Oleic acid biological activity

I. Oleic Acid Biological Activity AND Pharmaceutical Uses... 

Since Wallen et al. (1962) reported the first bioconversion of oleic acid to 10-hydroxystearic acid by a Pseudomonad, microbial conversions of unsaturated fatty acids from different substrates by various microbial strains have been widely exploited to produce new, value-added products. Among the unsaturated fatty acids used for microbial production of hydroxy fatty acids, three (oleic, linoleic, and linolenic acids) were well studied as substrates to produce mono-, di-, and trihydroxy fatty acids. Recently, a bacterial strain Pseudomonas aeruginosa NRRL B-18602 (PR3) has been studied to produce hydroxy fatty acids from several fatty acid substrates. In this review, we introduce the production of hydroxy fatty acids from their corresponding fatty acid substrates by P. aeruginosa PR3 and their industrially valuable biological activities. 

Allylic aeetates or carbonates can undergo nucleophilic substitutions via palla-dium(0)-catalysis (11). In this paper, we report on the extension of this reaction to unsaturated fatty aeids by the preparation of allyl carbonates and acetates of oleic, linoleic, and 10-undecenoic acid and their substitution with carbon- and heteroatom-nucleophiles by palladium(0)-catalysis. In this way, different substituents can be in-trodueed into the alkyl chain of fatty acids. This leads to fatty acid derivatives in which the properties of biologically active compounds may possibly be combined with the amphiphilic property of the fatty acid. 

Content of fatty acid components in the biologically active tGPI anchor fraction was found to be oleic acid (C18 l, 31%), linoleic acid (C18 2, 21%) and palmitic acid (C16 0,37%).f l... 

Huang, L., Cheng, X., Liu, C. et al. 2009. Preparation, characterization, and antibacterial activity of oleic acid-grafted chitosan oligosaccharide nanoparticles. Frontiers of Biology in China 4(3) 321-327. 

Chemical analysis of the psi factors resulted in the identification of a series of related compounds based on linoleic and oleic acid. PsiCa and psiCp, the most biologically active compounds, are (9Z,122)-(5S,8/i)-dihydroxyoctadeca-9,12,-dienoic acid (5,8-DiHODE) and (9Z)-(55,8ff)-dihydroxyoctadeca-9-(mono)enoic acid (5,8-DiHOME) respectively. Psi Act and psiAp, with lower biological activity, are the 1-5 lactones of PsiCa and psiCp. Finally, psiBa and psiBp are (9Z,12Z)-(8/ )-hydroxyoctadeca-9,12-dienoic acid (8-FIODE) and (92)-(8i )-hydroxy-octadeca-9-(mono)dienoic acid (8-HOME) respectively [11,12]. 

Fontana, A., Spolaore, B. Polverino de Laureto, P. (2013). The biological activities of protein/oleic acid complexes reside in the fatty acid. Biochimica et Biophysica Acta (BBA)-Proteins and Proteomics, 1834(6), 1125-43. 

There are several biologically active lipid derivatives of dopamine, including the amide of dopamine and oleic acid, iV-oleayldopamine (OLDA), 98. One study attempted to correlate the presence of 98 in brain tissues. Figure 23.8 shows the U V/VIS absorption spectra in membrane fractions of brain homogenates after 1 min, 18 h, and 20 h of incubation with AT-oleoyl-dopamine (curve... 

In addition to the negative response to oleic acid, Thomasson (1953) reported that the following closely related monoethenoid acids likewise lack any biopotency 11-octadecenoic acid 12-octadecenoic acid 13-docosenoic acid (erucic) and 12-hydroxy-9-octadecenoic acid (ricinoleic). Turpeinen (1938) also noted that 12-octadecenoic acid, erucic, and ricinoleic acids, as well as chaulmoogric acid, are without biological activity. Elaidic acid, the frans-isomer of oleic acid, has likewise been reported as without curative effect in fat deficiency. It is thus obvious that none of the monoethenoid acids affords protection from fat deficiency. 

Biological activity of vitamin E is related to antioxidant effects the most effective antioxidant in vivo) is a-tocopherol. In food lipids, the situation is more compHcated, because the antioxidant activity of tocopherols and tocotrienols depends on many factors. One important aspect is the amount and composition of unsaturated fatty acids. Under typical storage conditions, tocopherols are more effective antioxidants, for example, in animal fats (the main fatty acid is oleic acid) compared with vegetable oils that contain higher amounts of linoleic acid (e.g. soybean and sunflower oils). 

Coconut oil composition consists of 90% saturated fatty acids, 7.5% monounsaturated fatty acids and 1.8% polyimsaturated fatty acids (Zambiazi, et al., 2007) and it is as it follows 1% caproic acid (C6 0), 2% caprylic acid (C8 0), 4% capric acid (C10 0), 50% lauric acid (C12 0), 18% myristic acid (C14 0), 9% palmitic acid (C16 0), 8% oleic acid (C18 l), 5% stearic acid (C18 0) and 2% linoleic acid (C18 2) (Paiwan et al., 2013). The stmctured lipids (24%), which usually are difficult to find in nature are obtained by cmde oil biotransformation but another possibility to obtain them is by bioconversions in controlled conditions, in order to develop specific target compounds with biological activities that have different effects on microbial cells (Nugrahini et al., 2015). 

In the following chapters, examples are cited where fatty acid composition has been modified by biological methods—both traditional and modern. Well-known examples include low-erucic acid rapeseed oil (canola oil) and high-oleic sunflower oil, but attempts to develop oils with modified fatty acid are being actively pursued in many counties—in both academic and industrial laboratories—and substantial developments are likely in the next five to ten years. Some of have been described by the author (Gunstone 2001) and others are cited in the following chapters of this book. 

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