- Acyl flavonoids, biflavones, and flavonoids from Cephalotaxus harringtonia var. nana
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A methanol extract of the leaves of Cephalotaxus harringtonia var. nana and its ethyl acetate (EtOAc)-soluble fraction demonstrated strong antitumor activity against A549 and HT-29 cell lines. The EtOAc-soluble fraction was purified by column chromatography and high-performance liquid chromatography (HPLC) using a reverse-phase column to yield three novel acyl flavonoids and a biflavonoid, along with 15 other known compounds that included flavonoids, biflavonoids, and other phenolics. The structures of the new compounds were elucidated using spectral data from HR-MS and NMR, including two-dimensional NMR studies, as (2R,3R)-3-O-eicosanoyltaxifolin (1), (2R,3R)-3-O-docosanoyltaxifolin (2), (2R,3R)-3-O-tetracosanoyltaxifolin (3), and 6-methyl-4′,7,7′-tri-O-methylamentoflavone (4). The isolated compounds, including the known compounds, were tested for possible antitumor activity; some of the biflavones were found to be active. The potent antitumor activity of the extract was attributed to Cephalotaxus alkaloids, such as homoharringtonine (20).
- Komoto, Noriko,Nakane, Takahisa,Matsumoto, Sachiko,Hashimoto, Shusuke,Shirota, Osamu,Sekita, Setsuko,Kuroyanagi, Masanori
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- Valorization of Unconventional Lipids from Microalgae or Tall Oil via a Selective Dual Catalysis One-Pot Approach
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A dual catalysis approach enables selective functionalization of unconventional feedstocks composed of complex fatty acid mixtures with highly unsaturated portions like eicosapentaenoate (20:5) along with monounsaturated compounds. The degree of unsaturation is unified by selective heterogeneous hydrogenation on Pd/γ-Al2O3, complemented by effective activation to a homogeneous carbonylation catalyst [(dtbpx)PdH(L)]+ by addition of diprotonated diphosphine (dtbpxH2)(OTf)2. By this one-pot approach, neat 20:5 as a model substrate is hydrogenated to up to 80% to the monounsaturated analogue (20:1), this is functionalized to the desired C21 α,ω-diester building block with a linear selectivity of over 90%. This catalytic approach is demonstrated to be suitable for crude microalgae oil from Phaeodactylum tricornutum genetically engineered for this purpose, as well as tall oil, an abundant waste material. Both substrates were fully converted with an overall selectivity to the linear α,ω-diester of up to 75%.
- Hess, Sandra K.,Schunck, Natalie S.,Goldbach, Verena,Ewe, Daniela,Kroth, Peter G.,Mecking, Stefan
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- Dammarane triterpenoids from Carnauba, Copernicia prunifera (Miller) H. E. Moore (Arecaceae), wax
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Phytochemical investigation from carnauba (Copernicia prunifera) wax led to the identification of sixteen dammarane–type triterpenes, including thirteen new characterized as: (24R*)-methyldammara-20,25-dien-3α-ol and a mixture of alkyl (24R*)-methyldammar-25-en-20-ol-3β-carboxylates, together with three previously described triterpenes: carnaubadiol, (24R*)-methyldammara-20,25-dien-3β-ol and (24R*)-24-methyldammara-20,25-dien-3-one. Moreover, four fatty alcohols (eicosanol, docosanol, tetracosanol and hexacosanol) as well as four sterols (cholesterol, campesterol, stigmasterol, and sitosterol) were also obtained. These compounds were isolated using classical chromatographic methods and their structures were determined by spectroscopic and chemical methods.
- De Almeida, Buana C.,Araújo, Bruno Q.,Barros, Elcio D. S.,Freitas, Samya D. L.,Maciel, Dayany S. A.,Ferreira, Ari J. S.,Guadagnin, Rafael C.,Vieira, Gerardo M.,Lago, Jo?o H. G.,Chaves, Mariana H.
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- Isotope effects associated with the preparation and methylation of fatty acids by boron trifluoride in methanol for compound-specific stable hydrogen isotope analysis via gas chromatography/thermal conversion/isotope ratio mass spectrometry
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Rationale: Compound-specific stable hydrogen isotope analysis of fatty acids is being used increasingly as a means of deriving information from a diverse range of materials of archaeological, geological and environmental interest. Preparative steps required prior to isotope ratio mass spectrometry (IRMS) analysis have the potential to alter determined δD values and hence must be accounted for if accurate δD values for target compounds are to be obtained. METHODS Myristic, palmitic, stearic, arachidic and behenic saturated fatty acids were derivatised to their respective fatty acid methyl esters (FAMEs), using 14% (w/v) boron trifluoride in methanol then analysed by gas chromatography/thermal conversion/IRMS (GC/TC/IRMS). FAMEs generated from fatty acid sodium salts of unknown δD values were then used to test a correction factor determined for this method of derivatisation. RESULTS Derivatisation was found to alter the hydrogen isotopic composition of FAMEs although this effect was reproducible and can be accounted for. The difference between the mean corrected and mean bulk δD values was always less than 6.7 %. Extraction of saturated fatty acids and acyl lipids from samples, subsequent hydrolysis, then separation on a solid-phase extraction cartridge, was found to alter the determined δD values by less than one standard deviation. CONCLUSIONS Overall, it has been shown that for natural abundance hydrogen isotope determinations, the isolation and derivatisation of extracted fatty acids alters the determined δD values only by a numerical increment comparable with the experimental error. This supports the use of the described analytical protocol as an effective means of determining fatty acid δD values by GC/TC/IRMS. Copyright
- Chivall, David,Berstan, Robert,Bull, Ian D.,Evershed, Richard P.
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- New extracellular fatty acids in culture filtrates of Sporothrix flocculosa and S. rugulosa
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Two new and rare unsaturated, extracellular fatty acids were identified in the culture filtrates of the biocontrol fungi, Sporothrix flocculosa and S. rugulosa. 16-Methyl-9E-nonadecenoic acid (1) and (Z,Z)-10,14-eicosadienoic acid (2) were characterized on the basis of infrared (1R) and nuclear magnetic resonance spectra (13C and 1N NMR), and gas chromatographic - mass spectrometric data (GC-MS). The structure of compounds 1 and 2 was confirmed by oxidative degradation to the known standards, dimethyl azelate, dimethyl succinate, dimethyl sebacate, and methyl caproate.
- Choudhury,Traquair,Jarvis
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- Rapid differentiation of isomeric lipids by photodissociation mass spectrometry of fatty acid derivatives
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Rationale: Both traditional electron ionization and electrospray ionization tandem mass spectrometry have demonstrated limitations in the unambiguous identification of fatty acids. In the former case, high electron energies lead to extensive dissociation of the radical cations from which little specific structural information can be obtained. In the latter, conventional collision-induced dissociation (CID) of even-electron ions provides little intra-chain fragmentation and thus few structural diagnostics. New approaches that harness the desirable features of both methods, namely radical-driven dissociation with discrete energy deposition, are thus required. Methods: Herein we describe the derivatization of a structurally diverse suite of fatty acids as 4-iodobenzyl esters (FAIBE). Electrospray ionization of these derivatives in the presence of sodium acetate yields abundant [M + Na]+ ions that can be mass-selected and subjected to laser irradiation (λ = 266 nm) on a modified linear ion-trap mass spectrometer. Results: Photodissociation (PD) of the FAIBE derivatives yields abundant radical cations by loss of atomic iodine and in several cases selective dissociation of activated carbon-carbon bonds (e.g., at allylic positions) are also observed. Subsequent CID of the [M + Na - I]?+ radical cations yields radical-directed dissociation (RDD) mass spectra that reveal extensive carbon-carbon bond dissociation without scrambling of molecular information. Conclusions: Both PD and RDD spectra obtained from derivatized fatty acids provide a wealth of structural information including the position(s) of unsaturation, chain-branching and hydroxylation. The structural information obtained by this approach, in particular the ability to rapidly differentiate isomeric lipids, represents a useful addition to the lipidomics tool box. Copyright
- Pham, Huong T.,Trevitt, Adam J.,Mitchell, Todd W.,Blanksby, Stephen J.
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- Three new fatty acid esters from the mushroom Boletus pseudocalopus
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A bioassay-guided fractionation and chemical investigation of a MeOH extract of the Korean wild mushroom Boletus pseudocalopus resulted in the identification of three new fatty acid esters, named calopusins A-C (1-3), along with two known fatty acid methyl esters (4-5). These new compounds are structurally unique fatty acid esters with a 2,3-butanediol moiety. Their structures were elucidated through 1D- and 2D-NMR spectroscopic data and GC-MS analysis as well as a modified Mosher's method. The new compounds 1-3 showed significant inhibitory activity against the proliferation of the tested cancer cell lines with IC50 values in the range 2.77-12.51 μM. AOCS 2011.
- Kim, Ki Hyun,Choi, Sang Un,Lee, Kang Ro
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- Sphingolipids from Bombycis Corpus 101A and their neurotrophic effects
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Three new (2-4) and one known (1) sphingolipid were identified in the MeOH extract of Bombycis Corpus 101A. Their structures were elucidated as (4E,2S,3R)-2-N-octadecanoyl-4-tetradecasphingenine (1), (4E,6E,2S,3R)-2-N-eicosanoyl-4,6-tetradecasphingadienin
- Kwon, Hak Cheol,Lee, Kang Choon,Cho, Ock Ryun,Jung, I Yeon,Cho, Sae Yun,Kim, Sun Yeou,Lee, Kang Ro
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- PROCESS FOR PREPARATION OF ARACHIDIC ACID
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The present application relates to an improved process for preparation of arachidic acid.
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- GC-FID analysis of fatty acids and biological activity of Zanthoxylum rhetsa (Roxb.) DC seed oil
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The Fatty acid content and composition of fixed oil from Zanthoxylum rhetsa seeds was determined. The seeds were found to contain about ~19.5% of crude fixed oil on a dry weight basis. Fatty acids were converted into methyl esters and analyzed by GC-FID. Ten fatty acids were identified using GC-FID. The major monounsaturated and saturated fatty acids were oleic acid (41.6 - 43.5%) and palmitic acid (26.8-30.2%) respectively, whereas the α-linolenic acid (12.1 - 12.5%) and linoleic acid (10.0%) were polyunsaturated fatty acid. Stearic acid (5.2 - 6.0%), myristic acid (0.1%), traces of pentadecanoic, heptadecanoic and arachidic acid were also identified. These fatty acids have not been reported earlier from the oil of Z. rhetsa. Fixed oil exhibited significant free radical scavenging activity which was measured using DPPH, and is also known to inhibit the gastrointestinal motility significantly.
- Naik, Rajashri R.
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p. 1929 - 1935
(2016/02/27)
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- Anti-H5N1 virus new diglyceride ester from the Red Sea grass Thallasodendron ciliatum
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Some Egyptian plants were screened against highly pathogenic avian influenza strain H5N1 using plaque inhibition assay in Madin-Darby canine kidney. The results indicated that the extracts of Red Sea grass Thallasodendron ciliatum possessed potent antiviral activity (100% inhibition at the concentration of 1mgmL21). The bioactivityguided fractionations led to the isolation of a new diglyceride ester (1) along with asebotin (2) for the first time from the plant. The two isolates showed reduction of virus titre by 67.26% and 53.81% inhibition at concentration of 1 ngmL21, respectively.
- Ibrahim, Amany K.,Youssef, Ahmed I.,Arafa, Abdel Satar,Foad, Reda,Radwan, Mohamed M.,Ross, Samir,Hassanean, Hashim A.,Ahmed, Safwat A.
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supporting information
p. 1625 - 1632
(2013/10/01)
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- Solvent-free esterification of carboxylic acids and alcohols in the presence of silphos [PCl3-n(SiO2)n] as a heterogeneous phosphine reagent
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An efficient solvent-free method for the preparation of esters from various aromatic and aliphatic acids with primary, secondary, and tertiary alcohols using a heterogeneous phosphine reagent, silphos [PCl3-n(SiO 2)n], in good yields is reported.
- Rao, Ambati Narasimha,Ganesan, Kumaran,Shinde, Chandra Kant
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experimental part
p. 2299 - 2308
(2012/06/18)
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- Method of producing dicarboxylic acids
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A method of producing dicarboxylic acids (e.g., α,ω dicarboxylic acids) by reacting a compound having a terminal COOH (e.g., unsaturated fatty acid such as oleic acid) and containing at least one carbon-carbon double bond with a second generation Grubbs catalyst in the absence of solvent to produce dicarboxylic acids. The method is conducted in an inert atmosphere (e.g., argon, nitrogen). The process also works well with mixed unsaturated fatty acids obtained from soybean, rapeseed, tall, and linseed oils.
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Page/Page column 13; 19
(2009/05/29)
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- DIRECT METHOD AND REAGENT KITS FOR FATTY ACID ESTER SYNTHESIS
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Provided are efficient, cost-effective and water tolerant methods (e.g., single-vial methods) for preparing fatty acid esters from organic matter, comprising: obtaining organic matter comprising at least one fat substituent, contacting the organic matter in a reaction mixture with a basic solution under conditions suitable to provide for hydrolytic release of monomeric fatty acids from the at least one fat substituent to provide a base-treated reaction mixture, and esterifying the monomeric fatty acids of the base-treated reaction mixture by acidification of the reaction mixture and treating in the presence of an organic alcohol to provide fatty acid esters. The methods optionally further comprise, prior to esterifying, neutralizing the base-treated reaction mixture to provide for neutralized fatty acids, separating the neutralized fatty acids from the neutralized reaction mixture, and dissolving the separated fatty acids in the esterification reaction mixture. Also provided are related methods and kits for fat analysis.
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Page/Page column 18; 21-22; 29
(2008/12/07)
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- Novel galactolipids from the leaves of Ipomoea batatas L.: Characterization by liquid chromatography coupled with electrospray ionization-quadrupole time-of-flight tandem mass spectrometry
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Sixteen novel and ten known galactolipids have been isolated and characterized from the leaves of Ipomoea batatas L. (sweet potato) using an analytical method based on high-performance liquid chromatography coupled with electrospray ionization-quadrupole
- Napolitano, Assunta,Carbone, Virginia,Saggese, Paola,Takagaki, Kinya,Pizza, Cosimo
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experimental part
p. 10289 - 10297
(2009/10/02)
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- SINGLE-STAGE ESTERIFICATION OF OILS AND FATS
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A process for producing alkyl esters useful as biofuels and/or lubricants. An alkyl ester product produced by the process. The process comprises a single- stage reaction for esterifying a de-watered glyceride-containing feedstock with an anhydrous short chain alcohol in the presence of a basic esterification catalyst to produce a reaction product comprising alkyl esters and a reaction by-product comprising glycerol-containing substances and the catalyst-containing alcohol. The single-stage esterification reaction is conducted within a temperature and negative-pressure controllable vessel. The alkyl ester product is separated from the reaction by-product and may be further de-watered and/or purified. The catalyst-containing alcohol may be separated from the reaction by-product, de- watered and reused. The glycerol-containing substances may be separated from the reaction by-product and further purified. Useful glyceride-containing feedstocks include those prepared from plant or animal or fish materials, particularly those produced from seeds of mustard, canola, soybean, corn, cotton, flax and palm.
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Page/Page column 10-12
(2008/06/13)
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- SYNTHETIC MOLECULES HAVING IMMUNE ACTIVITY
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The present invention is directed to synthetic molecules having biological activity similar to PIM (acyl glycerol phosphatidylinositol manno-oligosaccharide) activity, for use in the treatment and prevention of inflammatory or immune cell mediated diseases or disorders.
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Page/Page column 41
(2010/02/12)
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- Method for commercial preparation of conjugated linoleic acid using recycled alkali transesterification catalyst
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Conjugated linoleic acid is readily prepared by mixing crude alkaline glycerol solution derived as a byproduct of triglyceride transesterification and a linoleate rich triglyceride, ester, soap, phospholipid, fatty acid, or wax and heating the mixture sufficiently to conjugate the linoleate double bonds. The reaction produces a favorable isomer mixture enriched in 10,12-trans,cis octadecadienoic and 9,11-cis,trans-octadecadienoic acids.
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(2008/06/13)
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- New spingosines from two soft corals of the Andaman & Nicobar Islands
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A new spingosine mixture in which the N-palmitoyl-2-amino-1,3-dihydroxyoctadeca-4,8-diene (6) is the major component has been isolated from two soft corals -a new species of Lobophytum and Sinularia conferta Dana sensu Tixier-Durivault 1951 of the Andaman & Nicobar Islands. The spingosine has been characterized by chemical and spectral studies.
- Subrahmanyam,Kulatheeswaran,Rao, C. Venkateswara
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p. 578 - 580
(2007/10/03)
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- A New Synthesis of Long Chain Acid Esters and Carbinols
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A versatile synthesis of difficulty accessible long chain acid esters and carbinols is described.The synthesis involves acylations at 2- and 5-positions of thiophene.Thioketalation of the resulting ketoesters followed by Raney nickel desulfurization yield acid esters which on LAH reduction give the corresponding carbinols.
- Rao, S. Jagadishwar,Bhalerao, U. T.,Tilak, B. D.
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p. 208 - 211
(2007/10/02)
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