2433-95-6

Usage

InChI:InChI=1/C25H50O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(26)25(27)28-2/h24,26H,3-23H2,1-2H3

Upstream product

• 152139-44-1 agelasphin-11 
• 67-56-1 methanol 
• 154801-30-6 (2S,3S,4R)-2-<(2R)-2-hydroxytetracosanoylamino>-1,3,4-octadecanetriol 
• 193412-78-1 1-O-β-D-glucopyranosyl-(2S,3S,4R,9Z)-2-[(2R)-2-hydroxytetracosanoylamino]-1,3,4-octadecanetriol 
• 148766-51-2 (2S,3S,4R)-1-O-(α-D-galctopyranosyl)-16-methyl-2--1,3,4-heptadecanetriol 
• 148289-27-4 agelasphin-9a 
• 148347-44-8 (2S,3S,4R,2''R)-1-O-α-D-galactopyranosyl-2-N-(2''-hydroxy-tetracosanoyl)hexadecane-3,4-diol 

Downstream Products

• 112146-61-9 methyl (2R)-2-(-)-α-methoxy-α-trifluoromethylphenylacetyloxytetracosanoate 
• 112146-59-5 methyl (2R)-2-tert-butyldiphenylsilyloxytetracosanoate 
• 112146-60-8 (2R)-2-tert-butyldiphenylsilyloxytetracosanoic acid 
• 64655-47-6 (2S,3R,4E)-N-(2'R)-2'-hydroxytetracosanoylsphingenine 
• 112146-62-0 (2S,3R,4E)-N-(2'R)-2'-tert-butyldiphenylsilyloxytetracosanoyl-1,3-di-O-(1-ethoxyethyl)-sphingenine 
• 112146-63-1 (2S,3R,4E)-N-(2'R)-2'-tert-butyldiphenylsilyloxytetracosanoylsphingenine 

Relevant academic research and scientific papers

Ceramide and cerebroside from the stem bark of Ficus mucuso (Moraceae)

Two new sphingolipids mucusamide (1) and mucusoside (2) have been isolated from methanol soluble part of the stem bark of Ficus mucuso WELW., together with fifteen known secondary metabolites including cellobiosylsterol (3), β-sitosterol (4), stigmasterol (5), β-sitosterol 3-O-β-D- glucopyranoside (6), lupeol acetate (7), ursolic acid (8), procatechuic acid (9), 2-methyl-5,7-dihydroxychromone 8-C-β-D-glucoside (10), apigenin (11), (-)-epicatechin (12), (+)-catechin (13), N-benzoyl-L-phenylalanilol (14), α-acetylamino-phenylpropyl α-benzoylaminophenylpropionate (15), asperphenamate (16) and bejaminamide (17). Structures of compounds 1 and 2 were elucidated by spectroscopic analysis and chemical methods.

Cytotoxic ceramides and glycerides from the roots of Livistona chinensis

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.

Preliminary biological assay on cerebroside mixture from Euphorbia nicaeensis All. Isolation and structure determination of five glucocerebrosides

Preliminary studies of in vitro cytostatic activity on less polar fraction of the MeOH extract of the plant Euphorbia nicaeensis All., carried out on KB cells, have evinced a relatively low ability of extract to inhibit cell growth. Successive, five glucocerebrosides were isolated from the cerebroside molecular species obtained from this extract using normal and reversed phase column 'flash-chromatography'. The structures of these cerebrosides were determined on the basis of chemical and spectroscopic evidences. Mass spectrometry of dimethyl disulfide derivatives was useful for the determination of the double-bond positions in the long-chain bases.

Regulosides A-C: Glycosphingolipids from the starfish Pentaceraster regulus

The glycosphingolipid (GSL) composition of the starfish Pentaceraster regulus has been studied. The structure of the major component, a new cerebroside named Reguloside A (1) and two minor homologues, Regulosides B (1a) and C (1b), are described. VCH Verlagsgesellschaft mbH, 1997.

Agelasphins, novel antitumor and immunostimulatory cerebrosides from the marine sponge Agelas mauritianus

New glycosphingolipids, named agelasphins (1-8), have been isolated by antitumor and immunostimulatory bioassay-guided purification from an extract of a marine sponge, Agelas mauritianus. Strongly active agents in agelasphins had characteristic α-galactosylceramide structures, the isolation of which from natural products has not previously been reported. The absolute configurations of agelasphins were elucidated by the total synthesis.