing recombinant mouse P-450 P1 and rabbit P-450 LM4 was screened using functional criteria to identify chimeras with shuffled substrate specificity. Restriction mapping of mosaic genes, biochemical analysis of the synthesized proteins, comparison of chimeric enzymes, and the alignment of sequences with bacterial P-450 camphor hydroxylase of known three-dimensional structure, all suggest that the P-450 P1 amino acid residues 203-238 play a major role in the control of cytochrome activity toward carcinogenic polycyclic aromatic hydrocarbons. Similar approaches to structure-function analysis are believed to be applicable to other protein families.

Cytochrome P-450 Enzyme System↗
PubMed1986

The intensely sweet herb, Lippia dulcis Trev.: historical uses, field inquiries, and constituents.

Lippia dulcis Trev. (Verbenaceae) is the source of hernandulcin, the first known intensely sweet sesquiterpenoid, a compound which is a volatile oil constituent. The literature on the uses of this species, dating back to early colonial times in Mexico, has been examined. This plant began to be used as an official drug in the late 19th century for the treatment of coughs and bronchitis, and at that time preliminary phytochemical investigations were undertaken. Field work carried out in Mexico in 1981 and 1982 has indicated that there is still an active trade involving L. dulcis, which is sold primarily in market places for its alleged abortifacient activity. We have obtained no evidence, either from the literature or from field inquiries, that L. dulcis has ever been used for sweetening foods or beverages. Fourteen L. dulcis volatile oil constituents, mainly mono- and sesquiterpenoids, were identified by gas chromatography/mass spectrometry. The toxic compound, camphor, was found to constitute 53% w/w of the volatile oil of this species. The potential use of L. dulcis for the extraction of hernandulcin is discussed.

Gas Chromatography-Mass Spectrometry↗
PubMed2004

Temperature-induced structural changes in putidaredoxin: a circular dichroism and UV-VIS absorption study.

Putidaredoxin (Pdx) is an 11,400-Da iron-sulfur protein that sequentially transfers two electrons to the cytochrome P450cam during the enzymatic cycle of the stereospecific camphor hydroxylation. We report two transitions in the Pdx UV-VIS absorption and circular dichroism (CD) temperature dependencies, occurring at 16.3+/-0.5 degrees C and 28.4+/-0.5 degrees C. The 16.3 degrees C transition is attributed to the disruption of the hydrogen bonding of the active center bridging sulfur atom with cysteine 45 and alanine 46. The transition at 28.4 degrees C occurs exclusively in the Pdx(ox) at very nearly the same temperature as the earlier reported biphasicity in the redox potential. The formal potential temperature slope constancy reflects the relative stability of the concentration ratio of both oxidation states. The lower temperature transition affects both Pdx(red) and Pdx(ox) to a comparable extent, and their concentration ratio remains constant. In contrast, the 28.4 degrees C transition preferentially destabilizes Pdx(ox) thereby accelerating the formal potential negative shift and lower redox reaction entropy. There is evidence to suggest that disrupting hydrogen bonding of the iron ligating cysteines 45, 39 with residues threonine 47, serine 44, glycine 41, and serine 42 causes the 28.4 degrees C transition. The sensitivity of the UV-VIS absorption and CD spectroscopy to subtle structural protein backbone transitions is demonstrated.

Alanine↗
PubMed2005

(+)- And (-)-borneol: efficacious positive modulators of GABA action at human recombinant alpha1beta2gamma2L GABA(A) receptors.

(+)-Borneol is a bicyclic monoterpene used for analgesia and anaesthesia in traditional Chinese and Japanese medicine and is found in the essential oils of medicinal herbs, such as valerian. (+)-Borneol was found to have a highly efficacious positive modulating action at GABA(A) receptors, as did its enantiomer (-)-borneol. The effects of these bicyclic monoterpenes alone and with GABA were evaluated at recombinant human alpha(1)beta(2)gamma(2L) GABA(A) receptors expressed in Xenopus laevis oocytes using two-electrode voltage-clamp electrophysiology. (+)-Borneol (EC(50) 248microM) and (-)-borneol (EC(50) 237microM) enhanced the action of low concentrations of GABA by more than 1000%. These enhancing effects were highly dependent on the relative concentrations of the borneol enantiomer and GABA, and were insensitive to flumazenil indicating that (+)- and (-)-borneol were not acting at classical benzodiazepine sites. The maximal responses to GABA were enhanced 19% by (+)-borneol and reduced 21% by (-)-borneol. The borneol analogues isoborneol, (-)-bornyl acetate and camphor, produced less marked effects. At high concentrations (>1.5mM) (+)- and (-)-borneol directly activated GABA(A) receptors producing 89% and 84%, respectively, of the maximal GABA response indicative of a weak partial agonist action. Although of lower potency, the highly efficacious positive modulatory actions of (+)- and (-)-borneol on GABA responses were at least equivalent to that of the anaesthetic etomidate and much greater than that of diazepam or 5alpha-pregnan-3alpha-ol-20-one. The relatively rigid cage structure of these bicyclic monoterpenes and their high efficacy may aid in a greater understanding of molecular aspects of positive modulation of the activation of GABA(A) receptors.

Camphanes↗
PubMed2006

Molecular targets of dietary agents for prevention and therapy of cancer.

While fruits and vegetables are recommended for prevention of cancer and other diseases, their active ingredients (at the molecular level) and their mechanisms of action less well understood. Extensive research during the last half century has identified various molecular targets that can potentially be used not only for the prevention of cancer but also for treatment. However, lack of success with targeted monotherapy resulting from bypass mechanisms has forced researchers to employ either combination therapy or agents that interfere with multiple cell-signaling pathways. In this review, we present evidence that numerous agents identified from fruits and vegetables can interfere with several cell-signaling pathways. The agents include curcumin (turmeric), resveratrol (red grapes, peanuts and berries), genistein (soybean), diallyl sulfide (allium), S-allyl cysteine (allium), allicin (garlic), lycopene (tomato), capsaicin (red chilli), diosgenin (fenugreek), 6-gingerol (ginger), ellagic acid (pomegranate), ursolic acid (apple, pears, prunes), silymarin (milk thistle), anethol (anise, camphor, and fennel), catechins (green tea), eugenol (cloves), indole-3-carbinol (cruciferous vegetables), limonene (citrus fruits), beta carotene (carrots), and dietary fiber. For instance, the cell-signaling pathways inhibited by curcumin alone include NF-kappaB, AP-1, STAT3, Akt, Bcl-2, Bcl-X(L), caspases, PARP, IKK, EGFR, HER2, JNK, MAPK, COX2, and 5-LOX. The active principle identified in fruit and vegetables and the molecular targets modulated may be the basis for how these dietary agents not only prevent but also treat cancer and other diseases. This work reaffirms what Hippocrates said 25 centuries ago, let food be thy medicine and medicine be thy food.

Animals↗
PubMed2004

Ion exchange resins as catalyst for the isomerization of alpha-pinene to camphene.

Camphene is an industrial intermediate compound for commercial chemicals such as isoborneol, isobornyl acetate and camphor. Industrially, the conventional process for camphene production consists of the isomerization of alpha-pinene using acidic TiO2 as catalyst. The use of this catalyst presents problems such as considerable time for preparation, reproducibility and recovery of catalyst from products after the alpha-pinene isomerization. For the first time, a commercial exchange resin was used as catalyst for this reaction. Based on the concentration of product as a function of the reaction time, the path of the alpha-pinene transformation to camphene and byproducts is proposed. Temperature and alpha-pinene/catalyst ratio were studied in order to optimize the yield to camphene production. The obtained results were comparable with those reported for acidic TiO2.

Bicyclic Monoterpenes↗
PubMed2005

Chemical polymorphism and antifungal activity of essential oils from leaves of different provenances of indigenous cinnamon (Cinnamomum osmophloeum).

The essential oils isolated from nine geographical provenances of indigenous cinnamon (Cinnamomum osmophloeum Kaneh.) leaves were examined by GC-MS and their chemical constituents were compared. According to GC-MS and cluster analyses the leaf essential oils of the nine provenances and their relative contents were classified into six chemotypes-cinnamaldehyde type, cinnamaldehyde/cinnamyl acetate type, cinnamyl acetate type, linalool type, camphor type and mixed type. In addition, the antifungal activities of leaf essential oils and their constituents from six chemotypes of indigenous cinnamon were investigated in this study. Results from the antifungal tests demonstrated that the leaf essential oils of cinnamaldehyde type and cinnamaldehyde/cinnamyl acetate type had an excellent inhibitory effect against white-rot fungi, Trametes versicolor and Lenzites betulina and brown-rot fungus Laetiporus sulphureus. The antifungal indices of leaf essential oils from these two chemotypes at the level of 200 micro/ml against T. versicolor, L. betulina and L. sulphureus were all 100%. Among them, the IC(50) (50% of inhibitory concentrations) value of the essential oil of cinnamaldehyde type leaf against L. sulphureus was 52-59microg/ml. Cinnamaldehyde possessed the strongest antifungal activities in comparison with other constituents of the essential oils from cinnamaldehyde type leaf, at the level of 100microg/ml its antifungal indices against T. versicolor, L. betulina and L. sulphureus were 100%. The IC50 values of cinnamaldehyde against T. versicolor, L. betulina and L. sulphureus were 73, 74 and 73microg/ml, respectively.

Antifungal Agents↗
PubMed2004

Occurrence of UV filter compounds from sunscreens in surface waters: regional mass balance in two Swiss lakes.

Consumer care products often contain UV filters, organic compounds which absorb ultraviolet light. These compounds may enter surface waters directly (when released from the skin during swimming and bathing) or indirectly via wastewater treatment plants (when released during showering or washed from textiles). Predicted and measured UV filter concentrations were compared in a regional mass balance study for two Swiss lakes: Lake Zurich, a typical midland lake which is also an important drinking water resource, and Hüttnersee, a small bathing lake. Both lakes are extensively used for recreational activities and considerable direct input of UV filters is thus expected. This input was estimated from the number of visitors at swimming areas around the lakes and a survey of the usage of sunscreen products among these visitors. Possible additional indirect input via wastewater treatment plants was not considered in this study. The quantitatively most important UV filters, as indicated by the survey data, ethylhexyl methoxycinnamate, octocrylene, 4-methylbenzylidene camphor, butyl methoxydibenzoylmethane, and benzophenone-3, all lipophilic compounds, were selected for analysis by gas chromatography-mass spectrometry. Concentrations of individual UV filters in water from Lake Zurich were low, ranging from <2 ng l(-1) (detection limit) to 29 ng l(-1), and somewhat higher at Hüttnersee, ranging from <2 to 125 ng l(-1), with the highest concentrations found in summer, consistent with direct inputs to the lakes during this time. The concentrations were clearly lower than predicted from input estimates based on the surveys. This may be in part due to (i) an overestimation of these inputs (e.g. less than the 50% wash-off of UV filters assumed to occur during swimming), and (ii) some removal of these compounds from the lakes by degradation and/or sorption/sedimentation. UV filters were also detected in semipermeable membrane devices (SPMDs) deployed at Lake Zurich and Greifensee, another midland lake, at concentrations of 80-950 ng SPMD(-1), confirming the presence of the compounds in surface waters and indicating a certain potential for bioaccumulation. SPMD-derived water concentrations were in the range of 1-10 ng l(-1) and thus corresponded well with those determined in water directly. No UV filters were detected above blank levels in SPMDs deployed at a remote mountain lake used for background measurements.

Fresh Water↗
PubMed2004

Analysis of volatile components of Lavandula luisieri L. by direct thermal desorption-gas chromatography-mass spectrometry.

Volatile components of wild samples of Lavandula luisieri collected in Central and Southern Spain have been analyzed by direct thermal desorption coupled to gas chromatography-mass spectrometry (DTD-GC-MS). This method requires only 10-20 mg of dry sample, allowing to obtain qualitative and quantitative results from different plant parts such as flowers and leaves. Average volatile yield calculated from 51 individual plants was higher for leaves (9.7mg g(-1)) than for flowers (2.9mg g(-1)). Samples presented a high variation in their yield and composition. Major components were camphor and 1,8-cineole (up to 80.9 and 76.7% in leaves; 87.8 and 85.2% in flowers, respectively); however, these compounds were not detected in several samples. Other major component (up to 60% in flowers and leaves) was 2,3,5,5-tetramethyl-4-methylene-2-cyclopenten-1-one. Multivariate analysis was applied to quantitative data from nine selected compounds in order to show the presence of several patterns in plant composition which were only partially related to the site of collection.

Discriminant Analysis↗
PubMed2006

Analysis by gas chromatography-mass spectrometry of the volatiles from the fruits of Ammodaucus leucotrichus subsp. leucotrichus and subsp. nanocarpus grown in North Africa and the Canary Islands, respectively.

The volatiles from the fruits of Ammodaucus leucotrichus subsp. leucotrichus and subsp. nanocarpus (two endemic species, the first from North Africa and the second from the Canary Islands, Spain) were studied by gas chromatography and gas chromatography-mass spectrometry. The major components of the volatiles of subsp. nanocarpus were found to be, beta-pinene (22.2-33.6%), bornyl angelate (20.6-21.8%) and camphor (8.3-11.7%) whereas in the fruits of subsp. leucotrichus, the main constituents were perillaldehyde (63.6%) and limonene (26.8%). We also suggest that subsp. nanocarpus should have the status of species and should be named Ammodaucus nanocarpus.

Apiaceae↗
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↗
PubMed2004

Modulation of human GABAA and glycine receptor currents by menthol and related monoterpenoids.

Effects of common monoterpenoid alcohols and ketones were investigated on recombinant human gamma-aminobutyric acid A (GABAA; alpha1beta2gamma2s) and glycine (alpha1 homomers) receptors expressed in Xenopus oocytes. GABA currents were enhanced by coapplications of 10-300 microM: (+)-menthol>(-)-menthol>(-)-borneol>>(-)-menthone=camphor enantiomers>carvone enantiomers, with menthol acting stereoselectively. By contrast, thujone diastereomers inhibited GABAA receptor currents while glycine currents were only markedly potentiated by menthol. Positive modulation by (+)-menthol was explored given its pronounced effects (e.g., at 100 microM, GABA and glycine EC20 responses increased by 496+/-113% and 135+/-56%, respectively). (+)-Menthol, 100 microM, reduced EC50 values for GABA and glycine from 82.8+/-9.9 to 25.0+/-1.8 microM, and from 98.7+/-8.6 to 75.7+/-9.4 microM respectively, with negligible effects on maximal currents. This study reveals a novel neuroactive role for menthol as a stereoselective modulator of inhibitory ligand-gated channels.

Animals↗
PubMed2005

Deramciclane in the treatment of generalized anxiety disorder: a placebo-controlled, double-blind, dose-finding study.

Deramciclane, a camphor derivative, is a novel anxiolytic agent with a unique mechanism of action. It acts as a potent and specific antagonist at serotonin 5-HT2A/2C receptors, and exhibits anxiolytic efficacy in animal models. The aim of this double-blind, placebo-controlled, parallel-group study was to evaluate the efficacy, safety, and tolerability of a range of doses of deramciclane in patients with generalized anxiety disorder (GAD). Adult patients with a diagnosis of GAD (DSM-IV) and a Hamilton Anxiety Rating Scale (HAM-A) total score >or=18; a score >or=2 for the HAM-A items 'Anxious Mood' and 'Tension'; a score >or=4 on the Clinical Global Impression of Severity of Illness (CGI-S) Scale; and a score <or=20 on the Montgomery-Asberg Depression Rating Scale (MADRS) were enrolled in the study. Following a 1-2 week placebo run-in period, patients were randomized to receive deramciclane (10, 30, or 60 mg/day in two divided doses) or placebo for 8 weeks, followed by a 2-week placebo wash-out period. The primary efficacy measure was change in HAM-A score from baseline to week 8. Adverse events were monitored throughout the study. Withdrawal reactions were assessed at the end of the study (week 8) and during the placebo wash-out period using the Physician's Withdrawal Checklist (34 items). In the intent-to-treat population (n=208), both the deramciclane 30 mg/day and 60 mg/day doses provided clinically relevant improvements in HAM-A total score after 8 weeks of treatment, reaching statistical significance compared with placebo in the 60 mg/day dose group (p=0.024) and a clear trend in the 30 mg/day group (p=0.059). On the HAM-A psychic anxiety factor, significant improvements were seen in patients in the deramciclane 30 mg/day and 60 mg/day treatment groups compared with those in the placebo group (p<0.05). Adverse events were reported at a similar frequency across all four treatment groups; the most commonly reported adverse event was headache. No withdrawal reactions were observed on abrupt discontinuation of deramciclane. In conclusion, deramciclane 60 mg/day showed significant evidence of efficacy for the treatment of GAD in adult patients. The efficacy for the 30 mg/day dose was close to the larger dose although not significant in the primary analysis, and there was no significant evidence of efficacy for the 10 mg/day dose. Deramciclane was safe and well-tolerated up to the 60 mg/day dose over an 8-week period.

Adolescent↗
PubMed2004

Antimicrobial activity of Artemisia douglasiana leaf essential oil.

Artemisia douglasiana leaf has been shown to be efficacious complementary herbal treatment for chronic bladder infection in a paraplegic youth. The leaf oil has been analyzed by GC-MS and the major components found to be camphor (29%), artemisia ketone (26%), artemisia alcohol (13%), alpha-thujone (10%), 1,8-cineole (8%), and hexanal (5%). The leaf oil and the major components have been tested for antimicrobial activity against Bacillus cereus, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Candida albicans, and Aspergillus niger. The essential oil shows limited antimicrobial activity in vitro, so it is unclear if the oil exerts a direct antimicrobial effect in vivo, or plays some role in stimulation of host defenses.

Adolescent↗
PubMed2005

In vitro anti-Vibrio cholerae activity of essential oil from Lepechinia caulescens.

Lepechinia caulescens is a plant employed by the Purepecha (a Mexican ethnic group) to treat infectious gastrointestinal ailments. The essential oil of this species was active against some strains of Vibrio cholerae with 4 microl/ml MIC and 6 microl/ml MBC. The major components of the oil found by GC-MS were borneol, camphor and trans-caryophyllene.

Anti-Bacterial Agents↗
PubMed2004

A preconcentrator coupled to a GC/FTMS: advantages of self-chemical ionization, mass measurement accuracy, and high mass resolving power for GC applications.

Coupling of a cryogenic preconcentrator (PC) to a gas chromatograph/Fourier transform ion cyclotron resonance mass spectrometer (GC/FT-ICR MS) is reported. To demonstrate the analytical capabilities of the PC/GC/FT-ICR MS, headspace samples containing volatile organic compounds (VOCs) emitted from detached pine tree twigs were analyzed. Sub-ppm mass measurement accuracy (MMA) for highly resolved (m/Deltam(50%) > 150 k) terpene ions was achieved. Direct PC/GC/FT-ICR MS analyses revealed that detached twigs from pine trees emit acetone, camphor, and four detectable hydrocarbon isomers with C(10)H(16) empirical formula. The unknown analytes were identified based on accurate mass measurement and their mass spectral appearances. Authentic samples were used to confirm initially unknown identifications. Self-chemical-ionization (SCI) reactions furnished an additional dimension for rapid isomer differentiation of GC eluents in real time.

Cyclotrons↗
PubMed2005

The in vitro pharmacological activities and a chemical investigation of three South African Salvia species.

Salvia species (sage) are well known in folk medicine throughout the world. In South Africa sage is used against fever and digestive disorders. Three closely related South African species (Salvia stenophylla, Salvia repens and Salvia runcinata) were investigated for their anti-oxidant (DPPH assay); anti-inflammatory (5-lipoxygenase and cyclo-oxygenase assays); antimalarial (tritiated hypoxanthine incorporation assay); antimicrobial (disc diffusion and micro-dilution assays) properties and toxicity profile (tetrazolium-based assay). The solvent extracts exhibited anti-oxidant, antimalarial and antibacterial and poor anti-inflammatory properties. The essential oils exhibited anti-inflammatory and antimalarial properties, but displayed poor anti-oxidant and antimicrobial activity. The extract of Salviastenophylla and the essential oil of Salvia runcinata displayed the highest toxicity profile. Overall, Salvia runcinata displayed the most favorable activity of all three taxa tested with an IC(50) value of 6.09 (anti-oxidant); 29.05 (antimalarial) and 22.82 microg/ml (anti-inflammatory). Analytical procedures (GC-MS and HPLC-UV) were employed to generate chromatographic profiles for the essential oils and solvent extracts respectively. The HPLC analysis revealed the presence of rosmarinic acid in all three taxa while carnosic acid was only present in Salvia repens and Salvia stenophylla. The GC-MS analysis showed that oils were qualitatively and quantitatively variable. beta-Caryophyllene was present in large amounts in all three taxa. Other components present include camphor, alpha-pinene and alpha-bisabolol. The results of the in vitro pharmacological activities provide a scientific basis to validate the use of these Salvia species in traditional medicine in South Africa.

Anti-Infective Agents↗
PubMed2006

Antrodia camphorata extract induces replicative senescence in superficial TCC, and inhibits the absolute migration capability in invasive bladder carcinoma cells.

The Antrodia camphorata crude extract (ACCE), an extract obtained from a precious traditional Chinese folkloric herbal medicine Zhan-Ku (a camphor tree mushroom) since the 18th century, has showed rather significant inhibitory effects on the growth and proliferation of the transitional cell carcinomas (TCC) cell lines RT4, TSGH-8301, and T24. On treatment with ACCE at 100 microg/mL, the p53-independent overexpression of p21 with simultaneous down alteration of pRb was observed in RT4, which was thus speculative of proceeding through a mechanism of replicative senescence. On the contrary treatment with ACCE, at 50 microg/mL, resulting in simultaneous down-regulations of Cdc2 and Cyclin B1, with suppression of the absolute migrating capability of the two cell lines TSGH-8301 and T24, and eventually the cell deaths. We conclude that ACCE can be rather effective and beneficial in suppression of both the superficial cancer cell line RT4 and the metastatic cell lines (TSGH-8301 and T24) through different mechanisms.

Antineoplastic Agents↗