H. W. Gardner

United States Department of Agriculture, Washington, D. C., DC, United States

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Publications (30)55.1 Total impact

  • H. W. Gardner · R. J. Bartelt · D. Weisleder ·
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    ABSTRACT: A facile, efficient synthesis of 4-hydroxy-2(E)-nonenal is presented as an alternative to the approaches published previously, which either employed four to six separate steps or furnished low yields. The commercially available 3(Z)-nonenol was sequentially oxidized into 3,4-epoxynonanol by 3-chloroperoxybenzoic acid followed by oxidation of the alcohol by periodinane to afford 4-hydroxy-2(E)-nonenal by this two-step procedure in 48±7% yield.
    Lipids 08/1992; 27(9):686-689. DOI:10.1007/BF02536025 · 1.85 Impact Factor
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    H W Gardner · D Weisleder · R D Plattner ·
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    ABSTRACT: Hydroperoxide lyase (HPLS) activity in soybean (Glycine max) seed/seedlings, leaves, and chloroplasts of leaves required detergent solubilization for maximum in vitro activity. On a per milligram of protein basis, more HPLS activity was found in leaves, especially chloroplasts, than in seeds or seedlings. The total yield of hexanal from 13(S)-hydroperoxy-cis-9,trans-11-octadecadienoic acid (13S-HPOD) from leaf or chloroplast preparations was 58 and 66 to 85%, respectively. Because of significant competing hydroperoxide-metabolizing activities from other enzymes in seed/seedling preparations, the hexanal yields from this source were lower (36-56%). Some of the products identified from the seed or seedling preparations indicated that the competing activity was mainly due to both a hydroperoxide peroxygenase and reactions catalyzed by lipoxygenase. Different HPLS isozyme compositions in the seed/seedling versus the leaf/chloroplast preparations were indicated by differences in the activity as a function of pH, the K(m) values, relative V(max) with 13S-HPOD and 13(S)-hydroperoxy-cis-9,trans-11,cis-15-octadecatrienoic acid (13S-HPOT), and the specificity with different substrates. With regard to the latter, both seed/seedling and chloroplast HPLS utilized the 13S-HPOD and 13S-HPOT substrates, but only seeds/seedlings were capable of metabolizing 9(S)-hydroperoxy-trans-10,cis-12-octadecadienoic acid into 9-oxononanoic acid, isomeric nonenals, and 4-hydroxynonenal. From 13S-HPOD and 13S-HPOT, the products were identified as 12-oxo-cis-9-dodecenoic acid, as well as hexanal from 13S-HPOD and cis-3-hexenal from 13S-HPOT. In seed preparations, there was partial isomerization of the cis-3 or cis-9 into trans-2 or trans-10 double bonds, respectively.
    Plant physiology 12/1991; 97(3):1059-72. DOI:10.1104/pp.97.3.1059 · 6.84 Impact Factor
  • R. D. Plattner · H. W. Gardner ·
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    ABSTRACT: Intact isomeric methyl 9- and 13-hydroperoxy linoleates are analyzed by chemical ionization (CI) mass spectrometry using a direct exposure probe. Both isobutane and ammonia CI spectra were obtained. With isobutane CI, ions are observed for protonated fragments that are indicative of an acid catalysis mechanism similar to that observed in solution, whereas ammonia CI yields primarily adduct ions. The collisionally activated decomposition daughters of the high mass ions can be used to identify the position of the hydroperoxy group in the isomers studied.
    Lipids 02/1985; 20(2):126-131. DOI:10.1007/BF02534219 · 1.85 Impact Factor
  • H.W. Gardner · E.C. Nelson · L.W. Tjarks · R.E. England ·
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    ABSTRACT: Acid treatment of (13S)-(9Z,11E)-13-hydroperoxy-9,11-octadecadienoic acid in tetrahydrofuran-water solvent afforded mainly (11R,12R,13S)-(Z)-12,13-epoxy-11-hydroxy-9-octadecenoic acid, diastereomeric (Z)-11,12,13-trihydroxy-9-octadecenoic acids and four isomers of (E)-9,12,13(9,10,13)-trihydroxy-10(11)-octadecenoic acid. Other minor products were oxooctadecadienoic, (E)-9(13)-hydroxy-13(9)-oxo-10(11)-octadecenoic and (E)-12-oxo-10-dodecenoic acids. A heterolytic mechanism for acid catalysis was indicated, even though most of the products characterized also have been observed as a result of homolytic decomposition of the hydroperoxide via an oxy radical. Most of the products found in this study have been observed as metabolites of (13S)-(9Z,11E)-13-hydroperoxy-9,11-octadecadenoic acid in biological systems, and analogous compounds have been reported as metabolites of (12S)-(5Z,8Z,10E, 14Z)-12-hydroperoxy-5,8,10,14-hydroperoxy-5,8,10,14-eicosatetraenoic acid in either blood platelets or lung tissue.
    Chemistry and Physics of Lipids 07/1984; 35(2):87-101. DOI:10.1016/0009-3084(84)90015-X · 2.42 Impact Factor
  • H. W. Gardner · R. D. Plattner ·
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    ABSTRACT: Treatment of isomeric methyl linoleate hydroperoxides with a Lewis acid, BF3, in anhydrous ether led to a carbon-to-oxygen rearrangement that caused cleavage into shorter-chain aldehydes. Methyl (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate afforded mainly hexanal and methyl (E)-12-oxo-10-dodecenoate, whereas methyl (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate cleaved into 2-nonenal and methyl 9-oxononanoate. The 2 aldehydes obtained from each hydroperoxide isomer were uncharacteristic of the complex volatile profile usually obtained by β-scission of oxy radicals derived from homolysis of the hydroperoxide group. Rather, the reaction resembled the one catalyzed by the plant enzyme, hydroperoxide lyase.
    Lipids 04/1984; 19(4):294-299. DOI:10.1007/BF02534458 · 1.85 Impact Factor
  • H. W. Gardner · D. Weisleder · E. C. Nelson ·
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    ABSTRACT: Acid catalysis (0.1 M H 2SO 4) of (13S)-(9Z,11E)-13-hydroperoxy-9,H-octadecadienoic acid (1) in methanol-water (9:1) did not afford appreciable yields of anticipated products, hexanal and (Z)-12-oxo-9-dodecenoic acid, via the known Hock rearrangement of hydroperoxides. Instead, intramolecular rearrangement of the 13-hydroperoxide into 12,13-epoxides, accompanied by solvent substitution, was the primary course of reaction (all products were isolated after conversion to methyl esters). Three isomeric methyl (Z)-12,13-epoxy-11-methoxy-9-octadecenoates were isolated in 20.2 mol % yield; methyl (11R,12R,13S)-(Z)-12,13-epoxy-11-methoxy-9-octadecenoate (2a) comprised 81% of the three. The stereoselectivity observed in the formation of 2a implied anchimeric assistance by the epoxide group in substitution by methanol. Kinetic evidence, as well as a 20.4 mol % yield of stereoisomers of methyl (E)-13-hydroxy-9,12-dimethoxy-10-octadecenoates, was indicative of intermediate (E)-12,13-epoxy-9-methoxy-10-octadecenoic acids. These allylic epoxides could not be isolated, presumably because they solvolyzed rapidly in the presence of acid. On the other hand, the nonallylic epoxides 2a-c solvolyzed more slowly. The following reaction mechanism is proposed: (a) a conjugate acid forms by addition of a proton to a hydroperoxy group; (b) electrophilic attack on C-12 by a partially positive-charged α-oxygen of the hydroperoxy group affords a 12,13-epoxy-9,11-allylic cation; (c) C-9 or C-11 undergoes substitution from methanol; (d) the products of substitution, isomeric epoxymethoxyoctadecenoic acids, are solvolyzed further to hydroxydimethoxyoctadecenoic acids. The possibility that heterolysis of 1, as well as of other hydroperoxides of polyunsaturated fatty acids, may have significance in biological transformations is discussed.
    The Journal of Organic Chemistry 02/1984; 49(3). DOI:10.1021/jo00177a024 · 4.72 Impact Factor
  • R. D. Plattner · H. W. Gardner · R. Kleiman ·
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    ABSTRACT: Chemical ionization (CI) mass spectra of functionally substituted fatty esters are a useful aid in determining molecular weight. Isobutane and ammonia CI mass spectra of various hydroxy, keto, epoxy and hydroperoxy fatty esters are reported and discussed.
    Journal of Oil & Fat Industries 06/1983; 60(7):1298-1303. DOI:10.1007/BF02702104 · 1.54 Impact Factor
  • H W Gardner · R Kleiman ·
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    ABSTRACT: 1. The degradation of linoleic acid hydroperoxide by cysteine and FeCl3 resulted in formation of a number of oxygenated fatty acids, among which isomeric epoxyoxooctadecenoic and epoxyhydroxyoctadecenoic acids were major products. Pure isomeric hydroperoxides, either 13-L(S)-hydroperoxy-cis-9,trans-11-octadecadienoic acid or 9-D(S)-hydroperoxy-trans-10,cis-12-octadecadienoic acid, were transformed into either 12,13-epoxides or 9,10-epoxides, respectively. 2. From 13-L(S)-hydroperoxy-cis-9,trans-11-octadecadienoic acid, the epoxides were identified as trans-12,13-epoxy-9-oxo-trans-10-octadecenoic acid, trans-12,13-epoxy-9-hydroxy-trans-10-octadecenoic acid, cis-12,13-epoxy-9-oxo-trans-10-octadecenoic acid, trans-12,13-epoxy-erythro-11-hydroxy-cis(trans)-9-octadecenoic acid and trans-12,13-epoxy-threo-11-hydroxy-cis(trans)-9-octadecenoic acid. 3. The 12,13-epoxides were found to be optically active, indicating that the chiral center of the 13-L(S)-hydroperoxy carbon was retained. 4. Although many epoxy fatty acids previously have been identified as linoleic acid hydroperoxide products, this study reports a more complete structural analysis of the various epoxides and allows an assessment of the mechanisms of their formation from hydroperoxides.
    Biochimica et Biophysica Acta 08/1981; 665(1):113-24. DOI:10.1016/0005-2760(81)90239-3 · 4.66 Impact Factor
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    H. W. Gardner · R. Kleiman ·
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    ABSTRACT: Either 9-hydroperoxy-trans-10,cis-12-octadecadienoic acid or 13-hydroperoxy-cis-9,trans-11-octadecadienoic acid was treated with the catalyst, cysteine-FeCl3, in the presence of oxygen. Oxohydroxyoctadecenoic acids were among the many products formed as a result of hydroperoxide decomposition. A mixture of 9(13)-oxo-13(9)-hydroxy-trans-11(10)-octadecenoic acids (δ-ketols) was produced from either isomeric hydroperoxide. The formation of isomeric δ-ketols from 9-hydroxy-trans-12,13-epoxy-trans-10-octadecenoic acid (epoxyol), a known product of 13-hydroperoxy-cis-9,trans-11-octadecadienoic acid decomposition, implies that the epoxyol is an intermediate. The mechanism was elucidated by the facile conversion of the epoxyol (methyl ester_ to methyl 9(13)-oxo-13(9)-hydroxy-trans-11(10)-octadecenoates with a Lewis acid, BF3-etherate.
    Lipids 09/1979; 14(10):848-851. DOI:10.1007/BF02534127 · 1.85 Impact Factor
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    H. W. Gardner · D. Weisleder · R. Kleiman ·
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    ABSTRACT: A soybean extract or an ethanolic solution of cysteine and ferric chloride catalyzed the conversion of 13-L-hydroperoxy-cis-9,trans-11-octadecadienoic acid to numerous products among which wastrans-12,13-epoxy-9-hydroperoxy-trans-10-octadecenoic acid. When this fatty acid was treated further with the cysteine-ferric chloride solution, 9-hydroxy-12,13-epoxy-10-octadecenoic and 9-oxo-12,13-epoxy-10-octadecenoic acids were formed. Thus,trans-12,13-epoxy-9-hydroperoxy-trans-10-octadecenoic acid probably is an intermediate in the formation of the latter two compounds. Additionally, theerythro andthreo isomers oftrans-12,13-epoxy-11-hydroperoxy-cis-9-octadecenoic acid tenatatively were identified as products.
    Lipids 04/1978; 13(4):246-252. DOI:10.1007/BF02533664 · 1.85 Impact Factor
  • H. W. Gardner · R. Kleiman ·
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    ABSTRACT: In the presence of oxygen, a crude soy extract converted 13-hydroperoxy-cis-9,trans-11-octadecadienoic acid into numerous products, from which 9-oxo-trans-12,13-epoxy-trans-10-octadecenoic acid was isolated. Additionally, the soy extract oxidized linoleic acid to the oxo-epoxyoctadecenoic acid, presumably via a sequential reaction involving lipoxygenase oxidation of linoleic acid followed by degradation of the resultant linoleic acid hydroperoxide. However, the linoleic acid substrate yielded two isomeric linoleic acid hydroperoxides and because of this, two isomeric oxoepoxyoctadecenoic acids.
    Lipids 11/1977; 12(11):941-944. DOI:10.1007/BF02533315 · 1.85 Impact Factor
  • H W Gardner · R Kleiman · D Weisleder · G E Inglett ·
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    ABSTRACT: Cysteine reacts with linoleic acid hydroperoxide to yield several products, some of which were identified as fatty acid-cysteine adducts. The addition was catalyzed by ferric chloride (10(-5) M) by initiating free radical reactions. When isomerically pure 13-hydroperoxy-cis-9,trans-11-octadecadienoic acid and cysteine were reacted in 80% ethanol under N2, the major adducts were 9-S-cysteine-13-hydroxy-10-ethoxy-trans-11-octadecenoic acid (I) and 9-S-cysteine-10,13-dihydroxy-trans-11-octadecenoic acid (II). When the reaction included both isomers of the hydroperoxide (13- and 9-hydroperoxide) and air, an adduct of 9-oxononanoic acid and cysteine also was isolated. Additional experiments gave information about possible mechanisms of I and II formation.
    Lipids 09/1977; 12(8):655-60. · 1.85 Impact Factor
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    D J Sessa · H W Gardner · R Kleiman · D Weisleder ·
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    ABSTRACT: Bitter-tasting phosphatidylcholines from hexane-defatted soybean flakes were chromatographically separable from ordinary soy phosphatidylcholines (SPC). The bitter-tasting SPC contain 32% oxygenated fatty acids in addition to palmitic, stearic, oleic, linoleic, and linolenic acids. Identification of these oxygenated acids was based on infrared, ultraviolet, proton nuclear magnetic resonance, and mass spectral characteristics of methyl ester derivatives which were separated and purified by column and thin layer chromatography. The fatty acid methyl esters identified were (a) 15, 16-epoxy-9, 12-octadecadienoate, (b) 12, 13-epoxy-9-octadecenoate, both with double bonds and epoxide groups predominantly ofcis configuration; (c) 13-oxo-9,11-and 9-oxo-10, 12-octadecadienoates; (d) 13-hydroxy-9, 11- and 9-hydroxy-10, 12-octadecadienoates; (e) 9, 10, 13-trihydroxy-11- and 9,12,13-trihydroxy-10-octadecenoates. In addition, trace amounts of (f) 11-hydroxy-9,10-epoxy-12-and 11-hydroxy-12,13-epoxy-9-octadecenoates; (g) 13-oxo-9-hydroxy-10-and 9-oxo-13-hydroxy-11-octadecenoates; (h) 9,10-dihydroxy-12- and 12, 13-dihydroxy-9-octadecenoates; and (i) 9,12,13-dihydroxyethoxy-10- and 9,10,13-dihydroxyethoxy-11-octadecenoates were indicated by mass spectrometry. Dihydroxyethoxy compounds (i) were possibly formed upon extraction of the SPC from flakes by 80% ethanol. Except for the first two epoxy compounds, labelled a and b, the oxygenated fatty acids are similar to the products formed by homolytic decomposition of linoleic acid hydroperoxide. The first two compounds with predominantlycis configuration may occur by action of fatty acid hydroperoxides on an unsaturated fatty acid.
    Lipids 08/1977; 12(7):613-9. DOI:10.1007/BF02533391 · 1.85 Impact Factor
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    H. W. Gardner · R. Kleiman · D. Weisleder · G. E. Inglett ·
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    ABSTRACT: Cysteine reacts with linoleic acid hydroperoxide to yield several products, some of which were identified as fatty acid-cysteine adducts. The addition was catalyzed by ferric chloride (10−5 M) by initiating free radical reactions. When isomerically pure 13-hydroperoxy-cis-9,trans-11-octadecadienoic acid and cysteine were reacted in 80% ethanol under N2, the major adducts were 9-S-cysteine-13-hydroxy-10-ethoxy-trans-11-octadecenoic acid (I) and 9-S-cysteine-10,13-dihydroxy-trans-11-octadecenoic acid (II). When the reaction included both isomers of the hydroperoxide (13-and 9-hydroperoxide) and air, an adduct of 9-oxononanoic acid and cysteine also was isolated. Additional experiments gave information about possible mechanisms of I and II formation.
    Lipids 07/1977; 12(8):655-660. DOI:10.1007/BF02533760 · 1.85 Impact Factor
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    H W Gardner · D Weisleder ·
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    ABSTRACT: Catalyzed by 10(-5)M ionic iron in 80% ethanol, N-acetylcysteine added to linoleic acid hydroperoxide, forming a thiobond. Reaction of a specific isomer of hydroperoxide, 13-hydroperoxy-trans-11, cis-9-octadecadienoic acid, and N-acetylcysteine, forms a number of products, of which two were identified as addition compounds. One addition product was 9-S-(N-acetylcysteine)-13-hydroxy-10-ethoxy-trans-11-octadecenoic acid, and the other was 9-S-(N-acetylcysteine)-10, 13-dihydroxy-trans-11-octadecenoic acid.
    Lipids 03/1976; 11(2):127-34. DOI:10.1007/BF02532662 · 1.85 Impact Factor
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    H W Gardner · R Kleiman · D D Christianson · D Weisleder ·
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    ABSTRACT: We have shown unequivocally that the positional specificity of gamma-ketol formation by a corn germ enzyme was different from that observed previously by others with an alfalfa seedling enzyme. When the pure positional isomers of linoleic acid hydroperoxide served as substrates, the corn germ enzyme formed one of two gamma-ketols: 12-oxo-9-hydroxy-trans-10-octadeconoic acid from 13-hydroperoxys-10-octadecenoic acid from 13-hydroperoxy-cis-9,trans-11-octadecadienoic acid (99+% pure) and 10-oxo-13-hydroxy-trans-11-octadecenoic acid from 9-hydroperoxy-trans-10,cis-12-octadecadienoic acid (96% pure). Also isolated from these reactions was one of two alpha-ketols commonly found as a result of catalysis by linoleic acid hydroperoxide isomerase: 12-oxo-13-hydroxy-cis-9-octadecenoic acid from the 13-hydroperoxide and 10-oxo-9-hydroxy-cis-12-octadecenoic acid from the 9-hydroperoxide. Evidence is offered that gamma-ketol formation is catalyzed by linoleic acid hydroperoxide isomerase, the same enzyme responsible for alpha-ketol production.
    Lipids 11/1975; 10(10):602-8. DOI:10.1007/BF02532724 · 1.85 Impact Factor
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    D D Christianson · H W Gardner ·
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    ABSTRACT: Linoleic acid hydroperoxide isomerase was extracted from corn germ and partially purified by differential centrifugation. This enzyme catalyzed the isomerization of linoleic acid hydroperoxide.(see article) Isomerase also catalyzed the substitution of various reagents at the carbon bearing the hydroperoxide group. These fatty acid products had the following functional groupings: (see article) where X is either oleoyloxy, ethylthio, or methoxy resulting from the presence of oleic acid, ethanethiol, or methanol, respectively. A crude wheat germ extract containing both lipoxygenase and isomerase enzymes reacted with linoleic acid to yield alpha-ketols, gamma-ketols, and a substitution product, the linoleoyloxy ester of alpha-ketol. Characterization of these products from wheat germ enzymes showed that the substitution reaction was not unique to corn germ. Because anions of the reagents tested are typical nucleophiles, the substitution reactions may proceed by a nucleophilic mechanism as mediated by the isomerase enzyme.
    Lipids 09/1975; 10(8):448-53. DOI:10.1007/BF02532427 · 1.85 Impact Factor
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    H. W. Gardner · R. Kleiman · D. Weisleder ·
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    ABSTRACT: An isomeric mixture of linoleic acid hydroperoxides, 13-hydroperoxy-cis-9,trans-11-octadecadienoic acid (79%) and 9-hydroperoxy-cis-12,trans-10-octadecadienoic acid (21%), was decomposed homolytically by Fe(II) in an ethanol-water solution. In one series of experiments, the hydroperoxides were decomposed by catalytic concentrations of Fe(II). The 10−5 M Fe(III) used to initiate the decomposition was kept reduced as Fe(II) by a high concentration of cysteine added to the reaction in molar excess of the hydroperoxides. Nine different monomeric (no detectable dimeric) fatty acids were identified from the reaction. Analyses of these fatty acids revealed that they were mixtures of positional isomers identified as follows: (I) 13-oxo-trans,trans-(andcis,trans-) 9,11-octadecadienoic and 9-oxo-trans,trans- (andcis,trans-) 10,12-octadecadienoic acids; (II) 13-oxo-trans-9,10-epoxy-trans-11-octadecenoic and 9-oxo-trans-12, 13-epoxy-trans-10-octadecenoic acids; (III) 13-oxo-cis-9,10-epoxy-trans-11-octadecenoic and 9-oxo-cis-12, 13-epoxy-trans-10-octadecenoic acids; (IV) 13-hydroxy-9,11-octadecadienoic and 9-hydroxy-10,12-octadecadienoic acids; (V) 11-hydroxy-trans-12, 13-epoxy-cis-9-octadecenoic and 11-hydroxy-trans-9, 10-epoxy-cis-12-octadecenoic acids; (VI) 11-hydroxy-trans-12, 13-epoxy-trans-9-octadecenoic and 11-hydroxy-trans-9,10-epoxy-trans-12-octadecenoic acids; (VII) 13-oxo-9-hydroxy-trans-10-octadecenoic acids; (VIII) isomeric mixtures of 9, 12, 13-dihydroxyethoxy-trans-10-octadecenoic and 9, 10, 13-dihydroxyethoxy-trans-11-octadecenoic acids; and (IX) 9, 12, 13-trihydroxy-trans-10-octadecenoic and 9, 10, 13-trihydroxy-trans-11-octadecenoic acids. In another experiment, equimolar amounts of Fe(II) and hydroperoxide were reacted in the absence of cysteine. A large proportion of dimeric fatty acids and a smaller amount of monomeric fatty acids resulted. The monomeric fatty acids were examined by gas liquid chromatography-mass spectroscopy. Spectra indicated that the monomers were largely similar to those produced by the Fe(III)-cysteine reaction.
    Lipids 08/1974; 9(9):696-706. DOI:10.1007/BF02532178 · 1.85 Impact Factor
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    D.D. Christianson · H.W. Gardner · K. Warner · B.K. Boundy · G.E. Inglett ·

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    H W Gardner · D D Christianson · R Kleiman ·
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    ABSTRACT: Lipoxygenase (EC from the seed ofDimorphotheca sinuata oxidized linoleic acid to predominantly 13-L-hydroperoxy-cis-9,trans-11-octadecadienoic acid. When the reaction proceeded at pH 6.9, the 13-hydroperoxide was the only isomer detected; but at pH 5.1, the 13-isomer was 92% of the total, the remaining 8% being the 9-hydroperoxide. At both pH's small amounts of hydroxyoctadecadienoic acid accumulated during the reaction. This acid from the pH 6.9 reaction was analyzed as 13-hydroxy-cis,trans-octadecadienoic. The postulate advanced by many workers that dimorphecolic acid, 9-D-hydroxy-trans-10,trans-12-octadecadienoic acid, is biosynthesized via a lipoxygenase product was not proved. Although the product specificity ofD. sinuata lipoxygenase is like that of lipoxygenase type 1 from soybeans, its inactivity at pH 9 demonstrated that it is a novel enzyme.
    Lipids 06/1973; 8(5):271-6. DOI:10.1007/BF02531904 · 1.85 Impact Factor

Publication Stats

882 Citations
55.10 Total Impact Points


  • 1984
    • United States Department of Agriculture
      • Agricultural Research Service (ARS)
      Washington, D. C., DC, United States