- New ceramide from marine sponge Haliclona koremella and related compounds as antifouling substances against macroalgae
-
A new ceramide N-docosanoyl-D-erythro-(2S,3R)-16-methyl- heptadecasphing-4(E)-enine (C22 ceramide) was isolated from the marine sponge Haliclona koremella as an antifouling substance against macroalgae. The structure of this substance was elucidated by spectral means. Antifouling activity of several related compounds was also examined.
- Hattori,Adachi,Shizuri
-
-
Read Online
- New sphingosines from a gorgonian, Pseudopterogorgia australiensis Ridley, of the Indian Ocean
-
Two new sphingosines, (2S,3R)-2-(docosanoyl amino)nonadecane-1,3-diol (1) and (2S,3S,4R)-2-[(2′R)-2′-hydroxynonadecanoylamino]nonadecane-1,3, 4-triol (3), along with the known (2S,3R,4E)-2-(heptadecanoylamino)octadec-4- ene-1,3-diol, have been isolated from Pseudopterogorgia australiensis, of the Indian Ocean. The structures were deduced from spectral and chemical methods. Compounds 1-3 showed moderate antibacterial activity.
- Krishna,Muralidhar,Muralikrishna Kumar,Venkata Rao,Bheemasankara Rao
-
-
Read Online
- Two triterpenyl fatty acid esters from fagonia cretica as lipoxygenase inhibitors
-
Two triterpenyl fatty acid esters were isolated from the chloroform soluble fraction of Fagonia cretica and their structures elucidated as 3β-12-ursen-3yl-docosanoate (1) and 3β-12-ursen-3yl-nonacosanoate (2) by 1D-NMR, 2D-NMR, mass spectrometric and chemical analyses. Both new compounds were also evaluated for their lipoxygenase inhibitory potential using Baicalein as a standard.
- Nawaz, Zahid,Ahmed, Ejaz,Sharif, Ahsan,Sajid, Anam,Arshed, Faiza,Arshad, Muhammad,Anjum, Muhammad Imran,Razaq, Abdul
-
p. 406 - 409
(2018/06/06)
-
- Methylation of Aliphatic and Aromatic Carboxylic Acids with Dimethyl Carbonate under the Influence of Manganese and Iron Carbonyls
-
The synthesis of methyl esters has been carried out via the reaction of aliphatic and aromatic carboxylic acids with dimethyl carbonate in the presence of manganese and iron carbonyls. The optimal ratio of catalyst and reagents and other conditions for the synthesis of methyl esters of carboxylic acids with high yield have been found.
- Khusnutdinov,Shchadneva,Mayakova, Yu. Yu.
-
-
- Dammarane triterpenoids from Carnauba, Copernicia prunifera (Miller) H. E. Moore (Arecaceae), wax
-
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.
-
p. 1371 - 1376
(2017/07/13)
-
- Methylation of mono- and dicarboxylic acids with dimethyl carbonate catalyzed with binder-free zeolite NaY
-
Synthesis of methyl mono- and dicarboxylates was developed consisting in treating the corresponding acids with dimethyl carbonate in the presence of a heterogenic catalyst, crystalline aluminosilicate whose mechanically strong granules to 90–95% were built of crystal aggregates of zeolite Y with modulus of about 5.0 in the Na-form. Optimum catalyst and reagents ratio and the reaction conditions were found for the preparation in high yields of methyl esters of mono- and dicarboxylic acids.
- Khusnutdinov,Shchadneva,Mayakova, Yu. Yu.,Konovalova, Yu. S.,Khazipova,Kutepov
-
p. 163 - 168
(2017/04/24)
-
- Improved protocol toward 1,3,4-oxadiazole-2(3H)-thiones and scale-up synthesis in the presence of SDS as a micelle promoted catalyst
-
Convenient procedure for in situ cyclization of hydrazinecarbodithioate potassium salts to 1,3,4-oxadiazole-2(3H)-thiones under normal phase micellar media catalysis promoted by sodium dodecyl sulfate (SDS) as an anionic surfactant is reported. The main advantage of this procedure is to provide shorter reaction time for the completion of cyclization; scale-up synthesis is possible and the oxadiazoles were obtained in high to excellent yields (87-100%), making the protocol an attractive alternative to the available methods.
- Yildirim, Ayhan
-
p. 473 - 478
(2015/06/30)
-
- Acyl flavonoids, biflavones, and flavonoids from Cephalotaxus harringtonia var. nana
-
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
-
p. 479 - 486
(2015/09/21)
-
- Branched Polymeric Emulsifiers
-
The present invention relates to esterified glycerylated alkyl glycoside and to a process for making same. The esterified glycerylated alkyl glycoside have one or more polyglyceryl moieties and one or more acyl moieties, wherein all of the one or more acyl moieties are situated on the one or more polyglyceryl moieties via an ester linkage. These compounds have been found to be useful as emulsifiers and coemulsifiers in the formulation of a phase stable emulsions suitable for use in personal care, home care, industrial and institutional, and health care applications.
- -
-
-
- New secondary metabolites from croton sparsiorus morong
-
Sparsioamide (1), a new sphingolipid, and sparsioside (2), a new diglyceride galactoside, have been isolated from the ethyl acetate soluble fraction of the 80% ethanolic extract of the whole plant of Croton sparsiorus Morong. Their structures were assigned by 1 H- and 13C-NMR spectra and DEPT, COSY, NOESY, HMQC, HMBC, and ESI-MS experiments. TUeBITAK.
- Mehmood, Rashad,Bibi, Amna,Malik, Abdul
-
p. 111 - 118
(2013/05/08)
-
- 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
-
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.
-
experimental part
p. 1232 - 1240
(2012/07/28)
-
- Iotrochotamides I and II: New ceramides from the Indonesian sponge Iotrochota purpurea
-
Our search for biologically active marine natural products led to the isolation of two new ceramides, iotrochotamide I (1) and iotrochotamide II (2), together with three known 6-bromoindole alkaloids (6-bromo-1H-indole-3-carbaldehyde (3), 6-bromo-1H-indole-3-carboxylic acid methyl ester (4), and 6-bromo-1H-indole-3-carboxylic acid ethyl ester (5)) from the sponge Iotrochota purpurea collected in Indonesia. The structure elucidation of these compounds was secured by spectroscopic methods (1H, 13C, DEPT, COSY, HMQC and HMBC), accurate mass measurements (ESI, EI and GS-MS) as well as comparison with known compounds.
- Ibrahim, Sabrin R.M.,Mohamed, Gamal A.,Fouad, Mostafa A.,El-Khayat, Ehab S.,Proksch, Peter
-
experimental part
p. 86 - 92
(2011/04/22)
-
- DIRECT METHOD AND REAGENT KITS FOR FATTY ACID ESTER SYNTHESIS
-
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.
- -
-
Page/Page column 18; 21-22; 29
(2008/12/07)
-
- SINGLE-STAGE ESTERIFICATION OF OILS AND FATS
-
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.
- -
-
Page/Page column 10-12
(2008/06/13)
-
- Constituents of Ocimum sanctum with antistress activity
-
Three new compounds, ocimumosides A (1) and B (2) and ocimarin (3), were isolated from an extract of the leaves of holy basil (Ocimum sanctum), together with eight known substances, apigenin, apigenin-7-O-β-D-glucopyranoside, apigenin-7-O-β-D-glucuronic acid (4), apigenin-7-O-β-D-glucuronic acid 6″-methyl ester, luteolin-7-O-β-D-glucuronic acid 6″-methyl ester, luteolin-7-O-β-D-glucopyranoside, luteolin-5-O-β-D- glucopyranoside, and 4-allyl-1-O-β-D-glucopyronosyl-2-hydroxybenzene (5), and two known cerebrosides. The structures of the new compounds were determined on the basis of extensive 1D and 2D NMR spectroscopic analysis. The new compounds (1-3) and the known compounds 4 and 5 were screened at a dose of 40 mg/kg body weight for acute stress-induced biochemical changes in male Sprague-Dawley rats. Compound 1 displayed promising antistress effects by normalizing hyperglycemia, plasma corticosterone, plasma creatine kinase, and adrenal hypertrophy. Compounds 2 and 5 were also effective in normalizing most of these stress parameters. In contrast, compounds 3 and 4 were ineffective in normalizing any of these effects.
- Gupta, Prasoon,Yadav, Dinesh Kumar,Siripurapu, Kiran Babu,Palit, Guatam,Maurya, Rakesh
-
p. 1410 - 1416
(2008/04/01)
-
- Sphingolipids from Bombycis Corpus 101A and their neurotrophic effects
-
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
-
p. 466 - 469
(2007/10/03)
-
- A facile synthesis of long chain acyclic alkanols via Kolbe coupling: 1-Docosanol and 1-triacontanol
-
A convenient synthesis of long chain acyclic alkanols viz., 1-docosanol and 1-triacontanol has been devised via Kolbe radical coupling of mono-methyl azelate 2, which has been synthesized from azelaic acid 1. The dimer viz. dimethyl thapsate 3, on Ba(OH)2 hydrolysis affords mono-methyl thapsate 4, which upon mixed Kolbe coupling with appropriate alkanoic acid [CH3(CH)2)nCOOH, n = 6 for 1-docosanol and n = 14 for 1-tri-acontanol] gives the cross coupled products methyl docosanoate 7 and methyl triacontanoate 8 along with the radical dimers dimethyl triacontanedioate 4′ and tetradecane 5′/triacontane 6′ as byproducts. Compounds 7 and 8 on LAH reduction in dry THF yield 1-docosanol 9 and 1- triacontanol 10, respectively in high yields. The mixed anodic coupling has been studied by varying parameters viz. degree of neutralization and molar ratio of compounds 4 and C8/C16 alkanoic acid, current density, anode material etc.
- Yadav, Ashok K.,Singh, Arpita
-
p. 1724 - 1726
(2007/10/03)
-
- Sphingolipid and Sterols of the sponge Callyspongia spinosissima
-
Isolation and structure elucidation of a new sphingolipid, ceramide 1 along with three known sterols cholesterol, poriferasterol and 24-methylene cholesterol as acetates from the lipid fraction of Callyspongia spinosissima (Dendy) are described.
- Agrawal, Shalini,Garg
-
p. 343 - 346
(2007/10/03)
-
- Synthesis of 1-docosanol
-
The synthesis of 1-docosanol 1, starting from palmitaldehyde 2 by dithiane 3 and Wittig approach, is described.
- Deshmukh,Veeresh
-
p. 1239 - 1241
(2007/10/03)
-
- Two amphoteric galactocerebrosides possessing a tri-unsaturated long-chain base from the leech (Hirudo nipponica)
-
Six amphoteric galactocerebrosides were isolated from the land annelid (Hirudo nipponica). Two of them have a tri-unsaturated long-chain base, D-erythro-(4E,8Z,11Z)-docosasphingatrienine. The position and geometry of the double bonds in the long-chain base unit were determined on the bases of chemical and spectral data.
- Noda,Tanaka,Tsujino,Miura,Miyahara,Hayakawa
-
p. 567 - 570
(2007/10/02)
-
- Oceanapins A-F, unique branched ceramides isolated from the haplosclerid sponge Oceanapia cf. tenuis of the Coral Sea
-
A series of ceramides, called oceanapins A-F, which are unique for branching at both the sphingosine and fatty-acid chains, have been isolated as pure compounds from the haplosclerid sponge Oceanapia cf. tenuis of the Coral Sea. Following acid hydrolysis, both the fatty-acid and the sphingosine portions were obtained separately, which allowed their unequivocal structural definition. The absolute configuration was secured via protection of C(l')-OH and Mosher's esterification at C(3')-OH of the oceanapins.
- Mancini,Guella,Debitus,Pietra
-
-
- HYDROGENATION CATALYSED BY PALLADIUM OR RHODIUM CHLORIDES IN THE PRESENCE OF TDA-1
-
Palladium or rhodium chlorides with TDA-1 catalyze the reduction of unsaturated substrates by hydrogen (1 atm.) at room temperature.
- Villemin, Didier,Letulle, Marguerite
-
p. 2833 - 2840
(2007/10/02)
-
- A CONVENIEN SYNTHESIS OF 1-TRIACONTANOL, A PLANT CROWTH GORMONE
-
A synthesis of 1-triacontanol, a plant growth regulator, starting from myristic acid and by two succesive additions of eight and nine carbon units from sebacic acid in Kolbe electro-organic process has been reported.
- Joshi, U. R.,Kapadi, A. H.
-
p. 681 - 686
(2007/10/02)
-
- Terpenoids and Phenolics from Cassia tora Stem Bark
-
The first natural occurance of 3,5,8,3',4',5'-hexahydroxyflavone and a hydroxycoumarin, aurapterol from Cassia tora stem bark is reported.Euphol, basseol, emodin, rhein, palmitic acid, isostearic acid, behenic acid, ethyl arachidate and β-sitosterol have also been isolated from this source the first time.
- Chakrabarty, Kakoli,Chawla, Mahindra H.
-
p. 1165 - 1166
(2007/10/02)
-
