Oxidation kinetics for <Emphasis Type="Italic">cis</Emphasis>-9,<Emphasis Type="Italic">trans</Emphasis>-11 and <Emphasis Type="Italic">trans</Emphasis>-10,<Emphasis Type="Italic">cis</Emphasis>-12 isomers of CLA

The autoxidation processes of the cis-9,trans-11 (c9,t11) and trans-10,cis-12 (t10,c12) isomers of CLA were separately observed at ca. 0% RH and different temperatures. The t10,c12 CLA oxidized faster than the c9,t11 isomer at all tested temperatures. The first half of the oxidation process of t10,c12 CLA obeyed an autocatalytic-type rate expression, but the latter half followed first-order kinetics. On the other hand, the entire oxidation process of c9,t11 CLA could be expressed by the autocatalytic-type rate expression. The apparent activation energies and frequency factors for the autoxidation of the isomers were estimated from the rate constants obtained at various temperatures based on the Arrhenius equation. The apparent activation energies for the CLA isomers were greater than those for the nonconjugated n−6 and n−3 PUFA or their esters. However, the enthalpyentropy compensation held during the autoxidation of both the CLA and PUFA. This suggested that the autoxidation mechanisms for the CLA and PUFA were essentially the same.     

Effect of <Emphasis Type="Italic">trans</Emphasis>8, <Emphasis Type="Italic">cis</Emphasis>10+<Emphasis Type="Italic">cis</Emphasis>9, <Emphasis Type="Italic">trans</Emphasis>11 Conjugated Linoleic Acid Mixture on Lipid Metabolism in 3T3-L1 Cells

Evidence suggests that minor isomers of conjugated linoleic acid (CLA), such as trans8, cis10 CLA, can elicit unique biological effects of their own. In order to determine the effect of a mixture of t8, c10+c9, t11 CLA isomers on selected aspects of lipid metabolism, 3T3-L1 preadipocytes were differentiated for 8 days in the presence of 100 μM linoleic acid (LA); t8, c10+c9, t11 CLA; t10, c12+c9, t11 CLA or purified c9, t11 CLA. Whereas supplementation with c9, t11 and t10, c12+c9, t11 CLA resulted in cellular triglyceride (TG) concentrations of 3.4 ± 0.26 and 1.3 ± 0.11 μg TG/μg protein, respectively (P < 0.05), TG accumulation following treatment with CLA mixture t8, c10+c9, t11 was significantly intermediate (2.5 ± 0.22 μg TG/μg protein, P < 0.05) between the two other CLA treatments. However, these effects were not attributable to an alteration of the Δ⁹ desaturation index. Adiponectin content of adipocytes treated with t8, c10+c9, t11 mixture was similar to the individual isomer c9, t11 CLA, and both the t8, c10+c9, t11 and c9, t11 CLA groups were greater (P < 0.05) than in the t10, c12+c9, t11 CLA group. Overall, these results suggest that t8, c10+c9, t11 CLA mixture affects TG accumulation in 3T3-L1 cells differently from the c9, t11 and t10, c12 isomers. Furthermore, the reductions in TG accumulation occur without adversely affecting the adiponectin content of these cells.     

Altered Lipid Response in Hamsters Fed <Emphasis Type="Italic">cis</Emphasis>-9,<Emphasis Type="Italic">trans</Emphasis>-11+<Emphasis Type="Italic">trans</Emphasis>-8,<Emphasis Type="Italic">cis</Emphasis>-10 Conjugated Linoleic Acid Mixture

The objective of the present study was to compare the effects of cis-9,trans-11 + trans-8,cis-10 conjugated linoleic acid (CLA) mixture to those of cis-9,trans-11 + trans-10,cis-12 CLA mixture and linoleic acid (LA) on lipoprotein profile, hepatic lipids, body composition and digestibility of dietary fat in hamsters (n = 17) fed diets containing 2% of experimental fat (w/w) for 28 days. The cis-9,trans-11 + trans-10,cis-12 CLA mixture showed higher LDL cholesterol concentrations than LA and the cis-9,trans-11 + trans-8,cis-10 CLA mixture. The cis-9,trans-11 + trans-8,cis-10 CLA mixture induced similar plasma LDL cholesterol and hepatic lipid concentrations, and coefficient of digestibility as LA, indicating no effect of the trans-8,cis-10 CLA isomer on these lipid parameters. On the other hand, the cis-9,trans-11 + trans-8,cis-10 CLA mixture induced higher plasma VLDL cholesterol and triglycerides than LA and the cis-9,trans-11 + trans-10,cis-12 CLA mixture. The cis-9,trans-11 + trans-8,cis-10 CLA mixture also induced the highest plasma glucose concentrations compared with the two other groups, indicating an impairment of glycemic control. No differences in body composition were noted between the three groups. The present results thus show that the cis-9,trans-11 + trans-8,cis-10 CLA mixture can deteriorate plasma VLDL cholesterol and triglycerides in hamsters, possibly due to an increased flux of glucose.     

<Emphasis Type="Italic">trans</Emphasis>-10,<Emphasis Type="Italic">cis</Emphasis>-12 Conjugated Linoleic Acid Enhances Endurance Capacity by Increasing Fatty Acid Oxidation and Reducing Glycogen Utilization in Mice

The supplementation of conjugated linoleic acid (CLA) has been shown to improve endurance by enhancing fat oxidation during exercise in rodents and humans. This study was designed to investigate the isomer-specific effects of CLA on endurance capacity and energy metabolism in mice during exercise. Male 129Sv/J mice were divided into three dietary groups and fed treatment diet for 6 weeks; control, 0.5 % cis-9,trans-11 (c9,t11) CLA, or 0.5 % trans-10,cis-12 (t10,c12) CLA. Dietary t10,c12 CLA induced a significant increase in maximum running time and distance until exhaustion with a dramatic reduction of total adipose depots compared to a control group, but there were no significant changes in endurance with the c9,t11 CLA treatment. Serum triacylglycerol and non-esterified fatty acid concentrations were significantly lower in the t10,c12 fed mice after exercise compared to control and the c9,t11 CLA fed-animals. Glycogen contents in livers of the t10,c12 fed-mice were higher than those in control mice, concomitant with reduction of serum l-lactate level. There were no differences in non-exercise physical activity among all treatment groups. In addition, the mRNA expression levels of carnitine palmitoyl transferase 1β, uncoupling protein 2 and peroxisome proliferator-activated receptor δ (PPARδ) in skeletal muscle during exercise were significantly up-regulated by the t10,c12 CLA but not the c9,t11 CLA. These results suggest that the t10,c12 CLA is responsible for improving endurance exercise capacity by promoting fat oxidation with a reduction of the consumption of stored liver glycogen, potentially mediated via PPARδ dependent mechanisms.     

Mechanical and thermal characterization of <Emphasis Type="Italic">cis</Emphasis>-polyisoprene and <Emphasis Type="Italic">trans</Emphasis>-polyisoprene blends

Measurements of mechanical and thermal transport properties have been made on the blends of cis-polyisoprene (CPI) and trans-polyisoprene (TPI) prepared by a solution casting method. Characterization of these blends has been done using wide angle X-ray scattering. Thermo-mechanical, mechanical, and thermal transport properties have been determined employing dynamic mechanical analyzer (DMA) and transient plane source. Storage modulus and tan δ as determined from DMA have been found to increase and decrease with the increase in TPI content, respectively. Mechanical properties such as Young’s modulus and tensile strength, as determined from strain–stress behavior of CPI/TPI blends, have been found to increase with increasing TPI content. This increase in properties has been explained on the basis of the crosslink density, calculated using theory of rubber elasticity. Thermal transport properties such as thermal conductivity, thermal diffusivity, and volumetric heat capacity are higher for all the three blends as compared to their pure components.     

Vaccenic Acid and <Emphasis Type="Italic">cis</Emphasis>-9,<Emphasis Type="Italic">trans</Emphasis>-11 CLA in the Rumen and Different Tissues of Pasture- and Concentrate-Fed Beef Cattle

The objective of present study was the comparison of trans-11 18:1 (VA) and cis-9,trans-11 CLA concentrations in the rumen and different tissues in beef cattle, and to examine the diet and breed effects on the compound concentration and deposition. Sixty-four German Holstein and German Simmental bulls were randomly assigned to two dietary treatments, based on concentrate or pasture. The concentration of cis-9,trans-11 CLA and VA in rumen, duodenal digesta and different tissues was determined by gas chromatography. The results showed that pasture relative to concentrate feeding significantly increased the concentration of VA in duodenal digesta, plasma and erythrocyte phospholipids. Pasture-based feeding resulted in a significant enrichment of cis-9,trans-11 CLA in plasma lipids and erythrocyte phospholipids, but not in rumen and duodenal digesta, compared to concentrate-fed diet. Diet did not affect the cis-9,trans-11 CLA concentrations (mg/100 g fresh tissue) in semitendinosus muscle and subcutaneous fat. There was a breed effect on the deposition of cis-9,trans-11 CLA in longissimus muscle with lower concentration in pasture-fed German Simmental bulls compared to concentrate-fed bulls. However, pasture feeding significantly increased both, the VA and cis-9,trans-11 CLA concentrations in liver and heart tissues. Both diet and breed effects on Δ⁹-desaturase index was observed in muscle and subcutaneous fat tissues. There was a linear relationship between the concentration of VA and cis-9,trans-11 CLA and the coefficients of determination (R ²) varied between 0.29 and 0.87 from rumen to the different tissues.     

Occurrence of the <Emphasis Type="Italic">cis</Emphasis>-4,7,10, <Emphasis Type="Italic">trans</Emphasis>-13-22:4 Fatty Acid in the Family Pectinidae (Mollusca: Bivalvia)

The present study aimed to elucidate the effective phylogenetic specificity of distribution of a cis-4,7,10, trans-13-22:4 (22:4(n-9)Δ13trans) among pectinids. For this purpose, we extended the analysis of membrane glycerophospholipids FA composition to 13 species of scallops, covering 11 genera and 7 tribes representatives of the three subfamilies Chlamydinae, Palliolinae and Pectininae and the subgroup Aequipecten. In species belonging to the subfamily Pectininae and the Aequipecten subgroup, 22:4(n-9)Δ13trans was found in substantial amounts, but it was absent in other species belonging to the subfamilies Chlamydinae and Palliolinae. Homologous non-methylene-interrupted (NMI) FA, also hypothesized to differ along phylogenetic lines in bivalves, were totally absent or present only in trace amounts in representatives of the Aequipecten subgroup but ranged from 0.3 to 4.5% of the total FA in Pectinidae, Chlamydinae, and Palliolinae subfamilies. The species-specific occurrence of NMI and 22:4(n-9)Δ13trans FA in membrane lipids of pectinids agrees with the most recent phylogenies based on shell morphology and molecular characteristics. We examined the potential timing of the appearance of 22:4(n-9)Δ13trans in pectinids on a geologic time scale.     

Butters Varying in <Emphasis Type="Italic">trans</Emphasis> 18:1 and <Emphasis Type="Italic">cis</Emphasis>-9,<Emphasis Type="Italic">trans-</Emphasis>11 Conjugated Linoleic Acid Modify Plasma Lipoproteins in the Hypercholesterolemic Rabbit

The experiment was designed to study the effects of butters differing in conjugated linoleic acid (CLA) and trans 18:1 contents on lipoproteins associated with the risk of atherogenesis. New Zealand White male rabbits (9.6 weeks; 2.1 kg) were assigned for 6 or 12 weeks to three diets (n = 6 per diet) made of conventional pellets with 0.2% cholesterol and with 12% fat provided from a butter poor in trans-10 and trans-11 18:1 and in CLA (standard group), or rich in trans-10 18:1 (trans-10 18:1 group) or rich in trans-11 18:1 and in cis-9,trans-11 CLA (trans-11 18:1/CLA group). Blood samples were collected at the end of dietary treatments. Lipoproteins were separated by gradient-density ultracentrifugation. Lipid classes were determined enzymatically and apolipoproteins A-I and B by radial immunodiffusion. Mainly in the 12-week rabbits, higher plasma triglycerides and apolipoprotein B levels shown in the standard and trans-10 18:1 groups compared with those in the trans-11 18:1/CLA group are associated with higher plasma levels of very low density lipoproteins (VLDL) and low density lipoproteins (LDL) also shown in these two groups. In the 12-week rabbits, a shift towards denser LDL, considered as more atherogenic, was shown only in the trans-10 18:1 group. In these animals, the VLDL + LDL to HDL ratio was 1.7-2.3 times higher in the trans-10 18:1 group than in the other groups (P = 0.076). These results suggest a rather neutral effect of trans-11 18:1/CLA butter towards the risk of atherogenesis, whereas trans-10 18:1 butter would tend to be detrimental.     

<Emphasis Type="Italic">cis</Emphasis>-, <Emphasis Type="Italic">trans</Emphasis>- and Saturated Fatty Acids in Selected Hydrogenated and Refined Vegetable Oils in the Indian Market

The fatty acid composition of 27 samples of commercial hydrogenated vegetable oils and 23 samples of refined oils such as sunflower oil, rice bran oil, soybean oil and RBD palmolein marketed in India were analyzed. Total cis, trans unsaturated fatty acids (TFA) and saturated fatty acids (SFA) were determined. Out of the 27 hydrogenated fats, 11 % had TFA about 1 % where as 11 % had more than 5 % TFA with an average value of about 13.1 %. The 18:1 trans isomers, elaidic acid was the major trans contributor found to have an average value of about 10.8 % among the fats. The unsaturated fatty acids like cis-oleic acid, linoleic acid and α-linolenic acid were in the range of 21.8–40.2, 1.9–12.2, 0.0–0.7 % respectively. Out of the samples, eight fats had fatty acid profiles of low TFA (less than 10 %) and high polyunsaturated fatty acids (PUFA) such as linoleic and α-linolenic acid. They had a maximum TFA content of 7.3 % and PUFA of 11.7 %. Among the samples of refined oils, rice bran oil (5.8 %) and sunflower oil (4.4 %) had the maximum TFA content. RBD palmolein and rice bran oils had maximum saturated fatty acids content of 45.1 and 24.4 % respectively. RBD palmolein had a high monounsaturated fatty acids (MUFA) content of about 43.4 %, sunflower oil had a high linoleic acid content of about 56.1 % and soybean oil had a high α-linolenic acid content of about 5.3 %.     

Preparative Separation of <Emphasis Type="Italic">cis</Emphasis>- and <Emphasis Type="Italic">trans</Emphasis>-Isomers of Unsaturated Fatty Acid Methyl Esters Contained in Edible Oils by Reversed-Phase High-Performance Liquid Chromatography

In order to measure exactly the trans-fatty acids content in food materials, a preparative group separation of cis- and trans-isomers of unsaturated fatty acid methyl esters (FAMEs) was achieved by an isocratic reversed-phase HPLC (RP-HPLC) method. The trans-isomers of 16:1, 18:1, 18:2, 18:3, 20:1 and 22:1 FAMEs were readily separated from the corresponding cis-isomers by a COSMOSIL Cholester C18 column (4.6 mm I.D. × 250 mm, Nacalai Tesque) or a TSKgel ODS-100Z column (4.6 mm I.D. × 250 mm, TOSOH), using acetonitrile as the mobile phase. This method was applied for determining the trans-18:1 fatty acid content in partially hydrogenated rapeseed oil. The methyl esters of cis- and trans-18:1 isomers of the oil were collected as two separate fractions by the developed RP-HPLC method. Each fraction was analyzed by gas chromatography (GC) for both qualitative and quantitative information on its positional isomers. By a combination of RP-HPLC and GC methods, a nearly complete separation of cis- and trans-18:1 positional isomers was achieved and the trans-18:1 fatty acid content was able to be evaluated more precisely than is possible by the direct GC method. The reproducibility of cis- and trans-18:1 isomers fractionated by the RP-HPLC method was better than 98%. These results suggested that the preparative RP-HPLC method developed in this study could be a powerful tool for trans-fatty acid analysis in edible oils and food products as an alternative to silver-ion chromatography.     

Dietary Docosahexaenoic Acid and <Emphasis Type="Italic">trans</Emphasis>-10, <Emphasis Type="Italic">cis</Emphasis>-12-Conjugated Linoleic Acid Differentially Alter Oxylipin Profiles in Mouse Periuterine Adipose Tissue

Diets containing high n-3 polyunsaturated fatty acids (PUFA) decrease inflammation and the incidence of chronic diseases including cardiovascular disease and nonalcoholic fatty liver disease while trans-fatty acids (TFA) intake increases the incidence of these conditions. Some health benefits of n-3 PUFA are mediated through the impact of their oxygenated metabolites, i.e. oxylipins. The TFA, trans-10, cis-12-conjugated linoleic acid (CLA; 18:2n-6) is associated with adipose tissue (AT) inflammation, oxidative stress, and wasting. We examined the impact of a 4-week feeding of 0, 0.5, and 1.5% docosahexaenoic acid (DHA; 22:6n-3) in the presence and absence of 0.5% CLA on AT oxylipin profiles in female C57BL/6N mice. Esterified oxylipins in AT derived from linoleic acid (LNA), alpha-linolenic acid (ALA), arachidonic acid (ARA), eicosapentaenoic acid (EPA), DHA, and putative from CLA were quantified. CLA containing diets reduced AT mass by ~62%. Compared with the control diet, the DHA diet elevated concentrations of EPA-and DHA-derived alcohols and epoxides and LNA-derived alcohols, reduced ARA-derived alcohols, ketones, epoxides, and 6-keto-prostaglandin (PG) F_1α (P < 0.05), and had mixed effects on ALA-derived alcohols. Dietary CLA lowered EPA-, DHA-, and ALA-derived epoxides, ARA-derived ketones and epoxides, and ALA-derived alcohols. While dietary CLA induced variable effects in EPA-, DHA-, and LNA-derived alcohols and LNA-derived ketones, it elevated ARA-derived alcohols and PGF_1α, PGF_2α, and F2-isoprostanes. DHA counteracted CLA-induced effects in 67, 57, 43, and 29% of total DHA-, ARA-, EPA-, and ALA-derived oxylipins, respectively. Thus, CLA elevated proinflammatory oxylipins while DHA increased anti-inflammatory oxylipins and diminished concentration of CLA-induced pro-inflammatory oxylipins in AT.     

Docosahexaenoic Acid and Eicosapentaenoic Acid Did not Alter <Emphasis Type="Italic">trans</Emphasis>-10,<Emphasis Type="Italic">cis</Emphasis>-12 Conjugated Linoleic Acid Incorporation into Mice Brain and Eye Lipids

trans 10,cis 12‐CLA has been reported to alter fatty acid composition in several non‐neurological tissues, but its effects are less known in neurological tissues. Therefore, the purpose of this study was to determine if CLA supplementation would alter brain and eye fatty acid composition and if those changes could be prevented by concomitant supplementation with docosahexaenoic acid (DHA; 22:6n3) or eicosapentaenoic acid (EPA; 20:5n3). Eight‐week‐old, pathogen‐free C57BL/6N female mice (n = 6/group) were fed either the control diet or diets containing 0.5% (w/w) t10,c12‐CLA in the presence or absence of either 1.5% DHA or 1.5% EPA for 8 weeks. CLA concentration was significantly (P < 0.05) greater in the eye but not in the brain lipids of the CLA group when compared with the control group. The sums of saturated, monounsaturated, polyunsaturated fatty acids, and n3:n6 ratio did not differ between these two groups for both tissues. The n3:n6 ratio and concentrations of 20:5n3 and 22:5n3 were significantly greater, and those of 20:4n6, 22:4n6, and 22:5n6 were lesser in the CLA + DHA and CLA + EPA groups than in the control and CLA groups for either tissue. DHA concentration was higher in the CLA + DHA group only but not in the CLA + EPA group when compared with the CLA group for both tissues. The dietary fatty acids generally induced similar changes in brain and eye fatty acid concentration and at the concentrations used both DHA and EPA fed individually with CLA were more potent than CLA alone in altering the tissue fatty acid concentration.     

Isomerization of Vaccenic Acid to <Emphasis Type="Italic">cis</Emphasis> and <Emphasis Type="Italic">trans</Emphasis> C18:1 Isomers During Biohydrogenation by Rumen Microbes

In ruminants, cis and trans C18:1 isomers are intermediates of fatty acid transformations in the rumen and their relative amounts shape the nutritional quality of ruminant products. However, their exact synthetic pathways are unclear and their proportions change with the forage:concentrate ratio in ruminant diets. This study traced the metabolism of vaccenic acid, the main trans C18:1 isomer found in the rumen, through the incubation of labeled vaccenic acid with mixed ruminal microbes adapted to different diets. [1-¹³C]trans-11 C18:1 was added to in vitro cultures with ruminal fluids of sheep fed either a forage or a concentrate diet. ¹³C enrichment in fatty acids was analyzed by gas-chromatography-mass spectrometry after 0, 5 and 24 h of incubation. ¹³C enrichment was found in stearic acid and in all cis and trans C18:1 isomers. Amounts of ¹³C found in fatty acids showed that 95% of vaccenic acid was saturated to stearic acid after 5 h of incubation with the concentrate diet, against 78% with the forage diet. We conclude that most vaccenic acid is saturated to stearic acid, but some is isomerized to all cis and trans C18:1 isomers, with probably more isomerization in sheep fed a forage diet.     

The Diversity of Health Effects of Individual <Emphasis Type="Italic">trans</Emphasis> Fatty Acid Isomers

There are multiple adverse effects of trans fatty acids (TFA) that are produced by partial hydrogenation (i.e., manufactured TFA), on CVD, blood lipids, inflammation, oxidative stress, endothelial health, body weight, insulin sensitivity, and cancer. It is not yet clear how specific TFA isomers vary in their biological activity and mechanisms of action. There is evidence of health benefits on some of the endpoints that have been studied for some animal TFA isomers, such as conjugated linoleic acid; however, these are not a major TFA source in the diet. Future research will bring clarity to our understanding of the biological effects of the individual TFA isomers. At this point, it is not possible to plan diets that emphasize individual TFA from animal sources at levels that would be expected to have significant health effects. Due to the multiple adverse effects of manufactured TFA, numerous agencies and governing bodies recommend limiting TFA in the diet and reducing TFA in the food supply. These initiatives and regulations, along with potential TFA alternatives, are presented herein.     

<Emphasis Type="Italic">Santalum </Emphasis><Emphasis Type="Italic">insulare</Emphasis> Acetylenic Fatty Acid Seed Oils: Comparison within the <Emphasis Type="Italic">Santalum</Emphasis> Genus

The sandalwood kernels of Santalum insulare (Santalaceae) collected in French Polynesia give seed oils containing significant amounts of ximenynic acid, E-11-octadecen-9-oic acid (64–86%). Fatty acid (FA) identifications were performed by gas chromatography/mass spectrometry (GC/MS) of FA methyl esters. Among the other main eight identified fatty acids, oleic acid was found at a 7–28% level. The content in stearolic acid, octadec-9-ynoic acid, was low (0.7–3.0%). An inverse relationship was demonstrated between ximenynic acid and oleic acid using 20 seed oils. Results obtained have been compared to other previously published data on species belonging to the Santalum genus, using multivariate statistical analysis. The relative FA S. insulare composition, rich in ximenynic acid is in the same order of those given for S. album or S. obtusifolium. The other compared species (S. acuminatum, S. lanceolatum, S. spicatum and S. murrayanum) are richer in oleic acid (40–59%) with some little differences in linolenic content.     

Comparison of Postprandial Oleic Acid, 9<Emphasis Type="Italic">c,</Emphasis>11<Emphasis Type="Italic">t</Emphasis> CLA and 10<Emphasis Type="Italic">t,</Emphasis>12<Emphasis Type="Italic">c</Emphasis> CLA Oxidation in Healthy Moderately Overweight Subjects

Few studies report the individual effect of 9c,11t- and 10t,12c-CLA on human energy metabolism. We compared the postprandial oxidative metabolism of 9c,11t- and 10t,12c-CLA and oleic acid (9c-18:1) in 22 healthy moderately overweight volunteers. After 24 weeks supplementation with 9c,11t-, 10t,12c-CLA or 9c-18:1 (3 g/day), subjects consumed a single oral bolus of the appropriate [1-¹³C]-labeled fatty acid. 8 h post-dose, cumulative oxidation was similar for 9c-18:1 and 10t,12c (P = 0.66), but significantly higher for 9c,11t (P < 0.01).     

(1<Emphasis Type="Italic">S</Emphasis>,3<Emphasis Type="Italic">R</Emphasis>)-<Emphasis Type="Italic">cis</Emphasis>-Chrysanthemyl Tiglate: Sex Pheromone of the Striped Mealybug, <Emphasis Type="Italic">Ferrisia virgata</Emphasis>

Derivatives of 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid (chrysanthemic acid) are classic natural pyrethroids discovered in pyrethrum plants and show insecticidal activity. Chrysanthemic acid, with two asymmetric carbons, has four possible stereoisomers, and most natural pyrethroids have the (1R,3R)-trans configuration. Interestingly, chrysanthemic acid–related structures are also found in insect sex pheromones; carboxylic esters of (1R,3R)-trans-(2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl)methanol (chrysanthemyl alcohol) have been reported from two mealybug species. In the present study, another ester of chrysanthemyl alcohol was discovered from the striped mealybug, Ferrisia virgata (Cockerell), as its pheromone. By means of gas chromatography–mass spectrometry, nuclear magnetic resonance spectrometry, and high-performance liquid chromatography analyses using a chiral stationary phase column and authentic standards, the pheromone was identified as (1S,3R)-(?)-cis-chrysanthemyl tiglate. The (1S,3R)-enantiomer strongly attracted adult males in a greenhouse trapping bioassay, whereas the other enantiomers showed only weak activity. The cis configuration of the chrysanthemic acid–related structure appears to be relatively scarce in nature, and this is the first example reported from arthropods.     

Lipid Rafts Promote <Emphasis Type="Italic">trans</Emphasis> Fatty Acid-Induced Inflammation in Human Umbilical Vein Endothelial Cells

The effects of two fatty acids, oleic acid (OLA) and elaidic acid (ELA) on normal human umbilical vein endothelial cells (HUVEC) and non-rafts HUVEC were investigated in this study. The expression levels of inflammatory cytokines (ICAM-1, VCAM-1 and IL-6) were analyzed. Western blot was used to analyze the expression levels of inflammation-related proteins (NF-κB, ERK1/2) and toll-like receptors 4 (TLR4). The results showed that the levels of nuclear translocation of NF-κB p65 and phosphorylated ERK1/2 were significantly decreased only in non-lipid rafts cells pretreated with trans fatty acid (TFA). The expression of TLR4 in the ELA-treated normal cells was higher than that in non-lipid rafts HUVEC. When the lipid rafts was destroyed by methyl-β-cyclodextrin, the levels of nuclear translocation of NF-κB p65, phosphorylated ERK1/2 and TLR4 were decreased significantly. Therefore, lipid rafts may be involved in TFA induced-inflammation in HUVEC through blocking the inflammatory signal pathway. Lipid rafts might be a platform for specific receptors such as TLR4 for TFA to activate the pro-inflammation on cell membranes.     

Fatty Acid Composition of Turkish <Emphasis Type="Italic">Rhododendron</Emphasis> Species

This study describes work aimed at the rapid evaluation of the fatty acid (FA) composition of Turkish Rhododendron species, particularly the leaves and the flowers of the toxic plants, R. ponticum and R. luteum. The FA profiles of the available parts of three other nonpoisonous Rhododendron species were also investigated. Subtotal extracts obtained (using n-hexane, chloroform and methanol) from total chloroform:methanol (1:1) extracts were analyzed and compared to each other. Palmitic acid was found to be the most abundant FA in almost all Rhododendron extracts, and the majority of leaf and flower extracts contained significant portions of C18 unsaturated FAs (18:1n-9, 18:2n-6, 18:3n-3). The n-hexane extracts of R. ponticum leaves and R. luteum flowers were unique, as they contained an unusual series of even-chain iso FAs (C16–C24). Especially the n-hexane extracts were found to comprise uncommon FAs with odd-numbered carbons (C13–C29). Overall, n-hexane proved to be the best solvent by representing the richest FA profile, whereas chloroform or methanol appeared less suitable for FA analyses. Appreciable intra-species variations in FA compositions among the leaves as well as other anatomical parts examined were observed. This study highlights the chemotaxonomical importance of the FAs for the genus Rhododendron.