Unsaturated hydroxy fatty acids

Kato, T., Yamaguchi, Y., Hirano, T., Yokoyama, T., Uyehara, T., Namai, T., Yamanaka, S., and Harada,N. 1984. Unsaturated Hydroxy Fatty-Acids, the Self Defensive Substances in Rice Plant against Rice Blast Disease. Chem. Lett., 409-412. 

Unsaturated hydroxy fatty acids, the self-defensive substances in rice plant against Rice Blast Disease. Chem. Lett., 25, 409 112. 

Klenk and Schorsch72 have elaborated an excellent method for the separation of the individual, genuine galactocerebrosides. The crude cerebroside fraction obtained by solvent extraction of a suitable tissue is separated by chromatography on silica gel. Cerebrosides containing saturated or unsaturated hydroxy fatty acids can be separated from those containing nonhydroxy fatty acids. In both of the separated parts, there are numerous individual cerebrosides. 

A similar structure was seen in Aspergillus oryzae, the Japanese yellow mold (75). Trans-unsaturated hydroxy fatty acids ( 2-hydroxyoctadec-3-enoic acid) found in F. amygdali and A. oryzae cerebrosides have not been detected in sphingolipids of animals and plants. 

German Patent 299992 (Chem Ze/iir., 1917, ii, 510) deals vitii the production of organic compounds of phosphorus. Unsaturated hydroxy-fatty acids of high molecular weight when treated with phosphorus tri- or oxy-halide yield as primary products acid... 

Koritala, S., and M.O. Bagby, Microbial Conversion of Linoleic and Linolenic Acids to Unsaturated Hydroxy Fatty Acids, J. Am. Oil. Chem. Soc. 69 575-578 (1992). 

There are two other HFA homologous series the ffl- and (co — 1). The general formula for co-hydroxy fatty acids is HOCH2(CH2) COOH and the general formula for (co —1) HFAs is CH3CH(OH) (CH2) C00H. Other functions, such as branches or double bonds, are often found in HFAs, for example, in 3-hydroxy-13-methyltetradecanoic and 3-hydroxy-15-methylhexadecanoic acids. An unsaturated hydroxy fatty acid is ricinoleic acid (12-hydro-xy-ds-9-octadecenoic acid). 

Introduction Primary Fatty Acids Fatty Acids of Plant Vegetative Parts Biosynthesis Fatty Acid Biosynthesis The Two-Pathway Model of Lipid Biosynthesis The Second 3-Ketoacyl ACP Synthase Isozyme Biosynthesis of Unsaturated Fatty Acids The Prokaryotic Pathway The Eukaryotic Pathway Biosynthesis of Triacylglycerides Degradation of Fatty Acids Unusual Fatty Acids in Plants Fatty Acids from Unusual Starter Units Fatty Acids with Unusual Patterns of Unsaturation Hydroxy Fatty Acids Epoxy Fatty Acids... 

The introduction of deuterium atom by deuteration of double or triple bonds of unsaturated hydroxy fatty acids has been reported [29, 36] without particular comments on the deuterium incorporation. 

Einhorn, J., et al.. Gas Phase lon/Molecule Reactions of Unsaturated Hydroxy Fatty Acid... 

Imai, H., Ohnishi, M., Kinoshita, M., Kojima, M. and Ito, S. Structure and distribution of cerebroside containing unsaturated hydroxy fatty acids in plant leaves, Biosci. Biotech. Biochem. 59 (1995), 1309-1313. 

In a few cases, 3-hydroxy fatty acids that contain additional functional groups were characterized. Thus (i )-3-hydroxydodec-(5Z)-enoic add [A5-12 l(3-OH)] was identified in ester linkage in lipid A of the chloridazon-de-grading bacterium P. immobile (105). Unsaturated 3-hydroxy fatty adds are also present in R. trifolii (81) and R. meliloti (82). In an extract of L. pneumophila, 2,3-dihydroxy-12-methyltridecanoic acid [12-Me-13 0(2,3-diOH)] and 2,3-dihydroxytetradecanoic acid [ 14 0(2,3-diOH)] were identified in amide-linkage (138). It remains, however, to be established, whether these 2,3-dihydroxylated fatty acids are lipid A constituents. Small amounts of 2-methyl-3-hydroxy-fatty adds have been detected in B. pertussis (139). 

Saturated and unsaturated y-lactones and 5-lactones which are synthesised from the corresponding acyclic hydroxy fatty acids by intramolecular esterification are important flavour compounds found ubiquitously in fruits and also in milk and fermentation products in parts-per-million concentrations. The natural lac-... 

Milk fat contains both keto (oxo) and hydroxy fatty acids, and earlier identifications are discussed by Jensen et al. (1967), Morrison (1970), and Kurtz (1974). In a more recent and careful study, Weihrauch et al. (1974) isolated 60 oxo acids from milk fat and positively and tentatively identified 47 with the aid of mass spectrometry. These data are presented in Table 4.9. About 85% (weight) of the oxo acids were stearates, mostly the 13-isomer, and 20% were palmitates, largely the 11-isomer. Of the unsaturated oxo acids, the 9-oxo, 12-ene, and 13-oxo, 9-ene were the predominant species. Other unsaturated oxo acids which are not listed in Table 4.9 but which were possibly present, are 15 1, 16 2, 17 1, 17 2, 17 3, 18 2, 18 3, 19 1, 19 2, and 20 1. 

There is a seemingly endless variety of fatty acids, but only a few of them predominate in any single organism. Most fatty acid chains contain an even number of carbon atoms. In higher plants the C16 palmitic acid and the C18 unsaturated oleic and linoleic acids predominate. The C18 saturated stearic acid is almost absent from plants and C20 to C24 acids are rarely present except in the outer cuticle of leaves. Certain plants contain unusual fatty acids which may be characteristic of a taxonomic group. For example, the Compositae (daisy family) contain acetylenic fatty acids and the castor bean contains the hydroxy fatty acid ricinoleic acid. 

Additionally, microbial systems convert unsaturated fatty acids to monohydroxy-, dihydroxy- and trihydroxy-fatty acids (Hou, 1995,2000). It is feasible to produce various value-added hydroxy fatty acids and derivatives for industrial applications by exploiting the unique reaction specificities of excep-... 

Production of hydroxy fatty acids from unsaturated fatty acids by PR3 558... 

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. 

PRODUCTION OF HYDROXY FATTY ACIDS FROM UNSATURATED FATTY ACIDS BY PR3... 

Various unsaturated fatty acids were efficiently used for the production of various hydroxy fatty acids by bacterial strain P. aeruginosa PR3. Among those unsaturated fatty acids, oleic acid, ricinoleic acid, linoleic acid, palmitoleic acid,... 

Hou, C. T. 1995b. Production of hydroxy fatty acids from unsaturated fatty acids by Flavobacterium sp. DS5 hydratase, a C 10 positional- and cis unsaturation-specific enzyme. /. Am. Oil Chem. Soc., 72,1265-1270. 

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