Manganese Lipoxygenase

Hámberg, Mats; Su, Chao; Oliw, Ernst H.

doi:10.1074/jbc.273.21.13080

Cited by 126 publications

(73 citation statements)

References 37 publications

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“…A few dioxygenase reactions deviate from this rule. Manganese lipoxygenase catalyzes suprafacial formation of linoleic acid 11-and 13-hydroperoxides (40), and the major ␣-DOX of tobacco and Arabidopsis produces ␣-hydroperoxides with retention of absolute configuration at C-2 (19). Furthermore, (10S)-DOX from the field mushroom (A. bisporus) catalyzes formation of (10S)-HPODE in a reaction that involves suprafacial stereochemistry.…”

Section: Tablementioning

confidence: 99%

Identification of Dioxygenases Required for Aspergillus Development

Garscha

Jernerén

Chung

et al. 2007

Journal of Biological Chemistry

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Aspergillus sp. contain ppoA, ppoB, and ppoC genes, which code for fatty acid oxygenases with homology to fungal linoleate 7,8-diol synthases (7,8-LDS) and cyclooxygenases. Our objective was to identify these enzymes, as ppo gene replacements show critical developmental aberrancies in sporulation and pathogenicity in the human pathogen Aspergillus fumigatus and the genetic model Aspergillus nidulans. The PpoAs of A. fumigatus and A. nidulans were identified as (8R)-dioxygenases with hydroperoxide isomerase activity, designated 5,8-LDS. 5,8-LDS transformed 18:2n-6 to (8R)-hydroperoxyoctadecadienoic acid ((8R)-HPODE) and (5S,8R)-dihydroxy-9Z,12Z-octadecadienoic acid ((5S,8R)-DiHODE). We also detected 8,11-LDS in A. fumigatus and (10R)-dioxygenases in both

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Section: Tablementioning

confidence: 99%

Identification of Dioxygenases Required for Aspergillus Development

Garscha

Jernerén

Chung

et al. 2007

Journal of Biological Chemistry

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“…Besides this product, upon incubation of CspLOX2 with 18:2(n-6) a mixture of typical LOX products 13S-and 9R-HPODE were formed. So far, the only LOXs that have been reported to produce bisallylic hydroperoxides are the Mn-LOX from the fungus G. graminis (10,40) and the LOX domain of the allene oxide synthase-LOX fusion protein from the coral Plexaura homomalla, which formed the 10-hydroperoxide out of 20:3(n-6) (41). Mn-LOX is the best studied example of a bisallylic LOX and can convert 18:2(n-6) to 11S-HPODE and 13R-HPODE in a 1:3 ratio with the latter accumulating as an end product (40).…”

Section: Discussionmentioning

confidence: 99%

“…Antarafacial oxygenation has been previously reported for all LOXs, with the exception of Mn-LOX, which also abstracts the pro-S hydrogen from the C11 of 18:2(n-6), but subsequently catalyzes the oxygen insertion on the same side of the (1Z,4Z)-pentadiene system (10). The fact that the amounts of bisallylic hydroperoxide product were reduced when [(11S)-2 H]-18:2(n-6) was used as CspLOX2 substrate may be indicative for a kinetically controlled formation of 11R-HPODE.…”

Section: Experiments With Labeled [(11s)-mentioning

confidence: 99%

“…The fact that the amounts of bisallylic hydroperoxide product were reduced when [(11S)-2 H]-18:2(n-6) was used as CspLOX2 substrate may be indicative for a kinetically controlled formation of 11R-HPODE. A strong primary isotope effect was also described for Mn-LOX, but for this enzyme the proportion of the bisallylic hydroperoxide product remained unaltered regardless of the isotopically labeled 18:2(n-6) used as substrate (10).…”

Section: Experiments With Labeled [(11s)-mentioning

confidence: 99%

“…Plant LOXs studied so far almost exclusively catalyze the insertion of oxygen with an S stereospecificity. 9R-products have mainly been identified in cyanobacteria, whereas 13R-hydroperoxide has been reported to be one of the hydroperoxides produced by a dual specificity LOX from olive (9) and is the end product of the fungal Mn-LOX (10). The latter enzyme is also the only as yet characterized LOX that produces the bisallylic 11S-hydroperoxide.…”

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A Bisallylic Mini-lipoxygenase from Cyanobacterium Cyanothece sp. That Has an Iron as Cofactor

Andreou¹,

Göbel²,

Hámberg

et al. 2010

Journal of Biological Chemistry

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Lipoxygenases are enzymes that are found ubiquitously in higher animals and plants, but have only recently been identified in a number of bacteria. The genome of the diazotrophic unicellular cyanobacterium Cyanothece sp. harbors two genes with homology to lipoxygenases. Here we describe the isolation of one gene, formerly named csplox2. It was cloned, and the protein was expressed in Escherichia coli and purified. The purified enzyme belongs to the group of prokaryotic mini lipoxygenases, because it had a molecular mass of 65 kDa. Interestingly, it catalyzed the conversion of linoleic acid, the only endogenously found polyunsaturated fatty acid, primarily to the bisallylic hydroperoxide 11R-hydroperoxyoctadecadienoic acid. This product had previously only been described for the manganese lipoxygenase from the take all fungus, Gaeumannomyces graminis. By contrast, CspLOX2 was shown to be an iron lipoxygenase. In addition, CspLOX2 formed a mixture of typical conjugated lipoxygenase products, e.g. 9R-and 13S-hydroperoxide. The conversion of linoleic acid took place with a maximum reaction rate of 31 s ؊1 . Incubation of the enzyme with [(11S)-2 H]linoleic acid led to the formation of hydroperoxides that had lost the deuterium label, thus suggesting that CspLOX2 catalyzes antarafacial oxygenation as opposed to the mechanism of manganese lipoxygenase. CspLOX2 could also oxidize diarachidonylglycerophosphatidylcholine with similar specificity as the free fatty acid, indicating that binding of the substrate takes place with a "tail-first" orientation. We conclude that CspLOX2 is a novel iron mini-lipoxygenase that catalyzes the formation of bisallylic hydroperoxide as the major product.

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Synthesis and Stability of Phosphatidylcholines Bearing Polyenoic Acid Hydroperoxides at the sn-2 Position

Onyango

Inoue²,

Nakajima³

et al. 2001

Angew. Chem. Int. Ed.

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Für die Aktivität von Fischölen gegen Krebs und Malaria könnten Phospholipidhydroperoxide eine Rolle spielen. Zwei derartige Phosphatidylcholine wurden synthetisiert: 1 und 2 mit den Hydroperoxiden von Docosahexaen‐ bzw. Icosapentaensäure – den beiden wichtigsten Fettsäuren in Fischölen. Trotz seiner hohen Ungesättigtheit ist 1 ausreichend stabil für den Einsatz in biologischen Studien.

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Manganese Lipoxygenase

Cited by 126 publications

References 37 publications

Identification of Dioxygenases Required for Aspergillus Development

Identification of Dioxygenases Required for Aspergillus Development

A Bisallylic Mini-lipoxygenase from Cyanobacterium Cyanothece sp. That Has an Iron as Cofactor

Synthesis and Stability of Phosphatidylcholines Bearing Polyenoic Acid Hydroperoxides at the sn-2 Position

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