Analysis of whole cellular fatty acids and anastomosis relationships of binucleate Rhizoctonia spp. associated with Ceratobasidium cornigerum

Previous research has demonstrated that whole cellular fatty acids analysis is a useful tool for identifying and establishing taxonomic relationships between anastomosis groups (AGs) and related Rhizoctonia isolates. In this experiment, the composition of fatty acid of 28 isolates of teleomorph genus Ceratobasidium cornigerum, consisting of binucleate Rhizoctonia, AG-A, AG-B(o), AG-C, AG-P, and AG-Q, was evaluated using gas chromatography. Eleven fatty acids identified, i.e., myristic, pentadecanoic, palmitic, 2-hydroxypalmitic, palmitoleic, heptadecanoic, 9-heptadecenoic, stearic, oleic, linoleic, and linolenic acids, were present in isolates of AG-A, AG-B(o), AG-C, AG-P, and AG-Q. The major fatty acids, palmitic, oleic, and linoleic acids, were common in all isolates, constituting 87.1% to 94.7% of the whole cellular fatty acids identified. Isolates within the same AG were closely clustered, whereas isolates from different AGs were clearly and distinctly clustered based on average linkage cluster analysis of whole cellular fatty acids. Principal-component analysis generated from all fatty acids also confirmed the divergent separation of the 5 AGs of binucleate Rhizoctonia.     

Chemotaxonomic Screening of Seed Oils from the Family Saxifragaceae and Comparison with Data on Seed Oils from Grossulariaceae Obtained from Literature

Seeds of 25 members of the family Saxifragaceae, 1 × Astilbe, 1 × Darmera, 1 × Leptarrhena, 1 × Tellima, 3 × Mitella, and 18 × Saxifraga were investigated regarding oil content, as well as composition and content of fatty acids and vitamin E active compounds. The results were compared with results obtained from literature for members of the genus Ribes belonging to the closely related family Grossulariaceae to find chemometric differences between the different genera and between members of the family Saxifragaceae and Grossulariaceae, respectively. Members of the family Saxifragaceae are dominated by high amounts of linoleic and α‐linolenic acid which together account for about 80% of the total fatty acids. While α‐linolenic acid is characteristic for members of the genus Saxifraga, in other genera, linoleic acid is predominant. In comparison to members of the family Saxifragaceae members of the family Grossulariaceae also contain γ‐linolenic acid and stearidonic acid which allow a significant differentiation between both families. By principle component analysis, members of both families were divided into three distinct groups, i) species with a high content of α‐linolenic acid (genus Saxifraga), ii) species with high amounts of γ‐linolenic acid and stearidonic acid (genus Ribes), and iii) species with higher amounts of linoleic acid (other members of the family Saxifragaceae). The composition of the vitamin E active compounds was characterized by a high content of γ‐tocopherol in most members of the family Saxifragaceae, but no chemotaxonomic relevance.     

Is the Profile of Fatty Acids,Tocopherols, and Amino Acids Suitable to Differentiate Pinus armandii Suspicious to Be Responsible for the Pine Nut Syndrome from Other Pinus Species?

Pinus armandii is suspicious to be responsible for the Pine Nut Syndrome, a long lasting bitter and metallic taste after the consumption of pine nuts. To find chemical characteristic features for the differentiation of P. armandii from other Pinus species, 41 seed samples of the genus Pinus from 22 plant species were investigated regarding the content and the composition of fatty acids, tocopherols, and amino acids. The predominant fatty acids in the seed oils were linoleic acid (35.2 – 58.2 g/100 g), oleic acid (14.6 – 48.5 g/100 g), and pinolenic acid (0.2 – 22.4 g/100 g), while the vitamin‐E‐active compounds were dominated by γ‐tocopherol. The amino acid composition was mainly characterized by arginine and glutamic acid with amounts between 0.9 and 8.9 g/100 g as well as 2.1 g/100 g and 8.3 g/100 mg. On the basis of this investigation, a Principle Component Analysis has been used to identify the most important components for the differentiation of P. armandii from other Pinus species. Using the data for glutamic acid, 20:2Δ^5,11, 18:3Δ^5,9,12, 18:1Δ⁹, and oil content, a classification of the 41 samples into four different groups by cluster analysis was possible, but the characteristic features of P. armandii were too close to some other members of the genus Pinus, making a clear differentiation of this species difficult. Nevertheless, the investigation showed the similarities of different members of the genus Pinus with regard to fatty acids, vitamin‐E‐active compounds, and amino acids.     

Fatty Acid Composition of Baobab Seed and Its Relationship with the Genus Adansonia Taxonomy

Baobab seed oil contains specific fatty acids. Most of the studies on baobab fatty acids have been carried out singly and in isolation from each other, making it difficult to compare results through different species. The objective of the present study is to establish the seed fatty acid composition of each Adansonia species in order to evaluate and understand the relationships between the oil chemical compositions, the baobabs’ taxonomy and, the ecological and geographical origin of each seed lot. The seed oils have been analysed using gas chromatography (GC). The oils of all baobab species contain three major fatty acids: palmitic, oleic and linoleic acids. They also contain specific fatty acids such as cyclopropenic and cyclopropanic acids, which are characteristic of the Malvaceae family seed oils. It was possible to distinguish three sections through principal components analysis using the eleven fatty acids identified by GC. The Adansonia section contains high rates of oleic acid (± 35%), the Brevitubae section is rich in palmitic acid (± 42%) and the Longitubae section contains high levels of dihydrosterulic acid (± 5%). The oil fatty acid composition, however, does not enable a definitive characterization of profiles according to species. The fatty acid composition is not significantly influenced by the geographical, soil and climate conditions of the collection sites.     

Fatty acid,lipid and cyanein production byPenicillium cyaneum

Summary The lipid constituents ofPenicillium cyaneum during the production phase of the macrolide antibiotic cyanein have been studied. Triglycerides were the main components of the neutral lipids and phosphatidyl ethanolamine was the major constituent of the polar lipids. The fatty acid pattern showed a similarity to those of several other fungi. No unusual fatty acids as possible precursors of the cyanein molecule were found. Palmitic, stearic, oleic and linoleic acids were the major fatty acids present. The course of linoleic acid production was very similar to that of cyanein, while the relative percentages of the other major fatty acids showed only slight variations during the cyanein production phase.     

Roots volatiles and fatty acids of coriander (<Emphasis Type="Italic">Coriandrum sativum</Emphasis> L.) grown in saline medium

An hydroponic culture was conducted to investigate the effect of saline stress on the essential oil and fatty acid composition of Tunisian coriander (Coriandrum sativum L.) roots. Ten days old coriander seedlings were treated during 3 weeks with different NaCl concentrations (0, 25, 50 and 75 mM). Roots volatile components and fatty acids were analyzed. The essential oil yield was 0.06% in the control, on the basis of dry matter weight, and did not changed at low concentration (25 mM), while it increased significantly with increasing NaCl concentrations to reach 0.12 and 0.21% at 50 and 75 mM NaCl, respectively. The major volatile component was (E)-2-dodecenal with 52% of total essential oil constituents, followed by decanal, dodecanal, (E)-2-tridecenal and (E)-2-dodecenal. Further, the amount of these compounds was affected differently by the NaCl level. Total fatty acid amount of coriander roots increased significantly only with 50 and 75 mM NaCl. Three major fatty acids: linoleic (43%), oleic (25.5%) and palmitic (21.6%) were identified. Linoleic acid amount remains unchanged at 25 mM, while it increased with raising NaCl concentrations. However, oleic acid amount decreased only at 25 mM and no effect was observed at 50 and 75 mM. Fatty acid percentages were differently affected by salt. The oleic/linoleic ratio was reduced with raising NaCl concentrations.     

Kinetic profile of the cellular lipid composition in an oleaginous Yarrowia lipolytica capable of producing a cocoa-butter substitute from industrial fats

Cell growth, lipid accumulation and cellular lipid composition of Yarrowia lipolytica growing on mixtures of industrial fats containing stearic, oleic, linoleic and palmitic acid have been studied. During growth, the strain incorporated oleic and linoleic acids more rapidly than the saturated fatty acids. Relatively high lipid accumulation (up to 0.44 g of lipids per g of dry matter) was observed when stearic acid was included in the culture medium. In contrast, substrates rich in oleic acid did not favor cellular lipid accumulation. The accumulated lipids, mainly composed of triacylglycerols (45-55% w/w), demonstrated a different total fatty acid composition compared with that of the substrate; in all cases, the microorganism showed the unusual capacity to increase its cellular stearic acid level, even if this fatty acid was not found in high concentrations in the substrate. This permitted the synthesis of interesting lipid profiles with high percentages of stearic acid and non-negligible percentages of palmitic and oleic acid, with a composition resembling that of cocoa-butter.     

Effect of Macrophomina phaseolina Infection on the Physico-Chemical Components of Groundnut Seed

Various aspects of groundnut seed deterioration due to M. phaseolina infection were studied. Fungal infection caused both quantitative and qualitative damage to the seed. It resulted in characteristic discoloration of pod and kernel. There was marked reduction in the pod and kernel yield, shelling percentage and oil content. The oil extracted from healthy kernels was barium yellow, whereas, oil from diseased kernels was amber yellow in color. The diseased kernels contained lesser amounts ofstearic and behenic acids but higher quantities of palmitic, oleic, linoleic and arachidic acids. Four fatty acids, namely, lauric, myristic, palmitoleic and eicosenoic acids were absent in diseased kernels.     

Myrtus communis berry color morphs: a comparative analysis of essential oils, fatty acids, phenolic compounds, and antioxidant activities

Extracts of mature dark blue and white berries from two Tunisian Myrtus communis morphs growing at the same site were assessed for their essential‐oil and fatty‐acid compositions, phenolic contents, and antioxidant activities. The GC and GC/MS analyses of the essential oils allowed the identification of 33 constituents. The oils from the dark blue fruits showed high percentages of α‐pinene (11.1%), linalool (11.6%), α‐terpineol (15.7%), methyl eugenol (6.2%), and geraniol (3.7%). Myrtenyl acetate (20.3%) was found to be the major compound in the oils from white berries. GC Analysis of the pericarp and seed fatty acids showed that the polyunsaturated fatty acids constituted the major fraction (54.3–78.1%). The highest percentages of linoleic acid (78.0%) and oleic acid (20.0%) were observed in the seeds and the pericarps of the white fruits, respectively. The total phenol, flavonoid, and flavonol contents and the concentration of the eight anthocyanins, identified by HPLC analysis, were significantly higher in the dark blue fruits. All extracts showed a substantial antioxidant activity, assessed by the free radical‐scavenging activity and the ferric reducing power, with the dark blue fruit extracts being more effective.     

Analysis of the total oil and fatty acid composition of seeds of some Boraginaceae taxa from Turkey

Mature seed samples of twenty-four Boraginaceae taxa collected from their natural habitats in Turkey were analysed by GC for total oil content and fatty acid composition. The range of total fat in the taxa varied between 7.0 and 35.7%. The amounts of palmitic (16:0) and stearic (18:0) acids determined were 5.65–17.81 and 1.49–5.08%, respectively. Mono-unsaturated fatty acids were in the range 8.83–55.32% for oleic, 0.22–6.21% for eicosenoic, 0.04–8.94% for erucic, and 0.08–2.71% for nervonic acid. Poly-unsaturated fatty acids were between 1.41 and 68.44% for linoleic, 0.12 and 43.0% for α-linolenic, 0.04 and 24.03% for γ-linolenic, and 0.02 and 14.59% for stearidonic acid. Total saturated (9.3–23.7%), mono-unsaturated (10.59–73.28%), and poly-unsaturated fatty acids (13.91–68.78%) varied substantially. Total unsaturated fatty acids ranged from 70.12 to 90.29%. There were significant differences between fatty acid profiles at taxa (P < 0.05) at genera levels, based on mono-unsaturated and poly-unsaturated fatty acid concentrations (P < 0.05). Segregation at the generic level by principle-component analysis was accomplished based on nine major fatty acids. The fatty acid patterns, their relative proportions, and quantities of unusual fatty acids as additional biochemical markers seem to be useful in the taxonomy of Boraginaceae at generic and infrageneric levels. All taxa are, in general, rich in linoleic and α-linolenic acids as essential fatty acids for dietary reference intakes. Seed oils of Symphytum, Anchusa, and Trachystemon orientalis for γ-linolenic acid and Echium for both γ-linolenic and stearidonic acid may be evaluated as alternative wild sources.     

Responses to oleic,linoleic and α-linolenic acids in high-carbohydrate,high-fat diet-induced metabolic syndrome in rats

We investigated the changes in adiposity, cardiovascular and liver structure and function, and tissue fatty acid compositions in response to oleic acid-rich macadamia oil, linoleic acid-rich safflower oil and α-linolenic acid-rich flaxseed oil (C18 unsaturated fatty acids) in rats fed either a diet high in simple sugars and mainly saturated fats or a diet high in polysaccharides (cornstarch) and low in fat. The fatty acids induced lipid redistribution away from the abdomen, more pronounced with increasing unsaturation; only oleic acid increased whole-body adiposity. Oleic acid decreased plasma total cholesterol without changing triglycerides and nonesterified fatty acids, whereas linoleic and α-linolenic acids decreased plasma triglycerides and nonesterified fatty acids but not cholesterol. α-Linolenic acid improved left ventricular structure and function, diastolic stiffness and systolic blood pressure. Neither oleic nor linoleic acid changed the left ventricular remodeling induced by high-carbohydrate, high-fat diet, but both induced dilation of the left ventricle and functional deterioration in low fat-diet-fed rats. α-Linolenic acid improved glucose tolerance, while oleic and linoleic acids increased basal plasma glucose concentrations. Oleic and α-linolenic acids, but not linoleic acid, normalized systolic blood pressure. Only oleic acid reduced plasma markers of liver damage. The C18 unsaturated fatty acids reduced trans fatty acids in the heart, liver and skeletal muscle with lowered stearoyl-CoA desaturase-1 activity index; linoleic and α-linolenic acids increased accumulation of their C22 elongated products. These results demonstrate different physiological and biochemical responses to primary C18 unsaturated fatty acids in a rat model of human metabolic syndrome.     

Evaluation of fatty acid composition among selected amaranth grains grown in two consecutive years

The oil of amaranth grain (Amaranthus spp.) is a rich source of poly-unsaturated fatty acids. In this study, we tested 10 amaranth samples representing two species (Amaranthus cruentus and Amaranthus hypochondriacus) in two consecutive years (2010, 2011). Grain oils were analysed by gas chromatography for their fatty acids profile. In 2010, oil content ranged from 6.4–8.2% for A. cruentus and 6.3–7.9% for A. hypochondriacus. In 2011, the level was 7.1–8.2% and 6.6–8.7% for A. cruentus and A. hypochondriacus, respectively. Linoleic, palmitic, and oleic acids were dominant fatty acids in all of the oil samples. The essential linoleic acid level was 33.3–38.7% (A. cruentus) and 31.7–47.5% (A. hypochondriacus) in 2010 and 34.6–39.9% (A. cruentus) and 34–44.5% (A. hypochondriacus) in 2011. The minority fatty acids, i.e. stearic, α-linolenic, and arachidic acids were also observed. Eicosenoic and behenic acids were present in the grain in trace amounts. Statistical evaluation showed a significant effect of year and species of amaranth on the levels of certain fatty acids. There was a strong positive correlation between oil content and oleic acid, and a negative correlation between oleic acid and either of the other two fatty acids, linoleic and α-linolenic ones.     

Fat Metabolism in the West 4frican Oil Palm (Elaeis guineensis): PART III. FATTY ACID FORMATION IN THE MATURING EXOCARP

Accumulation of fat in the oil-palm exocarp is delayed untilthe kernel has almost finished developing (at about 19 weeksafter pollination) and is then extremely rapid, a major partof the lipid being formed within a single week. Throughout theperiod studied (8 to 20 weeks after pollination) the fat-freedry weight remains approximately constant and carbohydrates(starch, sucrose, and reducing sugars) do not accumulate eitherprior to or during fat formation. Immature exocarps contain only a low proportion of fat (about1 per cent, of the dry weight) and this ‘protoplasmic’lipid has a different fatty acid composition (major componentspalmitic and linoleic acids accompanied by smaller amounts ofstearic and linolenic acids) from the later-formed oil (majorcomponents palmitic and oleic acids with smaller amounts ofstearic and linoleic acids). There is no evidence of fatty acidinterconversions at any stage of development.     

Fatty acids reduce the tensile strength of fungal hyphae during cephalosporin C production in Acremonium chrysogenum

Fragmentation rate constants, which can be used to estimate the tensile strength of fungal hyphae, were used to elucidate relationships between morphological changes and addition of fatty acids during cephalosporin C production in Acremonium chrysogenum M35. The number of arthrospores increased gradually during fermentation, and, in particular, was higher in the presence of rice oil, oleic acid or linoleic acid than in their absence. Because supplementation of rice oil or fatty acids increased cephalosporin C, we concluded that differentiation to arthrospores is related to cephalosporin C production. To estimate the relative tensile strengths of fungal hyphae, fragmentation rate constants (k _frag) were measured. When rice oil, oleic acid, or linoleic acid were added into medium, fragmentation rate constants were higher than for the control, and hyphal tensile strengths reduced. The relative tensile strength of fungal hyphae, however was not constant presumably due to differences in physiological state.     

Identification and characterization of Δ12 and Δ12/Δ15 bifunctional fatty acid desaturases in the oleaginous yeast Lipomyces starkeyi

Fatty acid desaturases play vital roles in the synthesis of unsaturated fatty acids. In this study, Δ12 and Δ12/Δ15 fatty acid desaturases of the oleaginous yeast Lipomyces starkeyi, termed LsFad2 and LsFad3, respectively, were identified and characterized. Saccharomyces cerevisiae expressing LsFAD2 converted oleic acid (C18:1) to linoleic acid (C18:2), while a strain of LsFAD3-expressing S. cerevisiae converted oleic acid to linoleic acid, and linoleic acid to α-linolenic acid (C18:3), indicating that LsFad2 and LsFad3 were Δ12 and bifunctional Δ12/Δ15 fatty acid desaturases, respectively. The overexpression of LsFAD2 in L. starkeyi caused an accumulation of linoleic acid and a reduction in oleic acid levels. In contrast, overexpression of LsFAD3 induced the production of α-linolenic acid. Deletion of LsFAD2 and LsFAD3 induced the accumulation of oleic acid and linoleic acid, respectively. Our findings are significant for the commercial production of polyunsaturated fatty acids, such as ω-3 polyunsaturated fatty acids, in L. starkeyi.

     

The Occurrence of Renin Inhibitor in Rice: Isolation,Identification, and Structure-Function Relationship

We found renin inhibitory activity in rice. The physico-chemical data on the isolated inhibitors were identical to those of oleic acid and linoleic acid. Oleic acid and linoleic acid competitively inhibited renin activity, with K_i values of 15.8 and 19.8 μM respectively. Other unsaturated free fatty acids also inhibited renin activity, but saturated fatty acids had no effect on it.     

Oviposition deterrents from the egg masses of the adzuki bean borer, Ostrinia scapulalis and Asian corn borer, O. furnacalis

Bioassays using gravid females of the adzuki bean borer, Ostrinia scapulalis (Walker), and the Asian corn borer, O. furnacalis (Guenée) (Lepidoptera: Crambidae), showed that the presence of an egg mass of a conspecific deters oviposition. Volatile chemicals emanating from the egg mass were responsible for the deterrence, and these deterrents could be extracted from the egg mass with hexane. When fractionated using a Sep‐Pak® Plus NH₂ cartridge, the deterrents were eluted with a 98 : 2 mixture of diethyl ether and acetic acid (polar lipid fraction). The polar lipid fraction contained free fatty acids with 14–20 carbons, and palmitic acid, palmitoleic acid, and oleic acid were predominant. A blend of all identified fatty acids, a blend of six major fatty acids (palmitic, palmitoleic, stearic, oleic, linoleic, and linolenic acids), a blend of the two Z‐9‐alkenoic acids (palmitoleic and oleic acids), palmitoleic acid alone, and oleic acid alone showed deterrence against O. scapulalis which was comparable to that provoked by the full egg extract. The dose‐dependency of the deterrent effects of palmitoleic acid and oleic acid was verified in O. scapulalis. The binary blend of palmitoleic acid and oleic acid was also confirmed to deter oviposition in O. furnacalis.     

The distribution of fatty acids including petroselinic and tariric acids in the fruit and seed oils of the Pittosporaceae, Araliaceae, Umbelliferae, Simarubaceae and Rutaceae

The fatty acid composition of the fruit oils or seed oils of Pittosporaceae (eight genera, 10 species), Araliaceae (two species), Simarubaceae (three species), and of one umbelliferous and one rutaceous species were determined by gas chromatography, argentation TLC and ozonolysis. In the Pittosporaceae, in which the major C₁₈ fatty acid of all species was either oleic acid (18:1, 9c) or linoleic acid (18:2, 9c, 12c), large amounts of C₂₀ and C₂₂ fatty acids seem to occur regularly. Petroselinic (18:1, 6c) and tariric (18:1, 6a) acids were absent. However, petroselinic acid was the major fatty acid in the Araliaceae and Umbelliferae. In these two families only small amounts of C₂₀ and C₂₂ acids were detected and tariric acid was absent. The Rutales contained relatively high amounts of trans-octadecenoic acids (18:1, 9t). Tariric acid was the major fatty acid in the two species of Picramnia (Simarubraceae), which also contained small amounts of petroselinic acid. The major fatty acids in Ailanthus glandulosa (Simarubaceae) and Phellodendron amurense (Rutaceae) were linoleic or linolenic acid (18:3, 9c, 12c, 15c); these species contained neither tariric nor petroselinic acid and the levels of C₂₀ and C₂₂ fatty acids were low. The appearance of schizogenous resin canals and polyacetylenes and the absence of iridoids and petroselinic acid allows the Pittosporaceae to be separated from the Rutales and Araliales and to be placed in an independent order, the Pittosporales. Arguments for a rather close relationship of the Pittosporales to the Araliales and Cornales (including the Escalloniaceae) are presented.     

Oleic,Linoleic and Linolenic Acids Increase ROS Production by Fibroblasts via NADPH Oxidase Activation

The effect of oleic, linoleic and γ-linolenic acids on ROS production by 3T3 Swiss and Rat 1 fibroblasts was investigated. Using lucigenin-amplified chemiluminescence, a dose-dependent increase in extracellular superoxide levels was observed during the treatment of fibroblasts with oleic, linoleic and γ-linolenic acids. ROS production was dependent on the addition of β-NADH or NADPH to the medium. Diphenyleneiodonium inhibited the effect of oleic, linoleic and γ-linolenic acids on fibroblast superoxide release by 79%, 92% and 82%, respectively. Increased levels of p47^phox phosphorylation due to fatty acid treatment were detected by Western blotting analyses of fibroblast proteins. Increased p47^phox mRNA expression was observed using real-time PCR. The rank order for the fatty acid stimulation of the fibroblast oxidative burst was as follows: γ-linolenic > linoleic > oleic. In conclusion, oleic, linoleic and γ-linolenic acids stimulated ROS production via activation of the NADPH oxidase enzyme complex in fibroblasts.     

The microspore-derived embryo ofBrassica napus L. as a tool for studying embryo-specific lipid biogenesis and regulation of oil quality

Summary A time-course study of lipid accumulation in microspore-derived embryos and developing zygotic embryos of rapeseed (Brassica napus L. ssp.oleifera) is presented. Rapid storage fat (triacylglycerol) biosynthesis was induced in microspore-derived embryos of oilseed rape (cv Topas) when the embryos were transferred from standing cultures (10 ml) to fresh medium (75 ml) and shake cultured. Triacylglycerols accumulated, after a lag period of 7 days, at a linear rate of approximately twice that of the developing zygotic embryo. The fatty acid composition of triacylglycerols in microspore-derived embryos closely parallelled that of the developing zygotic embryos. In the microspore-derived embryos, the amount of phosphatidylcholine, the major substrate for the production of polyunsaturated fatty acids in oilseeds, remained constant during the linear phase of triacylglycerol production, whereas it increased steadily in the zygotic embryos. The fatty acid composition of individual cotyledons from microspore embryos shake cultured for 15 days was compared with that of individual mature seeds. Relative amounts of the major fatty acids, i.e. palmitic, oleic and linoleic acids, were essentially the same, whereas the microspore-derived embryos had about 35% less stearic acid and 35% more linolenic acid than the mature seeds. Variation in the amounts of oleic, linoleic and linolenic acids between seeds was similar to that found between cotyledons of microspore-derived embryos, whereas variation in palmitic and stearic acid levels was significantly lower between microsporederived cotyledons than between the seeds. The results indicate that microspore-derived embryos from shake cultures should be convenient for use in studying the regulation of oil biosynthesis and for rapidly screening for oil quality in genetically altered rapeseed.