Regio- and stereochemical analysis of trihydroxyoctadecenoic acids derived from linoleic acid 9- and 13-hydroperoxides

No abstract is available for this paper.

• Publication year

  1991

• Venue

  Lipids

• Publication date

  1991-06-01

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1007/BF02536065PMID 27520964
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Hydroperoxide-dependent epoxidation of unsaturated fatty acids in the broad bean (Vicia faba L.).

  1990cited by this paper
• Fatty acid hydroperoxide isomerase inSaprolegnia parasitica: Structural studies of epoxy alcohols formed from isomeric hydroperoxyoctadecadienoates

  1989cited by this paper
• An antifungal compound, 9,12,13-trihydroxy-(E)-10-octadecenoic acid, from Colocasia antiquorum inoculated with Ceratocystis fimbriata

  1989cited by this paper
• Biosynthesis, catabolism, and biological properties of HPETEs, hydroperoxide derivatives of arachidonic acid.

  1989cited by this paper
• Vanadium-catalyzed transformation of 13(S)-hydroperoxy-9(Z), 11(E)-octadecadienoic acid: Structural studies on epoxy alcohols and trihydroxy acids

  1987cited by this paper
• Stereochemistry of two epoxy alcohols from Saprolegnia parasitica

  1986cited by this paper
• Novel biological transformations of 15-Ls-hydroperoxy-5,8,11,13-eicosatetraenoic acid.

  1986cited by this paper
• Isolation and structures of lipoxygenase products from Saprolegnia parasitica

  1986cited by this paper
• Structure and synthesis of unsaturaded trihydroxy c18 fatty

  1985cited by this paper
• Isolation and identification of two isomeric trihydroxy octadecenoic acids with prostaglandin E-like activity from onion bulbs (Allium cepa).

  1985cited by this paper
• Metabolic profile of linoleic acid in porcine leukocytes through the lipoxygenase pathway.

  1985cited by this paper
• Metabolism of linoleic acid and other essential fatty acids in the epidermis of the rat.

  1985cited by this paper
• Trihydroxy-C18-acids and a labdane from rudbeckia fulgida

  1985cited by this paper
• Acid-catalyzed transformation of 13(S)-hydroperoxylinoleic acid into epoxyhydroxyoctadecenoic and trihydroxyoctadecenoic acids

  1984cited by this paper
• Unsaturated polyhydroxy acids having prostaglandin-like activity from Bryonia alba II. Major components.

  1983cited by this paper
• Metabolism of linoleic acid by prostaglandin endoperoxide synthase from adult and fetal blood vessels.

  1983cited by this paper
• Malyngic acid, a new fatty acid from Lyngbya majuscula

  1980cited by this paper
• [Isomeric trihydroxy-octadecenoic acids in beer: Evidence for their presence and quantitative determination (author's transl)].

  1977cited by this paper
• A simple method for the preparation of pure 9-d-hydroperoxide of linoleic acid and methyl linoleate based on the positional specificity of lipoxygenase in tomato fruit

  1977cited by this paper
• Isomere Trihydroxy-octadecensäuren in Bier: Beweise für ihr Vorkommen und ihre quantitative Bestimmung

  1977cited by this paper
• Enzymatic oxydation of linoleic acid: Formation of bittertasting fatty acids

  1977cited by this paper
• Enzymic reactions of fatty acid hydroperoxides in extracts of potato tuber. II. Conversion of 9- and 13-hydroperoxy-octadecadienoic acids to monohydroxydienoic acid, epoxyhydroxy- and trihydroxymonoenoic acid derivatives.

  1975cited by this paper
• Homolytic decomposition of linoleic acid hydroperoxide: Identification of fatty acid products

  1974cited by this paper
• Über den enzymatischen Hydroperoxidabbau in Cerealien Enzymcharakterisierung und Reaktionsprodukte

  1973cited by this paper
• A new reaction of unsaturated fatty acid hydroperoxides: Formation of 11-hydroxy-12,13-epoxy-9-octadecenoic acid from 13-hydroperoxy-9,11-octadecadienoic acid

  1973cited by this paper
• Identification of Trihydroxy-Octadecenoates Derived from UV Irradiated or Autoxidized Sesame Oil and Methyl Linoleate and Mechanism of Their Formation

  1972cited by this paper
• Steric analysis of hydroperoxides formed by lipoxygenase oxygenation of linoleic acid.

  1971cited by this paper
• Enzymatic oxidations of linoleic acid and glycerol-1-monolinoleate in doughs and flour-water suspensions

  1970cited by this paper
• SEPARATION OF ISOMERIC LONG-CHAIN POLYHYDROXY ACIDS BY THIN-LAYER CHROMATOGRAPHY.

  1963cited by this paper

• Obtaining and Characterization of Nutraceuticals Based on Linoleic Acid Derivatives Obtained by Green Synthesis and Their Valorization in the Food Industry

  2025cites this paper
• Selenium-Enriched Aspergillus oryzae A02 Enhances Testicular Antioxidant Capacity in Mice by Regulating Intestinal Microbiota and Serum Metabolite

  2024cites this paper
• The versatile CYP74 clan enzyme CYP440A19 from the European lancelet Branchiostoma lanceolatum biosynthesizes novel macrolactone, epoxydiene, and related oxylipins.

  2024cites this paper
• The Octadecanoids: Synthesis and Bioactivity of 18-Carbon Oxygenated Fatty Acids in Mammals, Bacteria, and Fungi

  2024cites this paper
• Impact of feeding dried distillers’ grains with solubles diet on microbiome and metabolome of ruminal and cecal contents in Guanling yellow cattle

  2023cites this paper
• Stable analogs of 13‑hydroxy-9,10-trans-epoxy-(11E)-octadecenoate (13,9-HEL), an oxidized derivative of linoleic acid implicated in the epidermal skin barrier.

  2021cites this paper
• Detection of the First Epoxyalcohol Synthase/Allene Oxide Synthase (CYP74 Clan) in the Lancelet (Branchiostoma belcheri, Chordata)

  2021cites this paper
• Eosinophils synthesize trihydroxyoctadecenoic acids (TriHOMEs) via a 15-lipoxygenase dependent process.

  2020cites this paper
• Molecular level comparison of water extractives of maple and oak with negative and positive ion ESI FT-ICR mass spectrometry.

  2019cites this paper
• An LC-MS/MS workflow to characterize 16 regio- and stereoisomeric trihydroxyoctadecenoic acids[S]

  2018cites this paper
• Identification of CYP443D1 (CYP74 clan) of Nematostella vectensis as a first cnidarian epoxyalcohol synthase and insights into its catalytic mechanism.

  2017cites this paper
• The Precise Structures and Stereochemistry of Trihydroxy-linoleates Esterified in Human and Porcine Epidermis and Their Significance in Skin Barrier Function

  2016cites this paper
• The Reductase Activity of the Arabidopsis Caleosin RESPONSIVE TO DESSICATION20 Mediates Gibberellin-Dependent Flowering Time, Abscisic Acid Sensitivity, and Tolerance to Oxidative Stress1[W]

  2014influential citation
• WITHDRAWN: Structural and mechanistic studies of hydroperoxide conversions catalyzed by a CYP74 clan epoxy alcohol synthase from amphioxus (Branchiostoma floridae).

  2013cites this paper
• Steric analysis of epoxyalcohol and trihydroxy derivatives of 9-hydroperoxy-linoleic acid from hematin and enzymatic synthesis.

  2013influential citation
• Molecular characterization of NbEH1 and NbEH2, two epoxide hydrolases from Nicotiana benthamiana.

  2013cites this paper
• Spatiotemporal changes in the Content and Metabolism of 9, 12, 13 – Trihydorxy-10(E)-Octadecenoic Acid in Tomato ( Solanum Lycopersicum L. CV Balkonsar) fruits

  2013cites this paper
• Overexpression of hydroperoxide lyase, peroxygenase and epoxide hydrolase in tobacco for the biotechnological production of flavours and polymer precursors.

  2012cites this paper
• Selected Extracts of Chinese Herbal Medicines: Their Effect on NF-κB, PPARα and PPARγ and the Respective Bioactive Compounds

  2012influential citation
• Chapter 1 – ANALYSIS OF PLANT LIPOXYGENASE METABOLITES

  2012cites this paper
• Efficient and Specific Conversion of 9-Lipoxygenase Hydroperoxides in the Beetroot. Formation of Pinellic Acid

  2011influential citation
• Synthesis of (−)‐Pinellic Acid and Its (9R,12S,13S)‐Diastereoisomer

  2009cites this paper
• Roles of a membrane-bound caleosin and putative peroxygenase in biotic and abiotic stress responses in Arabidopsis.

  2009cites this paper
• High prevalence of hyperhomocysteinemia in critically ill patients: Vascular damage and adequate vitamin intake

  2008cites this paper
• Enantioselective synthesis of (-)-pinellic acid

  2007cites this paper
• Enantioselective syntheses of (−)-pinellic acid, α- and β-dimorphecolic acid

  2007cites this paper
• -octadecenoic acid from linoleic acid by Pseudomonas aeruginosa PR3

  2007cites this paper
• Epidermal lipoxygenase products of the hepoxilin pathway selectively activate the nuclear receptor PPARalpha.

  2007cites this paper
• Epidermal Lipoxygenase Products of the Hepoxilin Pathway Selectively Activate the Nuclear Receptor PPARα

  2007cites this paper
• Plant Seed Peroxygenase Is an Original Heme-oxygenase with an EF-hand Calcium Binding Motif*

  2006cites this paper
• The real radical generator other than main-product hydroperoxide in lipid autoxidation

  2006cites this paper
• Total synthesis, elucidation of absolute stereochemistry, and adjuvant activity of trihydroxy fatty acids

  2006cites this paper
• Technologische Einflussnahme auf den Lipidabbau im Sinne einer Verbesserung der Geschmacksstabilität des Bieres

  2006cites this paper
• Evaluation of the Antimicrobial Activities of Plant Oxylipins Supports Their Involvement in Defense

  2005cites this paper
• Discovery of a novel lipoxygenase pathway in skin.

  2005cites this paper
• Evaluation of the Antimicrobial Activities of Plant Oxylipins Supports Their Involvement in Defense against Pathogens1[W]

  2005cites this paper
• Freie und triglycerid-gebundene Hydroxyfettsäuren in Gerste und Malz und ihre Bedeutung für die Geschmacksstabilität des Bieres

  2005cites this paper
• Characterization and quantification of free and esterified 9- and 13-hydroxyoctadecadienoic acids (HODE) in barley, germinating barley, and finished malt.

  2005cites this paper
• Oxylipin profiling in pathogen-infected potato leaves.

  2002cites this paper
• An epoxy alcohol synthase pathway in higher plants: Biosynthesis of antifungal trihydroxy oxylipins in leaves of potato

  1999cites this paper
• Metabolic profile of linoleic acid in stored apples: Formation of 13(R)-hydroxy-9(Z),11(E)-octadecadienoic acid

  1999cites this paper
• Reactivity of lysine moieties toward an epoxyhydroxylinoleic acid derivative: aminolysis versus hydrolysis.

  1999cites this paper
• Linoleic acid peroxidation--the dominant lipid peroxidation process in low density lipoprotein--and its relationship to chronic diseases.

  1998cites this paper
• Microbial production of a novel trihydroxy unsaturated fatty acid from linoleic acid

  1997cites this paper
• Stereochemical aspects of fatty acid oxidation: hydroperoxide isomerases.

  1996cites this paper
• Sequential oxygenation of linoleic acid in the fungus Gaeumannomyces graminis: stereochemistry of dioxygenase and hydroperoxide isomerase reactions.

  1994cites this paper
• Trihydroxyoctadecadienoic acids exhibit antiatherosclerotic and antiatherogenic activity.

  1994cites this paper
• Transformation of fatty acid hydroperoxides by alkali and characterization of products

  1993cites this paper
• A method for determination of the absolute stereochemistry of α,β-epoxy alcohols derived from fatty acid hydroperoxides

  1992cites this paper
• Oxylipin pathway to jasmonates: biochemistry and biological significance.

  1992cites this paper
• Linoleic acid metabolism in the red algaLithothamnion corallioides: Biosynthesis of 11(R)-hydroxy-9(Z),12(Z)-octadecadienoic acid

  1992cites this paper
• A linoleic acid (8R)-dioxygenase and hydroperoxide isomerase of the fungus Gaeumannomyces graminis. Biosynthesis of (8R)-hydroxylinoleic acid and (7S,8S)-dihydroxylinoleic acid from (8R)-hydroperoxylinoleic acid.

  1992cites this paper
• On the Specificity of a Fatty Acid Epoxygenase in Broad Bean (Vicia faba L.).

  1992cites this paper
• Oxylipin metabolism in the red alga Gracilariopsis lemaneiformis: mechanism of formation of vicinal dihydroxy fatty acids.

  1991cites this paper
• OXYLIPINS AND RELEVANT ENZYMES IN PLANT DEFENCE

  year unknowncites this paper
• Fatty Acid Epoxygenase in Broad Bean

  year unknowncites this paper