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.     

Isomers of plamitoleic acid in lipids and volatile substances from the fruits ofZiziphus jujuba

Fatty acid from the dried pulp ofZiziphus jujuba Mill. Contain 33 components with a chain length from 7 to 28 carbon atoms and approximately equal ratio of total saturated and unsaturated, mainly monoenic, acids; among them, the isomers of palmitoleic acid 16:1(7) and 16:1(9) predominate, and sixteen fatty acids of the mixture, including 12:0, 16:0, 14:1(9).Published in Khimiya Prirodnykh Soedinenii, No. 4, 449–451, July–August, 1999.     

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.     

Uronic (hexenuronic) acid profile of ethanol–alkali delignification of giant reed Arundo donax L.

The effect of process variables on uronic acids (UAs) and hexenuronic acids (HexAs) in the annual crop Arundo donax L. during ethanol–alkali pulping has been examined. A substantial loss of UA moieties (up to 90%) was observed by the end of pulping (target kappa number 18) performed with 25% NaOH and 40% EtOH (by volume) within the temperature range of 130–150 °C. At the same time, the progressive formation of HexA in pulp was detected from the early phases of delignification. The proportion of HexA in the residual UA of the final pulp was found to be 84%, indicating almost complete conversion of 4-O-methylglucuronic acid side groups (MeGlcA) of heteroxylan into HexA. The kinetics of UA degradation and HexA formation has been described in terms of three consecutive first-order reaction stages. The overall rate of UA degradation was one order higher than the rate of UA conversion into HexA. The values of apparent activation energy were estimated as 68.6 and 94.7 kJ mol^–1, respectively. The reaction medium alkalinity was shown to be the controlling factor for UA and HexA stability during ethanol–alkali pulping. An increase in alkali charge from 5% to 35% (as NaOH) led to UA loss of 40%, but promoted HexA formation from 11.8 to 20.1 mol g^–1. The addition of organic solvent to the alkaline pulping solution had a similar effect, and about 10% of UA was lost and the content of HexA increased from 6.9 to 10.9 mol g^–1 with an increase in ethanol proportion in the liquor from 20% to 60%.     

Lipids from extracts ofChlorella vulgaris

The composition of ethanolic (I) and gasoline (II) extracts of the cultivated microalgaChlorella vulgaris has been studied. With the aid of CC, TLC, qualitative reactions, GLC, and UVS the following classes of compounds have been detected in them. From the neutral lipids: hydrocarbons, carotenoids, traces of sterols and their esters, fatty acid esters, tri- and diacylglycerols, free fatty acids, and chlorophylls; and from the polar lipids: di- and monogalactosylglycerols, phosphatidylethanolamine, lecithin, phosphatidylinositol, phosphatidylserine, and three sphingosine bases. The polar lipids I and II made up 52.4 and 50.2% of the total, respectively. As compared with extract I, extract II was somewhat enriched with neutral lipids, including provitamins of the A group and vitamins of the F group. In the fatty acids of chlorella, 19 components were detected, the main ones being the 16:0 acid and 18:2 and 18:3 acids.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 284–288, May–June, 1986.     

Comparative study on fatty acid composition of olive (Olea europaea L.), with emphasis on phytosterol contents

The present study was designed to determine the fatty acid composition and phytosterol contents of Turkish native olive cultivars, namely Kilis Yağlık and Nizip Yağlık cv. In this context, olive fruits from 34 locations were sampled and then screened for their components in comparison. Fifteen different fatty acids were found in both olive oils. In the order of abundance, the most important ones were oleic acid (18:1) > palmitic acid (16:0) > linoleic acid (18:2) > stearic acid (18:0). Significant differences were observed in the contents of oleic acid (18:1), palmitic acid (16:0), linoleic acid (18:2) but not for stearic acid content in comparison both oils (p < 0.01). There were significant differences in terms of unsaturated fatty acids, saturated fatty acids and polyunsaturated fatty acids (p < 0.01). The seven phytosterols – cholesterol, campesterol, stigmasterol, β ‐sitosterol, Δ‐5‐avenasterol, Δ‐7‐stigmastenol and Δ‐7‐avenasterol – were studied in both oil sources. The predominant sterols were β ‐sitosterol, Δ5‐avenasterol and campesterol in the samples analysed. However, no significant differences were found in the levels of the phytosterols between the two olive cultivars.     

Lipids of elaeagnus fruit

The composition of the classes of lipids of the fruit of three morphological forms of the elaeagnusElaeagnus angustifolia L. have been studied. Their compositions were identical. The amounts of the main lipid classes of extracts of the seeds and pericarps, the fatty acid compositions of the acyl-containing classes of lipids, and the compositions of the carbohydrates and sterols have been determined. The fatty oil of the seeds contained linoleic acid, while the main fatty acids of the pericarp extracts were the 16:0, 18:1, and 18:2 acids. The 16:1 acid that is characteristic for sea buckthorn oil was detected in the elaegnus fruit in insignificant amounts. The class of sterols, both in the free and in the esterified states, was represented by -sitosterol. The main hydrocarbon of the pericarps and seeds was nonacosane.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 17–21, January–February, 1990.     

High-Performance Liquid Chromatographic Analysis of Amino Acids in Edible Seaweeds after Derivatization with Phenyl Isothiocyanate

Summary A reversed-phase high-performance liquid-chromatographic method has been used for analysis of the amino acids in edible seaweed. Sample proteins were hydrolysed with hydrochloric acid and the amino acids produced were derivatized with phenyl isothiocyanate. The resulting phenylthiocarbamyl amino acids were chromatographed on an ODS2 column with UV detection at 254 nm. The mobile phase was a mixture of 0.14 M ammonium acetate buffer, pH 6.4, containing 0.05% triethylamine (A) and 60:40 (v/v) acetonitrile–water (B), at a flow rate of 1.1 mL min^–1; the elution gradient (min:A%) was: 0:90, 8:90, 10:70, 12:70, 18:52, 20:0, 25:0, 28:90, 35:90. Method precision for the different amino acids was between 1.33 and 3.88% (relative standard deviation); detection limits were between 6.9 and 14.3 ng mL^–1. The amino acid content of the algae analysed ranged from 22.4 ± 1.9 to 138.0 ± 5.6 mg g^–1 d.w. The amino acids present at highest concentrations were glutamic acid, alanine, and phenylalanine.     

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.     

Acids and their functionally substituted esters fromAmaranthus cruentus seed oil

The acid composition of seed oil ofAmaranthus cruentus and the synthesis of their glycidyl and pyridinecontaining esters are studied. It is demonstrated that 67% of the total acids are C₁₈-polyunsaturated linoleic and linolenic. A new method for preparing glycidyl esters of C₁₈-unsaturated carboxylic acids is developed by reacting their salts with ECG in an aprotic medium to produce the corresponding glycidyl esters. The reaction of the glycidyl esters and pyridine salts with carboxylic and phosphonic acids produces the propanolpyridine esters of the acids that combine the properties of the acids and pyridinium salts and are promising in the search for biologically active compounds.A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan' Scientific Center, Russian Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 217–219, May–June, 2000.     

Rapid Determination of Aristolochic Acids I and II in Some Medicinal Plants by High-Performance Liquid Chromatography

Aristolochic acids (AA) are toxic components of Aristolochia plants which result in diseases of the kidney such as urothelial cancer. It is, therefore, essential to monitor the amount of aristolochic acid in herbal medicines. In this study a reversed-phase high-performance liquid-chromatographic (HPLC) method has been developed for rapid determination of aristolochic acids I and II. Baseline separation was achieved within five minutes by use of an ODS C₁₈ column with methanol–water, 60:40, as mobile phase. Two kinds of aristolochic acid were successfully determined in 31 herbal samples of Aristolochia fangchi Wu and Caulis Aristolochiae Manshuriensis. The results indicated that in most samples the aristolochic acid I content is much higher than that of aristolochic acid II. The two kinds of aristolochic acid were not detected in Aristolochia fangchi from the Guangdong region, so Aristolochia fangchi from this region is recommended for use in herbal remedies.     

A new spot test for carboxylic acids

Summary A method for the detection ofg amounts of carboxylic acids, based on the conversion of carboxylic acids to hydroxamic acids using ethylene glycol or dicyclohexylcarbodiimide and subsequent detection as reddish-violet vanadium(V) complex, is presented. The method tolerates the presence of anions and cations including SO₄ ^2–, Br^–-, PC₄ ^3–, Mg(II), Ca(II), Na(I), Fe(II), Fe(III), Cu(II). The test for benzoic acid was independent of the presence of benzene, aniline, diethyl ether, benzenesulfonic acid and phenol. Aryl chlorides, esters, amides and anhydrides interfere with the test.

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Zusammenfassung Der Nachweis von Mikrogrammengen Carbonsäure läßt sich auf der Grundlage der Überführung in Hydroxamsäure und nachherige Bildung der rötlich-violetten Komplexverbindung mit Vanadin(V) durchführen. Dabei stören folgende Ionen nicht: SO₄ ^2–, Br^–, PO₄ ^3–, Mg(II), Ca(II), Na(I), Fe(II), Fe(III), Cu(II). Der Nachweis der Benzoesäure ist unabhängig von der gleichzeitigen Anwesenheit von Benzol, Anilin, Diäthyläther, Benzolsulfonsäure und Phenol. Arylchloride, Ester, Amide und Anhydride stören die Reaktion.

     

Lipids and essential oil ofOriganum onites

Neutral lipids, glycolipids, phospholipids, pigments, and essential oil of the above-ground part ofOriganum onites L. (Lamiaceae) are isolated and characterized for the first time. The fatty-acid composition of the lipids and the components of the hydrocarbons, sterols, and essential oil are determined by GC/MS. Linolenic and palmitic acids dominate in the acids of the lipids. The main components of the hydrocarbons are nonacosane; of the sterols, \-sitosterol; of the pigments, chlorophylls a and b. A total of 54 components are identified in the essential oil.Presented at the IIIrd International Symposium on the Chemistry of Natural Compounds, Bukhara, Uzbekistan, 19–22 December, 1998.Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 106–109, March–April, 2000.     

FT-midIR determination of fatty acid profiles, including trans fatty acids, in bakery products after focused microwave-assisted Soxhlet extraction

A study of the feasibility of Fourier transform medium infrared spectroscopy (FT-midIR) for analytical determination of fatty acid profiles, including trans fatty acids, is presented. The training and validation sets—75% (102 samples) and 25% (36 samples) of the samples once the spectral outliers have been removed—to develop FT-midIR general equations, were built with samples from 140 commercial and home-made bakery products. The concentration of the analytes in the samples used for this study is within the typical range found in these kinds of products. Both sets were independent; thus, the validation set was only used for testing the equations. The criterion used for the selection of the validation set was samples with the highest number of neighbours and the most separation between them (H<0.6). Partial least squares regression and cross validation were used for multivariate calibration. The FT-midIR method does not require post-extraction manipulation and gives information about the fatty acid profile in two min. The 14:0, 16:0, 18:0, 18:1 and 18:2 fatty acids can be determined with excellent precision and other fatty acids with good precision according to the Shenk criteria, R ²≥0.90, SEP=1–1.5 SEL and R ²=0.70-0.89, SEP=2–3 SEL, respectively. The results obtained with the proposed method were compared with those provided by the conventional method based on GC-MS. At 95% significance level, the differences between the values obtained for the different fatty acids were within the experimental error. Electronic Supplementary Material Supplementary material is available for this article at and is accessible for authorized users.     

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.     

Glycolipids from Capsicum annuum

The component and fatty-acid compositions of glycolipids from seeds and pulp of Capsicum annuum (Solanaceae) were established. The dominant acid of seed galactolipids was found to be linoleic; of pulp, linolenic. The content of medium-chain acids 9:0-15:0 was greater in seed glycolipids than in the analgous component of pulp lipids.     

Preparation and characterization of Cu(II)-N-salicylideneanthranilic acids,their reduction products and hydrolysis of the Schiff base

Copper (II) complexes ofN-salicylideneanthranilic acid (I) and its derivatives (II, III) as well as their NaBH₄ reduction products, namelyN-(2-hydroxybenzyl) anthranilic acids (IV–VI) have been prepared and their structures have been determined analytically. Tetracoordinated planar structures of the Cu(II) complexes of the Schiff bases and distorted tetrahedral structures of the Cu(II) complexes of compoundsV–VI have been elucidated by ESR and other spectral methods. During the preparation of the complex the hydrolysis of the Schiff base often takes place in the presence of water giving anthranilates and salicylaldehydates of metals to some extent along with the complexes of the Schiff base. The kinetic data for the hydrolysis ofN-salicylideneanthranilic acid (I) in methanol-water solution also are reported.Presented at the Sixth International Seminar on Inclusion Compounds, Istanbul, Turkey, 27–31 August, 1995.     

Lipids ofBryonia alba

The lipid composition of the roots ofBryonia alba (Cucurbitaceae) have been studied: It consists of fractions of 3-acyloxy-24-alkyl(alkenyl)-cholest-7-enes (I), triacylglycerols (II), 1,2-diacyl-3-monoglycopyranosyl-sn-glycerols (III), 1,2-diacyl-3-diglycopyranosyl-sn-glycerols (IV), 1,3-bis(3-sn-phosphatidyl)glycerols (V), 3-sn-phosphatidylethanolamines (VI), 3-sn-phosphatidylcholines (VII), and methyl esters of fatty acids (VIII). The amount of unsaturated fatty acids in the lipid fractions (I–VIII) is 60–94%, the main component being linolenic acid.A. L. Mndzhoyan Institute of Fine Organic Chemistry of the Academy of Sciences of the Armenian SSR, Erevan. Translated from Khimiya Pridodnykh Soedinenii, Vol. 6, pp. 781–785, November–December, 1980.     

Solvent extraction of amino acids into a room temperature ionic liquid with dicyclohexano-18-crown-6

Amino acids Trp, Gly, Ala, Leu are extracted efficiently from aqueous solution at pH 1.5–4.0 (Lys and Arg at pH 1.5–5.5) into the room temperature ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate (BmimPF₆) with dicyclohexano-18-crown-6 (CE). The most hydrophilic amino acids such as Gly are extracted as efficiently as the less hydrophilic (92–96%). The influence of pH, amino acid and crown ether concentration, volume ratio of aqueous and organic phases, and presence of some cations on amino acid recovery were studied. The ratio of amino acid to crown ether in the extracted species is 1:1 for cationic Trp, Leu, Ala, and Gly and to 1:2 for dicationic Arg and Lys. This ionic liquid extraction system was used successfully for the recovery of amino acids from pharmaceutical samples and fermentation broth, and was followed by fluorimetric determination.These results were published in part in Smirnova SV (2002) Ph.D. Thesis, Moscow State University.     

Metabolites of the pathogenic fungusVerticillium dahliae III. The lipid composition ofVerticillium dahliae

Summary The compositions of the neutral lipids of the mycelium and of the culture liquid from the pathogenic fungusVerticillium dahliae Kleb. have been investigated for the first time. The fatty-acid compositions of the main lipid fractions and the glyceride composition of the triglyceride fraction have been determined. The main acids of all the fractions are the 16:0 and 18:1 acids and in the triglyceride fraction, additionally, the 18:2 acid. Diisobutyl phthalate has been found in the combined neutral lipids of the fungal mycelium.V. I. Lenin Tashkent State University, Institute of the Chemistry of Plant Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 431–435, July–August, 1976.