16742-51-1Relevant articles and documents
Two new sphingolipids from the stem bark of Synsepalum msolo (Sapotaceae)
Ndifor, Ache Roland,Stanislaus, Njinga Ngaitad,Fru, Chi Godloves,Talontsi, Ferdinand,Tabopda, Turibio Kuiate,Menkem, Elisabeth Zeuko'o,Tchaleu, Ngadjui Bonaventure,Owusu, Yeboah Samuel
, (2021)
Synsepalum msolo commonly known as Bang Bali in Bali-Nguemba, Cameroon is used in traditional medicine against various diseases. The leaves and stem bark extracts were subjected to silica gel and Sephadex LH20 column chromatography to yield pur
Structural determination of glucosylceramides isolated from marine sponge by fast atom bombardment collision-induced dissociation linked scan at constant B/E
Ahn, Young Min,Lee, Won-Woong,Jung, Jee H.,Lee, Sang-Gi,Honga, Jongki
, p. 1698 - 1708 (2009)
Five glucosylceramides (GlcCers) were isolated by reversed phase high-performance liquid chromatography from the MeOH extracts of amarine sponge, Haliclona (Reniera) sp., collected from the coast of Ulleung Island, Korea, and analyzed by fast atom bombard
Pinelloside, an antimicrobial cerebroside from Pinellia ternata
Chen,Cui,Liu,Tan
, p. 903 - 906 (2003)
An antimicrobial cerebroside, pinelloside, was isolated from the dried tubers of Pinellia ternata (Thunb.) Breit. Its structure was determined as 1-O-β-D-glucopyranosyl-(2S,3R,4E, 11E) 2-(2′ R-hydroxyhexadecenoylamino)-4,11-octadecadiene-l,3 1,3-diol by chemical transformation and extensive spectroscopic analyses (IR, MS, 1H and 13C NMR, DEPT as well as 2D NMR techniques HMBC, HMQC, 1H-1H COSY and NOESY). The antimicrobial assay showed that this compound was inhibitory to the growth of Bacillus subtilis, Staphylococcus aureus, Aspergillus niger and Candida albicans, with minimum inhibitory concentrations (MICs) of 20, 50, 30 and 10 μg/ml, respectively. The MICs of penicillin G against bacteria B. subtilis, S. aureus, E. coli, P. fluorescens and H. pylori were 0.80, 0.34, 0.56, 1.34 and 0.92, and those of ketoconazole against fungi A. niger, C. albicans and T. rubrum 0.90, 0.65 and 1.0 μg/ml, respectively.
New cytotoxic cerebrosides from the red sea cucumber Holothuria spinifera supported by in-silico studies
Abdelhameed, Reda F.A.,Eltamany, Enas E.,Hal, Dina M.,Ibrahim, Amany K.,AboulMagd, Asmaa M.,Al-Warhi, Tarfah,Youssif, Khayrya A.,Abd El-Kader, Adel M.,Hassanean, Hashim A.,Fayez, Shaimaa,Bringmann, Gerhard,Ahmed, Safwat A.,Abdelmohsen, Usama Ramadan
, (2020/09/07)
Bioactivity-guided fractionation of a methanolic extract of the Red Sea cucumber Holothuria spinifera and LC-HRESIMS-assisted dereplication resulted in the isolation of four compounds, three new cerebrosides, spiniferosides A (1), B (2), and C (3), and cholesterol sulfate (4). The chemical structures of the isolated compounds were established on the basis of their 1D NMR and HRMS spectral data. Metabolic profiling of the H. spinifera extract indicated the presence of diverse secondary metabolites, mostly hydroxy fatty acids, diterpenes, triterpenes, and cerebrosides. The isolated compounds were tested for their in vitro cytotoxicities against the breast adenocarcinoma MCF-7 cell line. Compounds 1, 2, 3, and 4 displayed promising cytotoxic activities against MCF-7 cells, with IC50 values of 13.83, 8.13, 8.27, and 35.56 μM, respectively, compared to that of the standard drug doxorubicin (IC50 8.64 μM). Additionally, docking studies were performed for compounds 1, 2, 3, and 4 to elucidate their binding interactions with the active site of the SET protein, an inhibitor of protein phosphatase 2A (PP2A), which could explain their cytotoxic activity. This study highlights the important role of these metabolites in the defense mechanism of the sea cucumber against fouling organisms and the potential uses of these active molecules in the design of new anticancer agents.
Self gelating isoracemosol A, new racemosaceramide A, and racemosol E from Barringtonia racemosa
Ponnapalli, Mangala Gowri,Dangeti, Nalini,Sura, Madhu Babu,Kothapalli, Haribabu,Akella, V. S. Sarma,Shaik, Jeelani Basha
supporting information, p. 63 - 69 (2016/11/29)
Phytochemical investigation into the CHCl3extract of the fruits of Barringtonia racemosa resulted in the isolation of two new metabolites along with isoracemosol A and betulinic acid as known metabolites. The new compounds were characterised as phytosphingosine-type ceramide [(2S,3S,4R)-2-[(2R)-2-hydroxyhexadecanoyl amino]-hexacos-8(E)-ene-1,3,4-triol, 1] and racemosol E [21β-acetoxy-22α-(2-methylbutyroxy)-olean-12-ene-3β,16α,28-triol, 2] on the basis of extensive spectroscopic data analysis and chemical modifications. In addition, the self-gelating property of isoracemosol A (3) was investigated for the first time, which leads to the unexpected agglomerated porous-like morphology.
Synthesis of 6-Hydroxysphingosine and α-Hydroxy Ceramide Using a Cross-Metathesis Strategy
Wisse, Patrick,De Geus, Mark A. R.,Cross, Gen,Van Den Nieuwendijk, Adrianus M. C. H.,Van Rooden, Eva J.,Van Den Berg, Richard J. B. H. N.,Aerts, Johannes M. F. G.,Van Der Marel, Gijsbert A.,Codée, Jeroen D. C.,Overkleeft, Herman S.
, p. 7258 - 7265 (2015/07/27)
(Chemical Equation Presented) In this paper, a new synthetic route toward 6-hydroxysphingosine and α-hydroxy ceramide is described. The synthesis employs a cross-metathesis to unite a sphingosine head allylic alcohol with a long-chain fatty acid alkene that also bears an allylic alcohol group. To allow for a productive CM coupling, the sphingosine head allylic alcohol was protected with a cyclic carbonate moiety and a reactive CM catalyst system, consisting of Grubbs II catalyst and CuI, was employed.
Chiral Surfactant-Type Catalyst: Enantioselective Reduction of Long-Chain Aliphatic Ketoesters in Water
Lin, Zechao,Li, Jiahong,Huang, Qingfei,Huang, Qiuya,Wang, Qiwei,Tang, Lei,Gong, Deying,Yang, Jun,Zhu, Jin,Deng, Jingen
, p. 4419 - 4429 (2015/05/13)
A series of amphiphilic ligands were designed and synthesized. The rhodium complexes with the ligands were applied to the asymmetric transfer hydrogenation of broad range of long-chained aliphatic ketoesters in neat water. Quantitative conversion and excellent enantioselectivity (up to 99% ee) was observed for α-, β-, γ-, δ- and ε-ketoesters as well as for α- and β-acyloxyketone using chiral surfactant-type catalyst 2. The CH/π interaction and the strong hydrophobic interaction of long aliphatic chains between the catalyst and the substrate in the metallomicelle core played a key role in the catalytic transition state. Synergistic effects between the metal-catalyzed site and the hydrophobic microenvironment of the core in the micelle contributed to high stereoselectivity. (Chemical Equation Presented).
Lipid metabolites with free-radical scavenging activity from Euphorbia helioscopia L.
Cateni,Zilic,Altieri,Zacchigna,Procida,Gaggeri,Rossi,Collina
, p. 90 - 98 (2014/06/10)
The methanolic extract of the plant Euphorbia helioscopia L. exhibited an interesting free-radical scavenging activity. From the aerial parts of Euphorbia helioscopia L. (Euphorbiaceae), a complex mixture of seven cerebrosides together with glucoclionasterol, a digalactosyldiacylglycerol and a diacylmonogalactosylglycerol were identified. The structures of the cerebrosides were characterized as 1-O-β-d-glucosides of phytosphingosines, which comprised (2S, 3S, 4E, 8E)-2-amino-4(E),8(E)-octadecadiene-1,3-diol, (2S, 3S, 4E, 8Z)-2-amino-4(E),8(Z)-octadecadiene-1,3-diol, (2S, 3S, 4R, 8Z)-2-amino-8(Z)-octadecene-1,3,4-triol as long chain bases with seven 2-hydroxy fatty acids of varying chain lengths (C16, C24:1, C 26:1, C24, C26, C28:1) linked to the amino group. The glycosylglycerides were characterized as (2S)-2,3-O-di-(9,12, 15-octadecatrienoyl)-glyceryl-6-O-(α-d-galactopyranosyl) -β-d-galactopyranoside and (2S)-2,3-O-di-(9,12,15-octadecatrienoyl)- glyceryl-1-O-β-d-galactopyranoside. The structures were established on the basis of spectroscopic data and chemical reactions.
Neritinaceramides A-E, new ceramides from the marine bryozoan Bugula neritina inhabiting South China Sea and their cytotoxicity
Tian, Xiang-Rong,Tang, Hai-Feng,Feng, Jun-Tao,Li, Yu-Shan,Lin, Hou-Wen,Fan, Xiao-Pei,Zhang, Xing
, p. 1987 - 2003 (2014/06/09)
Five new ceramides, neritinaceramides A (1), B (2), C (3), D (4) and E (5), together with six known ceramides (6-11), two known alkyl glycerylethers (12 and 13) and a known nucleoside (14), were isolated from marine bryozoan Bugula neritina, which inhabits the South China Sea. The structures of the new compounds were elucidated as (2S,3R,3′S,4E,8E,10E)-2-(hexadecanoylamino)- 4,8,10-octadecatriene-l,3,3′-triol (1), (2S,3R,2′R,4E,8E,10E)-2- (hexadecanoylamino)-4,8,10-octadecatriene-l,3,2′-triol (2), (2S,3R,2′R,4E,8E,10E)-2-(octadecanoylamino)-4,8,10-octadecatriene-l,3, 2′-triol (3), (2S,3R,3′S,4E,8E)-2-(hexadecanoylamino)-4,8- octadecadiene-l,3,3′-triol (4) and (2S,3R,3′S,4E)-2- (hexadecanoylamino)-4-octadecene-l,3,3′-triol (5) on the basis of extensive spectral analysis and chemical evidences. The characteristic C-3′S hydroxyl group in the fatty acid moiety in compounds 1, 4 and 5, was a novel structural feature of ceramides. The rare 4E,8E,10E-triene structure in the sphingoid base of compounds 1-3, was found from marine bryozoans for the first time. The new ceramides 1-5 were evaluated for their cytotoxicity against HepG2, NCI-H460 and SGC7901 tumor cell lines, and all of them exhibited selective cytotoxicity against HepG2 and SGC7901 cells with a range of IC 50 values from 47.3 μM to 58.1 μM. These chemical and cytotoxic studies on the new neritinaceramides A-E (1-5) added to the chemical diversity of B. neritina and expanded our knowledge of the chemical modifications and biological activity of ceramides.
Asymmetric reduction of monoketo hexadecanoic acid methyl esters
Türker, Gülen,Yusufoglu, Ayse
, p. 1531 - 1535 (2013/06/26)
Methyl 2-,3-,6-,8-,14- and 15-keto hexadecanoates were reduced by using NaBH4 in presence of 1,2;5,6-di-O-isopropilydene-Dglucofuranose [DIPGH], R(+)-1,1′-binaphthyl-2,2′-diol [RBND] and pivalic acid [PA]. The reduction of 2- and 3-keto esters in the presence of (+)-1,1′-binaphthyl-2,2′-diol results in considerably higher stereoselectivities (95 % ee). Enantiometric excess (ee %) was determined by 1H and 13C NMR analyses using a shift reagent, Eu(tfc)3. Copyright
