Lipids from <Emphasis Type="Italic">Halostachys caspica</Emphasis> and <Emphasis Type="Italic">Halocharis hispida</Emphasis>

The composition of lipids from the aerial parts of two species of halophytes from the family Chenopodiaceae, Halostachys caspica C. A. Mey. and Halocharis hispida Bge. was determined. Neutral lipids (NL, 62.1 and 54.2%, respectively) dominated the total lipids (TL) of these plants. More than a third of the NL were esters of aliphatic alcohols and phytosterols (FAE). Fatty acids 16:0, 18:1, and 18:2 dominated the acids of FAE; 16:0, 18:1, and 18:3, the phospholipids. The principal fatty acids of glycolipids were unsaturated acids (68.3 and 75.1%) with linolenic acid dominating (44.9 and 43.5%). Presented at the 7th International Symposium on the Chemistry of Natural Compounds, Tashkent, October 16–18, 2007. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 276–278, May–June, 2009.     

Fatty acids from the Okhotsk sea sponge <Emphasis Type="Italic">Forcepia uschakowi</Emphasis>

The fatty-acid (FA) composition of total lipids from the Okhotsk sea marine sponge Forcepia uschakowi was studied. A total of 56 acids were identified by GC and GC—MS. The principal saturated acids were 16∶0 and 18∶0. The main monoene acid was 15-Me-24∶1(14), which was observed for the first time in sponge lipids. Polyunsaturated acids represented of 64.1% of the total FA of F. uschakowi. Of these, the principal ones were non-methylene-separated acids 26∶2(5,9) and 26∶3(5,9,19), which are typical of sponges, and bromo-acid 6-Br-26∶2(5,9). __________ Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 422–424, September–October, 2007.     

Composition of the lipophilic extract from the sponge <Emphasis Type="Italic">Axinella carteri</Emphasis> collected from the Bay of Bengal of the Orissa coast

The composition of the lipophilic extract from the two specimen of the sponge Axinella carteri (Dendy) collected from two different depths of the Bay of Bengal of the Orissa coast were investigated. Fatty acids, as well as volatile compounds and sterols, were identified. A high concentration of polyunsaturated fatty acids was identified from depth species compared to the species collected from shallow water. The presence of a high concentration of a polymethyl-branched fatty acid, i.e., phytanic acid, and a demospongic acid (C26:2, Δ 5,9) were identified in both specimen, but the % composition of both acids were more in the species collected from depth than the species collected from shallow water. Important polyunsaturated fatty acids like 5,8,11,14-eicosatetraenoic acid and 5,8,11,14,17-eicosapentaenoic acid (EPA) were also found in depth species which were absent in the species collected from shallow water. Antimicrobial screening of the lipid extracts of A. carteri was also studied against different pathogens. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 224–227, May–June, 2008.     

Fatty Acids from the Sponge <Emphasis Type="Italic">Tedania dirhaphis</Emphasis>

The fatty acid (FA) composition of total lipids from the marine sponge Tedania dirhaphis from the Sea of Okhotsk was studied. GC and GC-MS identified 50 acids, particular attention being paid to components with 14–22 C atoms. Acids 16-Me-19:0, 10,14-Me₂-15:1(Δ6), 18:1(Δ6), 18:1(Δ8), and 22:1(Δ16) were observed and identified for the first time in sponges. The main FA in lipids from T. dirhaphis was 28:3(Δ5,9,21), the relative content of which reached 63.3%.__________Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 233–236, May–June, 2005.     

Antibacterial study and fatty acid analysis of lipids of the sponge <Emphasis Type="Italic">Myrmekioderma granulata</Emphasis>

The composition of the lipophilic extract of the sponge Myrmekioderma granulata (Esper) collected from 13 m depth of the Bay of Bengal of the Orissa coast was investigated. Fatty acids as well as volatiles and sterols were identified. 4,8,12-Trimethyltridecanoic acid was identified for the first time along with the important PUFAs such as linoleic acid (n-6, C18:2), dihomo-γ-linolenic acid (n-6, C20:3), 5,8,11,14-eicosatetraenoic acid (n-3, C20:4), and 5,8,11,14,17-eicosapentaenoic acid (EPA) (n-3, C20:5) from this species. The branched polyunsaturated fatty acids like br-C26:2, 25-methyl-5,9-heptacosadienoic acid and 24-methyl-5,9heptacosadienoic acid were also identified by GC-MS. The lipid extract exhibited limited activity against different pathogens.     

Nutritional profile of food yeast kluyveromyces fragilis biomass grown on whey

Biomass of food yeast Kluyveromyces fragilis (MTCC 188) grown on deproteinized whey supplemented with 0.8% diammonium hydrogen phosphate and 10 ppm indole-3-acetic acid, had a crude protein content of 37%. The true protein content based on nitrogen fractionation procedure was 28.1%. Total nucleic acid content was 4.82%. This amount does not appear to be toxicologically offensive. Crude fiber, ash, and lipid content of K. fragilis dry cells were found to be 4.9%, 16%, and 7.8%, respectively. Essential fatty acids of both ω-3 and ω-6 series were found present in the fat of the yeast and represented 21.5% of the total fatty acids. All the essential amino acids were present in the proteins of K. fragilis; however, sulfur containing amino acids were found in lower amounts. Calculated protein scores indicate moderate biological value. Bvitamins in the biomass were present as expected, but folic acid and pyridoxine were present in high concentration.     

Lipids of <Emphasis Type="Italic">Thermopsis alterniflora</Emphasis> bean seeds and shells

The lipid groups and fatty-acid composition of Thermopsis alterniflora (Leguminosae) bean seeds and shells were established. It was shown that shell lipids have a greater content of unsaponified substances, galactolipids, and esterfied unsaturated 18:1, 18:2, and 18:3 acids (75% total) than seed lipids.Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 438–440, November–December, 2004.This revised version was published online in April 2005 with a corrected cover date.     

Interaction of functionally-substituted 4-alkyl-2,6-di-<Emphasis Type="Italic">tert</Emphasis>-butylphenols with hydrohalic acids

Reactions of 4-alkyl-2,6-di-tert-butylphenols containing OH, SH, COOH, and COOMe groups in their para substituents with hydrogen chloride and hydrohalic acids were studied. One-step transformations of 2,6-di-tert-butyl-4-(ω-hydroxyalkyl)phenols to the corresponding 4-(ω-halogenoalkyl)phenols, as well as of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid and its esters to phloretic acid were proposed. 4-(3-Mercaptopropyl)phenol upon heating with conc. HBr undergoes condensation to 3-(4-hydroxyphenyl)propyl 4-(3-mercaptopropyl)phenyl sulfide as the main product. Dedicated to the memory of Academician N. N. Vorozhtsov on the 100th anniversary of his birth. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1078–1083, June, 2007.     

Lipids from the Marine Alga <Emphasis Type="Italic">Gracilaria verrucosa</Emphasis>

The composition of lipids and fatty acids from the red alga Gracilaria verrucosa, for which a high content of 20:4n-6 acid is typical, was studied. The principal lipids were digalactosyldiacylglycerides, phosphatidylcholines (PC), monogalactosyldiacylglyderides (MGDG), and sulfoquinovosyldiacylglycerides, the fraction of each was approximately the same. Sphingophospholipids, inositephosphoceramides, were identified among the polar lipids. Each lipid class differed in the ratio of fatty acids (FA). The FA of all glycerolipids contained 20:4n-6 acid but its concentration was greatest in MGDG and PC, 67.2% and 56.5% of the acid mass.__________Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 230–232, May–June, 2005.     

Determination of cuticular and internal fatty acids of Chorthippus brunneus males and females using HPLC‐LLSD and GC–MS

Insects are of growing significance in veterinary medicine and human healthcare; therefore, an understanding of their biology is very important. The cuticular and internal fatty acid compositions of Chorthippus brunneus males and females have been studied for the first time. The lipids of males and females were separated into classes of compounds using high‐performance liquid chromatography with a laser light scattering detector. The free fatty acid (FFA) fractions obtained by HPLC were silylated and then analyzed by GC–MS. The cuticular lipids of males contained 15 saturated, four unsaturated with even‐numbered and two unsaturated with odd‐numbered carbon chains, FFAs ranging from C8 to C25. The major free fatty acids in males were C16 (20.8%), C18:2 (8.5%), C18:1 (32.9%) and C18 (24.4%). The cuticular lipids of females contained 17 saturated, four monounsaturated and two diunsaturated free fatty acids ranging from C8 to C30. The major cuticular fatty acids in females were C16 (25.1%), C18:2 (6.2%), C18:1 (23.7%) and C18:0 (33.2%). The internal FFAs of males consisted of 20 compounds ranging from C8 to C26. Four of these compounds were detected as major compounds: C16 (14.1%), C18:2 (21.6%), C18:1 (38.0%) and C18 (22.5%). Among 18 internal free fatty acids of females, C16 (22.3%), C18:2 (10.9%), C18:1 (40.2%) and C18 (20.5%) were the most abundant compounds. The following cuticular fatty acids present in the lipids of females were absent in the lipids of males: C26, C27 and C30. On the other hand, only C24 was absent from the cuticular lipids of females. Only C10 and C24 internal fatty acids present in the lipids of males were absent in the lipids of females. Copyright © 2016 John Wiley & Sons, Ltd.     

Enhancing the production of gamma-linolenic acid in <Emphasis Type="Italic">Hansenula polymorpha</Emphasis> by fed-batch fermentation using response surface methodology

Gamma-linolenic acid (GLA, C18:3Δ^6,9,12) is an n-6 polyunsaturated fatty acid (PUFA) that has been used for the alleviation and treatment of a number of symptoms and diseases. Increasing GLA demand has led to a search for alternative producers and potential strategies for GLA production. Based on the successful performance of Hansenula polymorpha, a methylotrophic yeast, as a “cell factory” for the production of valuable bioproducts, a bioprocess development approach was implemented for GLA production in the recombinant yeast carrying the mutated Δ⁶-desaturase gene of Mucor rouxii. Using a substrate-feeding strategy under glycerol-limited conditions, the physical-chemical variables during the fed-batch fermentation of the recombinant H. polymorpha were optimised for GLA production through response surface methodology using a Box-Behnken design. The medium composition, including yeast extract and trace elements, and dissolved oxygen tension (DOT) were targeted. We found that DOT was the most effective variable for enhancing GLA yield. These results also suggest that the optimum conditions for GLA production are 28 % saturation of DOT, 1 g L⁻¹ of yeast extract and 3.6 mL L⁻¹ of the Pichia trace metals 1 (PTM1).     

Lipids from the sand dollar <Emphasis Type="Italic">Scaphechinus mirabilis</Emphasis>

The composition of lipids and their fatty acids in tissues of scalp, gonads, and internal organs of the sand dollar Scaphechinus mirabilis was determined using one-and two-dimensional TLC and GC-MS. Lipids of S. mirabilis scalp consisting of several neutral and phospholipids were characterized for the first time. A significant quantity of eicosapentaenoic acid (20:5) was found in scalp lipids. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 320–323, July–August, 2007.     

Fatty-acid composition of rat brain lipids. Determined by support-coated open-tubular gas chromatography.

The nonhydroxy fatty acid composition of rat brain lipids (except gangliosides) was determined by support-coated open-tubular (SCOT) gas chromatography. Fatty acids of both odd and even chain lengths ranging from C14 to C26 were detected. Brain lipids contained 49% saturated, 29% monounsaturated, and 22% polyunsaturated fatty acids. Monoenoic fatty acids were mainly of the omega-9 and omega-7 series with minor amounts of omega-10 and amega-11 isomers. Dienes and trienes consisted of omega-6, amega-7, and omega-9 series. Tetraenes were of the omega-6 series. Small amounts of omega-6 and omega-3 pentaenes were detected. The most abundant polyunsaturated fatty acid was 22:6omega-3. The advantages of support-coated open-tubular columns over wall-coated open-tubular columns for the analysis of brain lipid fatty acids are discussed.     

Development of a Temperature Shift Strategy for Efficient Docosahexaenoic Acid Production by a Marine Fungoid Protist, <Emphasis Type="Italic">Schizochytrium</Emphasis> sp. HX-308

Temperature was one of the important environmental factors affecting the biosynthesis of docosahexaenoic acid (DHA; C22:6, ω−3). Generally, a low temperature would slow the strain growth, but promote the accumulation of unsaturated fatty acids. According to this information, the effects of temperature and different two-stage temperature shifting strategies on fatty acid production and DHA content of the marine fungoid protist, Schizochytrium sp. HX-308, were investigated in this study. Finally, the highest DHA percentage was up to 51.98% (per total fatty acids) with the DHA production of 6.05% (per dry cell weight), which was obtained with the method of shifting temperature from 30 °C for 32 h to 20 °C for 12 h.     

Differentiation of organically and conventionally produced milk by stable isotope and fatty acid analysis

Increasing sales of organic milk mean intensified tests for authenticity are required. In addition to comprehensive documentation, analytical methods to identify organic milk, and thus to differentiate it from conventional milk, are needed for consumer protection. Because the composition of milk is fundamentally dependent on the feeding of the cows, thirty-five samples from both production systems in Germany, including farm and retail milk, were collected within 12 months, to reflect seasonal variation, and appropriate properties were analysed. Fatty acid analysis enabled organic and conventional milk to be completely distinguished, because of the higher α-linolenic acid (C18:3ω3) and eicosapentaenoic acid (C20:5ω3) content of the former. Organic milk fat contained at least 0.56% C18:3ω3 whereas the maximum in conventional milk was 0.53%. Because of the parallel seasonal course of the C18:3ω3 content of organic and conventional retail samples, however, time-resolved comparison at the five sampling dates resulted in a clearer difference of 0.34 ± 0.06% on average. Analysis of stable carbon isotopes (δ¹³C) also enabled complete distinction of both types of milk; this can be explained by the different amounts of maize in the feed. For conventional milk fat δ¹³C values were −26.6‰ or higher whereas for organic milk fat values were always lower, with a maximum of −28.0‰. The time-resolved average difference was 4.5 ± 1.0‰. A strong negative correlation (r = −0.92) was found between C18:3ω3 and δ¹³C. Analysis of a larger number of samples is required to check the preliminary variation ranges obtained in this pilot study and, probably, to adjust the limits. Stable isotopes of nitrogen (δ¹⁵N) or sulfur (δ³⁴S) did not enable assignment of the origin of the milk; in cases of ambiguity, however, some trends observed might be useful in combination with other properties. Figure Correlation (r = −0.92) between δ¹³C value and C18:3ω3 content of milk fat from different production systems     

Polyunsaturated fatty acids from several plant species of the family Boraginaceae

Lipids from seeds of the plants Cynoglossum officinale (1), Echium vulgare (2), and Lappula squarrosa (3) of the family Boraginaceae growing in the Republic of Bashkortostan were studied. Four polyunsaturated acids, linoleic (LA), γ-linolenic (GLA), α-linolenic (ALA), and stearidonic (SA), were identified among the fatty acids. The principal acids of the neutral lipids (NL) were 18:1 and 18:2 in 1, ALA in 2 and 3, and GLA in approximately equal amounts in all three samples. The highest amount of SA (16.8 %) was found in 3. Unsaponified components of NL samples were identified by GC/MS. Alkaloids were observed in the pulp and polar lipids.     

Lipids from leaves ofEphedra equizetina

The content and composition by class and fatty acid of neutral (NL), glyco- (GL), and phospholipids (PL) in leaves ofEphedra equizetina Bunge (Ephedraceae) are determined. The acid composition of NL, GL, and PL includes saturated 12∶0–32∶0 acids and unsaturated 15∶1, 16∶1, 18∶1, 18∶2, and 18∶3 acids. Unsaponified components of the total lipids also contained biologically active substances such as α-tocopherol, carotenoids, high-molecular-weight fatty alcohols, triterpenes, and sterols. Academician S. Yu. Yunusov Institute of the Chemistry of Plant Substances. Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (371) 120 64 75. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 718–721, November–December, 1999.     

Fatty-acid composition and secondary metabolites from slightly polar extracts of the aerial part of <Emphasis Type="Italic">Primula macrocalyx</Emphasis>

Flavones 2′,5′-dimethoxyflavone, 3′-methoxy-4′,5′-methylenedioxyflavone, 3′,4′-dimethoxyflavone, 5,6,2′,3′,6′-pentamethoxyflavone, and 5,6,2′,3′,5′,6′-hexamethoxyflavone; salicylates, methyl-4-methoxysalicylate and peonol; and bisbibenzyl polyphenol riccardin C were isolated for the first time from the acetone extract of the aerial part of Primula macrocalyx Bge. The content of free and total fatty acids was determined by GC and GC—MS. Palmitic (16:0), octadecatetraenoic 18:4 (6,9,12,15), linoleic 18:2 (9,12), and α-linolenic 18:3 (9,12,15) were the principal acids from the aerial part of Primula macrocalyx. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 457–460, September-October, 2008.     

Lipids and flavolignans from <Emphasis Type="Italic">Silybum marianum</Emphasis>

Lipids from the air-dried aerial part (AP) and seeds of Silybum marianum (L.) Gaerth. (Asteraceae) were studied. The class and fatty acid compositions of neutral lipids (AP, seeds) and glyco- and phospholipids (AP) were determined. Neutral lipids (NL) with a complicated set of lipophilic components, mainly triterpenols, sterols, and their esters predominated in the AP. The fatty acids of the AP were dominated by 16:0, 18:2 (glycolipids), and 18:3 (neutral lipids, phospholipids); of seed NL, by 18:2 and 18:1. The content and composition of flavolignans isolated from defatted seeds and the content of total protein in the meal were found.     

Lipids of <Emphasis Type="Italic">Oenothera</Emphasis> seeds from different habitats. 1

The composition of lipids and fatty acids from seeds of Oenothera biennis growing in the RF near Kazan’ was determined. The content of γ-linolenic acid in all groups of acyl-containing lipids in the oil to be 4.4%. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 430–433, September–October, 2007.