Oxidative desaturation of eicosa-8,11-dienoic acid to eicosa-5,8,11-trienoic acid: comparison of different diets on oxidative desaturation at the 5,6 and 6,7 positions

7-Phenylhepta-2,4-dienoic acid and 7-phenylhepta-2,4,6-trienoic acid have been synthesized as their all-trans isomers. In addition p-(2-phenylethyl)benzoic acid has been prepared and the insecticidal activities of the isobutylamides of these three acids towards the housefly, Musca domestics, have been examined.

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Unusual Bioactive 4-Oxo-2-alkenoic Fatty Acids from Hygrophorus eburneus

Zeitschrift für Naturforschung B ◽

10.1515/znb-2005-0105 ◽

2005 ◽

Vol 60 (1) ◽

pp. 25-32 ◽

Cited By ~ 14

Author(s):

Axel Teichert ◽

Tilo Lübken ◽

Jürgen Schmidt ◽

Andrea Porzel ◽

Norbert Arnold ◽

...

Keyword(s):

Fatty Acids ◽

Spectroscopic Data ◽

Fungicidal Activity ◽

Dienoic Acid ◽

Trienoic Acid ◽

Enoic Acid ◽

Partial Structure

From fruit bodies of the basidiomycete Hygrophorus eburneus (Bull.: Fr.) Fr. (Tricholomataceae) eight fatty acids (C16, C18) with γ -oxocrotonate partial structure could be isolated. Initial tests demonstrate their bactericidal and fungicidal activity. The structures of (2E,9E)-4-oxooctadeca- 2,9,17-trienoic acid (1), (2E,11Z)-4-oxooctadeca-2,11,17-trienoic acid (2), (E)-4-oxohexadeca-2,15- dienoic acid (3), (E)-4-oxooctadeca-2,17-dienoic acid (4), (2E,9E)-4-oxooctadeca-2,9-dienoic acid (5), (2E,11Z)-4-oxooctadeca-2,11-dienoic acid (6), (E)-4-oxohexadec-2-enoic acid (7), and (E)-4- oxooctadec-2-enoic acid (8) were elucidated on the basis of their spectroscopic data.

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Large-scale preparation of (9Z,12E)-[1-13C]-octadeca-9,12-dienoic acid, (9Z,12Z,15E)-[1-13C]-octadeca-9,12,15-trienoic acid and their [1-13C] all-cis isomers

Chemistry and Physics of Lipids ◽

10.1016/s0009-3084(00)00137-7 ◽

2000 ◽

Vol 106 (1) ◽

pp. 65-78 ◽

Cited By ~ 13

Author(s):

O Loreau ◽

A Maret ◽

D Poullain ◽

J.M Chardigny ◽

J.L Sébédio ◽

...

Keyword(s):

Large Scale ◽

Dienoic Acid ◽

Trienoic Acid ◽

Large Scale Preparation ◽

Scale Preparation

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An in vitro and in vivo study of the conversion of eicosa-11, 14-dienoic acid to eicosa-5,11,14-trienoic acid and of the conversion of eicosa-11-enoic acid to eicosa-5,11-dienoic acid in the rat

Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism ◽

10.1016/0005-2760(71)90006-3 ◽

1971 ◽

Vol 248 (2) ◽

pp. 186-197 ◽

Cited By ~ 67

Author(s):

David Ullman ◽

Howard Sprecher

Keyword(s):

Dienoic Acid ◽

Trienoic Acid ◽

Enoic Acid ◽

In Vivo Study

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Evaluation of 5- and 6-fluoro derivatives of arachidonic acid and 5,8,14-eicosatrienoic acid as substrates and inhibitors of 5-lipoxygenase

Biochemical Journal ◽

10.1042/bj2780549 ◽

1991 ◽

Vol 278 (2) ◽

pp. 549-555 ◽

Cited By ~ 3

Author(s):

J F Navé ◽

D Jacobi ◽

C Gaget ◽

B Dulery ◽

J B Ducep

Keyword(s):

Arachidonic Acid ◽

Dienoic Acid ◽

Trienoic Acid ◽

Tetraenoic Acid ◽

Lipoxygenase Pathway ◽

Good Substrate ◽

Leukotriene A4 ◽

Derivatives Of ◽

Fluoro Derivatives

The 5- and 6-fluoro derivatives of arachidonic acid (5F-ETE and 6F-ETE) were evaluated as substrates of rat basophilic leukaemia cell (RBL-1) 5-lipoxygenase. 5F-ETE was found to be a poor substrate and was converted into a single product, 5-oxoeicosa-6,8,11,14-tetraenoic acid (5-oxo-ETE). 6F-ETE was a good substrate and was mainly converted into 5-hydroperoxy-6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-OOH-6F-ETE) with concomitant formation of a small amount of 5-oxo-6-fluoroeicosa-6,8,11,14-tetraenoic acid (5-oxo-6F-ETE). However the formation of 5,12-dihydroxy-6-fluoroeicosa-6,8,10,14-tetraenoic acids, epimeric at C-12, was not observed. Eicosa-5(Z),8(Z),14(Z)-trienoic acid (ET), previously described as a good substrate of 5-lipoxygenase, is oxidized mainly to 5-hydroperoxyeicosa-6,8,14-trienoic acid (5-OOH-ET), which does not serve as a substrate for the leukotriene A4 (LTA4) synthase activity of 5-lipoxygenase [Navé, Dulery, Gaget & Ducep (1988) Prostaglandins 36, 385-398]. To allow a better estimation of the effect of fluorine substitution on the rate of oxidation of the 5,8-cis,cis-diene moiety by 5-lipoxygenase, the 5- and 6-fluoro derivatives of ET were studied as substrates. Qualitatively, the metabolism of 5F-ET and 6F-ET was found to be similar to that observed for 5F-ETE and 6F-ETE. Quantitatively, 6F-ET proved to be a somewhat better substrate than ET, whereas 5F-ET was poorly metabolized. The relative ability of arachidonic acid, ET and the corresponding 5- and 6-fluoro derivatives to inhibit the 5-lipoxygenase-catalysed oxidation of eicosa-5(Z),8(Z)-dienoic acid (ED) was also investigated. 6F-ETE and 5F-ETE were found to be effective and about equipotent inhibitors of 5-lipoxygenase in the micromolar range. In view of their close structural similarity to arachidonic acid, these two inhibitors are expected to be important tools in the study of the 5-lipoxygenase pathway in vivo.

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CALENDIC ACID IN SEED OILS OF THE GENUS CALENDULA

Canadian Journal of Biochemistry ◽

10.1139/o67-028 ◽

1967 ◽

Vol 45 (2) ◽

pp. 251-254 ◽

Cited By ~ 8

Author(s):

Mary J. Chisholm ◽

C. Y. Hopkins

Keyword(s):

Fatty Acid ◽

Early Stage ◽

Continuous Process ◽

Dienoic Acid ◽

Major Fatty Acid ◽

Trienoic Acid ◽

Octadecatrienoic Acid ◽

Seed Oils ◽

Stage Of Development ◽

Putative Species

Seed oils of 17 definite and putative species of Calendula were examined. The major fatty acid of C. arvensis oil was identified as trans-8, trans-10, cis-12-octadecatrienoic acid (calendic acid). Spectrometric evidence demonstrated that all 17 species contained the same acid, in amounts varying from 38.9 to 58.4% of the oil.Seed was collected at intervals during maturation from growing plants of C. officinalis. Analysis of the seed and the oil showed that the conjugated trienoic acid was present at an early stage of development and increased steadily in amount to maturity. Accumulation of hydroxydienoic or conjugated dienoic acid in quantity was not observed at any stage although small amounts may have been present. It is concluded that calendic acid is formed in the seed by a rapid continuous process.

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