Oxygenated acids of the lipids ofOnopordum acanthium seeds

The structures of the oxygenated fatty acids of the lipids ofOnopordum acanthium L. seeds have been studied by the methods of chemical, chromatographic, and spectral analyses. Triepoxy acids of the C₁₈ series and 24 monohydroxy acids with chain lengths of C₁₄–C₁₈ have been identified, of which the 8-OH-9Z,12Z-18:2 and the 14-OH-9Z,12Z-18:2 acids have been isolated as natural compounds for the first time.     

Oxygenated acids of the reserve lipids of Rumex paulsenianus

The composition of the fatty mono- and dihydroxy acids of the fruit ofRumex paulsenianus Rech. fil. (familyPolygonaceae) has been determined by a combination of IRS, UVS, GLC, and mass-spectrometric methods. (22) Monohydroxy acids of the C₁₄–C₂₀ series, including isomers and isologues, and four dihydroxy acids from C₁₈ to C₂₀, including a new isomeric 9-OH-10, 12–17:2 acid have been detected.Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 762–765, November–December, 1991.     

Hydroxy acids of the reserve lipids of Galeopsis bifida

The structures of fatty monohydroxy acids of the lipids of the seeds ofGaleopsis bifida Boenn. have been studied by the methods of chromatographic, spectral, and chemical analysis. (31) Acids with chain lengths of from 14 to 20 carbon atoms, with from 0 to 3 double bonds, and with the hydrolyls in positions characteristic for the products of the direct hydroxylation and the lipoxygenase and photosensitized oxidation of unsaturated fatty acids were detected. Of them, the 13-OH-9Z, 11E-17:2, the 15-OH-9, 12-18:2, the 16-OH-9, 12-18:2, and 17-OH-11, 14-20:2 acids were new, while this is the first time that the 15-OH-9Z, 12Z, 16E-18:3 acid has been described as a natural compound. The behavior of the TMS derivatives of the hydroxy acids on a polyester phase in GLC is discussed.Institute of the Chemistry of Plant Substances, Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 744–753, November–December, 1991.     

Hydroxy acids of the reserve lipids of Galeopsis bifida

The structures of fatty monohydroxy acids of the lipids of the seeds ofGaleopsis bifida Boenn. have been studied by the methods of chromatographic, spectral, and chemical analysis. (31) Acids with chain lengths of from 14 to 20 carbon atoms, with from 0 to 3 double bonds, and with the hydrolyls in positions characteristic for the products of the direct hydroxylation and the lipoxygenase and photosensitized oxidation of unsaturated fatty acids were detected. Of them, the 13-OH-9Z, 11E-17:2, the 15-OH-9, 12-18:2, the 16-OH-9, 12-18:2, and 17-OH-11, 14-20:2 acids were new, while this is the first time that the 15-OH-9Z, 12Z, 16E-18:3 acid has been described as a natural compound. The behavior of the TMS derivatives of the hydroxy acids on a polyester phase in GLC is discussed.     

Oxygenated acids of the reserve lipids of Rumex paulsenianus

The composition of the fatty mono- and dihydroxy acids of the fruit ofRumex paulsenianus Rech. fil. (familyPolygonaceae) has been determined by a combination of IRS, UVS, GLC, and mass-spectrometric methods. (22) Monohydroxy acids of the C₁₄–C₂₀ series, including isomers and isologues, and four dihydroxy acids from C₁₈ to C₂₀, including a new isomeric 9-OH-10, 12–17:2 acid have been detected.     

Lipids of the seeds ofSecurinega suffruticosa

The lipid composition of the seeds ofSecurinega suffruticosa (Euphorbiaceae) has been studied, and eight classes of lipids have been identified with a predominance of triacylglycerols; the fatty acid compositions and structures of the triacylglycerols have been determined. Among the hydroxy acids of the hydroxyacylglycerols 13 components belonging to saturated, monoenic, and dienic acids of the C₁₇, C₁₈, and C₂₀ series have been identified; 12-hydroxyheptadecanoic and 12-hydroxyeicosanoic acids are new.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 277–281, May–June, 1986.     

Lipids of the fruit of Feijoa sellowiana

The composition and amounts of liposoluble substances in the flesh and peel of feijoa fruit has been investigated. About 30 groups of lipid substances have been identified. The main groups of lipids in the flesh were triacylglycerols, sterols, cerebrosides, ceramide phosphate inositol oligosides, sulfoquinovosyldiacylglycerols, phosphatidic acids, phosphotidylglycerols and phosphatidylcholines. In the peel, hydrocarbons, sterols, esters of fatty acids and lower alcohols, cerebrosides, digalactosyldiacylglycerols, ceramide oligosides, phosphatidylglycerols, and include predominated. The fatty acids of the flesh were found to include 15 representatives (C_12:0–C_28:0), and those of the flesh 11 representatives tives (C_12:0–C_18:3).M. V. Lomonosov Technological Institute of the Food Industry, Odessa. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 464–467, July–August, 1991.     

Additivity of atomic static polarizabilities and dispersion coefficients

A new empirical method is proposed to evaluate the average molecular polarizabilities assuming the additivity of atomic static polarizability. Atomic static polarizability for each atom in a particular valence state is obtained. Calculated molecular polarizabilities of 94 non-halogenated compounds and of the bases in nucleic acids show the excellent agreement with experimental data.To check the further validity of this method, dispersion coefficients for CH₄, C₂H₆, C₃H₈,n–C₄H₁₀,n–C₅H₁₂,n–C₆H₁₄,n–C₇H₁₆,n–C₈H₁₈, H₂, H₂O and NH₃ are obtained from a sum of atomic terms using a London-type formula, and are compared with the accurate values of dipole oscillator strength distribution (DOSD) method. The results show the excellent agreement between theory and experiment.     

Alkaloids ofAconitum coreanum. I. Structure of acorine

Two C₂₀-diterpene alkaloids have been isolated from the epigeal part ofAconitum coreanum (Levl.) Rapaics: the known 14-hydroxy-2-isobutyrylhetesine (I) (Guan-Fu base Z) and a new one — acorine (II), C₂₂H₂₉NO₅, mp 214–215°C (from acetone), _D ²⁰ +9° (c 0.01; methanol), for which the structure of 2-acetyl-14-hydroxy-hetesine has been established. Details of the IR, mass, and¹³C NMR spectrum of (I) and (II) and of the PMR spectrum of (II) are given.Institute of the Chemisry of Plant Substances of the Uzbek Academy of Sciences, Tashkent. All Union Scientific-Research Institute of Medicinal Plants. Translated from Khimiya Prirodnykh Soedenenii, No. 5, pp. 690–692, September–October, 1987.     

Analysis of the hydroxyacyldiacylglycerides of sea buckthorn seed oil

The TMS derivatives of the hydroxyacyldiacylglycerides of sea buckthorn seed oil have been analyzed by mass spectrometry. On the basis of characteristic fragments it has been established that an acyl residue of one of the seven hydroxy acids found previously in hydrolysis products by the GC-MS method is attached in one of the positions of the hydroxyacyldiacylglycerides. The remaining positions are substituted by acyl radicals of the C_18:1, C_18:2, C_18:3 and C_18:0 acids. The 24 most probable components of the triglycerides include these acyl and hydroxyacyl substituents. Features of the fragmentation of the components due to presence of polyunsaturated acids have been revealed.Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 176–182, March–April, 1991.     

Lactones ofFerula gigantea

The following substances have been isolated from an acetone extract ofFerula gigantea B. Fedtsch.: a coumarin — umbelliferone, C₉H₆O₂, mp 230–233°C; and sesquiterpene lactones — talassin A, C₂₅H₃₀O₇, mp 188–191°C; malaphyllinin, C₂₄H₂₄O₇, mp 231–235°C; malaphyll, C₂₉H₃₂O₉, mp 212–213°C; and malaphyllin, C₂₆H₂₈O₉, mp 216–218°C. Structures have been proposed for three new sesquiterpene lactones on the basis of an analysis of their spectral characteristics.All-Union Scientific-Research Institute of Medicinal Plants, Moscow. M. V. Lomonosov Moscow State University, Botanical Garden, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 490–495, July–August, 1979.     

Nonglyceride lipids of the seed coats ofArtemisia absinthium andOnopordum acanthium

The seed coats ofArtemisia absinthium andOnoporum acanthium have been shown to contain paraffinic hydrocarbons (C₃₁-C₂₅ and C₃₁-C₂₇, respectively), wax esters (C₃₂-C₂₃ and C₅₁-C₃₃), acetyltriterpenols (six types, five types), and acyltriterpenols with a predominance of palmitoyltriterpenols (esters of higher saturated unbranched C_32:0-C_12:0 fatty acids and triterpenols with a molecular weight of 426 belonging to the ursene group).Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 154–157, March–April, 1981.     

Vanilline Alkanoates in the Synthesis of Hexahydrobenzacridine and Octahydroxanthene Derivatives

Cascade heterocyclization of 1,3-cyclohexanedione and dimedone with 2-naphthylamine and vanilline esters gave derivatives of 2-methoxy-4-(alkyl-11-oxo-7,8,9,10,11,12-hexahydrobenz[a]acridin-12-yl)- and 2-methoxy-4-(alkyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl esters of aliphatic (C₁– C₄ ) carboxylic acids.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 4, 2005, pp. 654–658.Original Russian Text Copyright © 2005 by Kozlov, Basalaeva.     

Extended Hypervalent 5c–6e Interactions: Linear Alignment of Five C─Z- - -O- - -Z─C (Z = S,Se) Atoms in Anthraquinone and Anthracene Systems

Abstract

Structures of 1,8-(ArZ)₂C₁₄H₆O₂ and 9-(MeO)-1,8-(ArZ)₂C₁₄H₇ (Z = S, Se) are determined by X-ray crystallographic analysis. Five C─Z- - -O- - -Z─C atoms of the compounds align linearly, which are analyzed by the extended hypervalent 5c–6e model, based on QC calculations. CT of the 5c–6e occurs as the σ^*(C─Z) ← n _p (O)→ σ*(Z─C) direction.     

Small-angle neutron scattering from micelles of alkylpolyoxyethylene sulfate: Effect of chain length

Small-angle neutron scattering (SANS) data have been obtained for (i) a series of solutions of C _m H_2m+1(OCH₂–CH₂)₂SO₄Na, for m=18, 16, and 14; (ii) an approximately 0.07M solution of C₁₄H₂₉(OCH₂–CH₂)₂SO₄Na to which different amounts of NaCl were added; and (iii) a series of solutions of variable concentration of C₁₂H₂₅(OCH₂–CH₂)SO₄Na. The increase of the number of carbon atoms of the hydrocarbon chain produces a noticeable increase of the aggregation number of the micelles, while the salt tolerance decreases with increasing m. All the data can be described in terms of a monodispersed, charged, hard-spheres model interacting via a screened Coulombic potential, except the run at highest salt concentration, for which an ellipsoid model gives better results.     

Synthesis of hexylthiols C6H13SH−1/1, 2, 3, 4−14C1/4/' /1-thiol[35S]/ and C6H13SH−2/1, 2, 3, 4−14C1/4/, /2-thiol[35S]/

A synthesis of¹⁴C and³⁵S double labelled hexylthiols: C₆H₁₃SH–1/1, 2, 3, 4–¹⁴C_1/4/, /1-thiol[³⁵S]/ and C₆H₁₃SSH–2/1, 2, 3, 4–¹⁴C_1/4/, /2-thiol[³⁵S]/ based on H₂ ³⁵S and C₆H₁₂–/1, 2, 3, 4–¹⁴C_1/4/ has been developed and described.     

Nonglyceride complex of the seed oil ofOnopordum acanthium

Extraction of the comminuted seeds has yielded an oil from which have been isolated: C₃₃-C₂₅, C₁₈ and C₁₇ paraffinic hydrocarbons, C_18:1, C_18:2, C_18:3, C_17:1, C_17:2 and C_17:3 olefinic hydrocarbons, ethyl esters of C_32:0, C_31:0, C_30:0, C_29:0, and C_28:0 fatty acids, sterols with molecular weights of 414, 412, and 400, and the alcohols -amyrin and lupeol with their natural acetates. Extraction of the uncomminuted seeds has shown that the paraffinic hydrocarbons, ethyl esters, and alcohol acetates pass into the oil from the husks of the seeds. This is the first time that the C_31:0 and C_29:0 fatty acids have been detected as natural compounds, and it is the first time that the ethyl esters of C₃₄, C₃₃, C₃₂, C₃₁, and C₃₀ fatty acids have been isolated from seed oils of higher plants.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 612–615, September–October, 1979.     

Determination of fatty acids in atmospheric samples via GC/MS

Summary Atmospheric precipitation and aerosol samples are characterized by a complex mixture of several organic compounds. A simple method for the simultaneous determination of the main compound classes by GC/MS is presented. In detail, seasonal variations of C₈–C₃₂ fatty acids in precipitation in a semirural area have been studied. Total fatty acids concentrations of 7–53 g/l were detected. Summer rain is characterized by high amounts of fatty acids >C₂₀ and lower amounts of C₁₁–C₂₀ species. Two effects may be responsible: larger emission rates of fatty acids during vegetation periods and an increased influence of vapour phase due to higher temperatures during summer. CPI values showed no general trend; lower CPI values for winter rain could not be observed. This would be expected if anthropogenic sources play an important role. Monounsaturated fatty acids (C_16:1, C_18:1) were more abundant during winter than in summer. High concentrations of polyunsaturated fatty acids (C_18:x) could be detected during summer. High relative concentrations of the potential oxidation products of the unsaturated species, nonanedioic acid and w-oxononanoic acid, are associated with relatively low concentrations of their precursors.     

Positional isomers of monoenoic fatty acids from human milk

Summary Gas-liquid chromatographic analysis on capillary column in combination with mass spectrometry (LKB 9000) gave evidence for the occurence of positional isomers of monoenoic fatty acids in human milk. After high vacuum fractional distillation, mercury adducting and preparative gas-liquid chromatography the even numbered monoenoic fatty acid methyl esters from C₁₀–C₁₈ were obtained in a purity of better than 99.5%. Samples of 1 mg were oxidized by a modified reagent according to von Rudloff. Resulting mono- and dicarboxylic acids were analysed by gas-liquid chromatography. Overoxidation as determined with pure 9-octadecenoic acid was in the order of 1.5%. The number of isomers detected for C₁₀, C₁₂, C₁₄, C₁₆ and C₁₈ enoic acids were 8, 10, 10, 12, 9, respectively.

---

Stellungsisomere Monoenfettsäuren in der Muttermilch

Zusammenfassung Gas-Chromatographie auf Capillarsäule in Kombination mit Massenspektrometrie (LKB 9000) gab Anhaltspunkte für das Vorliegen stellungsisomerer Monoenfettsäuren in der Muttermilch. Die geradzahligen Monoenfettsäuren von C₁₀ bis C₁₈ wurden durch fraktionierte Destillation im Hochvakuum, Quecksilber-Adduktbildung und präparative Gas-Chromatographie in einer Reinheit von besser als 99,5% dargestellt. Trans-Fettsäuren konnten nicht nachgewiesen werden. Die oxydative Spaltung nach v. Rudloff erfolgte an Proben von je 1 mg, wobei die erhaltenen Mono- bzw. Dicarbonsäuren als Methylester gas-chromatographisch quantitativ analysiert wurden. Die Optimierung der Spaltansätze erfolgte mittels reiner 9-Octadecensäure. Unter den angegebenen Bedingungen war eine Überoxydation von maximal 1,5% zu beobachten. Die Zahlen der gefundenen Isomeren betragen 8, 10, 10, 12 und 9 für die C₁₀, C₁₂, C₁₄, C₁₆ und C₁₈ Monoensäuren in der angegebenen Reihenfolge.

     

Lipids of the vegetative and generative organs ofHibiscus sp.

The lipids of the leaves, stems, and roots ofHibiscus sp. have been studied. Their fatty acid compositions have been determined. The greatest amount of unsaturated fatty acids was present in the glycolipids of the leaves and the stems. More than 25% of low-molecular-mass C₁₀-C₁₂ fatty acids have been found in the neutral lipids of the roots.Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 705–708, September–October, 1996. Original article submitted March 11, 1996.