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PubMed2005

Anticariogenic activity of macelignan isolated from Myristica fragrans (nutmeg) against Streptococcus mutans.

The occurrence of dental caries is mainly associated with oral pathogens, especially cariogenic Streptococcus mutans. Preliminary antibacterial screening revealed that the extract of Myristica fragrans, widely cultivated for the spice and flavor of foods, possessed strong inhibitory activity against S. mutans. The anticariogenic compound was successfully isolated from the methanol extract of M. fragrans by repeated silica gel chromatography, and its structure was identified as macelignan by instrumental analysis using 1D-NMR, 2D-NMR and EI-MS. The minimum inhibitory concentration (MIC) of macelignan against S. mutans was 3.9 microg/ml, which was much lower than those of other natural anticariogenic agents such as 15.6 microg/ml of sanguinarine, 250 microg/ml of eucalyptol, 500 microg/ml of menthol and thymol, and 1000 microg/ml of methyl salicylate. Macelignan also possessed preferential activity against other oral microorganisms such as Streptococcus sobrinus, Streptococcus salivarius, Streptococcus sanguis, Lactobacillus acidophilus and Lactobacillus casei in the MIC range of 2-31.3 microg/ml. In particular, the bactericidal test showed that macelignan, at a concentration of 20 microg/ml, completely inactivated S. mutans in 1 min. The specific activity and fast-effectiveness of macelignan against oral bacteria strongly suggest that it could be employed as a natural antibacterial agent in functional foods or oral care products.

Anti-Bacterial Agents↗
PubMed2005

Gastrointestinal clinical pharmacology of peppermint oil.

In nine studies, 269 healthy subjects or patients underwent exposure to peppermint oil (PO) either by topical intraluminal (stomach or colon) or oral administration by single doses or 2 weeks treatment (n = 19). Methods used to detect effects were oro-cecal transit time by hydrogen expiration, total gastrointestinal transit time by carmine red method, gastric emptying time by radiolabelled test meal or sonography, direct observation of colonic motility or indirect recording through pressure changes or relieve of colonic spasms during barium enema examination. The dose range covered in single dose studies is 0.1-0.24ml of PO/subject. With one exception, which show an unexplained potentiation of neostigmine stimulated colon activity, all other studies result in effects, indicating a substantial spasmolytic effect of PO of the smooth muscles of the gastrointestinal tract. Pharmacokinetic studies reveal that fractionated urinary recovery of menthol is dependent on the kind of formulation used for the application of PO. Optimal pH triggered enteric coated formulations start releasing PO in the small intestine extending release over 10-12 h thus providing PO to the target organ in irritable bowel syndrome, i.e. the colon. The hypothesis is supported by anecdotal observations in patients with achlorhydria or ileostoma, respectively.

Administration, Oral↗
PubMed2004

Chemical composition and antimicrobial activity of the essential oil of Scutellaria barbata.

The essential oil of Scutellaria barbata was obtained by hydrodistillation with a 0.3% (v/w) yield and analysed by GC and GC-MS. The main compounds in the oil were hexahydrofarnesylacetone (11.0%), 3,7,11,15-tetramethyl-2-hexadecen-1-ol (7.8%), menthol (7.7%) and 1-octen-3-ol (7.1%). The antimicrobial activity of the oil was evaluated against 17 microorganisms using disc diffusion and broth microdilution methods. The gram-positive bacteria, including methicillin-resistant Staphlococcus aureus, were more sensitive to the oil than gram-negative bacteria and yeasts.

Anti-Infective Agents↗
PubMed2004

Kohl (surma): a toxic traditional eye cosmetic study in Saudi Arabia.

The use of kohl (surma) as eyeliner is a popular practice in Saudi Arabia and people firmly believe that it is safe to use. A total of 107 kohl samples (branded and unbranded) were collected from different regions of Saudi Arabia, and analysed for the presence of lead. In addition, aluminium and antimony levels were also determined. Lead levels up to 53% were detected in some kohl preparations, and some samples were found to contain camphor and menthol. The blood analyses of regular kohl users revealed a high lead concentration and relatively low haemoglobin levels. Due to the health risk, an official public awareness campaign is suggested to encourage the use of lead-free kohl.

Aluminum↗
PubMed2005

Exploring the association of John Henry active coping and education on smoking behavior and nicotine dependence among Blacks in the USA.

Although smoking is used as a coping tool in response to stress and Blacks have been found to report smoking more in response to stress than Whites, little research exists that has examined ethno-culturally specific constructs of stress and coping as they relate to smoking behavior and nicotine dependence among Blacks in the USA. This study explored the association between the ethno-culturally interactively defined construct of John Henryism, as well as the individual contributions of John Henry active coping and education on smoking behavior and nicotine dependence in a relatively urban-Midwestern Black population. Self-identified Black patients (n = 146) who had previously received a clinical intervention for nicotine dependence were followed to assess smoking status and John Henry active coping. Results revealed that patients with low levels of education who had low levels of John Henry active coping reported higher nicotine dependence scores than any other education by John Henry active coping group. Furthermore, low levels of John Henry active coping were associated with the use of menthol cigarettes and lower-educational level was associated with smoking greater than 20 cigarettes per day. Further community-based studies examining this construct among Black smokers in various socio-cultural contexts are needed to clarify the association between John Henry active coping and socioeconomic status on smoking behavior and nicotine dependence among Blacks.

Adaptation, Psychological↗
PubMed2004

Predictors of smoking cessation among African-Americans enrolled in a randomized controlled trial of bupropion.

OBJECTIVES: Identification of individual characteristics that predict successful smoking cessation treatment has been limited to studies with mostly white participants. This study identifies factors that predict successful quitting among African-Americans participating in a smoking cessation trial. METHODS: Twenty-one baseline variables were analyzed as potential predictors from a double-blind placebo-controlled, randomized trial that used bupropion SR for smoking cessation among 600 African-American smokers. Chi-square tests, two sample t tests, and multiple logistic regression procedures were employed to identify predictors of 7-day abstinence among the 535 participants who completed the 7-week medication phase. RESULTS: Univariate predictors of cessation were receiving bupropion (P < 0.0001), not smoking menthol cigarettes (P = 0.0062), smoking after 30 min of waking (P < 0.0001), older age (P = 0.0085), smoking fewer cigarettes per day (P = 0.0038), and lower cotinine levels (P = 0.0002). Logistic regression identified three significant independent predictors. Participants who received bupropion treatment were more than twice as likely to quit smoking at the end of treatment compared to participants who received placebo (OR = 2.62; 95% CI = 1.77-3.88, P < 0.0001), while smoking within 30 min of waking (OR = 0.40; 95% CI = 0.25-0.62, P < 0.0001) and higher salivary cotinine levels at baseline (OR = 0.799; 95% CI = 0.629-0.922, P < 0.0001) reduced the likelihood of quitting. CONCLUSIONS: This is the first report identifying predictors of smoking cessation among African-Americans participating in a clinical trial. Results indicate that, aside from bupropion treatment, various indicators of addiction were the strongest predictors. While this is similar to findings among white smokers, thresholds of addiction may need to be adjusted for African-American smoking patterns. Additional studies focused on diverse populations are needed to improve treatment approaches and to identify population-specific factors that are important for treatment-matching approaches.

Adult↗
PubMed2003

Monoterpenes affect chlorodiazepoxide-micelle interaction through micellar dipole potential modifications.

The ability of several natural terpenes to affect benzodiazepine (BZD)-micelle interaction through the membrane dipolar organization was investigated. The acid-base equilibrium of chlorodiazepoxide (CDX) and the spectroscopic behavior of the electrochromic dye merocyanine were tested in the presence and in the absence of Triton X-100 micelles (used to mimic a membrane environment) containing or not cineole, menthol, geraniol or camphor. CDX's apparent pK increased in the environment of terpene-containing micelles compared with pure Triton X-100 micelles. Decrements in electric potentials (between -111 and -128 mV with respect to pure detergent) were calculated from Boltzmann equation. This result suggested, that in the presence of terpenes, the tendency of CDXH(+) to remain in the membrane phase increased. The dielectric constant (D) of the microenvironment sensed by merocyanine within Triton X-100 micelles, determined from lambda(max,2) of merocyanine monomer, was D=9 and increased in the presence of all the terpenes assayed (D congruent with 11). The decrease in merocyanine partitioning (A(peak1)/A(peak2) increased) also reflected an increment in the negative dipole potential. The present results suggest that terpenes contributed to the whole dipolar arrangement of the micelle with a dipole moment vector which had an intense component oriented parallel to the intrinsic dipole of the Triton X-100 molecules in the micelles. This led to a more negative environment of the interface region where CDX was located, and increased the net polarity of the deepest micelle regions sensed by merocyanine.

Acid-Base Equilibrium↗
PubMed1990

Isotope dilution gas chromatography-mass spectrometry in the determination of benzene, toluene, styrene and acrylonitrile in mainstream cigarette smoke.

A cryogenic trapping method with isotope dilution gas chromatography-mass spectrometry analysis has been developed for the determination of benzene, toluene, styrene and acrylonitrile in mainstream vapor phase cigarette smoke. The method is simple, direct, and quantitative. Vapor phase samples are collected cryogenically in a series of four traps following removal of the particulate phase with a Cambridge filter pad. For all four analytes, 75-85% of the total amounts recovered were found in the initial trap and less than 1% in the final trap. Assessment of instrumental precision by multiple injections of a sample gave relative standard deviations of less than 2%. Linear calibration for all analytes over the analysis range gave an r2 value greater than 0.99 with average relative standard deviations at the mean ranging from 1.4 to 8.2%. The cigarettes analyzed include a reference cigarette (Kentucky 1R4F), a commercial ultra-low "tar" mentholated cigarette, and two cigarettes that heat but do not burn tobacco. The values determined for the four analytes in the 1R4F samples are comparable to reported values of similar cigarettes. The cigarettes which heat rather than burn tobacco yield less of all four analytes compared to the other cigarettes in the study.

Acrylonitrile↗
PubMed1987

High-performance liquid chromatographic analysis of glucuronic acid conjugates after derivatization with 4-bromomethyl-7-methoxycoumarin.

In order to enhance the detection sensitivity of various glucuronic acid conjugates (phenol, menthol borneol, estrone and testosterone) in high-performance liquid chromatography (HPLC), the compounds were esterified with 4-bromomethyl-7-methoxycoumarin in the presence of potassium carbonate and 18-crown-6 in acetone. The resulting esters were chromatographed on either a normal-phase (NP) column (LiChrospher DIOL) with hexane-ethanol mixtures as eluents or a reversed-phase column (LiChrospher CH-18) with methanol-water mixtures. They were detected by UV spectrophotometry at 328 nm. The structure of the derivatives was confirmed by mass spectrometry by direct introduction and chemical ionization. Prior to this step, their isolation on a semi-preparative scale was performed by NP-HPLC. The extraction of the studied glucuronides from microsomal solutions was tested by ion-suppression and ion-pair liquid-liquid partition and liquid-solid chromatography (on octadecylsilica cartridges). Extraction and chromatographic data are discussed with regard to the determination of glucuronyltransferase activity towards the aglycones cited above.

Chromatography, High Pressure Liquid↗
PubMed1999

The generalizability of capsaicin sensitization and desensitization.

Studies using capsaicin-saturated filter papers have shown that the intensity of oral irritation tends to grow over successive samples, a phenomenon known as sensitization. If a hiatus of 5-15 min is then introduced, the intensity of irritation produced by a subsequent capsaicin stimulus is much reduced, and desensitization is said to have occurred. The use of other methodologies such as whole-mouth rinses, either with capsaicin or the irritants menthol or zingerone, have not consistently shown this response pattern, casting doubt on the extent to which sensitization and desensitization are general phenomena. Experiment 1 addressed this issue by comparing responses to whole-mouth rinses of 0.6 and 3 ppm capsaicin with those to 3 ppm capsaicin filter papers. Over an initial series of 10 samples, sensitization was evident but only for the 3 ppm capsaicin stimuli. Following a 10-min hiatus, desensitization was observed for all stimulus types. An examination of the data of individual subjects revealed considerable variability in response patterns over the initial 10 samples between subjects and, within subjects, between the filter paper and rinse stimuli, and between the test replications. Desensitization to the posthiatus stimuli was more consistent. A second experiment examined whether the capsaicin sensitization and desensitization shown by stimulation with filter papers or solutions also occurred in the context of the consumption of foods containing capsaicin. Two foods--soup and chili con carne--were consumed under conditions in which the rate of consumption was timed, as in Experiment 1, or was self-paced. In neither of the two conditions or foods was there strong evidence of sensitization, although, again, desensitization following a hiatus was evident. Substantial individual variability in response patterns was again apparent. There is thus no evidence for sensitization occurring during normal food consumption.

Adult↗
PubMed2001

Candida Rugosa lipase reactions in nonionic w/o-microemulsion with a technical surfactant.

In enzyme catalysis there is a great interest in finding suitable organic media for less water soluble substrates in order to increase the substrate concentration and therefore the reaction rates. These requirements are fulfilled by using w/o-microemulsions as reaction media. The influences of pH, temperature, water concentration and the kinetic parameters of Candida Rugosa Lipase in a nonionic w/o-microemulsion with a surfactant of technical grade, Marlipal O13-60, are presented. In an example the enantiospecific esterification of racemic menthol with propionic anhydride using this nonionic microemulsion likely to be affordable in large scale applications is shown. For a continuous process an ultrafiltration unit is attached to a reactor within a loop. In this way, the reverse micelles containing the enzymes can be separated from the oil, containing the product, and reused afterwards.

Journal Article↗
PubMedDate not supplied

Modulation of plasminogen activator inhibitor type-1 biosynthesis in vitro and in vivo with oligo(nucleoside phosphorothioate)s and related constructs.

Oligonucleotides with a nucleotide sequence complementary to various regions of human plasminogen activator inhibitor type-1 (PAI-1) mRNA have been studied as antisense inhibitors of expression of PAI-1 protein in cultured cells [human umbilical vein endothelial cells (HUVEC), human aortic smooth muscle cells, human hybrid endothelial cells]. Hexadeca(deoxyribonucleoside phosphorothioate) 13 complementary to a fragment of a signal peptide PAI-1 mRNA was found to be most active, giving ca. 70% inhibition of PAI-1 release in a time- and dose-dependent way. The stereo-regular All-S(P) and All-R(P) diastereomers of 13 were studied and found to inhibit PAI-1 synthesis in HUVEC in a stereo-dependent manner, with the All-S(P) diastereomer considerably more active than the stereo-random construct and All-R(P) isomer. The observed stereo-dependent activity of oligonucleotide phosphorothioate constructs is presumably governed by their resistance to nucleases. The corresponding phosphodiester analogue of 13 was not active unless covalently bound at its 5'-end to a lipophilic alcohol residue (menthol, heptadecanol). The observed antisense activity of phosphodiester oligonucleotide bioconjugates in cultured human hybrid endothelial cells was paralleled by their increased stability in human plasma with respect to unconjugated oligonucleotide. The oligo(deoxyribonucleoside phosphorothioate) complementary to the same signal peptide region of rat PAI-1 mRNA was found to reduce the PAI-1 level in blood plasma of rats after intravenous administration into the tail vein. The effect was both time- and dose-dependent. The same oligonucleotide was found to protect against arterial thrombus formation in the rat (lower incidence of venous thrombosis, lower thrombus weight, and increased occlusion time in experimentally induced thrombosis). An anti-PAI-1 inhibitory activity has been independently reported for a 20-mer oligo(2'-O-methyl-ribonucleoside phosphorothioate) complementary to a 3'-untranslated region of human PAI-1 mRNA in cultured HUVEC and human aortic smooth muscle cells.

Animals↗
PubMed2002

Chiral recognition of terpenoids in some pharmaceuticals derived from natural sources.

Capillary gas chromatography was applied to explore the enantiomeric composition of some terpenoids in pharmaceuticals of natural origin. The drugs under investigation were produced in Germany (Rowachol, Rowatinex), Poland (Terpichol, Terpinex, Rub arom, Herbolen and Oleum Camphoratum), Slovenia (Uroterp, Mentoklar) and United Kingdom (Olbas oil, Vicks Vapo Rub). The model compounds tested were: menthone, isomenthone, menthol, fenchone, borneol and camphor. It has been found that depending on the manufacturer, pharmaceuticals possessing similar chemical composition may differ considerably in enantiomer composition. Exceptionally large discrepancies have been found for the content of borneol and fenchone enantiomers in pharmaceuticals applied in liver and kidney diseases. It seems that the changes in enantiomeric composition are the main reason of the lack of general acceptance of natural medicines by clinicians. The study of enantiomeric composition may sometimes lead to information concerning the origin of preparation, i.e. natural or synthetic.

Biological Factors↗
PubMed2001

The development of new methods for the recycling of chiral catalysts.

This article discusses different methods for the recycling of chiral catalysts, including heterogenization of the soluble catalyst on an insoluble inorganic or organic support, membrane filtration of homogeneously soluble catalysts, precipitation, and two-phase systems. In principle, all the methods presented enable the repeated use of a chiral catalyst without loss of activity and/or enantioselectivity. Examples will be given from laboratory and industrial processes, incuding hydrogenations, ketone reductions, epoxidations, dihydroxylations, diethylzinc additions and Diels-Alder reactions catalyzed by chemocatalysts or biocatalysts. Different approaches for cyanation, hydrogenation and epoxidation are compared. Data from industrial processes include the production of metalochlor, the production of (-)-menthol and the production of L-tert-leucine.

Catalysis↗
PubMed1999

Is odor processing related to oral breathing?

This paper addresses two questions related to the inherent association between breathing and odor perception: Does central nervous processing of odors change when an artificial breathing technique (velopharyngeal closure) is introduced and secondly, does odor processing vary with the oral breathing phase (inhalation or exhalation)? Chemosensory event-related potentials (CSERP) were obtained from eight female subjects while they were smelling an odor mixture (citral, eugenol, linalool, menthol and isoamylacetate). Each subject was required to perform spontaneous mouth breathing (120 trials) as well as the velopharyngeal closure technique (120 trials). Simultaneously, a thermistor monitored the phase of the respiratory cycle. The results reveal that the central nervous correlates of odor processing change with the breathing technique but not with the oral breathing cycle. The findings that early stimulus processing is faster (N1 latency) and late stimulus processing more pronounced (P3 amplitudes) when the subjects are breathing spontaneously are discussed with regard to attentional effects. The reduction of the N1 amplitude during the spontaneous breathing condition may be caused by larger latency variations and longer stimulus rise-times. Furthermore, it is concluded that the oral breathing cycle is less important than the nasal breathing cycle for olfactory information transmission.

Adult↗
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↗
PubMed2003

Transdermal iontophoresis of insulin. V. Effect of terpenes.

To increase the skin permeation of large peptides like insulin, it is necessary to utilize a combination of enhancement strategies. In this regard, this study investigated the effect of terpenes/EtOH combination in comparison to EtOH and neat terpene on transdermal iontophoretic permeation of insulin. Ex-vivo experiments were conducted using full thickness rat skin after pre-treatment for 2 h with 5% of menthol, menthone, cineole and pulegone in EtOH; EtOH alone; neat menthone with and without iontophoresis (0.5 mA/cm(2); 6 h). FT-IR studies were carried out using rat epidermal sheets after pre-treatment with enhancer solution for 2 h and tritiated water permeation studies was used to investigate the alteration in skin barrier property after enhancer or current treatment. The lag time was significantly reduced (P<0.05) with terpene/EtOH pre-treatment in comparison to passive control and EtOH pre-treatment, although there was no significant difference (P>0.05) among the terpenes. Synergistic enhancement in flux was observed with terpene/EtOH, and menthone/EtOH showed highest enhancement among the terpene/EtOH combinations. On the other hand, enhancement with neat menthone was higher than with menthone/EtOH. FT-IR studies showed that terpene/EtOH, EtOH and neat terpene act at the intercellular lipids. The skin barrier property was significantly (P<0.05) compromised with neat menthone treatment. Iontophoresis had a lesser effect on skin barrier property compared to chemical enhancer pre-treatment. Terpene/EtOH caused synergistic enhancement of insulin permeation when combined with iontophoresis and was influenced by the type and concentration of terpene.

Administration, Cutaneous↗
PubMed1999

Transdermal iontophoretic delivery of bovine insulin and monomeric human insulin analogue.

The present study was undertaken to explore the possibility of delivering bovine insulin in streptozocin (STZ)-induced diabetic rats by iontophoresis. Further, the effect of iontophoresis of monomeric human insulin analogue (r-DNA origin) on the plasma glucose level (PGL) of diabetic rats was studied. Iontophoresis of bovine insulin (10-200 IU/ml) was not effective in decreasing the PGL in untreated diabetic rats. Pretreatment of skin with oleic acid or menthol for 3 h followed by iontophoresis of bovine insulin also failed to produce a fall in PGL. Application of a depilatory cream for hair removal (24 h before the experiment), followed by iontophoresis of bovine insulin (10, 30 and 100 IU/ml) produced a concentration-dependent fall in PGL. Further, application of depilatory cream immediately before the experiment produced a substantial fall in PGL both by passive diffusion and iontophoresis. Depilatory cream might have drastically reduced the barrier function of skin such that conventional bovine insulin (dimer and hexamer) penetrates through the intact skin by iontophoresis and even by passive diffusion. Depilatory cream or the active components of depilatory cream may be useful as penetration enhancers for transdermal delivery of drugs especially macromolecules such as insulin. Iontophoresis of monomeric human insulin analogue (B9 Asp, B27 Glu) through intact skin (untreated) produced a significant fall in PGL in diabetic rats. Monomeric human insulin analogues which have low tendency to self aggregation may be promising candidates for the transdermal iontophoretic delivery of insulin.

Administration, Cutaneous↗