Synthesis and biological activity of hydroxylated derivatives of linoleic acid and conjugated linoleic acids
ABSTRACT Allylic hydroxylated derivatives of the C18 unsaturated fatty acids were prepared from linoleic acid (LA) and conjugated linoleic acids (CLAs). The reaction of LA methyl ester with selenium dioxide (SeO(2)) gave mono-hydroxylated derivatives, 13-hydroxy-9Z,11E-octadecadienoic acid, 13-hydroxy-9E,11E-octadecadienoic acid, 9-hydroxy-10E,12Z-octadecadienoic acid and 9-hydroxy-10E,12E-octadecadienoic acid methyl esters. In contrast, the reaction of CLA methyl ester with SeO(2) gave di-hydroxylated derivatives as novel products including, erythro-12,13-dihydroxy-10E-octadecenoic acid, erythro-11,12-dihydroxy-9E-octadecenoic acid, erythro-10,11-dihydroxy-12E-octadecenoic acid and erythro-9,10-dihydroxy-11E-octadecenoic acid methyl esters. These products were purified by normal-phase short column vacuum chromatography followed by high-performance liquid chromatography (HPLC). Their chemical structures were characterized by liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance spectroscopy (NMR). The allylic hydroxylated derivatives of LA and CLA exhibited moderate in vitro cytotoxicity against a panel of human cancer cell lines including chronic myelogenous leukemia K562, myeloma RPMI8226, hepatocellular carcinoma HepG2 and breast adenocarcinoma MCF-7 cells (IC(50) 10-75 microM). The allylic hydroxylated derivatives of LA and CLA also showed toxicity to brine shrimp with LD(50) values in the range of 2.30-13.8 microM. However these compounds showed insignificant toxicity to honeybee at doses up to 100 microg/bee.
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- "The precursor ion m/z 297 decomposes by CID and produces abundant m/z 279 in both MS/MS spectra, corresponding to a loss of water. The MS/ MS spectrum for each of the compounds 16 and 17 also contain abundant ions at m/z 171 ([M–H–C 9 H 18 ] À ) and 155 ([MÀHÀC 9 H 18- O] À ) respectively, arising from bond cleavage next to the hydroxyl group (Dufour and Loonis, 2005; Garscha and Oliw, 2007; Hou, 1995; Li et al., 2009). Thus, according to literature data (Rodr íguez et al., 2001), these hydroxyl-ene linoleates were identified as (10E)-9-hydroxy-10-octadecenoic (16) and (8E)-10-hydroxy-8- octadecenoic acid (17) acids. "
ABSTRACT: Bioassay-guided fractionation of Alternanthera brasiliana stem extracts resulted in the isolation of an antibiotically active fraction. Five human pathogenic bacteria were used to guide the fractionation process for the isolation of antimicrobial compounds. Finally, 17 linoleate oxylipins were identified by LC-MS/MS and NMR spectroscopy. Five of the isolated compounds present in A. brasiliana tissues were also detected to be synthesized by endophytic bacteria of the genus Bacillus that were isolated from A. brasiliana. It is speculated that the antibiotic oxylipins from A. brasiliana might derive from bacteria and be involved in an ecological relationship between this plant and its endophytes. Copyright © 2014 Elsevier Ltd. All rights reserved.Phytochemistry 11/2014; 110. DOI:10.1016/j.phytochem.2014.11.005 · 3.35 Impact Factor
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- "Hydroxy fatty acids (C18 or C20) are used as thickeners in a new generation of emulsifiers which require polyhydroxy fatty acids to reach new levels of performance (Hagemann and Rothfus, 1991). Various attempts have been made to synthesize such compounds , however the chemical pathway is tedious and produces a low yield (Rama Rao et al., 1987; Li et al., 2009). Pseudomonas aeruginosa 42A2 has been reported to accumulate hydroxy fatty acids in the cellular compartment in the form of polyhydroxyalkanoates (PHA) and oxylipins such as 10-hydroxy- 8E-octadecenoic acid and 7,10-dihydroxy-8E-octadecenoic acid, in the supernatant when cultivated in oily substrates (Culleré et al., 2001). "
ABSTRACT: In microorganisms hydroxy fatty acids are produced from the biotransformation of unsaturated fatty acids. Such compounds belong to a class of oxylipins which are reported to perform a variety of biological functions such as anti-inflammatory or cytotoxic activity. These compounds have been found in rice and timothy plants after being infected by specific fungus. When grown in submerged culture with linoleic acid, Pseudomonas 42A2 accumulated in the supernatant several hydroxy fatty acids. In this work LC-MS/MS has been used to elucidate the structure of the components form the organic extract: 9-hydroxy-10,12-octadecadienoic acid; 13-hydroxy-9,11-octadecadienoic acid; 7,10-dihydroxy-8E-octadecenoic acid; 9,10,13-trihydroxy-11-octadecenoic acid and 9,12,13-trihydroxy-10-octadecenoic acid. Antimicrobial activity against several pathogenic fungal strains is presented: MIC (microg/mL) Verticillium dhaliae, 32; Macrophonia phaesolina, 32; Arthroderma uncinatum, 32; Trycophyton mentagrophytes, 64.Chemistry and Physics of Lipids 02/2010; 163(4-5):341-6. DOI:10.1016/j.chemphyslip.2010.02.003 · 2.59 Impact Factor
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ABSTRACT: A novel derivative of glyceric acid (GA), dilinoleoyl-D-glyceric acid (LA₂-DGA), was synthesized from D-GA calcium salt and linoleoyl chloride and evaluated for cytotoxicity. The D-GA calcium salt was first reacted with 4-methoxybezylchloride, and the resulting compound was esterified with linoleoyl chloride. This reaction was followed by hydrolysis of the 4-methoxybenzyl moiety, yielding LA₂-DGA. LA₂-DGA was then subjected to cytotoxicity testing using normal human dermal fibroblasts and primary normal human dermal microvascular endothelial cells. LA₂-DGA showed no significant toxic effects in either type of cell.Journal of oleo science 09/2011; 60(9):483-7. DOI:10.5650/jos.60.483 · 1.24 Impact Factor