Lipoxygenases from soybean

Axelrod, B., Cheesebrough, T.M., and Laakso. S. 1981. Lipoxygenase from soybeans. EC... 

Considerable purification of lipoxygenase from soybeans was achieved by Balls et al (15), They used conventional protein purification methods and the carotene oxidase reaction to follow the enzyme activity. Theorell et al, (16), in 1947, crystallized the enzyme, or more correctly, one of the several isoenzymes in soybean. We believe this was lipoxygenase-1 as described later. 

Lipoxygenase is iron that contains dioxygenase and is found in plants and mammals, also produced by some microorganisms. It has been established that the lipoxygenase from soybeans can catalyse the oxidation of a wide range of endogenous chemicals (KuUcami 1996). 

Axelrod, B. T.M. Cheesbrough S. Laakso. Lipoxygenase from soybeans. Methods Enzymol. 1981, 71, 441-451. 

Fornaroli, S. S. Petrussa E. Braidot A. Vianello F. Macri. Purification of a plasma membrane-bound lipoxygenase from soybean cotyledons. Plant Sci. 1999, 145, 1—10. 

Figure 12. MR spectra (15.4 MHz) of [9,10,12,13- H]-linoleic acid in the presence of lipoxygenase from soybean. Spectra are for samples with fatty acid/enzyme mole ratios of (A) (B)...

Lipoxygenase-Catalyzed Oxidations. Lipoxygenase-1 catalyzes the incorporation of dioxygen into polyunsaturated fatty acids possessing a l(Z),4(Z)-pentadienyi moiety to yield ( ),(Z)-conjugated hydroperoxides. A highly active preparation of the enzyme from soybean is commercially available in purified form. From a practical standpoint it is important to mention that the substrate does not need to be in solution to undergo the oxidation. Indeed, the treatment of 28 g/L of linoleic acid [60-33-3] with 2 mg of the enzyme results in (135)-hydroperoxide of linoleic acid in 80% yield... 

A series of indolizines 281 and azaindolizines 282 were screened as possible inhibitors of 15-lipoxygenase (15-LO) from soybeans and rabbit reticulocytes. Most compounds studied were significantly more active than quercitin (IC50 51 pi) <2003BML5409>. The indolizine and azaindolizine sulfonates were particularly studied and showed high activity <2005BMC5409>. 

Human 15-lipoxygenase and soybean LO-1 H/D-atom transfer from per-H vs. per-D Unoleic acid Cll to Fe-O Soybean lipoxygenase-1, WT and L546A mutant, H-atom transfer from H, D labeled linoleic acid Cll to Fe-O... 

Additional lipoxygenases are known which oxygenate different positions on the arachidonic acid chain. 12-LO, resulting in the formation of 12-HETE (7), is best known in platelets, while the 15-LO from soybean has been studied in detail for many years [8]. 15-HETE (8) is also produced by mammalian cells the enzymes from neutrophils and particularly rabbit reticulocytes are the best characterized. 

Lipoxygenase (EC 1.13.11.12) is an enzyme that catalyzes the hydroperoxidation of polyunsaturated fatty acids and esters containing a cis-cis-l, 4-pentadiene system (Table 6). In 1947, Theorell et al. obtained the enzyme in a crystalline form from soybeans and reported that the enzyme neither contained nor required a metal cofactor192. Subsequent studies from three groups of investigators have demonstrated that the enzyme purified from soybeans in an iron-containing dioxygenase74-76 ... 

Lipoxygenase-Catalyzed Oxidations. Lipoxygenase-1 catalyzes the incorporation of diuxygen into polyunsaturated fatty acids possessing a l(Z).4(Z)-pentadienyl moiety to yield ( ).conjugated hydroperoxides. A highly active preparation of the enz.yme from soybean is commercially available in purified form. 

Srinivasulu, S. and Rao, A.G.A. 1993. Kinetic and structural studies on the interaction of surfactants with lipoxygenase LI from soybeans (Glycine max ). J. Agric. Food Chem. 41 366-371. 

Figure 6. (A) - The oxygenation of dilinoleoylphosphatidilcholine (DLPC) liposomes by C-15 plant (from soybeans) or animal (from rabbit reticulocytes) lipoxygenase ...

Scheme 3 Generation of 13-hydroperoxy-9Z-llE- octadeca-dienoic acid by action of soybean lipoxygenase from linoleic acid according to de Groot [154],...

Lipoxygenase derived from soybean transforms linoleic acid at pH 9.2 nearly exclusively into 13S-hydroperoxy-9Z-l lE-octadecadienoic acid (13S-HPODE, Scheme 4) and linoleinic acid into 16S-9Z 12Z,14E-octadecadienoic acid (13S-HPOTE, Scheme 5) [155]. 

For the first time bioactivation of aflatoxin B1 from soybeans lipoxygenase was demonstrated by Liu and Massey (Liu and Massey 1992). Datta and Kulkami have also investigated it, but in the presence of linoleic acid which is the natural substrate of the enzyme (Datta and Kulkami 1994). 

Figure 2.4 Phosphatidylcholine content of lecithin recovered from extruded-expelled (E-E) and solvent extracted (S-E) soybean oils. Abbreviations HO, high-oleic acid soybean oil LLL, low-linolenic acid soybean oil LOX, lipoxygenase-free soybean oil LS, low-saturated fatty acid soybean oil and CS, commodity soybean oil. Key , E-E B, S-E. 

The initial reaction of the pathway in which a-linolenic acid is converted to 12-oxo-PDA was catalysed with Oj in the presence of soybean lipoxygenase and the resultant hydroperoxide product was 13(S)-hydroperoxylinolenic acid [13(S)-HPOD a minor product was 9-HPOD [30]. A regiospecificity study using partially pure lipoxygenase from V. faba pericarp showed that 92% of the product was 13(S)-HPOD and 8% was the... 

Shen, N. W. Fehr P. White. High-temperature stabilities of oils from soybeans that lack lipoxygenases./. Am. Oil Chem. Soc. 1997, 74, 381-385. 

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