The structure of the glycerides of ergot oils

Morris, L. J.; Hall, Scott W.

doi:10.1007/bf02531871

Cited by 63 publications

(30 citation statements)

References 11 publications

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“…nonacylated form in the triacylglycerol fraction of castor oil; however, the occurrence of acylated ricinoleate residues (mono-, di-, and triestolides) in lipids from ergot oil has been described (13).…”

Section: Methodsmentioning

confidence: 99%

Isolation and structure of a new galactolipid from oat seeds

Hámberg

Лиепиньш

Otting

et al. 1998

Lipids

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Seeds of oat (Avena sativa L.) were recently shown to contain significant quantities of a new hydroxy acid, (15 R)-hydroxy-(9Z),(12Z)-octadecadienoic acid (trivial name, avenoleic acid). In the present work, avenoleate was found to be mainly (63%) localized in the glycolipid fraction of oat seed lipids. Fractionation of the glycolipids by thin-layer chromatography and reversed-phase high-performance liquid chromatography revealed the presence of a main molecular species which accounted for 20% of the total avenoleate content of oat seeds. Structural studies by chemical methods and mass spectrometry demonstrated that the avenoleate-containing glycolipid was a galactolipid assembled of one molecule of avenoleic acid, two molecules of linoleic acid, two molecules of D-galactose, and one molecule of glycerol. Degradation of the new galactolipid by chemical and enzymatic methods demonstrated the localization of acyl chains, i.e., linoleate at sn-1 and linoleoylavenoleate at sn-2. Nuclear magnetic resonance spectroscopy gave independent support for this structure and also demonstrated that the two galactoses formed an alpha-D-galactopyranosyl-1-6-beta-D-galactopyranosyl moiety which was bound to the sn-3 position. Based on these experiments, the new galactolipid could be formulated as 1-[(9'Z),(12'Z)-octadecadienoyl]-2-[(15''R)-[(9'''Z),(12'''Z)-o ctadecadienoyloxy]-(9''Z),(12''Z)-octadecadienoyl]-3-(alpha-D-g alactopyranosyl-1-6-beta-D-galactopyranosyl)-glycerol. Quantitatively, the amount of the avenoleate-containing galactolipid was of the same order of magnitude as those of individual molecular species of digalactosyldiacylglycerol containing nonoxygenated acyl chains. The content of the new galactolipid in oat seeds was 0.5-0.6 mg per g of seed.

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Section: Methodsmentioning

confidence: 99%

Isolation and structure of a new galactolipid from oat seeds

Hámberg

Лиепиньш

Otting

et al. 1998

Lipids

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“…The ricinoleic acid amount in the fat is given as approximately 30% (Bharucha and Gunstone 1957;Mantle et al 1969;Morris and Hall 1966;Whittemore et al 1976). …”

Section: Introductionmentioning

confidence: 98%

Distribution of ergot alkaloids and ricinoleic acid in different milling fractions

et al. 2010

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The sclerotia of the fungus Claviceps sp. are still a challenge for the milling industry. Ergot sclerotia are a constant contamination of the rye crop and have to be removed by modern milling technologies. Changing sizes and coloration of the sclerotia make it difficult to separate them from the grain. Ergot sclerotia are a problem when cleaning is insufficient and non-separated specimens or sclerotia fragments get into the milling stream and thus ergot alkaloids are distributed into the different cereal fractions. In model milling experiments, the residues of ergot in rye flour and the distribution of ergot into different milling fractions were investigated. Rye grains were mixed with whole ergot sclerotia and in another experiment with ergot powder and cleaned afterwards before milling. The ergot alkaloids ergometrine, ergosine, ergotamine, ergocornine, ergocryptine, ergocristineand their related isomeric forms (-inine-forms), and additionally ricinoleic acid as a characteristic component of ergot, were quantified in the different milling fractions. From the first experiment, it can be shown that after harvesting even simple contact of sclerotia with bulk grains during ordinary handling or movement of bulk grain in the granary is sufficient to contaminate all the healthy or sound rye grains with ergot alkaloids. Thereby, the amount of ergot residue correlates with the amount of peripheral layers of rye grains in the flour. In an additional experiment without sclerotia specimens, bulk rye grains were loaded with powder of sclerotia. After subsequent cleaning, aconcentration of ergot alkaloids was detected, which was tenfold higher than the ergot alkaloidconcentration of the experiment with intact ergot sclerotia.

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“…The main fatty acid was 18: 1 followed by 18: 2, and the contents of 16: 0, 18: 0 and 18: 3 were very low. Although multiacyl glycerides have been detected in ergot oi1 9 ) and kamala oil,lO) the existence of w-hydroxy fatty acids such as 18 : l-w-OH and 18: 2-w-OH in these multi acyl glycerides has not been reported.…”

Section: Discussionmentioning

confidence: 99%