1120-28-1Relevant articles and documents
Acyl flavonoids, biflavones, and flavonoids from Cephalotaxus harringtonia var. nana
Komoto, Noriko,Nakane, Takahisa,Matsumoto, Sachiko,Hashimoto, Shusuke,Shirota, Osamu,Sekita, Setsuko,Kuroyanagi, Masanori
, p. 479 - 486 (2015)
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).
Valorization of Unconventional Lipids from Microalgae or Tall Oil via a Selective Dual Catalysis One-Pot Approach
Hess, Sandra K.,Schunck, Natalie S.,Goldbach, Verena,Ewe, Daniela,Kroth, Peter G.,Mecking, Stefan
, p. 13487 - 13491 (2017)
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%.
Dammarane triterpenoids from Carnauba, Copernicia prunifera (Miller) H. E. Moore (Arecaceae), wax
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.
, p. 1371 - 1376 (2017)
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.
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
Chivall, David,Berstan, Robert,Bull, Ian D.,Evershed, Richard P.
, p. 1232 - 1240 (2012)
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
New extracellular fatty acids in culture filtrates of Sporothrix flocculosa and S. rugulosa
Choudhury,Traquair,Jarvis
, p. 84 - 87 (1995)
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.
Rapid differentiation of isomeric lipids by photodissociation mass spectrometry of fatty acid derivatives
Pham, Huong T.,Trevitt, Adam J.,Mitchell, Todd W.,Blanksby, Stephen J.
, p. 805 - 815 (2013)
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
Three new fatty acid esters from the mushroom Boletus pseudocalopus
Kim, Ki Hyun,Choi, Sang Un,Lee, Kang Ro
, p. 593 - 599 (2012)
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.
Sphingolipids from Bombycis Corpus 101A and their neurotrophic effects
Kwon, Hak Cheol,Lee, Kang Choon,Cho, Ock Ryun,Jung, I Yeon,Cho, Sae Yun,Kim, Sun Yeou,Lee, Kang Ro
, p. 466 - 469 (2003)
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
PROCESS FOR PREPARATION OF ARACHIDIC ACID
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, (2021/10/15)
The present application relates to an improved process for preparation of arachidic acid.
GC-FID analysis of fatty acids and biological activity of Zanthoxylum rhetsa (Roxb.) DC seed oil
Naik, Rajashri R.
, p. 1929 - 1935 (2016/02/27)
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.
