The fatty acid 8,11-diol synthase of Aspergillus fumigatus is inhibited by imidazole derivatives and unrelated to PpoB.

Abstract:

:(8R)-Hydroperoxy-(9Z,12Z)-octadecadienoic acid (8-HPODE) is formed by aspergilli as an intermediate in biosynthesis of oxylipins with effects on sporulation. 8-HPODE is transformed by separate diol synthases to (5S,8R)-dihydroxy- and (8R,11S)-dihydroxy-(9Z,12Z)-octadecadienoic acids (5,8- and 8,11-DiHODE). The former is formed by the cytochrome P450 (P450) domain of 5,8-linoleate diol synthase (5,8-LDS or PpoA). Our aim was to characterize the 8,11-diol synthase of Aspergillus fumigatus, which is prominent in many strains. The 8,11-diol synthase was soluble and had a larger molecular size (>100 kDa) than most P450. Miconazole, ketoconazole, and 1-benzylimidazole, classical inhibitors of P450, reduced the biosynthesis of 8,11-DiHODE from 8-HPODE (apparent IC(50) values ~0.8, ~5, and ~0.6 μM, respectively), but did not inhibit the biosynthesis of 5,8-DiHODE. Analysis of hydroperoxides of regioisomeric C(18) and C(20) fatty acids showed that the 8,11-diol synthase was specific for certain hydroperoxides with R configuration. The suprafacial hydrogen abstraction and oxygen insertion at C-11 of 8-HPODE was associated with a small deuterium kinetic isotope effect ((H) k (cat)/(D) k (cat) ~1.5), consistent with P450-catalyzed oxidation. The genome of A. fumigatus contains over 70 P450 sequences. The reaction mechanism, size, and solubility of 8,11-diol synthase pointed to PpoB, a homologue of 5,8-LDS, as a possible candidate of this activity. Gene deletion of ppoB of A. fumigatus strains AF:∆ku80 and J272 did not inhibit biosynthesis of 8,11-DiHODE and recombinant PpoB appeared to lack diol synthase activity. We conclude that 8,11-DiHODE is formed from 8-HPODE by a soluble and substrate-specific 8,11-diol synthase with catalytic characteristics of class III P450.

journal_name

Lipids

journal_title

Lipids

authors

Jernerén F,Oliw EH

doi

10.1007/s11745-012-3673-2

subject

Has Abstract

pub_date

2012-07-01 00:00:00

pages

707-17

issue

7

eissn

0024-4201

issn

1558-9307

journal_volume

47

pub_type

杂志文章

相关文献

LIPIDS文献大全
  • Nonessential fatty acids in formula fat blends influence essential fatty acid metabolism and composition in plasma and organ lipid classes in piglets.

    abstract::The n-6 and n-3 fatty acid status of developing organs is the cumulative result of the diet lipid composition and many complex events of lipid metabolism. Little information is available, however, on the potential effects of the saturated fatty acid chain length (8:0-16:0) or oleic acid (18:1) content of the diet on t...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02535583

    authors: Wall KM,Diersen-Schade D,Innis SM

    更新日期:1992-12-01 00:00:00

  • Effects of dietary fats on fatty acid composition and delta 5 desaturase in normal and diabetic rats.

    abstract::We have studied the effect of various diets on the phospholipid fatty acid composition and in vitro delta 5 desaturase activity of hepatic microsomes derived either from the normal or streptozotocin-induced diabetic rat. The diets studied were the standard rat chow diet and a basal fat-free diet supplemented either wi...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02535763

    authors: Dang AQ,Kemp K,Faas FH,Carter WJ

    更新日期:1989-10-01 00:00:00

  • A review of tobacco BY-2 cells as an excellent system to study the synthesis and function of sterols and other isoprenoids.

    abstract::In plants, two pathways are utilized for the synthesis of isopentenyl diphosphate (IPP), the universal precursor for isoprenoid biosynthesis. In this paper we review findings and observations made primarily with tobacco BY-2 cells (TBY-2), which have proven to be an excellent system in which to study the two biosynthe...

    journal_title:Lipids

    pub_type: 杂志文章,评审

    doi:10.1007/s11745-004-1289-0

    authors: Hemmerlin A,Gerber E,Feldtrauer JF,Wentzinger L,Hartmann MA,Tritsch D,Hoeffler JF,Rohmer M,Bach TJ

    更新日期:2004-08-01 00:00:00

  • The simultaneous separation and quantitation of human milk lipids.

    abstract::A protocol using a dry column method was modified for the extraction of total lipids and the simultaneous separation and quantitation of neutral and polar lipids in human milk. The triacylglycerol, cholesterol, phospholipid and vitamin E contents of the lipid extracts were determined and compared with lipids extracted...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02535216

    authors: Collins SE,Jackson MB,Lammi-Keefe CJ,Jensen RG

    更新日期:1989-08-01 00:00:00

  • High intake, but not low intake, of CLA impairs weight gain in growing mice.

    abstract::CLA has a range of biological properties, including effects on lipid metabolism and body composition in experimental animals. The prevalent isomer of CLA found in the human diet is 9c,11 t-CLA, and it is predominantly found in products containing fat from ruminant animals. This study investigated the effect of dietary...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-002-0950-y

    authors: Hayman A,MacGibbon A,Pack RJ,Rutherfurd K,Green JH

    更新日期:2002-07-01 00:00:00

  • Effects of dietary vitamin E, selenium, and polyunsaturated fats on in vivo lipid peroxidation in the rat as measured by pentane production.

    abstract::Starting at 21 days of age, groups of six rats each were fed a basal Torula yeast diet supplemented with 0.4% L-methionine and varying amounts of vitamin E as dl-alpha tocopherol acetate, selenium as sodium selenite, and with either 10% stripped corn oil, stripped lard, or coconut oil. By 7 wk, pentane production by r...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02533708

    authors: Dillard CJ,Litov RE,Tappel AL

    更新日期:1978-06-01 00:00:00

  • Eicosapentaenoic acid, but not oleic acid, stimulates beta-oxidation in adipocytes.

    abstract::The beneficial roles of dietary fish oil in lowering serum TAG levels in animals and humans have been attributed in part to the high content of two n-3 polyunsaturated very long-chain FA, EPA, and DHA. Recent studies show that EPA induces mitochondrial beta-oxidation in hepatocytes, which might contribute to the syste...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-005-1443-8

    authors: Guo W,Xie W,Lei T,Hamilton JA

    更新日期:2005-08-01 00:00:00

  • Dietary lipid level induced antioxidant response in Manchurian trout, Brachymystax lenok (Pallas) larvae.

    abstract::This study was designed to determine the nutritional lipid requirement of Manchurian trout and to investigate the effects of lipid concentrations on the antioxidant status in larvae with experimental diets with different lipid levels. Oxidative stress differences between different organs and tissues were also assessed...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-009-3313-7

    authors: Zhang H,Mu Z,Xu L,Xu G,Liu M,Shan A

    更新日期:2009-07-01 00:00:00

  • Alteration of 20:5n-3 and 22:6n-3 fat contents and liver peroxisomal activities in fenofibrate-treated rainbow trout.

    abstract::Fish easily accumulate n-3 PUFA of exogenous origin, but the underlying mechanisms are not well established in the whole animal. This study was undertaken to investigate whether this feature was physiologically associated with mitochondrial and peroxisomal capacities that differentially affect FA oxidation. For this p...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-004-1306-3

    authors: Du ZY,Demizieux L,Degrace P,Gresti J,Moindrot B,Liu YJ,Tian LX,Cao JM,Clouet P

    更新日期:2004-09-01 00:00:00

  • 1-14C-linoleic acid distribution in various tissue lipids of guinea pigs following an oral dose.

    abstract::A recent study on the metabolism of 1-14C-alpha-linolenic acid in the guinea pig revealed that the fur had the highest specific activity of all tissues examined, 48 h after dosing. The present study investigated the pattern of tissue lipid labeling following an oral dose of 1-14C-linoleic acid after the animals had be...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-001-0715-7

    authors: Fu Z,Attar-Bashi NM,Sinclair AJ

    更新日期:2001-03-01 00:00:00

  • Eicosapentaenoic and docosahexaenoic acid affect mitochondrial and peroxisomal fatty acid oxidation in relation to substrate preference.

    abstract::Decreased triacylglycerol synthesis within hepatocytes due to decreased diacylglycerol acyltransferase (DGAT) activity has been suggested to be an important mechanism by which diets rich in fish oil lower plasma triacylglycerol levels. New findings suggest that eicosapentaenoic acid (EPA), and not docosahexaenoic acid...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-999-0445-x

    authors: Madsen L,Rustan AC,Vaagenes H,Berge K,Dyrøy E,Berge RK

    更新日期:1999-09-01 00:00:00

  • Cardiopathogenicity of rapeseed oils and oil blends differing in erucic, linoleic, and linolenic acid content.

    abstract::Male Wistar rats were fed semipurifed diets containing 20% fat for 25 weeks. Ten different oils or oil blends were employed, including rapessed oils, simulated rapeseed-type oils, and modified rapeseed-type oils. Safflower, soybean, and hydrogenated coconut oils served as control oils. Histopathological examination of...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02532900

    authors: McCutcheon JS,Umermura T,Bhatnager MK,Walker BL

    更新日期:1976-07-01 00:00:00

  • Fatty acids bound to Fasciola hepatica 12 kDa fatty acid-binding protein, a candidate vaccine, differ from fatty acids in extracts of adult flukes.

    abstract::The FA composition of Fasciola hepatica 12 kDA purified native FA-binding protein (nFh12), a candidate vaccine against fascioliasis, is described. The FA chain lengths ranged between 12 and 24 carbons. The principal FA were 16:0, 18:1n-9, 18:0, 20:4n-6, and 20:1n-9. The acids 16:0, 18:1n-9, and 18:0 comprised over hal...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-003-1125-6

    authors: Carballeira NM,Cruz H,Hillyer GV

    更新日期:2003-07-01 00:00:00

  • The absolute configurations of hydroxy fatty acids from the royal jelly of honeybees (Apis mellifera).

    abstract::9-Hydroxy-2E-decenoic acid (9-HDA) is a precursor of the queen-produced substance, 9-oxo-2E-decenoic acid (9-ODA), which has various important functions and roles for caste maintenance in honeybee colonies (Apis mellifera). 9-HDA in royal jelly is considered to be a metabolite of 9-ODA produced by worker bees, and it ...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-010-3497-x

    authors: Kodai T,Nakatani T,Noda N

    更新日期:2011-03-01 00:00:00

  • Successful utilization of lyophilized lipoprotein(a) as a biological reagent.

    abstract::Lipoprotein(a) [Lp(a)] represents a class of lipoprotein particles having as a protein moiety apoB-100 linked by a single disulfide bond to apolipoprotein(a) [apo(a)], a multikringle structure with a high degree of homology with plasminogen. A recognized feature of Lp(a) is its instability on storage caused by attenda...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-004-1268-5

    authors: Scanu AM,Hinman J,Pfaffinger D,Edelstein C

    更新日期:2004-06-01 00:00:00

  • Lung lipid composition in zinc-deficient rats.

    abstract::There have been a limited number of studies investigating surfactant lipid changes in lung with trace elements. The present investigation was designed to examine the effect of moderate zinc deficiency on the lipid metabolism in rat lung. We also evaluated whether zinc deficiency, which is a wide-spread problem, could ...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-002-0893-3

    authors: Gomez NN,Ojeda MS,Gimenez MS

    更新日期:2002-03-01 00:00:00

  • Effect of human mammary MX-1 tumor on plasma free fatty acids in fasted and fasted-refed nude mice.

    abstract::We hypothesized that tumor-bearing (TB) nude mice, because they are reported to have no detectable, circulating tumor necrosis factor (TNF)/cachectin, would regulate their plasma free fatty acid (FFA) levels normally when fasted and refed. We compared levels of individual plasma FFA in response to fasting (24 hr) and ...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02537055

    authors: Lin C,Blank W,Ceriani RL,Baker N

    更新日期:1992-01-01 00:00:00

  • Conjugated linoleic acid modulation of phorbol ester-induced events in murine keratinocytes.

    abstract::Recent work in our lab has shown that the chemoprotective fatty acid, conjugated linoleic acid (CLA), inhibits phorbol ester skin tumor promotion in mice. Because little is known about the deposition of CLA into tissues as well as its biological activity, this study compared the incorporation and biological activity o...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-997-0092-2

    authors: Liu KL,Belury MA

    更新日期:1997-07-01 00:00:00

  • Rapid three-step purification of a hepatic neutral cholesteryl ester hydrolase which is not the pancreatic enzyme.

    abstract::A rat liver cytosolic cholesteryl ester hydrolase (CEH) was purified 12,600-fold by ammonium sulfate precipitation, cation exchange chromatography and gel permeation high-performance liquid chromatography, with an overall yield of 20%. Its properties are compared to those of pancreatic CEH, with which it has sometimes...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02536160

    authors: Ghosh S,Grogan WM

    更新日期:1991-10-01 00:00:00

  • Mechanisms of linoleic acid uptake by rabbit small intestinal brush border membrane vesicles.

    abstract::We examined the initial transport of a long-chain unsaturated fatty acid, linoleic acid, by brush border membrane vesicles isolated from rabbit small intestine. This preparation allowed us to examine the transport of linoleic acid across the brush border membrane without the effect of the unstirred water layer or cyto...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02535264

    authors: Ling KY,Lee HY,Hollander D

    更新日期:1989-01-01 00:00:00

  • Polyunsaturated phosphatidylinositol and diacylglycerol substantially modify the fluidity and polymorphism of biomembranes: a solid-state deuterium NMR study.

    abstract::One of the main biological systems that can be used as a model for studying the molecular mechanisms involved in membrane fusion is the formation of the nuclear envelope (NE). NE assembly to form the male pronucleus at fertilization occurs by binding of NE membrane precursor vesicles to chromatin and their fusion. MV1...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-006-5045-2

    authors: Larijani B,Dufourc EJ

    更新日期:2006-10-01 00:00:00

  • alpha-Tocopherol oxidation mediated by superoxide anion (O2-). I. Reactions in aprotic and protic conditions.

    abstract::The reaction of alpha-tocopherol (alpha-T) with superoxide anion (O2-) in both dry acetonitrile and in aqueous acetonitrile solution is described. The O2- was generated by the electrochemical reduction of molecular oxygen in acetonitrile, using tetrabutylammonium bromide as an electrolyte. alpha-T was reacted with O2-...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02536178

    authors: Csallany AS,Ha YL

    更新日期:1992-03-01 00:00:00

  • The effects of trans fatty acids on fatty acyl delta 5 desaturation by human skin fibroblasts.

    abstract::The effectiveness of different fatty acids as inhibitors of fatty acyl delta 5 desaturation activity in human skin fibroblasts has been investigated. When incubated with 2.25 microM [14C] eicosatrienoate (20:3 omega 6) in otherwise lipid-free medium, these cells rapidly incorporate the radiolabeled fatty acid into cel...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02534517

    authors: Rosenthal MD,Doloresco MA

    更新日期:1984-11-01 00:00:00

  • Search for new seed oils. XV. Oils of boraginaceae.

    abstract::In a search for a preferred source of gamma-linolenic (all-cis-6,9,12-octadecatrienoic) acid, seed oils of 33 species of Boraginaceae were examined. The desired triene was found primarily in the subfamily Boraginoideae in amounts ranging from 0.2 to 18%. Oils of this subfamily also contain 0.2 to 15% of the tetraene, ...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02530967

    authors: Miller RW,Earle FR,Wolff IA,Barclay AS

    更新日期:1968-01-01 00:00:00

  • Glucose-sensitive liposomes incorporating hydrophobically modified glucose oxidase.

    abstract::Glucose-sensitive liposomes were prepared by incorporating hydrophobically modified glucose oxidase (EC 1.1.3.4.) into the liposomal bilayer of dioleoylphosphatidylethanolamine and cholesteryl hemisuccinate. For the release test, calcein, a fluorescence marker, was entrapped in the liposomes. The liposomes were stable...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-008-3223-0

    authors: Jo SM,Lee HY,Kim JC

    更新日期:2008-10-01 00:00:00

  • Modification of odd-chain length unsaturated fatty acids by hepatocytes of rainbow trout (Oncorhynchus mykiss) fed diets containing fish oil or olive oil.

    abstract::Hepatocytes isolated from rainbow trout fed on diets containing either fish oil or olive oil were incubated with individual odd-chain length unsaturated fatty acids (19:1n-9, 19:2n-6, 19:3n-3, 21:2n-6, 21:3n-6, 21:4n-6, 21:3n-3, and 21:5n-3) to examine whether these fatty acids were substrates for modification by desa...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-997-0078-0

    authors: Rodríguez C,Henderson RJ,Porter AE,Dick JR

    更新日期:1997-06-01 00:00:00

  • Structural characterization of a "signature" phosphatidylethanolamine as the major 10-hydroxy stearic acid-containing lipid of Cryptosporidium parvum oocysts.

    abstract::A 10-hydroxy stearic acid-containing lipid from Cryptosporidium parvum was purified by thin-layer chromatography and analyzed by infrared spectroscopy, fast-atom bombardment mass spectrometry, 1H and 31P nuclear magnetic resonance spectroscopy, and was identified as phosphatidyl-ethanolamine. ...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-997-0102-4

    authors: Schrum DP,Alugupalli S,Kelly ST,White DC,Fayer R

    更新日期:1997-07-01 00:00:00

  • Foam fractionation of exo-lipases from a growing fungus (Pleurotus sapidus).

    abstract::Active lipases were isolated from the culture supernatant of the basidiomycetous fungus Pleurotus sapidus by foam fractionation. The pH value, the gas flow, and the foaming period were systematically varied to optimize the transport of the enzymes into the foam phase. On a 70-mL scale, a maximum recovery of hydrolytic...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-005-1389-x

    authors: Linke D,Zorn H,Gerken B,Parlar H,Berger RG

    更新日期:2005-03-01 00:00:00

  • Carnitine palmitoyltransferase I, carnitine palmitoyltransferase II, and acyl-CoA oxidase activities in Atlantic salmon (Salmo salar).

    abstract::Salmon farmers are currently using high-energy feeds containing up to 35% fat; the fish's capability of fully utilizing these high-energy feeds has received little attention. Carnitine is an essential component in the process of mitochondrial fatty acid oxidation and, with the cooperation of two carnitine palmitoyltra...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/s11745-998-0289-4

    authors: Frøyland L,Madsen L,Eckhoff KM,Lie O,Berge RK

    更新日期:1998-09-01 00:00:00

  • Effect of dietary linseed oil on tumoricidal activity and eicosanoid production in murine macrophages.

    abstract::Diets that contain high levels of n-3 fatty acids from fish oil have been shown to significantly effect macrophage cytolytic capacity, tumor necrosis factor alpha production and eicosanoid production. The present study was undertaken to determine whether n-3 fatty acids from vegetable origin [linseed oil (LIN)] would ...

    journal_title:Lipids

    pub_type: 杂志文章

    doi:10.1007/BF02536100

    authors: Hubbard NE,Chapkin RS,Erickson KL

    更新日期:1994-09-01 00:00:00