The structures of triacylglycerols from sclerotia of the rye ergot Claviceps purpurea (Fries) Tul.

Batrakov, S. G.; Толкачев, О. Н.

doi:10.1016/s0009-3084(96)02653-9

Cited by 11 publications

(14 citation statements)

References 14 publications

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“…However, as far as we know, no further study of these ricinoleatecontaining AG was reported. RRRR was not previously suggested in sclerotia of the rye eregot (9) and is reported here for the first time. For positive identification of RRRR, we have shown the clean spectrum of HR-MS/MS with significant original precursor ion (nonhydrogenated), diglyceride and acyl ions, and their exact masses.…”

Section: Resultssupporting

confidence: 53%

“…Therefore, one of the two ricinoleoyl chain losses on [RRRR + Na -RCOOH -RCOOH] + was the fourth ricinoleoyl chain attached to a ricinoleoyl chain, and the other ricinoleoyl chain (Figures 1 and 4-6 AG with four acyl chains have previously been tentatively identified (2-9) as estolides. In sclerotia of the rye ergot, the AG containing four to nine acyl chains including ricinoleate and nonhydroxylated FA have been suggested (9). However, as far as we know, no further study of these ricinoleatecontaining AG was reported.…”

Section: Resultsmentioning

confidence: 97%

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Identification of (12-Ricinoleoylricinoleoyl)diricinoleoylglycerol, an Acylglycerol Containing Four Acyl Chains, in Castor (Ricinus communis L.) Oil by LC-ESI-MS

Lin

Arcinas

Harden

et al. 2006

J. Agric. Food Chem.

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An acylglycerol (AG) containing four acyl chains, (12-ricinoleoylricinoleoyl)diricinoleoylglycerol (RRRR), was positively identified for the first time in a natural source in castor oil using electrospray ionization tandem mass spectrometry (ESI-MS/MS). HPLC-purified RRRR from castor oil was subjected to ion trap and high-resolution ESI-MS/MS. The precursor and fragment ions of [RRRR + Na]+ showed the expected masses, and the sodiated fragment ions of both diacylglycerols and fatty acids were detected. Because fragment ions of fatty acids from [AG + NH4]+ adducts cannot be detected by ESI-MS/MS, [AG + Na]+ adducts are more informative. Radiolabeled triricinolein (RRR) was incorporated into RRRR in castor microsomes, indicating that RRRR is biosynthesized in castor bean. This newly identified and biosynthesized RRRR represents a new AG subclass of tetra-acylglycerols (or acylacyldiacylglycerol).

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Section: Resultssupporting

confidence: 53%

Section: Resultsmentioning

confidence: 97%

Identification of (12-Ricinoleoylricinoleoyl)diricinoleoylglycerol, an Acylglycerol Containing Four Acyl Chains, in Castor (Ricinus communis L.) Oil by LC-ESI-MS

Lin

Arcinas

Harden

et al. 2006

J. Agric. Food Chem.

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“…The substrate preference of CpDGAT2 toward ricinoleic acid was not unexpected, given that ricinoleic acid can represent up to 50% of the total fatty acids in the sclerotium oil of this fungus (2). DGAT2 previously has been implicated in the preferential utilization of unusual fatty acids for TAG formation.…”

Section: Discussionmentioning

confidence: 80%

“…The radiolabeled glycerolipids were resuspended in chloroform and subjected to thin-layer chromatography (TLC) separation on silica gel-G plates. The experimental conditions for the acyl acceptor assay were the same as those described above, except that [1][2][3][4][5][6][7][8][9][10][11][12][13][14] C]ricinoleoyl-CoA was incubated with different acyl acceptors.…”

Section: Methodsmentioning

confidence: 99%

“…It infects young flowers by mimicking pollen grains to penetrate style tissues. After reaching the ovary of the inflorescence, it forms a specialized structure called a sclerotium, in which high levels of ricinoleic acid accumulate, in some cases amounting to as much as 50% of the total fatty acids in sclerotium oil (2). Ricinoleic acid, a hydroxyl fatty acid [(R)-12-hydroxyoctadeccis-9-enoic acid] with many specialized uses in the chemical industry, has been the subject of a great deal of scientific interest in recent years.…”

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confidence: 99%

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Type II Diacylglycerol Acyltransferase fromClaviceps purpureawith Ricinoleic Acid, a Hydroxyl Fatty Acid of Industrial Importance, as Preferred Substrate

Mavraganis

Meesapyodsuk

Vrinten³

et al. 2010

Appl Environ Microbiol

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Diacylglycerol acyltransferase (DGAT) catalyzes the final and committed step in triacylglycerol (TAG) biosynthesis from the substrates diacylglycerol (DAG) and fatty acyl-coenzyme A (CoA). Although DGAT activity was reported first in chicken liver in 1956 (30), only in the last few years have DGAT genes been cloned and characterized at the molecular level. Cases et al. (7) cloned the first DGAT gene from the mouse by using homology searches of expressed sequence tag (EST) databases with a mammalian acyl-CoA:cholesterol acyltransferase (ACAT) as the query sequence. The DGAT identified shared 20% identity at the amino acid level with the ACAT translation product. The mouse DGAT later was named DGAT1, so as to distinguish it from subsequently identified types of DGATs. An in vitro assay of mouse DGAT1 showed that, in addition to DGAT activity, this enzyme also could catalyze the esterification of a fatty acyl-CoA with monoacylglycerol, generating diacylglycerols (31). Mice lacking DGAT1 have reduced levels of wax esters in their fur (8), and

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Characterization of Polyglycerol Polyricinoleate Formulations Using NMR Spectroscopy, Mass Spectrometry and Dynamic Light Scattering

Orfanakis

Hatzakis

Kanaki

et al. 2012

J Americ Oil Chem Soc

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Three different analytical techniques, namely NMR spectroscopy, mass spectrometry and dynamic light scattering, were used to unravel the structure and morphology of polyglycerol polyricinoleate (PGPR). This material is used as an emulsifier in the preparation of chocolate and other confectionary products. The use of 1D and 2D NMR techniques led to the distinction of two separate entities in commercial ricinoleic acid (RA) and PGPR samples, namely the monomeric and oligomeric RA (estolides). 1H and 13C spectra of PGPR confirmed the presence of polyglycerol moieties of various lengths being esterified by RA and estolides and to a lesser extent by oleic and linoleic acids. 13C‐NMR DOSY experiments demonstrated the occurrence of several species in PGPR. Electrospray Ionization and tandem Mass Spectrometry succeeded in identifying the presence of over 30 glycerol/polyglycerol species containing n glycerol moieties with n = 1–6 esterified by monomeric and oligomeric RA molecules. Dynamic light scattering contributed to the characterization of PGPR morphology. The PGPR mixture contains relatively small‐sized entities (monomers, dimmers, trimmers) and larger aggregates resulted from chain association. The percentage of larger aggregates is minimal compared to small‐sized species.

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The structures of triacylglycerols from sclerotia of the rye ergot Claviceps purpurea (Fries) Tul.

Cited by 11 publications

References 14 publications

Identification of (12-Ricinoleoylricinoleoyl)diricinoleoylglycerol, an Acylglycerol Containing Four Acyl Chains, in Castor (Ricinus communis L.) Oil by LC-ESI-MS

Identification of (12-Ricinoleoylricinoleoyl)diricinoleoylglycerol, an Acylglycerol Containing Four Acyl Chains, in Castor (Ricinus communis L.) Oil by LC-ESI-MS

Type II Diacylglycerol Acyltransferase fromClaviceps purpureawith Ricinoleic Acid, a Hydroxyl Fatty Acid of Industrial Importance, as Preferred Substrate

Characterization of Polyglycerol Polyricinoleate Formulations Using NMR Spectroscopy, Mass Spectrometry and Dynamic Light Scattering

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