- New lipoxygenase inhibitory sphingolipids from Chrozophora plicata
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Two new sphingolipids plicatin A [(2S,3S,4R)-2-{[(2R)-2-hydroxyoctdecanoyl] amino}hexaeicosane-1,3,4-triol (1)] and plicatin B [(2S,3S,4R,10E)-2-{[(2R)-2- hydroxyoctdecanoyl]amino}tricont-10-ene-1,3,4-triol (2)], together with 4-hydroxybenzaldehyde, scopoletin, uracil, and dl-threonolactone were isolated from the methanolic extract of the whole plant of Chrozophora plicata. The structures of these compounds were established using 1D (1H, 13C) and 2D NMR (HMQC, HMBC, and COSY) spectroscopy and mass spectrometry (EI-MS and HR-EI-MS) and in comparison with the reported data in the literature. Compounds 1 and 2 showed inhibitory potential against enzyme lipoxygenase with IC50 values 195.1 and 102.3 μM, respectively.
- Riaz, Naheed,Tabussum, Asia,Saleem, Muhammad,Ashraf, Muhammad,Nasar, Romana,Jabeen, Bushra,Malik, Abdul,Jabbar, Abdul
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- New n-nonadecanoyl-β-sitosterol and other constituents from the stem-bark of Anacardium occidentale
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A new steroidal ester bearing n-nonadecanoyl moiety (1) and a mixture of isomeric cerebrosides (2) along with two known compounds were isolated from the methanol extract of the stem-bark of Anacardium occidentale. The structure of the new steroidal ester was determined as 3-n-nonadecanoyl-β-sitosterol on the basis of modern spectroscopic techniques (IR, ESI-MS, HR-ESIMS, 1D and 2D NMR) and chemical degradation studies. The structures of the known compounds were identified as gallic acid and tanacetene by comparison of the spectroscopic data with those of reported data. The mixture of cerebrosides was confirmed based on the analysis of 1D and 2D NMR. These compounds were evaluated for cytotoxicity against human cancer cell lines A549, SCOV3 and rat normal cell line NRK49f.
- Shehu, Abdullahi,Ponnapalli, Mangala Gowri,Mahboob,Prabhakar,Olatunji, Gabriel Ademola
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- Cytotoxic ceramides and glycerides from the roots of Livistona chinensis
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A 70% ethanol extract of the roots of Livistona chinensis has been investigated, led to the isolation of 13 compounds, including a new ceramide, (2S,3S,4R,9Z)-2-[(2R)-2-hydroxytricosanoylamino]-9-octadecene-1,3,4-triol (2), a new glycosyl ceramide, 1-O-β-d-glucopyranosyl-(2S,3S,4R,9Z)-2-[(2R)-2- hydroxydocosanoylamino]-9-octadecene-1,3,4-triol (3), three new monoacylglycerols, 1-(34-hydroxytetratriacontanoyl)-sn-glycerol (9), 1-[nonadeca-(9Z,12Z)-dienoyl]-sn-glycerol (10), and 1-[12-hydroxypentatriaconta- (13E,15Z)-dienoyl]-sn-glycerol (11), a new diacylglycerol, 1-(heptadeca-6Z,9Z- dienoyl)-3-(octadeca-6Z,9Z,12Z-trienoyl)-sn-glycerol (12), as well as a new diacylglycerol aminoglycoside, 1-octadecanoyl-2-nonadecanoyl-3-O-(6-amino-6- deoxy)-β-d-glucopyranosyl-sn-glycerol (13). The structures of new compounds were elucidated, based on spectroscopic, zymologic and chemical methods. Among the compounds tested, compounds 3, 4 and 13 showed significantly antiproliferative effects against the human tumor cell lines (K562, HL-60, HepG2, and CNE-1) with the IC50 of 10-65 μM. To our knowledge, this is first report of the occurrence of ceramides and acylglycerols in the genus Livistona.
- Zeng, Xiaobin,Xiang, Limin,Li, Chen-Yang,Wang, Yihai,Qiu, Guofu,Zhang, Zhen-Xue,He, Xiangjiu
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experimental part
p. 609 - 616
(2012/06/04)
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- Syntheses of All Four Stereoisomers Which Are Conformationally Constrained 1,4-Dioxanyl Analogs of the Antineoplastic Ether Lipid ET-18-OCH3
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The syntheses of each of the four nearly optically pure stereoisomers of oxy>phosphocholine (2,3,2',3') were performed by two parallel divergent sequences.Phosphocholines 2 and 3 were prepared via the corresponding 5-heptadecyl-2-(hydroxymethyl)-1,4-dioxanes 21 and 23, respectively, from the completely regiospecific mixed-hydride reductions of (1R,4S,5S)-4-heptadecyl-3,6,8-trioxabicyclooctane (19) and (1R,4R,5S)-4-heptadecyl-3,6,8-trioxabicyclooctane (20), respectively.The two 4-heptadecyl-3,6,8-trioxabicyclooctanes 19 and 20 were the two separable products from an intramolecular cyclization reaction.By a parallel divergent sequence from the enantiomeric starting material, 3-O-benzyl-sn-glycerol (16'), the other two diastereomeric oxy>phosphocholines 2' and 3' were prepared.These four monocyclic oxy>phosphocholines (2,3,2',3') are conformationally constrained analogs of the antineoplastic and immunomodulatory ether lipid rac-2-O-methyl-1-O-octadecylglycero-3-phosphocholine (rac-1) (rac-ET-18-OCH3, rac-Edelfosine).
- Duclos, Richard I.,Makriyannis, Alexandros
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p. 6156 - 6163
(2007/10/02)
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- Selective Mono- and Bis(alkoxycarbonylation)s of Olefins Catalyzed by Palladium in the Presence of Cu(I) or Cu(II) Chloride under Remarkably Mild Conditions. Application to the Synthesis of γ-Butyrolactone Derivatives
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Palladium-catalyzed mono- and bis(alkoxycarbonylation)s of the olefins were controlled by the use of copper(II) and copper(I) chloride, respectively, in alcohol under normal pressure of carbon monoxide and oxygen at room temperature without any other additives. 3-Buten-1-ols gave the corresponding γ-butyrolactones and 2-oxotetrahydrofuran-3-acetic acid esters, respectively, in high yields.
- Toda, Shiho,Miyamoto, Masanori,Kinoshita, Hideki,Inomata, Katsuhiko
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p. 3600 - 3606
(2007/10/02)
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