Regiospecific identification of 2-(12-ricinoleoylricinoleoyl)-1,3- diricinoleoyl-sn-glycerol in castor (Ricinus communis L.) oil by ESI-MS

Jiann Tsyh Lin, Arthur J. Arcinas

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

(12-Ricinoleoylricinoleoyl)diricinoleoylglycerol (RRRR), a tetraacylglycerol, was identified earlier in castor oil. Using ESI-MS 4, 95% of the 12-ricinoleoylricinoleoyl chain was identified at the sn-2 position of the glycerol backbone of RRRR. Regiospecific location of the 12-ricinoleoylricinoleoyl chain of RRRR on the glycerol backbone was identified and quantified by the ions from the losses of the acyl chains at the sn-2 position as α,β-unsaturated fatty acids from the lithium adduct of RRRR. The regiospecific location was confirmed by hydrolysis of RRRR using sn-1,3 specific lipase. By comparison to the mass spectrum of 1-O-palmityl-2,3-palmitoyl-rac-glycerol containing one ether bond, the 12-ricinoleoylricinoleoyl chain of RRRR is indeed the ester bond between the two ricinoleoyl chains, not the ether bond formed from the two hydroxyl groups of the two ricinoleoyl chains. The structure of RRRR is 2-(12- ricinoleoylricinoleoyl)-1,3-diricinoleoyl-sn-glycerol.

Original languageEnglish (US)
Pages (from-to)3616-3622
Number of pages7
JournalJournal of Agricultural and Food Chemistry
Volume56
Issue number10
DOIs
StatePublished - May 28 2008
Externally publishedYes

Fingerprint

Ricinus
Ricinus communis
glycerol
Oils
oils
ethers
Glycerol
castor oil
lithium
unsaturated fatty acids
Ether
hydrolysis
esters
Castor Oil
ions
electrospray ionization mass spectrometry
2-(12-ricinoleoylricinoleoyl)-1,3-diricinoleoylglycerol
Lipase
Unsaturated Fatty Acids
Lithium

Keywords

  • 1-O-palmityl-2,3- palmitoyl-rac-glycerol
  • 2-(12-ricinoleoylricinoleoyl)-1,3-diricinoleoyl-sn- glycerol
  • Castor oil
  • ESI-MS
  • Lipase
  • Regiospecific
  • Ricinoleate
  • Ricinus communis L.
  • Tetraacylglycerol
  • Tetraricinolein

ASJC Scopus subject areas

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

Cite this

@article{71d73d697eec4d7d92e8d56c257617b0,
title = "Regiospecific identification of 2-(12-ricinoleoylricinoleoyl)-1,3- diricinoleoyl-sn-glycerol in castor (Ricinus communis L.) oil by ESI-MS",
abstract = "(12-Ricinoleoylricinoleoyl)diricinoleoylglycerol (RRRR), a tetraacylglycerol, was identified earlier in castor oil. Using ESI-MS 4, 95{\%} of the 12-ricinoleoylricinoleoyl chain was identified at the sn-2 position of the glycerol backbone of RRRR. Regiospecific location of the 12-ricinoleoylricinoleoyl chain of RRRR on the glycerol backbone was identified and quantified by the ions from the losses of the acyl chains at the sn-2 position as α,β-unsaturated fatty acids from the lithium adduct of RRRR. The regiospecific location was confirmed by hydrolysis of RRRR using sn-1,3 specific lipase. By comparison to the mass spectrum of 1-O-palmityl-2,3-palmitoyl-rac-glycerol containing one ether bond, the 12-ricinoleoylricinoleoyl chain of RRRR is indeed the ester bond between the two ricinoleoyl chains, not the ether bond formed from the two hydroxyl groups of the two ricinoleoyl chains. The structure of RRRR is 2-(12- ricinoleoylricinoleoyl)-1,3-diricinoleoyl-sn-glycerol.",
keywords = "1-O-palmityl-2,3- palmitoyl-rac-glycerol, 2-(12-ricinoleoylricinoleoyl)-1,3-diricinoleoyl-sn- glycerol, Castor oil, ESI-MS, Lipase, Regiospecific, Ricinoleate, Ricinus communis L., Tetraacylglycerol, Tetraricinolein",
author = "Lin, {Jiann Tsyh} and Arcinas, {Arthur J.}",
year = "2008",
month = "5",
day = "28",
doi = "10.1021/jf072750z",
language = "English (US)",
volume = "56",
pages = "3616--3622",
journal = "Journal of Agricultural and Food Chemistry",
issn = "0021-8561",
publisher = "American Chemical Society",
number = "10",

}

TY - JOUR

T1 - Regiospecific identification of 2-(12-ricinoleoylricinoleoyl)-1,3- diricinoleoyl-sn-glycerol in castor (Ricinus communis L.) oil by ESI-MS

AU - Lin, Jiann Tsyh

AU - Arcinas, Arthur J.

PY - 2008/5/28

Y1 - 2008/5/28

N2 - (12-Ricinoleoylricinoleoyl)diricinoleoylglycerol (RRRR), a tetraacylglycerol, was identified earlier in castor oil. Using ESI-MS 4, 95% of the 12-ricinoleoylricinoleoyl chain was identified at the sn-2 position of the glycerol backbone of RRRR. Regiospecific location of the 12-ricinoleoylricinoleoyl chain of RRRR on the glycerol backbone was identified and quantified by the ions from the losses of the acyl chains at the sn-2 position as α,β-unsaturated fatty acids from the lithium adduct of RRRR. The regiospecific location was confirmed by hydrolysis of RRRR using sn-1,3 specific lipase. By comparison to the mass spectrum of 1-O-palmityl-2,3-palmitoyl-rac-glycerol containing one ether bond, the 12-ricinoleoylricinoleoyl chain of RRRR is indeed the ester bond between the two ricinoleoyl chains, not the ether bond formed from the two hydroxyl groups of the two ricinoleoyl chains. The structure of RRRR is 2-(12- ricinoleoylricinoleoyl)-1,3-diricinoleoyl-sn-glycerol.

AB - (12-Ricinoleoylricinoleoyl)diricinoleoylglycerol (RRRR), a tetraacylglycerol, was identified earlier in castor oil. Using ESI-MS 4, 95% of the 12-ricinoleoylricinoleoyl chain was identified at the sn-2 position of the glycerol backbone of RRRR. Regiospecific location of the 12-ricinoleoylricinoleoyl chain of RRRR on the glycerol backbone was identified and quantified by the ions from the losses of the acyl chains at the sn-2 position as α,β-unsaturated fatty acids from the lithium adduct of RRRR. The regiospecific location was confirmed by hydrolysis of RRRR using sn-1,3 specific lipase. By comparison to the mass spectrum of 1-O-palmityl-2,3-palmitoyl-rac-glycerol containing one ether bond, the 12-ricinoleoylricinoleoyl chain of RRRR is indeed the ester bond between the two ricinoleoyl chains, not the ether bond formed from the two hydroxyl groups of the two ricinoleoyl chains. The structure of RRRR is 2-(12- ricinoleoylricinoleoyl)-1,3-diricinoleoyl-sn-glycerol.

KW - 1-O-palmityl-2,3- palmitoyl-rac-glycerol

KW - 2-(12-ricinoleoylricinoleoyl)-1,3-diricinoleoyl-sn- glycerol

KW - Castor oil

KW - ESI-MS

KW - Lipase

KW - Regiospecific

KW - Ricinoleate

KW - Ricinus communis L.

KW - Tetraacylglycerol

KW - Tetraricinolein

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U2 - 10.1021/jf072750z

DO - 10.1021/jf072750z

M3 - Article

C2 - 18442250

AN - SCOPUS:45549105444

VL - 56

SP - 3616

EP - 3622

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

SN - 0021-8561

IS - 10

ER -