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PubMed2005

Stereoisomer composition of the chiral UV filter 4-methylbenzylidene camphor in environmental samples.

4-Methylbenzylidene camphor (4-MBC) is an important organic UV filter used in many personal care products such as sunscreens and cosmetics. After use, 4-MBC may enter the aquatic environment due to its release from skin during recreational activities (swimming, bathing) and from personal hygiene measures (washing, laundering of cloths) via wastewater treatment plants (WWTPs). In fact, 4-MBC has been detected in wastewater, in surface waters, and even in fish. 4-MBC can exist as distinct cis-(Z)- and trans-(E)-isomers, both of which are chiral. Despite the fact that stereoisomers often show a different biological behavior, the stereochemistry of 4-MBC has hardly ever been considered in environmental or biological studies. In this study, enantioselective gas chromatography-mass spectrometry (GC-MS) was used to determine the stereoisomer composition of 4-MBC. For stereoisomer assignment, the pure enantiomers of (E)-4-MBC were synthesized from (+)- and (-)-camphor. The photochemical isomerization (sunlight) of these (E)-isomers to the corresponding (Z)-isomers eventually allowed the configurational assignment of all four stereoisomers of 4-MBC. In a technical material and in a major brand sun lotion, 4-MBC was shown to consist entirely (>99%) of (E)-isomers and to be racemic (R/S, 1.00 +/- 0.02). Wastewater showed the presence of both (E)- and (Z)-4-MBC with a clear excess of (E)-isomers (E > Z). Untreated wastewater showed a nearly racemic composition (R/S= 0.95-1.09), suggesting that most if not all commercial 4-MBC is racemic. Treated wastewater indicated some excess of (R)- or (S)-stereoisomers (R/S, 0.89-1.17), likely as a result of some enantioselective (bio)degradation in WWTPs. Residues of 4-MBC in lakes and in a river with inputs from WWTPs and/or recreational activities consisted mainly of (E)-4-MBC and, with exception of one lake (Greifensee), showed a small enantiomer excess (R/S, 1.04-1.16). In Greifensee, 4-MBC showed a higher enantiomer excess (R/S, 1.70-1.83), probably as a result of more extensive biotic degradation in this lake. The analysis of 4-MBC in a small number of fish from these lakes indicated residues with nearly racemic compositions or a moderate enantiomer excess (R/S, approximately 1.0-1.2) in roach (Rutilus rutilus), whereas in perch (Perca fluviatilis) a much higher enantiomer excess (R/S, approximately 5) was observed. The data indicate that the stereoisomer composition of 4-MBC in environmental samples is not only a function of initial product composition but is also modified by enantioselective processes in lakes and biota (fish).

Animals↗
PubMed2004

Thermodynamics of the molecular and chiral recognition of cycloalkanols and camphor by modified beta-cyclodextrins possessing simple aromatic tethers.

The complex stability constants (K(S)) and thermodynamic parameters (DeltaG degrees, DeltaH degrees, and TDeltaS degrees ) for 1:1 inclusion complexation of beta-cyclodextrin (beta-CD) derivatives, 6-O-phenyl-beta-CD (2) 6-O-(4-formyl-phenyl)-beta-CD (3), 6-O-(4-nitrophenyl)-beta-CD (4), 6-O-(4-bromophenyl)-beta-CD (5), 6-O-(4-chlorophenyl)]-beta-CD (6), and 6-O-(4-hydroxybenzoyl)-beta-CD (7) with representative guest molecules, cyclic alcohols (cyclopentanol, cyclohexanol, cycloheptanol, cyclooctanol), (+/-)-borneol, and (+/-)-camphor, have been determined by means of titration microcalorimetry in an aqueous phosphate buffer solution (pH = 7.20) at 298.15 K. The results obtained indicate that the introduction to beta-CD of an aromatic ring bearing different substituent groups significantly enhances the molecular binding ability and moderately alters the chiral discrimination ability for the guests examined here, displaying the highest enantioselectivity of up to 4.01 for the inclusion complexation of 6 with (+/-)-camphor. The enhanced molecular/chiral discrimination ability caused by derivatization is attributed solely to increased positive entropy changes due to the expanding hydrophobic interaction and desolvation effects. The binding modes of host-guest interactions derived from ROESY spectroscopy data show that the resulting complex of 4 and (+)-borneol possesses better induced-fit interaction as compared to (-)-borneol, which is responsible for the enhanced molecular/chiral recognition ability.

Alcohols↗
PubMed2005

Practical and efficient multigram preparation of a camphor-derived diol for the enantioselective Lewis acid catalyzed allylboration of aldehydes.

[reaction: see text] Chiral diols are important molecules with widespread use as chiral auxiliaries and ligands in enantioselective synthesis. Therefore, efficient and practical syntheses of highly dissymmetrical nonracemic diols are still a meaningful pursuit. Two new routes to access camphor-derived chiral diol 1 have been developed. One route employs camphorquinone (3) as the starting material, affording in only two steps the desired diol in 55% overall yield. The second route, from camphor (2), leads to the desired diol in an efficient four-step synthesis, with an overall yield of 55%.

Alcohols↗
PubMed1999

Camphor toxicity.

Camphor ingestion led to status epilepticus in a 20-month-old girl who required intubation and ventilation. She was treated with intravenous valium and phenobarbitone, and nasogastric activated charcoal. She made a complete neurological recovery. A number of products containing a high concentration of camphor were found to be available in the local community.

Anticonvulsants↗
PubMed2000

[Effects of an herbal crataegus-camphor combination on the symptoms of cardiovascular diseases].

One hundred and ninety (190) patients presenting with "functional cardiovascular disorders" (ICD 10, F 45.3) received purely herbal combination therapy comprising crataegus and camphor (Korodin Herz-Kreislauf-Tropfen) or a placebo, identical in colour and taste to the active treatment, over a period of four weeks within the scope of a multi-centre, placebo-controlled, double-blind study. The principal criterion was the fall in the overall score obtained for a heart-related symptom complex (HSK) during administration of the herbal combination or randomly allocated placebo. The overall score fell significantly by 5.5 or 4.5 points, respectively, from a baseline value of 10.0 points each (p = 0.0165). The sub-score for exhaustion, joint pain, heart disorders, pain on pressure and the total score on the Giessen discomfort chart (GBB) indicated better efficacy with the crataegus-camphor combination than with the placebo. On completion of treatment, the investigators assessed the efficacy of the active drug as "very good to good" in 70.5% of their patients compared with a similar evaluation in just 49.5% of the placebo patients. The degree of satisfaction with the drug therapy according to physician and patient reflected the objective results obtained. 71.6% of subjects in the active drug group were satisfied with their treatment compared with just 52.7% in the placebo group. Adverse events (undesirable side effects) were recorded in 8.3% and 8.5% of patients, respectively. A correlation with the active drug therapy was established in only two cases. Tolerance was therefore positively assessed.

Adult↗
PubMed1973

A transmissible plasmid controlling camphor oxidation in Pseudomonas putida.

Earlier papers demonstrated an extensive genetic exchange among fluorescent Pseudomonads; this one documents for genes specifying enzymes of peripheral dissimilation an extrachromosomal array, segregation, and frequent interstrain transfer. An hypothesis is presented of a general mechanism for the formation and maintenance of metabolic diversity. The example used, the path of oxidative cleavage of the carbocyclic rings of the bicyclic monoterpene D- and L-camphor, terminates in acetate release and isobutyrate chain debranching. By transduction, two gene linkage groups are shown for the reactions before and after isobutyrate. The group for reactions before isobutyrate is plasmid borne, contransferable by conjugation, mitomycin curable, and shows a higher segregation rate from cells that are multiplasmid rather than carrying a single plasmid. The genes that code for isobutyrate and essential anaplerotic and amphibolic metabolism are chromosomal. By conjugation plasmid-borne genes are transferred at a higher frequency than are chromosomal, and are transferred in homologous crosses more frequently than between heterologous species. Most isobutyrate-positive fluorescent pseudomonad strains will accept and express the camphor plasmid.

Camphor↗
PubMed1984

Camphor hydroxylase of Pseudomonas putida: vestiges of sequence homology in cytochrome P-450CAM, putidaredoxin, and related proteins.

The amino acid sequences of cytochrome P-450CAM and putidaredoxin of the camphor hydroxylase [camphor, reduced-putida-ferredoxin:oxygen oxidoreductase (5-hydroxylating), EC 1.14.15.1] of Pseudomonas putida are compared to each other and then to the sequences of bovine adrenodoxin and cytochrome b5. The comparisons reveal areas of homology indicating that these four proteins may share a common evolutionary origin. Moreover, homologous segments can be recognized by proper alignment of the sequence of cytochrome P-450CAM to recently determined sequences of other P-450 hemeproteins. Further scrutiny indicates vestiges of internal sequence duplications that have been conserved in limited segments by the constraints of selection over a long time period, while other segments of the sequence diverged. It is predicted that the corresponding reductases will show a similar sequence pattern. The conserved regions of internal sequence repetition may serve a special purpose in protein-protein interactions within the multienzyme systems.

Amino Acid Sequence↗
PubMed2002

Camphor-Crataegus berry extract combination dose-dependently reduces tilt induced fall in blood pressure in orthostatic hypotension.

In order to test the efficacy of a combination of natural D-camphor and an extract of fresh crataegus berries (Korodin Herz-Kreislauf-Tropfen) on orthostatic hypotension, two similar, controlled, randomized studies were carried out in a balanced crossover design in 24 patients each with orthostatic dysregulation. The camphor-crataegus berry combination (CCC) was orally administered as a single regimen in 3 different dosages of 5 drops, 20 drops and 80 drops; a placebo with 20 drops of a 60% alcoholic solution served as control. Orthostatic hypotension was assessed with the tilt table test before and after medication. Source data of both studies were pooled and meta-analytically evaluated for all 48 patients. CCC drops decreased the orthostatic fall in blood pressure versus placebo, as almost uniformly established at all times by mean arterial pressure and diastolic blood pressure. Mean arterial pressure demonstrated the very fast onset of action by a clearly dose-dependent statistically significant effect even after 1-minute orthostasis. Increase of mean arterial pressure as compared to the orthostasis test before medication was on average 4.5 mmHg. CCC affected diastolic blood pressure after 1 minute of orthostasis in all dosages as compared to placebo. A statistically significant effect of the highest dose of 80 drops on diastolic blood pressure could be demonstrated after 1-, 3-, and 5-minute orthostasis. The hemodynamic findings of a stabilizing effect on arterial pressure in orthostasis corroborate the long-term medical experience with CCC and justify the indication orthostatic hypotension.

Adult↗
PubMed1977

The low-spin/high-spin transition equilibrium of camphor-bound cytochrome P-450. Effects of medium and temperature on equilibrium data.

The spin state of camphor-bound cytochrome P-450 is shown to depend largely on medium and temperature in aqueous as well as in mixed organic buffer. At sub-zero temperatures a variation of paH, ionic strength or camphor concentration modifies the spin equilibrium from nearly pure high-spin form to nearly pure low-spin form. Since the apparent pKa of transition is a linear function of log I, the spin state seems to be controlled by the electrostatic potential in the heme proximity. K+ is found to have a specific effect on the spin state. The change of enthalpy, deltaH, of the spin transition depends on the same parameters as the equilibrium constant, in the organic cosolvent as well as in aqueous buffer. As the cosolvent effect is reflected by higher deltaH values, and KCl and pH tend to lower deltaH, the cosolvent effect can easily be compensated. Therefore kinetic studies of the spin conversion might well be undertaken at sub-zero temperature in this solvent.

Camphor↗
PubMed2005

Impaired thermosensation in mice lacking TRPV3, a heat and camphor sensor in the skin.

Environmental temperature is thought to be directly sensed by neurons through their projections in the skin. A subset of the mammalian transient receptor potential (TRP) family of ion channels has been implicated in this process. These "thermoTRPs" are activated at distinct temperature thresholds and are typically expressed in sensory neurons. TRPV3 is activated by heat (>33 degrees C) and, unlike most thermoTRPs, is expressed in mouse keratinocytes. We found that TRPV3 null mice have strong deficits in responses to innocuous and noxious heat but not in other sensory modalities; hence, TRPV3 has a specific role in thermosensation. The natural compound camphor, which modulates sensations of warmth in humans, proved to be a specific activator of TRPV3. Camphor activated cultured primary keratinocytes but not sensory neurons, and this activity was abolished in TRPV3 null mice. Therefore, heat-activated receptors in keratinocytes are important for mammalian thermosensation.

Animals↗
PubMed2005

Estrogen target gene regulation and coactivator expression in rat uterus after developmental exposure to the ultraviolet filter 4-methylbenzylidene camphor.

Because the estrogen receptor (ER) ligand type influences transactivation, it is important to obtain information on molecular actions of nonclassical ER agonists. UV filters from cosmetics represent new classes of endocrine active chemicals, including the preferential ER beta ligands 4-methylbenzylidene camphor (4-MBC) and 3-benzylidene camphor. We studied estrogen target gene expression in uterus of Long Evans rats after developmental exposure to 4-MBC (0.7, 7, 24, and 47 mg/kg x d) administered in feed to the parent generation before mating, during pregnancy and lactation, and to the offspring until adulthood. 4-MBC altered steady-state levels of mRNAs encoding for ER alpha, ER beta, progesterone receptor (PR), IGF-I, androgen receptor, determined by real-time RT-PCR in uterus of 12-wk-old offspring. Western-blot analyses of the same tissue homogenates indicated changes in ER alpha and PR but not ER beta proteins. To assess sensitivity to estradiol (E2), offspring were ovariectomized on d 70, injected with E2 (10 or 50 microg/kg sc) on d 84, and killed 6 h later. Acute up-regulation of PR and IGF-I and down-regulation of ER alpha and androgen receptor by E2 were dose-dependently reduced in 4-MBC-exposed rats. The reduced response to E2 was accompanied by reduced coactivator SRC-1 mRNA and protein levels. Our data indicate that developmental exposure to 4-MBC affects the regulation of estrogen target genes and the expression of nuclear receptor coregulators in uterus at mRNA and protein levels.

Animals↗
PubMed2002

Confirmation of uterotrophic activity of 3-(4-methylbenzylidine)camphor in the immature rat.

In this study we found that the ultraviolet sunscreen component 3-(4-methylbenzylidine)camphor (4MBC) is uterotrophic in immature rats when administered by either subcutaneous injection or oral gavage. These data confirm earlier reports of uterotrophic activity for this agent when administered to immature rats in the diet or by whole-body immersion; however, they are in contrast to negative unpublished immature rat uterotrophic assay results. Data also indicate that 4MBC binds to isolated rat uterine estrogen receptors and shows activity in a human estrogen receptor yeast transactivation assay; however, we considered both of these effects equivocal. In this study, we confirmed the original observation that 4MBC was active as a mitogen to MCF-7 breast cancer cells. We evaluated and discounted the possibility that the estrogenic activity of 4MBC is related to its bulky camphor group, which is of similar molecular dimensions to that of the weak estrogen kepone. Uncertainty remains regarding the mechanism of the uterotrophic activity of 4MBC.

Administration, Oral↗
PubMed2004

Efficacy of camphorated paramonochlorophenol to a mixture of honey and mustard oil as a root canal medicament.

OBJECTIVE: To compare the efficacy of camphorated paramonochlorophenol to a mixture of honey and mustard oil as a root canal medicament. DESIGN: An in vitro comparative study. PLACE AND DURATION OF STUDY: This study was carried out in collaboration with microbiology department of Armed Forces Institute of Pathology, Rawalpindi and was conducted from Aug-2001 to Nov-2001. MATERIALS AND METHODS: A sample of 90 infected root canal contents of decayed teeth was collected from Operative Dentistry Department of Armed Forces Institute of Dentistry, Rawalpindi. Each sample was inoculated aerobically as well as an-aerobically. Organisms were identified and isolates were preserved and refrigerated for experiments. Medicaments were procured and prepared in comparable dilutions. Minimum inhibitory concentration of both medicaments was compared by susceptibility testing against already preserved isolates. RESULTS: The tested mixture (honey and mustard oil equal v/v ) demonstrated antibacterial activity against all isolates at concentration of 12.5%(mean of effective conc.17.11%) while that of camphorated paramonochlorophenol was comparably at higher concentration 3.1%(mean of effective conc. 3.35%). However the mixture revealed better results than that of individual agents, which was 12.5% to 25% respectively. CONCLUSION: Mixture (honey and mustard oil) was effective, viable alternate endodontic medicament.

Anti-Infective Agents, Local↗
PubMed1977

Camphorated and castor oil confusion and its toxic results.

Three cases of camphorated oil ingestion occurring over a 20-month period are discussed. Two of the three ingestions resulted in hospitalization, and the clinical course of the ingestions are presented. Follow-up investigations were performed to determine the causes of the confusion between castor and camphorated oil. Also presented are descriptions of efforts made to improve labeling and packaging of this potentially lethal household product.

Adolescent↗
PubMed1998

DSC and NMR spectroscopic studies of the interaction between camphorated phenol and phospholipid liposomes.

To clarify the interaction mechanism of biological activities induced by camphorated phenol (CP), the interactions between CP and phospholipid liposomes [dipalmitoyl phosphatidylcholine (DPPC) liposomes, dimyristoyl phosphatidylcholine (DMPC) liposomes and DMPC/dilauloyl phosphatidylethanolamine (DLEA) liposomes] were studies by DSC and NMR spectroscopy. CP exhibited a larger DSC phase transition properties [shift of phase transition temperature to a lower temperature and decrease in Height/Half-Height Width (H/HHW) of DSC peak)] than phenol in the various liposome systems. It was concluded from the NMR studies that CP is highly incorporated into the DPPC bilayer, the 1H and 13C signals of phenol in a complex between phenol and camphor being markedly broadened but shielded in the presence of DPPC liposomes. It was clear that CP is incorporated as a complex into the lipid bilayers.

Anti-Infective Agents, Local↗
PubMed2001

[Camphor in the Edo era fireworks].

Guns and gunpowder were introduced into Japan in 1543 by the Portuguese, and they soon began to be made in Japan by the Japanese. The powder was used also for making fireworks. The brilliance of fireworks was darker and the scale was less in the Edo period. Various materials were added to the powder to make the fireworks more brilliant. Camphor was one of them, though the volume was slight and the frequency of adding it was small. Camphor had been used for torch-light materials before the Edo period, so it seems logical that it would be added to powder for fireworks.

Camphor↗
PubMed2001

[Historical study of a moth repellent, "Fujisawa Camphor" (2) manufacture of borneol].

The manufacture of borneol started in about 1890 by the reduction of camphor at a rural chemical work in Osaka. Fujisawa Company, which refined and sold crude camphor, began to study the techniques necessary to manufacture borneol. In 1912, Fujisawa had succeeded in producing high-quality borneol in its plant. They tried to export it to China, from where they imported it before. The company replaced natural borneol on the market, supplying large amounts of high-quality borneol produced by the reduction method.

Animals↗
PubMed2000

[Gas chromatographic determination of camphor, menthol, methyl salicylate, thymol in JEIL COOL PAP].

The contents of camphor, menthol, methyl salicylate and thymol in JEIL COOL PAP were determined with gas chromatography by using a stainless steel column (2 m x 3 mm i.d.) packed with 15% DEGS, Chromosorb W (AW-DMCS) 80-100 mesh. Temperature programming was from 70 degrees C to 180 degrees C. The quantitative determination was performed with diphenyl as the internal standard. The internal standard method showed good linearity (r = 0.9995-0.9999). The average recoveries were 99.63% (camphor), 99.83% (menthol), 100.0% (methyl salicylate) and 100.4% (thymol).

Camphor↗