- One-pot synthesis of polyunsaturated fatty acid amides with anti-proliferative properties
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A one-pot environmentally friendly transamidation of ω-3 fatty acid ethyl esters to amides and mono- or diacylglycerols was investigated via the use of a polymer-supported lipase. The method was used to synthesize a library of fatty acid monoglyceryl esters and amides. These new derivatives were found to have potent growth inhibition effects against A549 lung cancer cells.
- Tremblay, Hugo,St-Georges, Catherine,Legault, Marc-Andr,Morin, Caroline,Fortin, Samuel,Marsault, Eric
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p. 5635 - 5638
(2015/01/09)
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- Monoglycerides from the brown alga Sargassum sagamianum: Isolation, synthesis, and biological activity
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Polyunsaturated fatty acid-derived monoglycerides were characterized from the marine brown alga Sargassum sagamianum, collected from Jeju Island, Korea. A new compound of this structural class was isolated and determined to be 1-octadecatetraenoyl glycerol, by combined spectroscopic methods. Based on the structures and bioactivity of these compounds, a series of monoglycerides were synthesized using glycerol and various fatty acids. Several compounds exhibited moderate to significant inhibition of phospholipase A2 and cyclooxygenase-2.
- Chang, Hyeun Wook,Jang, Kyoung Hwa,Lee, Doohyun,Kang, Hee Ryong,Kim, Tae-Yoon,Lee, Bong Ho,Choi, Byoung Wook,Kim, Sanghee,Shin, Jongheon
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body text
p. 3589 - 3592
(2009/04/11)
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- POLYUNSATURATED FATTY ACID MONOGLYCERIDES, DERIVATIVES, AND USES THEREOF
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The invention emcompasses polyunsaturated fatty acid monoglycerides and derivatives thereof, having the formulae (I), (II), (III) and (IV), pharmaceutically acceptable salts thereof, compositions thereof and processes of preparing said compounds. These compounds can be useful as cancer chemopreventive agents, cancer treating agents, or radioenhencers for radiotherapy of cancer, or for inhibiting tumor growth or cell proliferation, or reducing tumor growth.
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Page/Page column 22
(2008/12/08)
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- COMPOSITIONS COMPRISING POLYUNSATURATED FATTY ACID MONOGLYCERIDES OR DERIVATIVES THEREOF AND USES THEREOF
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There are provided various compounds and compositions comprising polyunsaturated fatty acid monoglycerides and derivatives thereof. These compounds and compositions can be useful as cancer chemopreventive agents. They can also be useful for enhancing solubility of various active agents and enhancing their bioavailability.
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Page/Page column 27
(2008/12/07)
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- Synthesis of Triacylglycerol from Polyunsaturated Fatty Acid by Immobilized Lipase
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More than 95percent of polyunsaturated acid (PUFA) was converted to triacylglycerol by immobilized lipase from Candida antarctica or Rhizomucor miehei.The esterification was carried out at 50-60 deg C with shaking and dehydration for 24 h.The substrates consisted of glycerol and free fatty acid or ethyl esters of the fatty acid at a 1:3 molar ratio.The docosahexaenoic acid (DHA) or eicosapentaenoic acid (EPA) in the substrate polymerized during the reaction, and they required 5-10percent more than the stoichiometric amount to compensate for the PUFA loss.On the contrary, ethyl esters of DHA and EPA were not polymerized.Pure tridocosahexaenoyl, trieicosapentaenoyl and triarachidonoyl glycerol were isolated after passing the product through a basic aluminum oxide column.Industrial feasibility of this process was discussed for the ethyl ester as substrate. KEY WORDS: Docosahexaenoic acid, docosahexaenoyl ethyl ester, eicosapentaenoic acid, immobilized lipase, lipase, polyunsaturated fatty acid, triacylglycerol, triarachidonoyl glycerol, tridocosahexaenoyl glycerol, trieicosapentaenoyl glycerol.
- Kosugi, Yoshitsugu,Azuma, Naoki
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p. 1397 - 1403
(2007/10/02)
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