Metabolism of <i>trans</i>‐3‐Hexadecenoic Acid by <i>Chlorella vulgaris</i> and by Lettuce Leaf

Bartels, C. T.; James, A.T.; Nichols, B.W.

doi:10.1111/j.1432-1033.1967.tb19492.x

Cited by 27 publications

(6 citation statements)

References 18 publications

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“…In some cases there was no further movement of label from oleate even after 92 hr, and the only change that took place was a decrease in labeling of palmitate accompanying an almost equivalent increase in labeling of trans-Zk3-hexadecenoic acid. This is quite consistent with the suggestion, based on different data (21), that this unique fatty acid L1PIDS, VOL. 10, NO.…”

Section: Discussionsupporting

confidence: 93%

Phosphatidyl choline: Donor of 18‐carbon unsaturated fatty acids for glycerolipid biosynthesis

Roughan¹

1975

Lipids

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Kinetics of radiocarbon inforporation into the phyosphatidyl choline of pumpkin leaf fed 1(-14)C-acetate at low light intensity were strongly suggestive of lipid bound fatty acids acting as substrates for desaturase enzymes. After pulse labeling in direct sunlight with the same precursor, phosphatidyl choline and phosphatidyl glycerol contained up to 90% of total glycerolipid radiocarbon at the shortest sampling times. Subsequent loss of radiocarbon from phyosphatidyl choline and a corresponding gain in other glycerolipids is taken to indicate a net flow of long chain fatty acids through phosphatidyl choline and into other lipids. It is proposed that there may be 2 separate synthetases in leaf tissue, one producing oleic and the other palmitic acids as their end products. Oleic acid is transferred almost exclusively to phosphatidyl choline where it is further desaturated to linoleic and linolenic acids before being made available for the biosynthesis of other lipids. Palmitic acid is transferred mainly to phosphatidyl glycerol, where it is desaturated to trans-delta3-hexadecenoic acid.

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Section: Discussionsupporting

confidence: 93%

Phosphatidyl choline: Donor of 18‐carbon unsaturated fatty acids for glycerolipid biosynthesis

Roughan¹

1975

Lipids

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“…Clearly under conditions producing marked inhibition of the total counts in the C,, monoenoic acids, no inhibition of formation of the trans-acid can be detected. It has been shown by Bartels et al [31] that either leaf tissue or Chlorella cells, when given labeled A3-trans-hexadecenoic acid, rapidly incorporate a small proportion of this compound into all the lipids. There is thus no selectivity of esterification that can account for the specific localisation of this acid in phosphatidyl glycerol.…”

Section: Inhibition Of Unsaturated Fatty Acid Biosynthesis By Sterculmentioning

confidence: 99%

The Inhibition of Unsaturated Fatty Acid Biosynthesis in Plants by Sterculic Acid

James

Harris

Bézard

1968

European Journal of Biochemistry

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Sterculic acid, 8-(2-octyl-I -cyclopropenyl)octanoic acid, is a potent inhibitor of the enzyme system converting stearic acid to oleic acid in Chlorella vulgaris. No inhibition of oleic acid formation from acetate, is, however, observed. With the C,, C,, or C, acids as precursor, inhibition increases with chain length. The enzyme system converting oleic acid to linoleic acid js also less sensitive than the stearate-oleate system. Stearic acid generated internally in leaf preparations anaerobically from acetate is still converted to oleic acid on transference to air in the presence of sterculic acid. Desaturation of added palmitic acid is readily inhibited by sterculic acid, so far as formation of the A' and A9 acids are concerned. Desaturation of palmitic acid to the 3-trans-hexadecenoic acid is unaffected by sterculic acid.Two possible schemes to account for the effects of sterculic acid on stearate desaturation are suggested.The addition of sterculic acid, 8-(2-octyl-l-cyclopropenyl) octanoic acid, to animal diets is known to produce profound biological effects [I]. These are believed t o be due to the cyclopropene ring itself since alcohols, methyl esters, methyl ethers, and hydrocarbons containing this group are also effective [2-61. The mechanisms involved are not yet clear although Kircher [7] has demonstrated that reactions between cyclopropenes and thiol compounds such as mercaptans occur readily to produce thiolethers. Ory and Altschul [S] showed marked inhibition of the lipase from Ricinus communis by sterculic acid and suggested that it might be a general inhibitor for other SH-containing enzymes.Dietary sterculic acid causes increased levels of stearic acid and decreased levels of oleic acid in the lipids of various chicken tissues [9-121. Reiser and Raju [13] showed that an in vivo effect of dietary sterculic acid on monoene biosynthesis in rats could be demonstrated only when labelled acetate as precursor was replaced by labelled stearic acid. These studies were extended by Johnson [14] who showed that sterculic acid inhibited the desaturation of stearic to oleic acid by chicken liver preparations.Since sterculic acid is a plant product, it was of interest to study its effect on fatty acid biosynthesis in photosynthetic systems, particularly since oleic acid has now been shown to be produced in plants by desaturation of stearic acid [15--17, 271.Xon-Standard Abbreviation. ACP, acyl carrier protein. MATERIALS AND METHODS ChemicalsAll solvents were redistilled before use and chemicals were of analytical grade. Methyl sterculate, as the urea adduct, was generously donated by Dr.A. R. Johnson, C. S. I. R. O., Division of Food Preservation, Ryde, N. S. W., Australia. The labelled compounds used had a specific activity of approximately 40mC/mmole and were obtained from the Radiochemical Centre (Amersham, Bucks). They were each dispersed in distilled water (about 4ml) containing a trace of sodium carbonate (1 drop of a 1 solution) and, where necessary, a drop of Tween 20 was added and ultrasonication ...

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“…This acid is synthesized from palmitic acid in Chlorella vulgaris, the synthesis being directly light dependent 42 . This compound is also hydrogenated to give again palmitic acid in the same organism 43 . The functions of both SL and PG in fatty acid biosynthesis are still unknown.…”

Section: (Mgdg Dgdg)mentioning

confidence: 99%

Control of Fatty Acid and Lipid Biosynthesis in Euglena gracilis by Ammonia, Light and DCMU

Pohl¹,

Wagner²

1972

Zeitschrift Für Naturforschung B

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When Euglena gracilis was grown under white (fluorescent) light in media containing high concentrations of ammonium chloride (more than 0.005%), the main lipids synthesized were monogalactosyl diglyceride, digalactosyl diglyceride, phosphatidyl glycerol, sulfolipid and the all eis 47, [10][11][12][13][14][15][16]47,10,[13][14][15][16] Zl4,7,10,[13][14][15][16] A9,[12][13][14][15][16][17][18]12,[15][16][17][18]:3 fatty acids. At low levels of ammonium (less than 0.002%) these compounds were produced only in small amounts, while neutral lipids, phosphatidyl choline, phosphatidyl ethanolamine and the 14:0, 16:0 and 16:1 fatty acids predominated.When Euglena gracilis was grown in white light in the presence of dichlorophenyldimethylurea (DCMU) or in the dark, fatty acid and lipid biosyntheses followed the same pattern as in white light at low levels of ammonium. Similar results were obtained when nitrate served as the only nitrogen source in the light and in the dark.The results indicate that in Euglena gracilis there are a light independent and a light and ammonium dependent pathway of fatty acid biosynthesis. Both pathways seem to be in association with specific lipids.Green algae 1-8 and the phytoflagellates Euglena gracilis 9-1 'and Ochromonas danica 18 synthesize predominantly unsaturated C16 and C18 fatty acids with 1-4 double bonds. Lesser amounts of unsaturated C20 and C2, fatty acids are found. Red and brown algae 3 ' 7 mainly produce unsaturated C18 and C20 fatty acids and only small quantities of C16 fatty acids with one or two double bonds. They lack the 16:3 and 16:4 fatty acids which are characteristic constituents of the green algae and phytoflagellates. In an investigation 19 carried out on various green algae we observed that the biosynthesis of these compounds depends on the ammonium or nitrate level in the nutrient medium. The low nitrogen content of seawater could be responsible for their absence in red and brown algae. The biosynthesis of these unsaturated fatty acids is influenced by light 12-14 ' 16 . Since they are predominantly found in galactolipids 13 ' 14 ' 16 ' 17 we were interested to study the influence of light and of the nitrogen content of the nutrient medium on both fatty acid and lipid biosynthesis. Euglena gracilis was chosen for our experiments because it can be Requests for reprints should be sent to Dr. PETER POHL, Institut für Pharmazeutische Arzneimittellehre der Universität, D-8000 München 2, Karl-Str. 29, Germany. Abbreviations:GLC: gas liquid chromatography TLC: thin layer chromatography; DCMU: (3-(3,4-dichlorophenyl)-1,1-dimethyl urea; Card.: cardiolipin; DGDG: digalactosyl diglyceride; MGDG: monogalactosyl diglyceride; PC: phosphatidyl choline; PE: phosphatidyl ethanolamine; PG: phosphatidyl glycerol; SL: sulfolipid; NL 1 (see Figs. 2 and 3) : neutral lipids (mainly wax esters and triglycerides) ; NL 2: neutral lipids (mainly diglycerides). grown in the dark and in the light and contains polyunsaturated C16 , C18 , C20 and C22 fatty acids 10 . Material and MethodsEuglen...

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Metabolism of trans‐3‐Hexadecenoic Acid by Chlorella vulgaris and by Lettuce Leaf

Cited by 27 publications

References 18 publications

Phosphatidyl choline: Donor of 18‐carbon unsaturated fatty acids for glycerolipid biosynthesis

Phosphatidyl choline: Donor of 18‐carbon unsaturated fatty acids for glycerolipid biosynthesis

The Inhibition of Unsaturated Fatty Acid Biosynthesis in Plants by Sterculic Acid

Control of Fatty Acid and Lipid Biosynthesis in Euglena gracilis by Ammonia, Light and DCMU

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