Phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 Conjugated Linoleic Acid Isomers: Synthesis and Cytotoxic Studies

Niezgoda, Natalia; Gliszczyńska, Anna; Gładkowski, Witold; Kempińska, Katarzyna; Wietrzyk, Joanna; Wawrzeńczyk, Czesław

doi:10.1071/ch14606

Cited by 12 publications

(10 citation statements)

References 51 publications

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“…Hydrolysis of 1,2-dipalmitoyl- sn -glycero-3-phosphocholine ( 5 ) was carried out according to the method described by Morgado et al [ 21 ]. The detailed data were described earlier [ 22 ]. 1-Palmitoyl-2-hydroxy- sn -glycero-3-phosphocholine (6) was obtained in 99% yield and its physical and spectroscopic data were consistent with those found in literature [ 23 ].…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Biological Evaluation of Novel Phosphatidylcholine Analogues Containing Monoterpene Acids as Potent Antiproliferative Agents

et al. 2016

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The synthesis of novel phosphatidylcholines with geranic and citronellic acids in sn-1 and sn-2 positions is described. The structured phospholipids were obtained in high yields (59–87%) and evaluated in vitro for their cytotoxic activity against several cancer cell lines of different origin: MV4-11, A-549, MCF-7, LOVO, LOVO/DX, HepG2 and also towards non-cancer cell line BALB/3T3 (normal mice fibroblasts). The phosphatidylcholines modified with monoterpene acid showed a significantly higher antiproliferative activity than free monoterpene acids. The highest activity was observed for the terpene-phospholipids containing the isoprenoid acids in sn-1 position of phosphatidylcholine and palmitic acid in sn-2.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Biological Evaluation of Novel Phosphatidylcholine Analogues Containing Monoterpene Acids as Potent Antiproliferative Agents

et al. 2016

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“…Mono-and digalactosyldiacylglycerols also play roles in the regulation of systemic acquired resistance in plants (Gao et al, 2014). Perhaps the best candidate to explain the decreased herbivore performance is the linoleoyl lysophosphocholine, as some compounds in this class have been shown to be highly cytotoxic to human cancer cell lines (Niezgoda et al, 2015).…”

Section: Resultsmentioning

confidence: 99%

Root herbivore performance suppressed when feeding on a jasmonate‐induced pasture grass

Johnson

Glauser

Hiltpold

et al. 2018

Ecological Entomology

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1. Plants defend themselves from insect herbivore attack using a range of physical and chemical defences which are in many cases regulated by phytohormones such as jasmonates. While much more is known about how jasmonates regulate defence against above‐ground herbivores (e.g. herbivores of leaves), there is increasing interest in how they influence below‐ground defences. 2. For the Poaceae, most below‐ground studies focus on highly domesticated cereals. Here it is demonstrated how exogenous application of methyl jasmonate (MeJA) to the leaf blades of a non‐domesticated pasture grass (Microlaena stipoides) caused a more than two‐fold decrease in relative growth rate (RGR) of a root‐feeding chafer (Dermolepida albohirtum). MeJA treatment did not affect root consumption rates, but substantially reduced the efficiency of conversion of ingested food to body mass. 3. Non‐targeted metabolomics identified significant changes in the metabolome of MeJA‐induced plants, with three compounds (a galactolipid, a trihydroxy fatty acid and a lysophospholipid) found to be correlated with herbivore RGR, although their roles in herbivore defence remain uncertain. 4. This study suggests that an important Australian pasture grass can become better defended against root herbivores via enhanced jasmonate activity.

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“…1II), since such esters react faster than acids. For the reduction an Data derived from earlier experiment [29]. equivalent of LAH in anhydrous diethyl ether was used and the reaction was conducted at room temperature.…”

Section: Chemical Synthesis Of Fatty Acid Derivativesmentioning

confidence: 99%

“…Also phospholipids can be used as an alternative carriers for conjugated linoleic acid. Recently we developed chemical and enzymatic methods for effective synthesis of phosphatidylcholine with conjugated linoleic acid isomers . Studies have shown that supplementation of essential fatty acids in the form of phosphatidylcholines and ethyl esters were more effective than in the TAG form or free fatty acids itself .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of cytotoxic activity of conjugated linoleic acid derivatives (esters, alcohols, and their acetates) toward cancer cell lines

Niezgoda¹,

Gliszczyńska²,

Kempińska

et al. 2017

Euro J Lipid Sci & Tech

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Conjugated linoleic acid (CLA) is natural unsaturated fatty acid known for the wide biological properties therefore is available in functional food and cosmetics and as a dietary supplements. In this study a series of simple derivatives of cis-9,trans-11 and trans-10,cis-12 CLA and a mixture of those isomers have been proposed as alternative for free CLA preparations. Obtained in high yields (>72%) ethyl esters, alcohols and their acetates have been subjected to in vitro cytotoxic assay against human tumor cells (human promyelocytic leukemia, breast cancer and colon cancer) and compered with stearic and linoleic derivatives. Studies showed that the growth inhibitory activities depended on the degree of unsaturation. All CLA derivatives except ethyl esters showed similar activities compared to free CLA isomers. Moreover, this study showed that trans-10,cis-12 CLA derivatives have better anticancer properties against all tested tumour cells than derivatives of cis-9,trans-11 isomer and a mixture of both isomers. Practical applications:This paper make a contribution in the field of study of biological activity of CLA derivatives and completes deficiencies in spectroscopic data of known isomers of ethyl esters of CLA isomers, conjugated octadecadienoic alcohols and their acetates. Obtained compounds can be used as a components of cosmetics and food supplements.

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Phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 Conjugated Linoleic Acid Isomers: Synthesis and Cytotoxic Studies

Cited by 12 publications

References 51 publications

Synthesis and Biological Evaluation of Novel Phosphatidylcholine Analogues Containing Monoterpene Acids as Potent Antiproliferative Agents

Synthesis and Biological Evaluation of Novel Phosphatidylcholine Analogues Containing Monoterpene Acids as Potent Antiproliferative Agents

Root herbivore performance suppressed when feeding on a jasmonate‐induced pasture grass

Synthesis and evaluation of cytotoxic activity of conjugated linoleic acid derivatives (esters, alcohols, and their acetates) toward cancer cell lines

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