scholarly journals The enzymic conversion of linoleic acid into 9-(nona-1′,3′-dienoxy)non-8-enoic acid, a novel unsaturated ether derivative isolated from homogenates of Solanum tuberosum tubers

1972 ◽  
Vol 129 (3) ◽  
pp. 743-753 ◽  
Author(s):  
T. Galliard ◽  
D. R. Phillips
Keyword(s):  
Solanum Tuberosum ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Fatty Acid Derivative ◽  
Dienoic Acid ◽  
Enoic Acid ◽  
Ph Optimum ◽  
Ether Derivative ◽  
Unsaturated Ether ◽  
Acid Hydroperoxide

1. A major component of the lipids in aqueous (pH7.5) homogenates of tuber tissue from Solanum tuberosum was isolated and characterized as 9-(nona-1′,3′-dienoxy)non-8-enoic acid. 2. This novel unsaturated ether fatty acid derivative, which contains a butadienylvinyl ether function, has the structure: [Formula: see text] and is formed from linoleic acid by a sequence of enzymic reactions. 3. A precursor of the unsaturated ether derivative is 9-d-hydroperoxyoctadeca-10,12-dienoic acid, formed by the action of S. tuberosum lipoxygenase on linoleic acid. 4. An enzyme that converts the fatty acid hydroperoxide into the unsaturated ether derivative was isolated from S. tuberosum. The pH optimum of this enzyme is approx. 9, although the overall conversion of linoleic acid into the ether derivative is maximal at pH7.5. 5. An unusual feature of this pathway is the insertion of an oxygen atom into the alkyl chain of a fatty acid. 6. This novel mechanism may play a role in the breakdown of polyunsaturated fatty acids to volatile products in plants.

Separation, Partial Purification and Characterization of a Fatty Acid Hydroperoxide Cleaving Enzyme from Apple and Tomato Fruits

1982 ◽  
Vol 37 (3-4) ◽  
pp. 165-173 ◽  
Author(s):  
P. Schreier ◽  
G. Lorenz
Keyword(s):  
Fatty Acid ◽  
Inhibitory Effect ◽  
Fatty Acid Hydroperoxide ◽  
Partial Purification ◽  
Purification And Characterization ◽  
Ph Optimum ◽  
Isoelectric Points ◽  
Acid Hydroperoxide ◽  
Membrane Bound

Abstract A membrane-bound enzyme catalysing the cleavage of 13-hydroperoxy-(Z)-9,(E)-11-oc-tadecadienoic acid (13-LHPO) and 13-hydroperoxy-(Z)-9,(E)-11,(Z)-15-octadecadienoic acid (13-LnHPO) to C6-aldehydes was isolated and partially purified from apples and tomatoes. Attempts to employ Ultrogel AcA 34 and AcA 22 in a gel chromatographic purification step were partially frustrated by reaggregation phenomena. However, by using Sepharose CL-4 B an enzyme fraction (MW 200 000 Da) with lipoxygenase and fatty acid hydroperoxide cleaving activity could be separated from a high molecular-weight active eluate. By applying preparative isoelec­ tric focussing to the tomato protein we succeeded in separating the fatty acid cleaving activity from the lipoxygenase, because o f their different isoelectric points of pH 5.8 -6 .1 and pH 5.0, respectively, An 8.4-fold purification of the fatty acid cleaving activity was achieved. A pH-optimum of 5.5 and a Km-value of 2.6 × 10-5 м/1 for the 13-hydroperoxide of linoleic acid were measured. p-Chloromercuribenzoic acid (1 mм) showed significant inhibitory effect on the fatty acid hydroperoxide cleaving enzyme, but no evidence o f inhibition was found with 1 mм H2O2, KCN, DABCO and EDTA or superoxide dismutase (270 U). The maximum amount of fatty acid hydroperoxide decomposition (C6-aldehyde formation) was determined to be 59%.

scholarly journals The origin and structures of dimeric fatty acids from the anaerobic reaction between soya-bean lipoxygenase, linoleic acid and its hydroperoxide

1972 ◽  
Vol 130 (2) ◽  
pp. 435-442 ◽  
Author(s):  
G. J. Garssen ◽  
J. F. G. Vliegenthart ◽  
J. Boldingh
Keyword(s):  
Fatty Acids ◽  
Linoleic Acid ◽  
Carbonyl Compounds ◽  
Dienoic Acid ◽  
Soya Bean ◽  
Linoleic Acid Hydroperoxide ◽  
Acid Hydroperoxide ◽  
Epoxy Groups ◽  
Anaerobic Reaction ◽  
Anaerobic System

In an anaerobic system soya-bean lipoxygenase catalyses in the presence of linoleic acid and l-13-hydroperoxyoctadeca-cis-9-trans-11-dienoic acid the formation of dimeric fatty acids and of carbonyl compounds. The analogous reaction does not take place when d-9-hydroperoxyoctadeca-trans-10-cis-12-dienoic acid is used instead of the 13-hydroperoxy isomer. Non-oxygenated dimers stem directly from linoleic acid and have C(11)–C(13′) or –C(9′) and C(13)–C(13′) or –C(9′) linkages. Dimers that contain oxygen originate from linoleic acid and linoleic acid hydroperoxide. It is most likely that the oxygen is present in epoxy groups.

C6-Aldehyde Formation by Fatty Acid Hydroperoxide Lyase in the Brown Alga Laminaria angustata

2003 ◽  
Vol 58 (3-4) ◽  
pp. 207-214 ◽  
Author(s):  
Kangsadan Boonprab ◽  
Kenji Matsuia ◽  
Miyuki Yoshida ◽  
Yoshihiko Akakabe ◽  
Anong Chirapart ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Brown Alga ◽  
Marine Algae ◽  
Higher Plants ◽  
Fatty Acid Hydroperoxide ◽  
Hydroperoxide Lyase ◽  
Acid Hydroperoxide ◽  
Fatty Acid Hydroperoxide Lyase

Some marine algae can form volatile aldehydes such as n-hexanal, hexenals, and nonenals. In higher plants it is well established that these short-chain aldehydes are formed from C18 fatty acids via actions of lipoxygenase and fatty acid hydroperoxide lyase, however, the biosynthetic pathway in marine algae has not been fully established yet. A brown alga, Laminaria angustata, forms relatively higher amounts of C6- and C9-aldehydes. When linoleic acid was added to a homogenate prepared from the fronds of this algae, formation of n-hexanal was observed. When glutathione peroxidase was added to the reaction mixture concomitant with glutathione, the formation of n-hexanal from linoleic acid was inhibited, and oxygenated fatty acids accumulated. By chemical analyses one of the major oxygenated fatty acids was shown to be (S)-13-hydroxy-(Z, E)-9, 11-octadecadienoic acid. Therefore, it is assumed that n-hexanal is formed from linoleic acid via a sequential action of lipoxygenase and fatty acid hydroperoxide lyase (HPL), by an almost similar pathway as the counterpart found in higher plants. HPL partially purified from the fronds has a rather strict substrate specificity, and only 13-hydroperoxide of linoleic acid, and 15-hydroperoxide of arachidonic acid are the essentially suitable substrates for the enzyme. By surveying various species of marine algae including Phaeophyta, Rhodophyta and Chlorophyta it was shown that almost all the marine algae have HPL activity. Thus, a wide distribution of the enzyme is expected.

scholarly journals The enzymic conversion of linoleic acid hydroperoxide by flax-seed hydroperoxide isomerase

1970 ◽  
Vol 120 (1) ◽  
pp. 55-60 ◽  
Author(s):  
G. A. Veldink ◽  
J. F. G. Vliegenthart ◽  
J. Boldingh
Keyword(s):  
Linoleic Acid ◽  
Functional Relationship ◽  
Dienoic Acid ◽  
Soya Bean ◽  
Isomerization Reaction ◽  
Spectroscopic Methods ◽  
Linoleic Acid Hydroperoxide ◽  
Flax Seed ◽  
Acid Hydroperoxide

1. The mode of action of flax-seed hydroperoxide isomerase was studied in vitro by using as substrates linoleic acid hydroperoxides formed by soya-bean lipoxygenase. 2. The enzyme converts only 13-hydroperoxyoctadeca-cis-9-trans-11-dienoic acid, whereas the 9-hydroperoxy isomer does not react. 3. The isomerization product was identified by chemical and spectroscopic methods as 13-hydroxy-12-oxo-octadec-cis-9-enoic acid. 4. 12,13-Epoxyoleic acid isomers do not act as intermediates in the isomerization reaction. 5. Suggestions for a functional relationship between hydroperoxide isomerase and lipoxygenase are discussed.

scholarly journals Lipoxygenase from potato tubers. Partial purification and properties of an enzyme that specifically oxygenates the 9-position of linoleic acid

1971 ◽  
Vol 124 (2) ◽  
pp. 431-438 ◽  
Author(s):  
T. Galliard ◽  
D. R. Phillips
Keyword(s):  
Linoleic Acid ◽  
Gel Filtration ◽  
Dienoic Acid ◽  
Preliminary Evidence ◽  
Partial Purification ◽  
Maximal Velocity ◽  
Potato Tubers ◽  
Ph Optimum ◽  
Purification And Properties ◽  
A Minor

A lipoxygenase (EC 1.13.1.13) was partially purified from potato tubers and was shown to differ from previously characterized soya-bean lipoxygenases in the positional specificity and pH characteristics of the oxygenation reaction. The potato enzyme converted linoleic acid almost exclusively (95%) into 9-d-hydroperoxyoctadeca-trans-10,cis-12-dienoic acid. The 13-hydroperoxy isomer was only a minor product (5%). Linolenic acid was an equally effective substrate, which was also oxygenated specifically at the 9-position. The enzyme had a pH optimum at 5.5–6.0 and was inactive at pH9.0. A half-maximal velocity was obtained at a linoleic acid concentration of 0.1mm. No inhibition was observed with EDTA (1mm) and cyanide (1mm) or with p-chloromercuribenzoate (0.2mm). Haemoproteins were not involved in the lipoxygenase activity. The molecular weight of the enzyme was estimated from gel filtration to be approx. 105. Preliminary evidence suggested that the enzyme oxygenated the n–10 position of fatty acids containing a penta(n–3, n–6)diene structure.

FEATURES OF THE OIL-BEARING-CROP (CHARTHAMUS) CULTIVATION UNDER THE CONTRASTIVE EDAPHIC-CLIMATIC CONDITIONS

2018 ◽  
pp. 31-37
Author(s):  
S. К. Temirbekova ◽  
Yu. V. Afanaseva ◽  
I. M. Kulikov ◽  
G. V. Metlina ◽  
S. A. Vasilchenko
Keyword(s):  
Fatty Acid Composition ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Acid Composition ◽  
Oil Content ◽  
Moscow Region ◽  
Average Weight ◽  
North Caucasus ◽  
Saratov Region ◽  
Rostov Region

The results of long-term studies of the biological, morphological and phenological features of the introduced new culture of safflower in the Central, Volga and North Caucasus regions are presented. Optimum parameters of depth of seeding (5-6 cm), seeding rates (300-350 thousand pieces/hectare or 12-14 kg), ensuring high productivity, oil content and quality of seeds are established. For the first time, the relationship between moisture availability of vegetation periods with accumulation of oil content and a change in the fatty acid composition was established. Oilseed (in untreated seeds) in the regions was from 14,5 to 31,2%, in excessively wet 2013 – 6,4% in the Moscow region and 8,6% in the Saratov region. Fatty acid composition revealed a high content of oleic acid in Krasa Stupinskaya variety – 13,6-16,8%, linoleic acid – 68,5-75,7%. The yield of oil in the Moscow region was 240 kg/ha. The yield of Krasa Stupinskaya in the Moscow Region was 0,6 t/ha, the Rostov Region 0,8 t/ha and Saratov Region 1,2 t/ha, with an average weight of 1000 seeds, respectively, by regions: 40,0 g, 47,3 g and 40,9 g. The growing season for growing seeds was 105 days in the Moscow Region, 94 days in the Rostov Region and 95 days in the Saratov Region. It has been established that excessive moistening during the flowering and seed filling period increases the harmfulness of enzyme-mycosis seed depletion (EMIS) – biological injury during maturation (enzymatic stage), followed by the seeding of the seeds with the phytopathogen Alternaria carthami Chowdhury. In the breeding programs for productivity and oil content, it is recommended to use the varieties Moldir (Kazakhstan) and Krasa Stupinskaya (FGBNU VSTISP), the fatty acid composition of which is characterized by an increased content of oleic and linoleic acid, which is of particular value for storage and use for food purposes.

scholarly journals Explore the gene network regulating the composition of fatty acids in cottonseed

2021 ◽  
Vol 21 (1) ◽  
Author(s):  
Lihong Ma ◽  
Xinqi Cheng ◽  
Chuan Wang ◽  
Xinyu Zhang ◽  
Fei Xue ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Linolenic Acid ◽  
Gene Network ◽  
Unsaturated Fatty Acids ◽  
Saturated Fatty Acids ◽  
Accumulation Pattern ◽  
Time Points ◽  
Expression Characteristics

Abstract Background Cottonseed is one of the major sources of vegetable oil. Analysis of the dynamic changes of fatty acid components and the genes regulating the composition of fatty acids of cottonseed oil is of great significance for understanding the biological processes underlying biosynthesis of fatty acids and for genetic improving the oil nutritional qualities. Results In this study, we investigated the dynamic relationship of 13 fatty acid components at 12 developmental time points of cottonseed (Gossypium hirsutum L.) and generated cottonseed transcriptome of the 12 time points. At 5–15 day post anthesis (DPA), the contents of polyunsaturated linolenic acid (C18:3n-3) and saturated stearic acid (C18:0) were higher, while linoleic acid (C18:2n-6) was mainly synthesized after 15 DPA. Using 5 DPA as a reference, 15,647 non-redundant differentially expressed genes were identified in 10–60 DPA cottonseed. Co-expression gene network analysis identified six modules containing 3275 genes significantly associated with middle-late seed developmental stages and enriched with genes related to the linoleic acid metabolic pathway and α-linolenic acid metabolism. Genes (Gh_D03G0588 and Gh_A02G1788) encoding stearoyl-ACP desaturase were identified as hub genes and significantly up-regulated at 25 DPA. They seemed to play a decisive role in determining the ratio of saturated fatty acids to unsaturated fatty acids. FAD2 genes (Gh_A13G1850 and Gh_D13G2238) were highly expressed at 25–50 DPA, eventually leading to the high content of C18:2n-6 in cottonseed. The content of C18:3n-3 was significantly decreased from 5 DPA (7.44%) to 25 DPA (0.11%) and correlated with the expression characteristics of Gh_A09G0848 and Gh_D09G0870. Conclusions These results contribute to our understanding on the relationship between the accumulation pattern of fatty acid components and the expression characteristics of key genes involved in fatty acid biosynthesis during the entire period of cottonseed development.

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