- Epoxy-acetogenins and other polyketide epoxy derivatives as inhibitors of the mitochondrial respiratory chain complex I
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Annonaceous acetogenins (ACG), an extensive group of cytotoxic natural products, are antitumor agents whose main mode of action is inhibition of the mammalian mitochondrial complex I. Herein we describe the importance of the different chemical groups along the alkyl chain for optimal inhibitory potency, discussing the structurally relevant factors present in these compounds. For this purpose, a series of epoxide derivatives from α- linolenic acid were prepared and their activity compared with that of epoxy- acetogenins and tetrahydrofuranic (THF) acetogenins isolated from Rollinia membranacea.
- Tormo, Jose R.,Zafra-Polo,Serrano, Angel,Estornell, Ernesto,Cortes, Diego
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Read Online
- Chemical constituents and antibacterial activity of Melastoma malabathricum L.
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The aqueous methanolic extracts of Melastoma malabathricum L. exhibited antibacterial activity when assayed against seven microorganisms by the agar diffusion method. Solvent fractionation afforded active chloroform and ethyl acetate fractions from the leaves and the flowers, respectively. A phytochemical study resulted in the identification of ursolic acid (1), 2α- hydroxyursolic acid (2), asiatic acid (3), β-sitosterol 3-O-β-D-glucopyranoside (4) and the glycolipid glycerol 1,2-dilinolenyl-3-O-β-D-galactopyanoside (5) from the chloroform fraction. Kaempferol (6), kaempferol 3-O-α-L-rhamnopyranoside (7), kaempferol 3-O-β-D-glucopyranoside (8), kaempferol 3-O-β-D-galactopyranoside (9), kaempferol 3-O-(2 ,6 -di-O-E-p-coumaryl)-β-D-galactopyranoside (10), quercetin (11) and ellagic acid (12) were found in the ethyl acetate fraction. The structures of these compounds were determined by chemical and spectral analyses. Compounds 1-4, the flavonols (6 and 11) and ellagic acid (12) were found to be active against some of the tested microorganisms, while the kaempferol 3-O-glycosides (7-9) did not show any activity, indicating the role of the free 3-OH for antibacterial activity. Addition of p-coumaryl groups results in mild activity for 10 against Staphylococcus aureus and Bacillus cereus. Compounds 2-5, 7 and 9-12 are reported for the first time from M. malabathricum. Compound 10 is rare, being reported only once before from a plant, without assignment of the double bond geometry in the p-coumaryl moiety.
- Wong, Keng-Chong,Hag Ali, Dafaalla Mohamed,Boey, Peng-Lim
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- Secondary metabolites of Astragalus danicus Retz. and A. inopinatus Boriss
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The chemical composition of the above-ground parts of Astragalus danicus and A. inopinatus collected in the Baikal region (Eastern Siberia) was studied for the first time. From A. danicus, pentacyclic triterpene saponins were isolated and identified, viz., 3-O-(β-glucuronopyranosyl)-3β,22β,24-trihydroxyolean-12-ene, 3-O-[O-(β-D-xylopyranosyl)-(1→2)-(β-glucuronopyranosyl)]-3β, 22β,24-trihydroxyolean-12-ene, 3-O-[O-(β-D-glucopyranosyl)-(1→2)-(β-glucuronopyranosyl)]-3β ,22β,24-trihydroxyolean-12-ene, 3-O-[O-(α-L-rhamnopyranosyl)-(1→2)-O-(β-D-xylopyranosyl) -(1→2)-(β-glucuronopyranosyl)]-3β,22β,24-trihydroxyolean-12-ene, 3-O-[O-(α-L-rhamnopyranosyl)-(1→2)-O-(β-D-glucopyranosyl)-(l-2)-(β-glucuronopyranosyl)]-3β,22β,24-trihydroxyolean-12-ene, 3-O-methyl-D-chiro-inositol, and linolenic acid. In A. inopinatus, the same saponins were identified as well as tricosan-1-ol and tetracosan-1-ol, 5,7,4′-trihydroxyflavon (apigenin), and atetracyclic triterpenoid, 20(R),24(S)-epoxycyclolanost-9(11)-ene-3β,6α, 16β, 25-tetrol (cycloastragenol). All reported compounds from the both genus of Astragalus were isolated for the first time. Methanolic extracts of A. danicus and A. inopinatus exhibited low inhibitory activity with respect to the growth of HeLa cells. The chloroform fraction of A. danicus showed a strong antimicrobial activity against Staphylococcus aureus and a strong cytotoxic activity against HeLa cells.
- Gromova,Lutsky,Cannon,Li,Owen
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Read Online
- Linoleic acid, α-linolenic acid, and monolinolenins as antibacterial substances in the heat-processed soybean fermented with Rhizopus oligosporus
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Antibacterial activities against Staphylococcus aureus and Bacillus subtilis were found in an ethanol fraction of tempe, an Indonesian fermented soybean produced using Rhizopus oligosporus. The ethanol fraction contained free fatty acids, monoglycerides, and fatty acid ethyl esters. Among these substances, linoleic acid and α-linolenic acid exhibited antibacterial activities against S. aureus and B. subtilis, whereas 1-monolinolenin and 2-monolinolenin exhibited antibacterial activity against B. subtilis. The other free fatty acids, 1-monoolein, monolinoleins, ethyl linoleate, and ethyl linolenate did not exhibit bactericidal activities. These results revealed that R. oligosporus produced the long-chain polyunsaturated fatty acids and monolinolenins as antibacterial substances against the Gram-positive bacteria during the fungal growth and fermentation of heat-processed soybean.
- Kusumah, Dewi,Maeda, Isamu,Murakami, Mai,Wakui, Misaki,Xie, Xiaonan,Yukihito, Kabuyama
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p. 1285 - 1290
(2020/03/03)
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- Detection and identification of complex oxylipins in meadow buttercup (Ranunculus acris) leaves
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Screening of linolipins, i.e. galactolipids containing esterified residues of divinyl ether oxylipins, in the leaves of several higher plants revealed the presence of these complex oxylipins in the meadow buttercup leaves. The rapid accumulation of linoli
- Chechetkin, Ivan R.,Blufard, Alexander S.,Yarin, Andrey Y.,Fedina, Evgenia O.,Khairutdinov, Bulat I.,Grechkin, Alexander N.
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- Fatty acid based biocarbonates: Al-mediated stereoselective preparation of mono-, di- and tricarbonates under mild and solvent-less conditions
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A catalytic method for the preparation of a series of fatty acid derived biocarbonates has been developed using a binary Al-complex/PPNCl catalyst. This catalyst system allows conversion of fatty acid derived epoxides under comparatively mild reaction conditions (70-85 °C, 10 bar) while maintaining high levels of diastereospecificity with cis/trans ratios of up to 97:3 in the products. The comparative catalysis data obtained for the reactions catalysed only by the nucleophilic halide based components show that the presence of the Al-complex is crucial for the retention of the original stereochemistry.
- Pe?a Carrodeguas,Cristòfol,Fraile,Mayoral,Dorado,Herrerías,Kleij
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supporting information
p. 3535 - 3541
(2017/08/15)
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- Stereoselective Synthesis of Z Fluoroalkenes through Copper-Catalyzed Hydrodefluorination of gem-Difluoroalkenes with Water
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A copper catalytic system was established for the stereoselective hydrodefluorination of gem-difluoroalkenes through C?F activation to synthesize various Z fluoroalkenes. H2O is used as the hydrogen source for the fluorine acceptor moiety. This mild catalytic system shows good-functional group compatibility, accepting a range of carbonyls as precursors to the gem-difluoroalkenes, including aliphatic, aromatic, and α,β-unsaturated aldehydes and even ketones. It serves as a powerful synthetic method for the late-stage modification of complex compounds.
- Hu, Jiefeng,Han, Xiaowei,Yuan, Yu,Shi, Zhuangzhi
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supporting information
p. 13342 - 13346
(2017/10/17)
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- Methanolysis of Jatropha curcas oil using K2CO3/CaO as a solid base catalyst
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Biodiesel, fatty acid methyl ester produced by the transesterification of vegetable oil with methanol, is a promising alternative to petroleum-based diesel fuel. In the present study, the methanolysis of high free fatty acid (FFA) Jatropha curcas oil in a transesterification reaction using K 2 CO 3 /CaO solid base catalyst was studied. The various reaction parameters in the transesterification reaction were also discussed. The catalyst was characterized by means of Fourier transform infrared, X-ray diffraction, temperature programmed desorption of CO 2, scanning electron microscopy, particle size analyzer, true density, and surface area analyzer. The optimum conversion of jatropha oil was 92% when the transesterification reaction was carried out at 70? C with 10:1 molar ratio of methanol to oil at reaction time of 3 h and catalyst amount of 6 wt%. The efficiency of catalysts in the methanolysis of jatropha oil was also investigated.
- Sahu, Gajanan,Saha, Sujan,Datta, Sudipta,Chavan, Prakash,Naik, Satyanarayan
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p. 845 - 861
(2018/01/12)
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- Plasticizer and surfactant formation from food-waste- and algal biomass-derived lipids
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The potential of lipids derived from food-waste and algal biomass (produced from food-waste hydrolysate) for the formation of plasticizers and surfactants is investigated herein. Plasticizers were formed by epoxidation of double bonds of methylated unsaturated fatty acids with in situ generated peroxoformic acid. Assuming that all unsaturated fatty acids are convertible, 0.35 and 0.40 g of plasticizer can be obtained from 1 g of crude algae- or food-waste-derived lipids, respectively. Surfactants were formed by transesterification of saturated and epoxidized fatty acid methyl esters (FAMEs) with polyglycerol. The addition of polyglycerol would result in a complete conversion of saturated and epoxidized FAMEs to fatty acid polyglycerol esters. This study successfully demonstrates the conversion of food-waste into value-added chemicals using simple and conventional chemical reactions.
- Pleissner, Daniel,Lau, Kin Yan,Zhang, Chengwu,Lin, Carol Sze Ki
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p. 1686 - 1691
(2015/06/02)
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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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- Selective ethenolysis and oestrogenicity of compounds from cashew nut shell liquid
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The ethenolysis of cardanol (2), a waste product from cashew kernel production, was carried out using a variety of metathesis catalysts. Surprisingly, the best activities and selectivities could be observed with ruthenium based 1st generation type catalysts converting cardanol (2) almost completely to the corresponding 1-octene (6) and 3-non-8-enylphenol (4), a potential detergent precursor. Detailed investigation of the reaction system showed that the high activity and selectivity were due to a combination of ethenolysis and internal self-metathesis of the unsaturated cardanol mixture, 2. Self-metathesis of cardanol (2) containing three double bonds led to the formation of 3-non-8-enylphenol (4) and 1,4-cyclohexadiene (7). The latter was crucial for a high selectivity and activity in the ethenolysis, not only of cardanol (2), but also of other substrates like methyl oleate (10) when using ruthenium based 1st generation catalysts. The endocrine disrupting properties of 3-nonylphenol and related compounds are compared. the Partner Organisations 2014.
- Julis, Jennifer,Bartlett, Stuart A.,Baader, Sabrina,Beresford, Nicola,Routledge, Edwin J.,Cazin, Catherine S.J.,Cole-Hamilton, David J.
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p. 2846 - 2856
(2014/05/06)
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- Compositions and methods of omega polyunsaturated fatty acids for the treatment of oral diseases
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The invention discloses a novel discovery of anti-microbial activity against oral bacteria, which can be applied for controlling and preventing oral diseases, of omega-3, omega-6, and omega-9 fatty acids, but not limited to omega-3, omega-6, and omega-9 fatty acids; omega-3, omega-6, and omega-9 fatty acid methyl esters, and omega-3, omega-6, omega-9 fatty acid ethyl esters and their application method. The application of this discovery includes the preparation of drugs, dietary supplements, food and daily necessities with oral health care and therapeutic effects.
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Page/Page column 2-3
(2011/05/05)
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- Fatty acid desaturation and elongation reactions of trichoderma sp. 1-OH-2-3
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The fatty acid desaturation and elongation reactions catalyzed by Trichoderma sp. 1-OH-2-3 were investigated. This strain converted palmitic acid (16:0) mainly to stearic acid (18:0), and further to oleic acid (c9-18:1), linoleic acid (c9,c12-18:2), and α-linolenic acid (c9,c12,c15-18:3) through elongation, and Δ9, Δ12, and Δ15 desaturation reactions, respectively. Palmitoleic acid (c9-16:1) and cis-9,cis-12- hexadecadienoic acid were also produced from 16:0 by the strain. This strain converted n-tridecanoic acid (13:0) to cis-9-heptadecenoic acid and further to cis-9,cis-12-heptadecadienoic acid through elongation, and Δ9 and Δ12 desaturation reactions, respectively. trans-Vaccenic acid (t11-18:1) and trans-12-octadecenoic acid (t12-18:1) were desaturated by the strain through Δ9 desaturation. The products derived from t11-18:1 were identified as the conjugated linoleic acids (CLAs) of cis-9,trans-11-octadecadienoic acid and trans-9,trans-11-octadecadienoic acid. The product derived from t12-18:1 was identified as cis-9,trans-12-octadecadienoic acid. cis-6,cis-9-Octadecadienoic acid was desaturated to cis-6,cis-9,cis-12-octadecatrienoic acid by this strain through Δ12 desaturation. The broad substrate specificity of the elongation, and Δ9 and Δ12 desaturation reactions of the strain is useful for fatty acid biotransformation.
- Ando, Akinori,Ogawa, Jun,Kishino, Shigenobu,Ito, Taiyo,Shirasaka, Norifumi,Sakuradani, Eiji,Yokozeki, Kenzo,Shimizu, Sakayu
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experimental part
p. 227 - 233
(2010/06/16)
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- Two new glyceroglycolipids from the fruits of Cucurbita moschata
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Aphytochemical study of Cucurbita moschata resulted in the characterisation of two new glyceroglycolipids, 1-O-(9Z, 12Z,15Z-octadecatrienoyl)-3-0-[β- D-galactopyranosyl-(1-6)-0-p-D-galactopyranosyl-(1?6)-O-p-D-galactopyranosyl] glycerol (1) and 1-0-(9Z,12
- Jianga, Zhi-Guo,Dua, Qi-Zhen
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experimental part
p. 157 - 159
(2009/10/15)
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- Glycerogalactolipids from the fruit of Lycium barbarum
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Four glycerogalactolipids (1-4), together with 11 other previously known homologues were isolated from the fruit of Lycium barbarum. Their structures were elucidated by chemical analyses including regio-selective enzymatic, alkaline and acidic hydrolyses and spectroscopic methods involving GCMS, HRESIMS and 1D and 2D NMR, respectively.
- Gao, Zengping,Ali, Zulfiqar,Khan, Ikhlas A.
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experimental part
p. 2856 - 2861
(2009/04/07)
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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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- Process for producing fatty acid alkyl ester composition
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An object of the present invention is to solve a problem of separation and recovery of catalysts present in an alkali metal catalytic method currently often used, a problem of excess consumption of a catalyst by a free fatty acid in a raw material, and other problems, and to solve a problem of the presence of a large excess amount of alcohol in a conventional supercritical methanol method, and to provide a method for producing a fatty acid alkyl ester composition in a reaction system containing water and free fatty acid present. The present invention has attained the above-mentioned object by provided a method for producing a fatty acid alkyl ester composition using fats and oils containing a fatty acid glyceride and/or fatty acid, wherein alcohol and/or water is allowed to co-exist with the above-mentioned fats and oils and the reaction is conducted under conditions of a temperature of 100° C. to 370° C. and a pressure of 1 to 100 MPa.
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Page/Page column 6; 7-8
(2008/06/13)
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- Biodiesel additive and method of preparation thereof
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Fuel oxygenates comprised of fatty acid or fatty acid ester derivatives which have been reacted with ozone; a base; and a lower alkanol (1 to 8 carbon atoms) are described. The oxygenates comprise ester groups at a point of cleavage by the ozone which provide oxygen in the oxygenate.
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Page/Page column 4-5
(2008/06/13)
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- Enantioselective epoxidation of linolenic acid catalysed by cytochrome P450BM3 from Bacillus megaterium
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Cytochrome P450BM3, from Bacillus megaterium, catalyses the epoxidation of linolenic acid 1 yielding 15,16-epoxyoctadeca-9,12-dienoic acid 2 with complete regioand moderate enantio-selectivity (60% ee). The absolute configuration of the product is tentatively assigned as 15(R),16(S)-. The Michaelis-Menten parameters kcat and Km for the reaction were determined to be 3126 ± 226 min-1 and 24 ± 6 μM respectively. The Royal Society of Chemistry 2005.
- Celik, Ayhan,Sperandio, Davide,Speight, Robert E.,Turner, Nicholas J.
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p. 2688 - 2690
(2007/10/03)
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- PROCESS FOR EXTRACTION AND CATALYTIC ESTERIFICATION OF FATTY ACIDS FOUND IN SEWAGE SCUM
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The innovation proposed herein describes the process of a fatty acids esterification presents in the sewage scum namely the surface phase of sewage rich in fatty matter, being that this fatty acids are extracted from the scum and esterified by acid catalysts and reagents like as methanol or ethanol.
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- Secondary metabolites from the leaves of Feijoa sellowiana Berg.
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The investigation of the lipid extract of leaves of Feijoa sellowiana cultivated along the east coast of Sicily has yielded in addition to the widespread secondary metabolites: α-tocopherol, flavone, stigmasterol and β-carotene, an inseparable mixture of tyrosol esters of lignoceric (1a), cerotic (1b) and montanic (1c) acids, and a novel galactolipid identified as (2S)-1,2,6′-tri-O-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl] -3-O-β-d-galactopyranosyl glycerol (2).
- Ruberto, Giuseppe,Tringali, Corrado
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p. 2947 - 2951
(2007/10/03)
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- Cerebrosides and a monoacylmonogalactosylglycerol from Clinacanthus nutans
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A mixture of nine cerebrosides and a monoacylmonogalactosylglycerol were seperated from the leaves of Clinacanthus nutans. The structures of the cerebrosides were characterized as 1-O-β-D-glucosides of phytosphingosines, which comprised a common long-chain base, (2S,3S,4R,8Z)-2-amino-8(Z)- octadecene-1,3,4-triol with nine 2-hydroxy fatty acids of varying chain lengths (C16, C18, C20-26) linked to the amino group. The glycosylglyceride was characterized as (2S)-1-O-linolenoyl-3-O-β-D- galactopyranosylglycerol. The structures were established on the basis of the spectroscopic data and chemical reactions.
- Tuntiwachwuttikul, Pittaya,Pootaeng-On, Yupa,Phansa, Photchana,Taylor, Walter Charles
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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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- Direct preparation of (Z,Z)-1,4-dienic units with a new C6 homologating agent: Synthesis of α-linolenic acid
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Syntheses of two C6 homologating agents 2a and 2f are described. These agents allow direct access to the (Z,Z)-1,4-diene unit 3, a moiety present in a wide number of natural compounds. Compound 2a is prepared in 40% overall yield by selective epoxidation of methoxycyclohexa-1,4-diene followed by oxidative ring cleavage and transatalization. Compound 2f is obtained in 90% yield by a one-step oxidative dimerization of phosphonium salt 1. A short synthetic application of these two new C6 homologating agents to the synthesis of α-linolenic acid is described.
- Sandri,Viala
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p. 271 - 275
(2007/10/02)
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- A MONOACYL GALACTOSYLGLYCEROL FROM SONCHUS ARVENSIS
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The major lipids isolated in a phytochemical study of Sonchus arvensis were 1,2-dilinolenyl-3-O-β-D-galactopyranosyl-sn-glycerol, 1,2-dilinolenyl-3-O-(α-D-galactopyranosyl-(1->6)-O-β-D-galactopyrasonyl-sn-glycerol and the previously undescribed 1-linolenyl-3-O-β-D-galactopyranosyl-sn-glycerol.Key word Index-Sonchus arvensis; Compositae; glycosylglycerides; 1-linolenyl-3-O-β-D-galactopyranosyl-sn-glycerol
- Baruah, Putul,Baruah,Nabin C.,Sharma, Ram P.,Baruah, Jogendra N.,Kulanthaivel, Palianappan,Herz, Werner
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p. 1741 - 1744
(2007/10/02)
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- 1,1'-OXALYLDIIMIDAZOLE, A NEW REAGENT FOR ACTIVATION OF CARBOXYLIC ACID
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Carboxylic acids and their salts are converted into the 1-acylimidazoles by the title reagent.This reaction is applied for esterification of fatty acids.
- Murata, Shizuaki
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p. 1819 - 1820
(2007/10/02)
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