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 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.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 515–518, July–August, 1993.     

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.     

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.     

Lipids of the seeds of Cynoglossum officinale

The compositions of the lipids and fatty acids of the seeds ofCynoglossum officinale, familyBoraginaceae have been established. The bulk of the lipids consisted of netural compounds (95.2%), while the amounts of glycolipids and phospholipids were 3.1 and 1.7%, respectively. Among the fatty acids, in addition to the usual components, acids characteristic for theBoraginaceae family have been found: 18:3 (6, 9, 12), 18:3 (9, 12, 15), 18:4 (6, 9, 12, 15), 20:1 (11), 22:1 (13), and 24:1 (15).Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. South Urals Reservation, Bashkir. Institute of Chemistry, Bashkir Scientific-Center, Urals Branch, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 758–762, November–December, 1991.     

Lipids of the seeds ofPaliurus spina-christi

The composition of the unsaturated and oxidized fatty acids and steroids of the lipids of the seeds ofPaliurus spina-christi has been determined. Among the unsaturated acids the 20:1 (11) was detected, while the 18:1 and 18:2 acids predominate. The oxidized acids are represented by the sum of the 9,10(12,13)-epoxy-12(9)-18:1, the 9,10-epoxy-18:0, the oxo-18:1, the oxo-18:2, the 12-hydroxy-9-18:1, and the 9-hydroxy-10,11-18:2 acids. The main component of the sterols is -sitosterol. It has been found that the composition of the acylglycerols of the lipids of the seeds ofP. spina-christi gathered in different years is variable.I. G. Kutateladze Institute of Pharmatochemistry, Academy of Sciences of the Georgian SSR, Tbilisi. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 322–326, May–June, 1985.     

Synthesis of Fatty-Acid Ethanolamides from Linum catharticum Oils and Cololabis saira Fats

Ethanolamides of polyunsaturated fatty acids (9Z,12Z,15Z-octadecatrienoic; 5Z,8Z,11Z,14Z,17Z-eicosapentaenoic; and 4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic) and mixtures of ethanolamides of fatty acids from natural fats (oils) were synthesized. It was found that the polyunsaturated fatty acids did not isomerize under the proposed conditions for aminolysis of the ester bond. Conditions for analyzing the complicated mixtures of ethanolamides of fatty acids by HPLC-MS were determined.     

New hydroxy fatty acids of Acanthopanax sessiliflorus

The structures of six new hydroxy fatty acids from the hydroxyacyldiacylglycerols of the fruit ofAcanthopanax sessiliflorus (Rupr. et amaxim.) Seem. (family Araliaceae have been established as 6-hydroxyhexadeca-12Z-enoic, 6-hydroxyhexadeca-9Z,12Z-dienoic, and the isomeric 6- and 7-hydroxyoctadeca-12-Z-enoic, and 6- and 7-hydroxyoctadeca-9Z,12Z-dienoic acids and their quantitative amounts have been determined with the aid of spectral, chromatographic, and chemical methods of analysis.Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 616–619, September–October, 1991.     

Lipids of the seeds of Cynoglossum officinale

The compositions of the lipids and fatty acids of the seeds ofCynoglossum officinale, familyBoraginaceae have been established. The bulk of the lipids consisted of netural compounds (95.2%), while the amounts of glycolipids and phospholipids were 3.1 and 1.7%, respectively. Among the fatty acids, in addition to the usual components, acids characteristic for theBoraginaceae family have been found: 18:3 (6, 9, 12), 18:3 (9, 12, 15), 18:4 (6, 9, 12, 15), 20:1 (11), 22:1 (13), and 24:1 (15). Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. South Urals Reservation, Bashkir. Institute of Chemistry, Bashkir Scientific-Center, Urals Branch, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 758–762, November–December, 1991.     

Cellular Fatty Acid Composition of Vibrio parahaemolyticus by Reversed-Phase High-Performance Liquid Chromatography

Abstract

High-performance liquid chromatography was used to separate and identify cellular fatty acids isolated from Vibrio parahaemolyticus, a gram-negative estuarine microorganism associated with seafood-borne enteritis in man. Fatty acids were isolated from statically grown bacterial cultures, saponified, and derivatized with an ultraviolet tag. Aliquots of derivatized fatty acids were injected onto a reversed-phase column with water:acetonitrile gradient as the mobile phase and ultraviolet detection at 254 nm. The predominant fatty acids found for the V. parahaemolyticus strains studied were C12, C14, C16:1, C16, C18:1, and C18. In addition, previously unreported fatty acids C13, C17, C19, and C21 were identified. Comparison of HPLC with GLC fatty acid separations showed good agreement with the exception that HPLC was able to resolve previously unidentified fatty acid constituents.     

碱催化法衍生化气相色谱/质谱法分析青海湖裸鲤鱼油中的脂肪酸

用碱催化法将青海湖裸鲤鱼油甲酯化,以气相色谱/质谱法分析鱼油中的脂肪酸。青海湖裸鲤可食用部分中鱼油含量为25.13%。从鱼油中共鉴定出47种脂肪酸,包括直链、单支链、多支链饱和脂肪酸,单不饱和、多不饱和脂肪酸,环丙烷基、呋喃基脂肪酸等。不饱和脂肪酸含量为73.6%,其中多不饱和脂肪酸含量为25.4%,以C18∶2(4.9%),C18∶3(3.1%),C20∶4(1.3%),C20∶5(二十碳五烯酸（EPA）, 9.4%)和C22∶6(二十二碳六烯酸（DHA）, 6.7%)为主。单不饱和脂肪酸含量为48.2%,主要由C16∶1(20.3%),C18∶1(25.9%)构成。饱和脂肪酸含量为25.7%,主要有C14∶0(3.4%),C16∶0 (19.4%)和C18∶0(1.1%)。青海湖裸鲤鱼油中还存在不常见的环丙烷基和呋喃基脂肪酸及多种奇数碳链和支链脂肪酸。因此,青海湖裸鲤是功能性脂肪酸的重要膳食来源。     

The fatty acid composition of the phospholipids of cottonseed oil

Summary 1. The phospholipids of cottonseed oil contain ten fatty acids.2. The positions of the double bonds in the aliphatic chain in the newly discovered unsaturated fatty acids — palmitlinoleic, palmitlinolenic, linolenic, and eicosadienic — have been established by the method of gas-liquid chromatography: they are present at the 6, 9; 6, 9, 12; 9, 12, 15; and 11, 14 carbon atoms, respectively, counting from the carboxyl end of the chain. A saturated fatty acid (myristic) has been found in the phospholipids of cottonseed oil for the first time.Khimiya Prirodnykh Soedinenii, Vol. 1, No. 3, pp. 199–201, 1965     

Structures of two new diterpenoids from Teucrium polium

Two new acids of the neoclerodane series have been isolated fromTeucrium polium L. (Lamiaceae); they have been called tepolin A and tepolin B and their structures have been established on the basis of spectral characteristics as 7,12,19-trihydroxy-6,18:15,16-diepoxycleroda-3,13(16),14-triene-9-carboxylic acid and 12,19-dihydroxy-6,18:15,16-diepoxycleroda-3,13(16)-14-triene-9-carboxylic acid, respectively.Institute of Fine Organic Chemistry, Armenian Academy of Sciences, Erevan. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 503–508, September–October, 1992.     

Liquid chromatographic–electrospray mass spectrometric study of the phthalides of Angelica sinensis and chemical changes of Z-ligustilide

High-performance liquid chromatography–electrospray ionization–mass spectrometry has been applied to analyze the chemical constituents of Danggui (the rhizome of Angelica sinensis) and to study chemical changes of Z-ligustilide. Twelve phthalides were unambiguously identified as senkyunolide I (3), senkyunolide H (4), sedanenolide (8), butylphthalide (9), E-ligustilide (13), Z-ligustilide (14), Z-butylidenephthalide (15), Z,Z′-6.8′,7.3′-diligustilide (16), angelicide (17), levistolide A (18), Z-ligustilide dimer E-232 (19) and Z,Z′-3.3′,8.8′-diligustilide (20) in Danggui extract. The existence of 12 other phthalides (2, 5–7, 11, 12, 22–27), ferulic acid (1) and coniferyl ferulate (10) in Danggui extract has also been demonstrated. Phthalides 3, 4, 16–18 and 20 were determined to be the products from chemical change of Z-ligustilide. This is the first report of the existence of 16 compounds (2–8, 10–12, 20, 22–25 and 27) in Danggui extract.     

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.     

The seed oil of Rindera oblongifolia

Summary The oil of the seeds ofRindera oblongifolia, family Boraginaceae, growing in Central Asia, has been studied for the first time. Among the acids of the triglycerides of the oil five types of monoenoic acid differing by the length of the carbon chain but having the same length of the terminal carbon chain — 18:1⁹, 20:1¹¹, 22:1¹³, 24:1¹⁵, and 26:1¹⁷ — have been detected for the first time. This is the first time that the last of these acids has been found in a seed oil of this family.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 26–29, January–February, 1976.     

Thermospray-mass spectrometric analysis of underivatized monohydroxy fatty acids: application to stimulated platelets

Monohydroxylated fatty acids prepared from polyunsaturated fatty acids of nutritional value were analysed by thermospray-mass spectrometry without prior chemical derivatization. Positive and negative ionization modes were compared. The highest sensitivity was observed with the negative ionization mode with detection limits of 10 pmol based on the 12-hydroxy derivative of eicosatrienoic acid (12-OH-8,10,14-20:3). This is comparable to that obtained by high-performance liquid chromatography with UV detection at 234 nm. Selected ion monitoring based on the fragment [M-H]- allowed a variety of standard monohydroxy fatty acids to be detected. This approach makes possible the analysis of various derivatives generated by thrombin-stimulated platelets (10(9) cells) pre-enriched with minor polyunsaturated fatty acids, even when these derivatives co-elute from the column (e.g., 12-HETE and 14-OH-22:6).     

Polyunsaturated fatty acids of the α-linolenic series from insulin production wastes

The following polyenic acids has been isolated from insulin production waste and have been determined quantitatively: eicosa-5Z,8Z,11Z,14Z-pentaenoic, docosa-7Z,10Z,13Z,16Z,19Z-pentaenoic, and docosa-4Z,7Z,10Z,13Z,16Z,19Z-hexaenoic acids. They were identified by PMR and¹³C NMR.All-Union Scientific-Research Institute of the Technology of Blood Substitutes and Hormone Preparations, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 205–212, March–April, 1987.     

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.     

Influence of infection by Verticillium dahliae on the cuticular lipids of the leaves of cotton plants of variety 175

The composition of the cuticular lipids of young leaves of cotton plants of the wilt-resistant variety 175-F has been determined and it has been established that on artificial infection of the plant with cotton wilt(Verticilliuim dahliae) the component composition of these lipids did not change but the level of the 18:0, 18:1, and 18:2 acids in esters of fatty acids with alkanol, sterols, and triterpenols fell.Institute of the Chemistry of Plant Substances, Uzbek. Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 765–768, November–December, 1991.