Optimized Production of MLM Triacylglycerols Catalyzed by Immobilized Heterologous <Emphasis Type="Italic">Rhizopus oryzae</Emphasis> Lipase

Response surface methodology was used to model and optimize the acidolysis of virgin olive oil with caprylic (C8:0) or capric (C10:0) acids, aimed at the production of low caloric triacylglycerols (TAG) of MLM type, in solvent free media, catalyzed by the heterologous Rhizopus oryzae lipase (r-ROL) immobilized in Eupergit^® C. This lipase was produced in the methylotrophic yeast Pichia pastoris Mut^s phenotype (experiments with C10:0) or a Mut⁺ phenotype (experiments with C8:0), under different operational conditions. The r-ROL used in experiments with C10:0 presented a hydrolytic activity about 5 times of that presented by r-ROL used in acidolysis with C8:0. The experiments were carried out following a central composite rotatable design, as a function of the molar ratio (MR) medium chain fatty acid/TAG (1.6–4.4) and temperature (25–55 °C). Convex surfaces described by second order polynomials as a function of MR and temperature were well fitted to fatty acid incorporation values. After 24-h reaction, the predicted maximum incorporation of caprylic (15.5 mol%) or capric (33.3 mol%) acids in olive oil occurs at 37 and 35 °C, respectively, and at C8:0/TAG of 2.8:1 or C10:0/TAG of 3:1. These predicted optima were experimentally validated. Fermentation conditions used in r-ROL production highly affected hydrolytic activity and to a lesser extent interesterification activity.     

Evaluation of <Emphasis Type="Italic">Rhizopus oryzae</Emphasis> Lipase for the Determination of Regiodistribution in Triacylglycerols with Medium Chain Fatty Acids

The nutritional profile and rheological behaviors of lipids is both due to fatty acid composition and regiodistribution on external and internal positions of triacylglycerol. Actual methods for regiodistribution analysis having some restrictions, there is still a need for investigating a safe, simple and environmentally friendly method for the sn-2 position analysis that could especially be used for the analysis of fats containing medium and short chain fatty acids. The objective of this study was to evaluate the 1,3-selectivity and typoselectivity of Rhizopus oryzae lipase in the presence of short/medium chain fatty acids in partial hydrolysis conditions used for regiodistribution analysis. Structured triacylglycerols containing eight-carbon-chain length fatty acids in the sn -2 position were chemically synthesized using DCC/DMAP coupling agent and purification steps by flash-chromatography. The final product showed very high purity and was used as the substrate for 1,3-selectivity evaluation. Typoselectivity was assessed by investigating partial hydrolysis of equimolar blends of homogeneous TAG. This study confirmed the 1,3-selectivity of Rhizopus oryzae lipase in the hydrolysis conditions used, and revealed that this lipase was less influenced by fatty acids chain length than pancreatic lipase. Considering this, Rhizopus oryzae lipase appeared to be a good candidate for regiodistribution analysis of fats containing medium and short chain fatty acids.     

(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.     

<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.     

Phospholipid Composition of <Emphasis Type="Italic">Jatropha curcus</Emphasis> Seed Lipids

Jatropha curcus L. oil has emerged as one of the most important raw materials for biodiesel production. However, no detailed study has been reported on characterizing the lipid constituents of jatropha oil. The present study revealed that the total oil content of jatropha seeds was 32% with a composition of 97.6% neutral lipids, 0.95% glycolipids and 1.45% phospholipids. The fatty acid composition of total lipids, neutral lipids, phospholipids and glycolipids was also determined and found to contain oleic acid (18:1) and linoleic acids (18:2) as major fatty acids. The phospholipids fraction was further characterized and quantified and found to contain phosphatidyl choline (PC) 60.5%, phosphatidyl inositol (PI) 24% and phosphatidyl ethanolamine (PE) 15.5%. The fatty acid composition and the positional distribution of the fatty acids of individual phospholipids were also reported.     

Synthesis of <Emphasis Type="Italic">p</Emphasis><Emphasis Type="Bold">-</Emphasis> and <Emphasis Type="Italic">n</Emphasis>-type Gels Doped with Ionic Charge Carriers

In this study, we synthesized the new kinds of semiconducting polymeric gels having negative (n-type) and positive (p-type) counter ions as charge carriers. The polyacrylamide gel was doped with pyranine (8-hydroxypyrene-1,3,6-trisulfonic acid, trisodium salt), having \textSO₃ ^- {\text{SO}}_{3}^{ - } ions as side groups and Na⁺ as counter ions, so-called p-type semiconducting gel. The doping process was performed during the polymerization where the pyranine binds to the polymer strands over OH group chemically via radical addition. In a similar way, N-isopropylacrylamide (NIPA) gel was doped with methacrylamidopropyltrimethyl ammonium chloride (MAPTAC), having Cl⁻ as counter ions, so-called n-type semiconducting gel. Here MAPTAC was embedded by copolymerization within the polymer network (NIPA). These semiconducting gels can show different electrical properties by changing the concentration of the doping agents, swelling ratio etc. We have shown that the pn junction, formed by combining p-type and n-type gels together in close contact, rectifies the current similar to the conventional Si and Ge diodes.     

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).     

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.     

Production of rhamnolipids-producing enzymes of <Emphasis Type="Italic">Pseudomonas</Emphasis> in <Emphasis Type="Italic">E. coli</Emphasis> and structural characterization

Rhamnolipids are a class of biosurfactants that have a great potential to be used in industries. Five proteins/enzymes, namely RhlA, RhlB, RhlC, RhlG and RhlI, are critical for the production of rhamnolipids in Pseudomonas aeruginosa. Four of the 5 proteins except RhlC were successfully over-expressed in E. coli and three of them (RhlA, RhlB and RhlI) were purified and obtained in milligram quantities. The purified proteins were shown to be folded in solution. Homology models were built for RhlA, RhlB and RhlI. These results lay a basis for further structural and functional characterization of these proteins in vitro to favor the construction of super strains for rhamnolipids production.

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Biosynthesis of (3<Emphasis Type="Italic">Z</Emphasis>,6<Emphasis Type="Italic">Z</Emphasis>,9<Emphasis Type="Italic">Z</Emphasis>)-3,6,9-Octadecatriene: The Main Component of the Pheromone Blend of <Emphasis Type="Italic">Erannis bajaria</Emphasis>

The hydrocarbons (3Z,6Z,9Z)-3,6,9-octadecatriene (3Z,6Z,9Z-18:H) and (3Z,6Z,9Z)-3,6,9-nonadecatriene (3Z,6Z,9Z-19:H) constitute the pheromone of the winter moth, Erannis bajaria. These compounds belong to a large group of lepidopteran pheromones which consist of unsaturated hydrocarbons and their corresponding oxygenated derivatives. The biosynthesis of such hydrocarbons with an odd number of carbons in the chain is well understood. In contrast, knowledge about the biosynthesis of even numbered derivatives is lacking. We investigated the biosynthesis of 3Z,6Z,9Z-18:H by applying deuterium-labeled precursors to females of E. bajaria followed by gas chromatography–mass spectrometry analysis of extracts of the pheromone gland. A mixture of deuterium-labeled [17,17,18,18-²H₄]-3Z,6Z,9Z-18:H and the unlabeled 3Z,6Z,9Z-18:H was obtained after topical application and injection of (10Z,13Z,16Z)-[2,2,3,3-²H₄]-10,13,16-nonadecatrienoic acid ([2,2,3,3-²H₄]-10Z,13Z,16Z-19:acid) or (11Z,14Z,17Z)-[3,3,4,4-²H₄]-11,14,17-icosatrienoic acid ([3,3,4,4-²H₄]-11Z,14Z,17Z-20:acid). These results are consistent with a biosynthetic pathway that starts with α-linolenic acid (9Z,12Z,15Z-18:acid). Chain elongation leads to 11Z,14Z,17Z-20:acid, which is shortened by α-oxidation as the key step to yield 10Z,13Z,16Z-19:acid. This acid can be finally reduced to an aldehyde and decarbonylated or decarboxylated to furnish the pheromone component 3Z,6Z,9Z-18:H. A similar transformation of 11Z,14Z,17Z-20:acid yields the second pheromone component, 3Z,6Z,9Z-19:H.     

Roquefortine/Oxaline Biosynthesis Pathway Metabolites in <Emphasis Type="Italic">Penicillium</Emphasis> ser. <Emphasis Type="Italic">Corymbifera</Emphasis>: <Emphasis Type="Italic">In Planta</Emphasis> Production and Implications for Competitive Fitness

Three strains of each of the seven taxa comprising the Penicillium series Corymbifera were surveyed by direct injection mass spectrometry (MS) and liquid chromatography–MS for the production of terrestric acid and roquefortine/oxaline biosynthesis pathway metabolites when cultured upon macerated tissue agars prepared from Allium cepa, Zingiber officinale, and Tulipa gesneriana, and on the defined medium Czapek yeast autolysate agar (CYA). A novel solid-phase extraction methodology was applied for the rapid purification of roquefortine metabolites from a complex matrix. Penicillium hordei and P. venetum produced roquefortine D and C, whereas P. hirsutum produced roquefortine D and C and glandicolines A and B. P. albocoremium, P. allii, and P. radicicola carried the pathway through to meleagrin, producing roquefortine D and C, glandicolines A and B, and meleagrin. P. tulipae produced all previously mentioned metabolites yet carried the pathway through to an end product recognized as epi-neoxaline, prompting the proposal of a roquefortine/epi-neoxaline biogenesis pathway. Terrestric acid production was stimulated by all Corymbifera strains on plant-derived media compared to CYA controls. In planta, production of terrestric acid, roquefortine C, glandicolines A and B, meleagrin, epi-neoxaline, and several other species-related secondary metabolites were confirmed from A. cepa bulbs infected with Corymbifera strains. The deposition of roquefortine/oxaline pathway metabolites as an extracellular nitrogen reserve for uptake and metabolism into growing mycelia and the synergistic role of terrestric acid and other Corymbifera secondary metabolites in enhancing the competitive fitness of Corymbifera species in planta are proposed.     

Laboratory Evaluation of <Emphasis Type="Italic">Artemisia annua</Emphasis> L. Extract and Artemisinin Activity against <Emphasis Type="Italic">Epilachna paenulata</Emphasis> and <Emphasis Type="Italic">Spodoptera eridania</Emphasis>

Ethanolic extract of aerial parts of Artemisia annua L. and artemisinin were evaluated as anti-insect products. In a feeding deterrence assay on Epilachna paenulata Germ (Coleoptera: Coccinellidae) larvae, complete feeding rejection was observed at an extract concentration of 1.5 mg/cm² on pumpkin leaf tissue. The same concentration produced a feeding inhibition of 87% in Spodoptera eridania (Cramer) (Lepidoptera: Noctuidae). In a no-choice assay, both species ate less and gained less weight when fed on leaves treated with the extract. Complete mortality in E. paenulata and 50% mortality in S. eridania were observed with extract at 1.5 mg/cm². Artemisinin exhibited a moderate antifeedant effect on E. paenulata and S. eridania at 0.03–0.375 mg/cm². However, a strong effect on survival and body weight was observed when E. paenulata larvae were forced to feed on leaves treated at 0.03 and 0.075 mg/cm². Artemisia annua ethanolic extract of aerial parts at 1.5 mg/cm² showed no phytotoxic effect on pumpkin seedlings.     

Ammonia Released by <Emphasis Type="Italic">Streptomyces aburaviensis</Emphasis> Induces Droplet Formation in <Emphasis Type="Italic">Streptomyces violaceoruber</Emphasis>

Streptomyces violaceoruber grown in co-culture with Streptomyces aburaviensis produces an about 17-fold higher volume of droplets on its aerial mycelium than in single-culture. Physical separation of the Streptomyces strains by either a plastic barrier or by a dialysis membrane, which allowed communication only by the exchange of volatile compounds or diffusible compounds in the medium, respectively, still resulted in enhanced droplet formation. The application of molecular sieves to bioassays resulted in the attenuation of the droplet-inducing effect of S. aburaviensis indicating the absorption of the compound. ¹H-NMR analysis of molecular-sieve extracts and the selective indophenol-blue reaction revealed that the volatile droplet-inducing compound is ammonia. The external supply of ammonia in biologically relevant concentrations of ≥8 mM enhanced droplet formation in S. violaceoruber in a similar way to S. aburaviensis. Ammonia appears to trigger droplet production in many Streptomyces strains because four out of six Streptomyces strains exposed to ammonia exhibited induced droplet production.     

Solvent-gradient SMB to separate <Emphasis Type="Italic">o</Emphasis>-xylene and <Emphasis Type="Italic">p</Emphasis>-xylene

In batch chromatography, solvent-gradient operations (SG) produce significant improvement in terms of the enrichment of products and the separation time and the solvent consumption as compared with isocratic operations. This work studied solvent-gradient operation in reversed-phase simulated moving bed unit to separate ortho-xylene and para-xylene. In a solvent-gradient mode, different mobile phase compositions lead to a different retention behavior of solutes, i.e., different adsorption isotherms. Frontal analysis experiments for ortho-xylene and para-xylene were carried out with a reversed-phase column to measure adsorption parameters at several different mobile phase compositions, such as 45%, 50%, 60%, 75% and 90% acetonitrile. Therefore, the parameters in the retention model for solvent-gradient operation in the case of reversed-phase chromatography were estimated and applied to the design of an SMB system. A modified design method for solvent-gradient simulated moving bed chromatography (SG-SMB) was proposed. The robust operating conditions were obtained within the separation region on (φ _R , φ _E ) plane (φ _R and φ _E are the volumetric content of organic modifier in the raffinate and the extract streams, respectively). The performance results of isocratic and solvent-gradient SMB were compared. A partial-discard strategy and increasing of the solvent gradient level were also applied to improve the performance of the SG-SMB.     

Effects of Root Isoquinoline Alkaloids from <Emphasis Type="Italic">Hydrastis canadensis</Emphasis> on <Emphasis Type="Italic">Fusarium oxysporum</Emphasis> Isolated from <Emphasis Type="Italic">Hydrastis</Emphasis> Root Tissue

Goldenseal (Hydrastis canadensis L.) is a popular medicinal plant distributed widely in North America. The rhizome, rootlets, and root hairs produce medicinally active alkaloids. Berberine, one of the Hydrastis alkaloids, has shown antifungal activity. The influence of a combination of the major Hydrastis alkaloids on the plant rhizosphere fungal ecology has not been investigated. A bioassay was developed to study the effect of goldenseal isoquinoline alkaloids on three Fusarium isolates, including the two species isolated from Hydrastis rhizosphere. The findings suggest that the Hydrastis root extract influences macroconidia germination, but that only the combined alkaloids—berberine, canadine, and hydrastine—appear to synergistically stimulate production of the mycotoxin zearalenone in the Fusarium oxysporum isolate. The Hydrastis root rhizosphere effect provided a selective advantage to the Fusarium isolates closely associated with the root tissue in comparison with the Fusarium isolate that had never been exposed to Hydrastis.     

Geographic Variation in Alkaloid Production in <Emphasis Type="Italic">Conium maculatum</Emphasis> Populations Experiencing Differential Herbivory by <Emphasis Type="Italic">Agonopterix alstroemeriana</Emphasis>

Conium maculatum, a Eurasian weed naturalized in North America, contains high concentrations of piperidine alkaloids that act as chemical defenses against herbivores. C. maculatum was largely free from herbivory in the United States, until approximately 30 yr ago, when it was reassociated via accidental introduction with a monophagous European herbivore, the oecophorid caterpillar Agonopterix alstroemeriana. At present, A. alstroemeriana is found in a continuum of reassociation time and intensities with C. maculatum across the continent; in the Pacific Northwest, A. alstroemeriana can cause severe damage, resulting in some cases in complete defoliation. Studies in biological control and invasion biology have yet to determine whether plants reassociated with a significant herbivore from the area of indigeneity increase their chemical defense investment in areas of introduction. In this study, we compared three locations in the United States (New York, Washington, and Illinois) where C. maculatum experiences different levels of herbivory by A. alstroemeriana to determine the association between the intensity of the interaction, as measured by damage, and chemical defense production. Total alkaloid production in C. maculatum was positively correlated with A. alstroemeriana herbivory levels: plants from New York and Washington, with higher herbivory levels, invested two and four times more N to alkaloid synthesis than did plants from Illinois. Individual plants with lower concentrations of alkaloids from a single location in Illinois experienced more damage by A. alstroemeriana, indicative of a preference on the part of the insect for plants with less chemical defense. These results suggest that A. alstroemeriana may act either as a selective agent or inducing agent for C. maculatum and increase its toxicity in its introduced range.     

Epicuticle Lipids Mediate Mate Recognition in <Emphasis Type="Italic">Triatoma infestans</Emphasis>

Epicuticular lipids are contact cues in intraspecific chemical communication in insects, both for aggregation and sexual behavior. Triatomine bugs are vectors of the parasite Trypanosoma cruzi, the cause of Chagas disease. In Triatoma infestans, the major epicuticular lipids are hydrocarbons, fatty alcohols, and free and esterified fatty acids. Previously, we found that epicuticular lipid extracts, or selected fatty acid components, trigger aggregation and arrestment behavior in this bug. Using headspace solid phase microextraction, we found no sexual dimorphism in epicuticular hydrocarbons, but found female-specific fatty alcohols (eicosanol and docosanol). The role of epicuticular lipids in T. infestans copulation behavior was tested by observing male responses to live or various treatments of freeze-killed females. We report that hexane-soluble contact cues on females trigger copulation by males. Freeze-killed intact females were attractive to males, but no response was observed when males were exposed to hexane-washed females. Responses were partially recovered when epicuticular extract was applied to the dorsal surface of dead, hexane-washed females. One female equivalent of docosanol, evoked similar responses.     

<Emphasis Type="Italic">N</Emphasis>-Acylated Bacteriohopanehexol-Mannosamides from the Thermophilic Bacterium <Emphasis Type="Italic">Alicyclobacillus acidoterrestris</Emphasis>

Identification of molecular species of various N-acylated bacteriohopanehexol-mannosamides from the thermophilic bacterium Alicyclobacillus acidoterrestris by semipreparative HPLC and by RP-HPLC with ESI is described. We used triple-quadrupole type mass spectrometer, ¹H and ¹³C NMR for analyzing this complex lipid. CD spectra of two compounds (model compound—7-deoxy-d-glycero-d-allo-heptitol obtained by stereospecific synthesis, and an isolated derivative of hopane) were also measured and the absolute configuration of both compounds was determined. On the basis of all the above methods, we identified the full structure of a new class of bacteriohopanes, represented by various N-acylated bacteriohopanehexol-mannosamides.     

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.     

Yellow-Cedar, <Emphasis Type="Italic">Callitropsis</Emphasis> (<Emphasis Type="Italic">Chamaecyparis</Emphasis>) <Emphasis Type="Italic">nootkatensis</Emphasis>, Secondary Metabolites,Biological Activities,and Chemical Ecology

Yellow-cedar, Callitropsis nootkatensis, is prevalent in coastal forests of southeast Alaska, western Canada, and inland forests along the Cascades to northern California, USA. These trees have few microbial or animal pests, attributable in part to the distinct groups of biologically active secondary metabolites their tissues store for chemical defense. Here we summarize the new yellow-cedar compounds identified and their biological activities, plus new or expanded activities for tissues, extracts, essential oils and previously known compounds since the last review more than 40 years ago. Monoterpene hydrocarbons are the most abundant compounds in foliage, while heartwood contains substantial quantities of oxygenated monoterpenes and oxygenated sesquiterpenes, with one or more tropolones. Diterpenes occur in foliage and bark, whereas condensed tannins have been isolated from inner bark. Biological activities expressed by one or more compounds in these groups include fungicide, bactericide, sporicide, acaricide, insecticide, general cytotoxicity, antioxidant and human anticancer. The diversity of organisms impacted by whole tissues, essential oils, extracts, or individual compounds now encompasses ticks, fleas, termites, ants, mosquitoes, bacteria, a water mold, fungi and browsing animals. Nootkatone, is a heartwood component with sufficient activity against arthropods to warrant research focused toward potential development as a commercial repellent and biopesticide for ticks, mosquitoes and possibly other arthropods that vector human and animal pathogens.