Fatty acids,Part 44 The preparation of some long-chain hydroperoxides and t-butyl peroxides

A number of long-chain hydroperoxides and t-butyl peroxides have been prepared — some of them for the first time — by the application of known procedures.     

Fatty acids of some algae from the Bohai Sea.

The fatty acid compositions of 22 species of marine macrophytes, belonging to the Ceramiales, Cryptonemiales, Nemalionales, Laminariales, Chordariales, Scytosiphonales, Desmarestiales, Dictyosiphonales, Fucales, Dictyotales and Ulvales and collected from the Bohai Sea, were determined by capillary gas chromatography. The contents of polyunsaturated fatty acids (FAs) in the Bohai Sea algae, in comparison with the same species from the Yellow Sea were found to be lower. Red algae had relatively high levels of the acids 16:0, 18:1(n-7), 18:1(n-9), 20:5(n-3) and 20:4(n-6), and those examined were rich in C(20) PUFAs, these chiefly being arachidonic and eicosapentaenoic acids. The major FAs encountered in the Phaeophyta were 14:0, 16:0, 18:1(n-9), 18:2(n-6), 18:3(n-3), 18:4(n-3), 20:4(n-6) and 20:5(n-3). C(18)PUFAs are of greater abundance in the brown algae than in the red algae examined. All three green algae from the Ulvales had similar fatty acid patterns with major components, 16:0, 16:4(n-3), 18:1(n-7), 18:2(n-6), 18:3(n-3), and 18:4(n-3). They contained 16:3(n-3) and more 16:4(n-3), were rich in C(18)PUFAs, chiefly 18:3(n-3) and 18:4(n-3) and had 18:1(n-7)/18:1(n-9) ratios higher than 1.     

Fatty acids. part 42 The preparation and properties of methyl monomercaptostearates. some related thiols, and some methyl epithiostearates

Some saturated and unsaturated mercapto C₁₈ esters have been obtained for the first time. Such compounds are prepared from hydroxy esters via their mesyloxy derivatives by reaction with sodium hydrogen sulphide or with potassium thioacetate (followed by deacetylation) or from alkene esters by radical addition of thioacetic acid. The mercapto esters are readily identified by infrared, nuclear magnetic resonance, and mass spectroscopic procedures, preferably after acetylation or trifluoroacetylation.γ-Mesyloxy alkenes furnish tetrahydrothiophen rather than mercapto alkenes and methyl 9,12-epithiostearate was synthesised by an independent route from thiophen.     

Fatty acids,resin acids and phenols in Pinus muricata

Acetone-soluble extractives of “blue” and “green” strain Pinus muricata D. Don were found to consist of free and “combined” fatty acids, resin acids, and phenols. The composition of the extractives from the two strains was similar though “green” strain P. muricata contained more Δ^8(9),15 isopimaric acid than “blue” strain. This difference may be used to identify these muricata strains if the age of the wood precludes a monoterpene examination.     

Fatty acids ofStreptomyces cinnamonensis,producer of monensin

Using the gas chromatography-mass spectrometry (GC-MS) method we found inStreptomyces cinnamonensis saturated fatty acids of iso-and anteiso-types, cyclopropyl acids, and unsaturated fatty acids where the double bond position was determined by MS of their pyrrolidine derivatives.     

Fatty acids. part 43. The preparation and properties of some methyl dimercaptostearates and of some related methyl epithio-and epidithiostearates

The methods described for converting mesyloxy esters to mercapto esters (see previous paper) have been applied to appropriate dimesyloxy derivatives as a route to the 9,10; 10,12 and 9,12-dimercapostearates. Some reactions furnish epithio and epidithio esters in place of mercapto esters. The dithiols are converted to acetyl, trifluoroacetyl, and isopropylidene derivatives. The products are identified mainly by infrared, nuclear magnetic resonance, and mass spectroscopic procedures.     

Fatty acids, membrane permeability, and sugars of stored potato tubers

The relationships of potato (Solanum tuberosum L.) tuber membrane permeability and membrane lipid composition to sugar accumulation were examined. Tubers from four potato cultivars were stored for 40 weeks at 3°C and 9°C. Rates of tuber membrane electrolyte leakage, total fatty acid composition, free fatty acid composition, and sugar content were measured throughout the storage period. Storage of tubers at 3°C caused dramatic increases in total fatty acid unsaturation, membrane permeability, and sugar content compared to tubers stored at 9°C. Cultivars with higher levels of fatty acid unsaturation had lower rates of membrane electrolyte leakage and lower sugar contents. We propose that high initial levels or high induced levels of membrane lipid unsaturation mitigate increases in tuber membrane permeability during storage, thus positively influencing the processing quality of stored potato tubers.     

Fatty acids of actinomycete phospholipids

The fatty acid composition of phospholipids was studied in different actinomycetes growing in two media in order to detect their biological activity. The total phospholipids of the actinomycetes did not differ qualitatively and their composition was represented by the same series of fatty acids (C13--C19). The qualitative composition and the quantitative content of fatty acids in phospholipids depended on the composition of the growth medium. When the actinomycetes were cultivated in a complex medium, the proportion between fatty acids (C14:0, C14:1, C16:0, C17:0, C17:1, C18:1, C18:2) changed. The qualitative composition of fatty acids in phospholipids varied among the cultures. However, the content of palmitoleic, palmitic and oleic acids was elevated in all of the cultures. Under the given experimental conditions, the actinomycetes were found to synthesize phospholipids containing fatty acids with a high degree of unsaturation (mainly at the account of C16:1 and C18:1 acids).     

Fatty acids filamentous green algae

Fatty acid analyses of several filamentous green algae were conducted using gas-liquid chromatography. Two bryophytes were also examined. Qualitatively, the genera of algae studied were divided into two groups: (A) algae that have significant amounts of polyunsaturated C₂₀ fatty acids and (B) algae that lack or only have very small amounts of the C₂₀ acids. On the basis of fatty acid content, the algae of Group A more closely resemble the bryophytes than do the algae of Group B. Culture age was shown to cause quantitative but not qualitative variations in fatty acid content. It is evident from this study that extrapolation to land plants, from studies on the fatty acid content of the green algae, should include the filamentous forms.     

Fatty acids trigger mitochondrion-dependent necrosis

Obesity is characterized by lipid accumulation in non-adipose tissues, leading to organ degeneration and a wide range of diseases, including diabetes, heart attack, and liver cirrhosis. Free fatty acids (FFA) are believed to be the principal toxic triggers mediating the adverse cellular effects of lipids. Here, we show that various cooking oils used in human nutrition cause cell death in yeast in the presence of a triacylglycerol lipase, mimicking the physiological microenvironment of the small intestine. Combining genetic and cell death assays, we demonstrate that elevated FFA concentrations lead to necrotic cell death, as evidenced by loss of membrane integrity and release of nuclear HMGB1. FFA-mediated necrosis depends on functional mitochondria and leads to the accumulation of reactive oxygen species. We conclude that lipotoxicity is executed via a mitochondrial necrotic pathway, challenging the dogma that the adverse effects of lipid stress are exclusively apoptotic.     

Fatty acids and other lipids of corals: Composition, distribution, and biosynthesis

This paper reviews the literature data on the composition, structure, and distribution of the main lipid classes and their fatty acids in reef-building and soft corals and in hydrocorals of the genus Millepora. The review presents information about more than 150 coral species from tropical and cold waters of the World Ocean, as well as data on the influence of environmental factors on the lipid compositions of corals. The possible pathways of polyunsaturated fatty acid biosynthesis in corals are discussed.