Wax Alcohols Research Articles

A 8-week, randomized, double-blind, placebo-controlled human trial to evaluate the efficacy and safety of Saccharum officinarum wax alcohols (Policosanol) on improvement of blood cholesterol

BackgroundThe prevalence of atherosclerotic cardiovascular disease appears to be reduced, according to a large body of research, by lowering blood levels of the ratio of low-density lipoprotein cholesterol (LDL-C)/ high-density lipoprotein cholesterol (HDL-C), triglyceride (TG)/HDL-C, and LDL-C. ObjectiveThe objective of the investigation was to determine the safety and endurance of policosanol (20 mg/d), as well as its efficacy in healthy individuals. Two parallel groups in this randomized, double-blind, placebo-controlled human experiment received either a policosanol (20 mg/d) or a placebo for eight weeks. 80 people were randomly assigned, with a mean (SD) age (years) of 42.61 (13.51), a mean (SD) BMI (kg/m2) of 24.53 (3.57), a mean (SD) weight (kg) of 66.71 (14.30), and a mean (SD) height (cm) of 164.21. (7.99). ResultsAt 8 weeks, when compared to the baselinegroup, the policosanol (20 mg/d) batch displayed considerably greater LDL-C (-4.87 ± 11.30 mg/dL; p = 0.014), total cholesterol (-6.82 ± 14.32 mg/dL; p = 0.007), triglyceride (-9.37 ± 19.27 mg/dL; p = 0.008), non HDL-C reductions (-10.32 ± 13.75 mg/dL; p = 0.0001), and significantly greater augmentation of HDL-C (3.50 ± 4.55 mg/dL; p = 0.010). Policosanol (20 mg/d) treatment also significantly reducing the serum levels of TC/HDL-C (p = 0.0001) and LDL-C/HDL-C (p = 0.0002), triglyceride/HDL-C (p = 0.001), and T-cholesterol-HDL-C/HDL-C (p = 0.0001) ratios. ConclusionIn humans, policosanol delivery resulted in a lowering of LDL-C levels and an improvement in other lipid markers, demonstrating the product potential to regulate hypercholesterolemia.

Enhancement of High-Density Lipoprotein Cholesterol Functions by Encapsulation of Policosanol Exerts Anti-Senescence and Tissue Regeneration Effects Via Improvement of Anti-Glycation, Anti-Apoptosis, and Cholesteryl Ester Transfer Inhibition

Consumption of policosanol (PCO), a refined mixture of sugar cane wax alcohols, can elevate serum levels of high-density lipoprotein cholesterol (HDL-C), although the molecular mechanism is still unknown. To investigate the mechanism of action responsible for the anti-senescence effects of PCO on lipoprotein metabolism and HDL functionality, we synthesized reconstituted HDL (rHDL) containing PCO. Encapsulation of PCO by rHDL (PCO-rHDL) enhanced anti-oxidant activity against cupric ion-mediated low-density lipoprotein (LDL) oxidation. PCO-rHDL (final concentration, 9 μM PCO) showed more potent anti-oxidant activity than vitamin C treatment (final concentration, 100 μM). PCO-rHDL inhibited fructose-mediated glycation, which is a major pathological mechanism of diabetic complications, in a dose-dependent manner. PCO also showed cytoprotective effects in monocytes and macrophages with less triggering of apoptotic processes and reactive oxygen species (ROS) production in the presence of hydrogen peroxide (H2O2). PCO-rHDL strongly inhibited uptake of acetylated LDL into macrophages, which is an initial atherosclerotic process. Surprisingly, PCO-rHDL inhibited human serum cholesteryl ester transfer protein (CETP) activity by up to 47% (final concentration, 10 μM PCO). Subcutaneous injection of PCO-rHDL dose-dependently enhanced tissue regeneration activity by 2.4-fold and 3.6-fold compared to that of the phosphate-buffered saline (PBS) control. In conclusion, PCO in HDL showed potent anti-oxidant, anti-glycation, and CETP inhibitory activities along with tissue regenerative activity, especially upon incorporation into HDL. These results suggest that PCO can enhance functionality of HDL in serum to exert anti-senescence and longevity effects.

Identification of β-hydroxy fatty acid esters and primary, secondary-alkanediol esters in cuticular waxes of the moss Funaria hygrometrica

The plant cuticle, a multi-layered membrane that covers plant aerial surfaces to prevent desiccation, consists of the structural polymer cutin and surface-sealing waxes. Cuticular waxes are complex mixtures of ubiquitous, typically monofunctional fatty acid derivatives and taxon-specific, frequently bifunctional specialty compounds. To further our understanding of the chemical diversity of specialty compounds, the waxes on the aerial structures of the leafy gametophyte, sporophyte capsule, and calyptra of the moss Funaria hygrometrica were surveyed. Respective moss surfaces were extracted, and resulting lipid mixtures were analyzed by gas chromatography–mass spectrometry (GC–MS). The extracts contained ubiquitous wax compound classes along with two prominent, unidentified classes of compounds that exhibited some characteristics of bifunctional structures. Microscale transformations led to derivatives with characteristic MS fragmentation patterns suggesting possible structures for these compounds. To confirm the tentative structure assignments, one compound in each of the suspected homologous series was synthesized. Based on GC–MS comparison with the authentic standards, the first series of compounds was identified as containing esters formed by β-hydroxy fatty acids and wax alcohols, with ester chain lengths varying from C42 to C50 and the most prominent homolog being C46. The second series consisted of fatty acid esters of 1,7-alkanediols, linked via the primary hydroxyl group, with ester chain lengths C40–C52 also dominated by the C46 homolog. The β-hydroxy acid esters were restricted to the sporophyte capsule, and the diol esters to the leafy gametophyte and calyptra. Based on their homolog and isomer distributions, and the presence of free 1,7-triacontanediol, possible biosynthetic reactions leading to these compounds are discussed.

Pathophysiologic Treatment Approach to Irritant Contact Dermatitis

Irritant contact dermatitis (ICD) is a commonly occurring non-specific cutaneous inflammatory response to topical chemical, physiologic, and biologic toxins. Direct damage to the skin induces barrier dysfunction, epidermal cell stimulation, and pro-inflammatory mediator release leading to a visibly variable, itchy cutaneous reaction. Workplace exposure of the hands to water, cleansers, and solvents remains the most common source of ICD. There is no diagnostic test for ICD, as such a diagnosis is based on history and clinical findings. Exclusion of allergic contact dermatitis, atopic dermatitis, and other xerotic conditions is a key part of the work-up. Prevention and treatment of ICD lies in the utilization of barrier protectants, incorporation of hydrating cleansers to decrease disruption of the barrier, and avoidance protocols and protective gear (fabrics, gloves, etc.). Therapeutic tools to treat ICD include acute anti-pruritic and antibacterial soaks, cutaneous barrier protectants such as petrolatum, paraffin, and dimethicone; lipid-laden moisturizers rich in wool wax alcohols, ceramides, and cholesterol esters and colloidal oatmeal based creams; and, when there is an eczematous component, the restrained use of anti-inflammatory agents such as topical corticosteroids may be warranted. Future research in ICD pathophysiology will yield more precise treatment options for future patients and clinicians.

Effects Of Policosanol Plus Aspirin Therapy On The Neurological Recovery And Plasma Oxidative Markers Of Patients With Ischemic Stroke

Background. Oxidative stress (OS) contributes to brain reperfusion injury after ischemic stroke. Policosanol, a mixture of 8 higher aliphatic sugarcane wax alcohols, has shown to protect against experimental brain ischemia. Objectives. To investigate the effect of policosanol plus aspirin (AS) therapy on the neurological outcome and plasma oxidative variables in patients post-ischemic stroke Methods. Post-ischemic stroke (≤ 30 days evolution) sufferers with a modified Rankin Scale score (mRSs) ≥2 ≤4 were randomized to placebo or policosanol (20 mg/day) + aspirin (AS) (125 mg/day) (pla + AS) or placebo + AS (pla + AS) for 24 weeks. The primary efficacy variable was to significantly increase the patients with a favourable stroke outcome (mRSs ≤1) versus pla +AS. Plasma oxidative markers (malondialdehyde –MDA-, sulphidril groups –SHG-, total antioxidant capacity –TAC-) were secondary variables. Results. Sixty-one (61) patients (mean age: 64 years) were randomized. No significant changes occurred with pla +AS. After 6 weeks on treatment poli + AS reduced significantly the mean mRSs value (p0.001 vs pla + AS), and this effect was not wear off, but enhanced, throughout the study. More (p0.0001) poli + AS patients (29/31, 93.5%) achieved mRSs values ≤1 at study completion as compared to pla + AS patients (2/30, 6.7%). Also, poli + AS treatment produced significant reductions of plasma MDA and SHG, while increased plasma TAC. Treatments were well tolerated. There were not study withdrawals. Conclusions. Poli + AS therapy improved the neurological recovery and favourably modified plasma oxidative markers versus pla + AS in patients post-ischemic stroke KEYWORDSAspirin, Ischemic stroke, Oxidative stress, Policosanol, Rankin-modified scale, Stroke

Effects of policosanol on the recovery of ischemic stroke: a randomized controlled study

Background. Antiplatelet therapy lowers the risk of recurrent stroke. Policosanol, a mixture of 8 high molecular weight sugar cane wax alcohols, has shown to reduce platelet aggregation. Objectives. To investigate whether the therapy with policosanol plus aspirin (AS) could improve the neurological outcome as compared to placebo + AS in patients with a recent ischemic stroke. Methods. Ninety-two (92) patients with a modified Rankin Scale score (mRSs) ≥2 ≤4 after suffering an ischemic stroke within 30 days before enrollment were randomized to placebo or policosanol (20 mg/day) + AS (125 mg/day) (pla + AS or poli + AS) for 24 weeks. The primary efficacy variable was to obtain a better stroke outcome (mRSs ≤1) as compared to pla +AS. Reduction of platelet aggregation was a secondary variable. Results. After 12 and 24 weeks on therapy, the rates of patients treated with poli + AS (10/46, 21.7% and 32/46, 69.6%, respectively) who achieved mRSs ≤1 were significantly (p0.01 and p0.0001, respectively) greater than those treated with pla + AS (0/46, 0.0% and 7/46, 15.2%, respectively). Poli + AS treatment given for 6 weeks reduced significantly (p0.00001 vs baseline, p0.01 vs pla + AS) the mean mRSs value (24.1%), and this effect improved thereafter, so that it was reduced by 31.0% and 55.2% after 12 and 24 weeks on therapy, respectively. Poli + AS treatment also reduced significantly arachidonic acidand adenosine diphosphateinduced platelet aggregation by 41.0% and 24.8%, respectively. Treatments were well tolerated. There were not withdrawals due to adverse experiences. Conclusions. In patients with recent ischemic stroke, poli + AS treatment improved the neurological recovery and decreased platelet aggregation as compared to pla + AS.

Ontogenetic variation in chemical and physical characteristics of adaxial apple leaf surfaces

The reaction of plants to environmental factors often varies with developmental stage. It was hypothesized, that also the cuticle, the outer surface layer of plants is modified during ontogenesis. Apple plantlets, cv. Golden Delicious, were grown under controlled conditions avoiding biotic and abiotic stress factors. The cuticular wax surface of adaxial apple leaves was analyzed for its chemical composition as well as for its micromorphology and hydrophobicity just after unfolding of leaves ending in the seventh leaf insertion. The outer surface of apple leaves was formed by a thin amorphous layer of epicuticular waxes. Epidermal cells of young leaves exhibited a distinctive curvature of the periclinal cell walls resulting in an undulated surface of the cuticle including pronounced lamellae, with the highest density at the centre of cells. As epidermal cells expanded during ontogenesis, the upper surface showed only minor surface sculpturing and a decrease in lamellae. With increasing leaf age the hydrophobicity of adaxial leaf side decreased significantly indicated by a decrease in contact angle. Extracted from plants, the amount of apolar cuticular wax per area unit ranged from only 0.9 μg cm −2 for the oldest studied leaf to 1.5 μg cm −2 for the youngest studied leaf. Differences in the total amount of cuticular waxes per leaf were not significant for older leaves. For young leaves, triterpenes (ursolic acid and oleanolic acid), esters and alcohols were the main wax components. During ontogenesis, the proportion of triterpenes in total mass of apolar waxes decreased from 32% (leaf 1) to 13% (leaf 7); absolute amounts decreased by more than 50%. The proportion of wax alcohols and esters, and alkanes to a lesser degree, increased with leaf age, whereas the proportion of acids decreased. The epicuticular wax layer also contained α-tocopherol described for the first time to be present also in the epicuticular wax. The modifications in the chemical composition of cuticular waxes are discussed in relation to the varying physical characteristics of the cuticle during ontogenesis of apple leaves.

Gill lipid metabolism and unidirectional Na + flux in the European eel ( Anguilla anguilla) after transfer to dilute media: the formation of wax alcohols as a primary response

The present study investigated the mechanism involved when fish tighten their gill membrane after transfer to dilute media. Ten individually assayed eels adapted to fresh water (FW) and labelled with radioactive 22 Na in the plasma showed mean exchange rates in equilibrium with ambient radioactive 24 Na in FW at 70 μmol kg −1 h −1. Just after transfer to demineralized water (DW), the mean Na + release rate went up to 120 μmol kg −1 h −1; after 24 h in DW it came down again and levelled off at 40 μmol kg −1 h −1 during a period of up to 2 weeks. During the same period the mean Na + uptake rate was 12 μmol kg −1 h −1, i.e., the general picture in DW was a net Na + loss. In another similar experiment, groups of three FW-adapted eels were incubated in vivo for up to 24 h with ( 14 C ) acetate added as lipid precursor to the ambient water. Incubation in FW showed about 20% of the total 14 C -activity incorporated into gill lipids as ( 14 C ) wax alcohols (WA; octadecanol and eicosanol). This percentage went up to 50% shortly after transfer to DW and came down again to about 20% after 2 weeks in DW. Single eels labelled with 22 Na in the plasma showed a statistically significant positive linear correlation of percentage ( 14 C ) wax alcohols with log [ 22 Na efflux]. Based on the observed parallel between Na + flux and gill lipid metabolism, it is suggested that the eel reacts at first to a loss of Na + by synthesizing wax alcohols that can tighten the gill membrane.

KCS1 encodes a fatty acid elongase 3-ketoacyl-CoA synthase affecting wax biosynthesis in Arabidopsis thaliana.

An Arabidopsis fatty acid elongase gene, KCS1, with a high degree of sequence identity to FAE1, encodes a 3-ketoacyl-CoA synthase which is involved in very long chain fatty acid synthesis in vegetative tissues, and which also plays a role in wax biosynthesis. Sequence analysis of KCS1 predicted that this synthase was anchored to a membrane by two adjacent N-terminal, membrane-spanning domains. Analysis of a T-DNA tagged kcs1-1 mutant demonstrated the involvement of the KCS1 in wax biosynthesis. Phenotypic changes in the kcs1-1 mutant included thinner stems and less resistance to low humidity stress at a young age. Complete loss of KCS1 expression resulted in decreases of up to 80% in the levels of C26 to C30 wax alcohols and aldehydes, but much smaller effects were observed on the major wax components, i.e. the C29 alkanes and C29 ketones on leaves, stems and siliques. In no case did the loss of KCS1 expression result in complete loss of any individual wax component or significantly decrease the total wax load. This indicated that there was redundancy in the elongase KCS activities involved in wax synthesis. Furthermore, since alcohol, aldehyde, alkane and ketone levels were affected to varying degrees, involvement of the KCS1 synthase in both the decarbonylation and acyl-reduction wax synthesis pathways was demonstrated.

The myth of lanolin allergy.

Lanolin has the reputation of being an important contact sensitizer. The market place abounds with products that are labeled "lanolin free". In fact, lanolin is at most a weak contact allergen. The supposed hazards of sensitization to lanolin products are a resultant of faulty science and failure to appreciate the limitations of patch testing. Lanolin allergy is a myth created mainly by overzealous professional patch testers. No one has succeeded in sensitizing animals or humans to lanolin or wool wax alcohols. Most of the case reports are false positives, in association with the angry back syndrome.

Contact sensitization in chronic venous insufficiency: modern wound dressings.

Patch tests with an expanded European standard series and 20 different wound dressings revealed sensitization in 78% of all (36) patients. The charts of allergens were headed by ointment bases (wool wax alcohols sensitization in 33% of all patients; Amerchol L-101 19.4%; cetearyl alcohol 13.9%; propylene glycol 8.3%), followed by plant resins/ethereal oils (balsam of Peru 22.2%; colophony 13.9%, fragrance mix 8.3%; propolis 5.6%) and topical antibiotics (neomycin sulfate 16.7%, chloramphenicol 13.9%), while usually common sensitizers like metal salts were not found as often (nickel sulfate 16.7%; potassium dichromate 13.9%; cobalt chloride 5.6%). Sensitization to modern wound dressings was found in 8.3% (3 cases) and was caused by propylene glycol as an ingredient of hydrogels; no sensitization was found to hydrocolloids, alginates or polyurethane foams. The overall sensitization rate in 2nd degree CVI was nearly as high as in 3rd degree CVI, but sensitization to ointments, their additives and topical antibiotics was significantly higher in 3rd degree CVI. Significant differences in sensitization frequencies to individual allergens were found between male and female patients. Our investigation points out the high risk of sensitization in 2nd as well as 3rd degree CVI, especially to ointment bases and active principles of topical drugs. Even wound dressings may cause allergic contact reactions.

Wool wax alcohols and lanolin sensitization

Wool wax alcohols and lanolin sensitization

The lanolin paradox.

Several puzzling aspects of the use of lanolin are discussed as "lanolin paradoxes', in analogy with the 'paraben paradoxes'. Lanolin in topical therapeutic agents sensitizes a high proportion of patients, whereas the same lanolin is 'safe' in cosmetics so widely used by millions of individuals. Patients with an allergic contact dermatitis to lanolin in a medication applied to a stasis ulcer can nevertheless use lanolin-containing cosmetics and not experience a reaction. Lanolin-sensitive individuals often show false-negative patch test reactions to unaltered lanolin. Patch testing with 30% wool wax alcohols used in the standard patch test tray cannot be considered a reliable method for detecting and confirming lanolin allergies. There are too many false-positive and false-negative results using the standard patch test tray.

Leaf wax alcohols inCoincya (Brassicaceae)

AbstractFree and ester alcohol compositions have been determined for leaf waxes in ten taxa belonging to the genusCoincya (Brassicaceae) on the Iberian Peninsula (Spain and Portugal). Size of leaf wax alcohols in the genusCoincya varies between 20 and 31 carbon atoms. This series is dominated by alcohols with an even number of carbon atoms. The most abundant alcohols are C24, C26 and C28 among even and C25, C27 and C29 among odd alcohols, both in free alcohols and in wax esters.

Thermoanalytical and gas chromatographic evaluation of wool wax alcohols supported by principal component analysis

Three commercial and three non-commercial samples of wool wax alcohols were analysed using thermoanalytical and gas chromatographic techniques. For further characterisation using a chemometric procedure, concentrations of 28 individual components and 14 thermoanalytical parameters were considered. The data were processed using principal component analysis. Our results demonstrate the comparable classification ability of gas chromatographic and thermoanalytical methods. However, in the case of thermal analysis the sample patterns are more complex. This suggests that the thermoanalytical data contain additional information on the contents of non-volatile compounds which cannot be determined by gas chromatography.

Gas chromatographic evaluation of wool wax alcohols supported by principal component analysis

Capillary gas chromatography with flame ionization detection has been applied to the separation of the components of wool wax alcohols. Twenty-six commercial and non-commercial (laboratory) samples were investigated. Twenty-eight components found in the samples were used as variables for further characterization by a chemometric procedure. Principal component analysis was applied to the differentiation of samples from different sources and obtained by different technologies.

Digestive lipolytic enzymes in cod ( Gadus morrhua): Fatty acid specificity

1. 1. Digestive juice from cod ( Gadus morrhua) pyloric ceca and anterior ileum was tested for specificity using marine triglycerides (TG) and marine wax esters (WE) as substrates. 2. 2. The lipolysis was bile stimulated, active at 7°C, had an optimum at 37°C, hydrolysed TG faster than WE and this was not affected by mixing the substrates. 3. 3. The lipolytic activity was clearly fatty acid specific, in that short chain saturated fatty acids accumulated in the residual di- and monoglycerides whereas polyenoic fatty acids accumulated in the free fatty acid fraction and monoenoic fatty acids were evenly distributed. 4. 4. The same pattern was found for the fatty acid from the wax esters as substrate whereas no specificity was shown towards the wax alcohols.

High Pressure Extraction of Crude Montan Wax

AbstractThe high pressure extraction of crude montan wax was investigated at 20 to 100°C and at 150 to 500 bar with CO2 and ethylene and also with the fluorinated hydrocarbons Frigen 13, 13 B1 and 23. – In some cases the acid numbers, saponification numbers and setting points of the extracts differed markedly from those of the starting material. Especially at low extraction temperatures and pressures, where however solubilities are relatively low mainly low‐molecular weight wax components, such as free wax acids, wax alcohols and paraffins, as well as low‐molecular weight resin components were extracted. The corresponding high‐molecular weight components remain preferentially in the extraction residues.

Separation and analysis of steryl and wax esters from Dicranum elongatum

Abstract Complete separation of the steryl and wax esters in the subarctic moss Dicranum elongatum was achieved on MgO thin‐layer plates without any notable alteration of the acyl and alkyl moieties of the esters. Gas chromatography‐mass spectrometry of the hydrolyzed fraction showed that the sterols (campesterol, stigmasterol, sitosterol, cycloartenol, 24‐methylene cycloartanol and an unidentified sterol) were primarily esterified with unsaturated fatty acids 18:2 ω 6, 18:3 ω 3 and 20:4 ω 6. In contrast, the wax alcohols (l‐octadecanol, phytol and geranylgeraniol) were mainly esterified with saturated fatty acids with 16:0, 18:0 and 20:0 as major components. No great differences were found in the fatty acid pattern of the steryl esters between different portions of the shoot. Slight differences, however, were found in the proportions of ω 3 and ω 6 fatty acids. In the wax esters a clear decrease was found in the proportions of 18:0 and 20:0 acids with increased shoot age accompanied by a slight increase in the proportions of 14:0, 20:4 ω 6 and phytenic acid.

Terpenoid and other extractives of western white pine bark

Abstract A detailed chemical analysis of the benzene extract of western white pine bark was conducted. The extract consisted of 13% phlobaphenes, 18% strong acids, 21% polar weak acids, 6.5% fatty acids, 9.5% resin acids, and 32% neutrals. The fatty acids consisted mainly of C 20:0 , C 22:0 , and C 24:0 acids. The resin acids were identified as: isopimaric, anticopalic, dehydroabietic, sandaracopimaric, abietic, 6,8,11,13-abietatetraen-18-oic and pimaric acids. The neutrals on saponification gave fatty acids, sterols, wax alcohols, nonsaponifiables, and other components. The esterified fatty acids consisted primarily of the C 16:0 , C 18:0 , C 20:0 and C 24:0 acids. The sterols included major amounts of sitosterol, campesterol, and stigmasterol, and traces of cholesterol. Over 70 individual compounds were isolated and identified from the nonsaponifiables. These included borneol, sesquiterpenes, diterpenes, steroidal ketones, as well as lanostane and serratane triterpenes. The characterization of12 new natural products or natural products isolated for the first time from Pinus species is reported.