Identification of (12-ricinoleoylricinoleoyl)diricinoleoylglycerol, an acylglycerol containing four acyl chains, in castor (Ricinus communis L.) oil by LC-ESI-MS

Jiann Tsyh Lin, Arthur J. Arcinas, Leslie R. Harden, Clifton K. Fagerquist

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

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).

Original languageEnglish (US)
Pages (from-to)3498-3504
Number of pages7
JournalJournal of Agricultural and Food Chemistry
Volume54
Issue number10
DOIs
StatePublished - May 17 2006
Externally publishedYes

Fingerprint

Ricinus
Glycerides
Ricinus communis
acylglycerols
Oils
oils
ions
castor oil
Ions
Castor Oil
fatty acids
Fatty Acids
Castor Bean
castor beans
microsomes
diacylglycerols
Electrospray ionization
Electrospray Ionization Mass Spectrometry
Diglycerides
Microsomes

Keywords

  • Acylacyldiacylglycerol
  • Acylglycerol
  • Biosynthesis
  • Castor oil
  • HPLC
  • Ricinoleate
  • Ricinus communis L.
  • Tetra-acylglycerol

ASJC Scopus subject areas

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)

Cite this

Identification of (12-ricinoleoylricinoleoyl)diricinoleoylglycerol, an acylglycerol containing four acyl chains, in castor (Ricinus communis L.) oil by LC-ESI-MS. / Lin, Jiann Tsyh; Arcinas, Arthur J.; Harden, Leslie R.; Fagerquist, Clifton K.

In: Journal of Agricultural and Food Chemistry, Vol. 54, No. 10, 17.05.2006, p. 3498-3504.

Research output: Contribution to journalArticle

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abstract = "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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