Regiospecific analysis of diricinoleoylacylglycerols in castor (Ricinus communis L.) oil by electrospray ionization-mass spectrometry

Jiann Tsyh Lin, Arthur J. Arcinas

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

HPLC fractions of diricinoleoylacylglycerols containing one non-ricinoleoyl chain from castor oil were used to identify the regiospecific location of this non-ricinoleoyl chain on the glycerol backbone using electrospray ionization-MS3 of lithium adducts. The regiospecific ions used were from the loss of α,β-unsaturated fatty acid specific at the sn-2 position. The content of 1,3-diricinoleoyl-2-oleoyl-sn-glycerols (ROR) among the three stereospecific isomers, RRO, ROR and ORR, was about 91%. The contents of other 1,3-diricinoleoyl-2-acyl-glycerols among the three stereospecific isomers were as follows: 1,3-diricinoleoyl-2-linoleoyl-sn-glycerol, 95%; 1,3-diricinoleoyl-2-linolenoyl-sn-glycerol, 96%; 1,3-diricinoleoyl-2-stearoyl- sn-glycerol, 96%; 1,3-diricinoleoyl-2-palmitoyl-sn-glycerol, 78%; and 1,3-diricinoleoyl-2-lesqueroloyl-sn-glycerol, 31%. These non-hydroxyl fatty acids were mostly at the sn-2 position of triacylglycerols in castor oil. These results suggest that phospholipase A2 hydrolysis of phosphatidylcholine (PC) containing non-hydroxyl fatty acid at the sn-2 position is either blocked or partially blocked in vivo. Phospholipase A2 hydrolysis of 2-lesqueroloyl-PC is not blocked and is similar to that of 2-ricinoleoyl-PC. Transgenic inhibition of phospholipase C hydrolysis of PC might be used to block the incorporation of non-hydroxyl fatty acids into triacylglycerols, thus increasing the content of ricinoleate in seed oil.

Original languageEnglish (US)
Pages (from-to)2209-2216
Number of pages8
JournalJournal of Agricultural and Food Chemistry
Volume55
Issue number6
DOIs
StatePublished - Mar 21 2007
Externally publishedYes

Fingerprint

Ricinus
Electrospray ionization
Electrospray Ionization Mass Spectrometry
Ricinus communis
Glycerol
Mass spectrometry
glycerol
Oils
Phosphatidylcholines
oils
phosphatidylcholines
Castor Oil
Hydrolysis
Fatty Acids
Phospholipases A2
castor oil
phospholipase A2
hydrolysis
Triglycerides
fatty acids

Keywords

  • Castor oil
  • Diricinoleoylacylglycerols
  • Diricinoleoyloleoylglycerol
  • LC-MS
  • Phospholipase A
  • Phospholipase C
  • Regiospecific analysis
  • Ricinoleate
  • Ricinus communis L.
  • Triacylglycerols

ASJC Scopus subject areas

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

Cite this

@article{6eae2f8821764d85ab40d1eb13b2771f,
title = "Regiospecific analysis of diricinoleoylacylglycerols in castor (Ricinus communis L.) oil by electrospray ionization-mass spectrometry",
abstract = "HPLC fractions of diricinoleoylacylglycerols containing one non-ricinoleoyl chain from castor oil were used to identify the regiospecific location of this non-ricinoleoyl chain on the glycerol backbone using electrospray ionization-MS3 of lithium adducts. The regiospecific ions used were from the loss of α,β-unsaturated fatty acid specific at the sn-2 position. The content of 1,3-diricinoleoyl-2-oleoyl-sn-glycerols (ROR) among the three stereospecific isomers, RRO, ROR and ORR, was about 91{\%}. The contents of other 1,3-diricinoleoyl-2-acyl-glycerols among the three stereospecific isomers were as follows: 1,3-diricinoleoyl-2-linoleoyl-sn-glycerol, 95{\%}; 1,3-diricinoleoyl-2-linolenoyl-sn-glycerol, 96{\%}; 1,3-diricinoleoyl-2-stearoyl- sn-glycerol, 96{\%}; 1,3-diricinoleoyl-2-palmitoyl-sn-glycerol, 78{\%}; and 1,3-diricinoleoyl-2-lesqueroloyl-sn-glycerol, 31{\%}. These non-hydroxyl fatty acids were mostly at the sn-2 position of triacylglycerols in castor oil. These results suggest that phospholipase A2 hydrolysis of phosphatidylcholine (PC) containing non-hydroxyl fatty acid at the sn-2 position is either blocked or partially blocked in vivo. Phospholipase A2 hydrolysis of 2-lesqueroloyl-PC is not blocked and is similar to that of 2-ricinoleoyl-PC. Transgenic inhibition of phospholipase C hydrolysis of PC might be used to block the incorporation of non-hydroxyl fatty acids into triacylglycerols, thus increasing the content of ricinoleate in seed oil.",
keywords = "Castor oil, Diricinoleoylacylglycerols, Diricinoleoyloleoylglycerol, LC-MS, Phospholipase A, Phospholipase C, Regiospecific analysis, Ricinoleate, Ricinus communis L., Triacylglycerols",
author = "Lin, {Jiann Tsyh} and Arcinas, {Arthur J.}",
year = "2007",
month = "3",
day = "21",
doi = "10.1021/jf063105f",
language = "English (US)",
volume = "55",
pages = "2209--2216",
journal = "Journal of Agricultural and Food Chemistry",
issn = "0021-8561",
publisher = "American Chemical Society",
number = "6",

}

TY - JOUR

T1 - Regiospecific analysis of diricinoleoylacylglycerols in castor (Ricinus communis L.) oil by electrospray ionization-mass spectrometry

AU - Lin, Jiann Tsyh

AU - Arcinas, Arthur J.

PY - 2007/3/21

Y1 - 2007/3/21

N2 - HPLC fractions of diricinoleoylacylglycerols containing one non-ricinoleoyl chain from castor oil were used to identify the regiospecific location of this non-ricinoleoyl chain on the glycerol backbone using electrospray ionization-MS3 of lithium adducts. The regiospecific ions used were from the loss of α,β-unsaturated fatty acid specific at the sn-2 position. The content of 1,3-diricinoleoyl-2-oleoyl-sn-glycerols (ROR) among the three stereospecific isomers, RRO, ROR and ORR, was about 91%. The contents of other 1,3-diricinoleoyl-2-acyl-glycerols among the three stereospecific isomers were as follows: 1,3-diricinoleoyl-2-linoleoyl-sn-glycerol, 95%; 1,3-diricinoleoyl-2-linolenoyl-sn-glycerol, 96%; 1,3-diricinoleoyl-2-stearoyl- sn-glycerol, 96%; 1,3-diricinoleoyl-2-palmitoyl-sn-glycerol, 78%; and 1,3-diricinoleoyl-2-lesqueroloyl-sn-glycerol, 31%. These non-hydroxyl fatty acids were mostly at the sn-2 position of triacylglycerols in castor oil. These results suggest that phospholipase A2 hydrolysis of phosphatidylcholine (PC) containing non-hydroxyl fatty acid at the sn-2 position is either blocked or partially blocked in vivo. Phospholipase A2 hydrolysis of 2-lesqueroloyl-PC is not blocked and is similar to that of 2-ricinoleoyl-PC. Transgenic inhibition of phospholipase C hydrolysis of PC might be used to block the incorporation of non-hydroxyl fatty acids into triacylglycerols, thus increasing the content of ricinoleate in seed oil.

AB - HPLC fractions of diricinoleoylacylglycerols containing one non-ricinoleoyl chain from castor oil were used to identify the regiospecific location of this non-ricinoleoyl chain on the glycerol backbone using electrospray ionization-MS3 of lithium adducts. The regiospecific ions used were from the loss of α,β-unsaturated fatty acid specific at the sn-2 position. The content of 1,3-diricinoleoyl-2-oleoyl-sn-glycerols (ROR) among the three stereospecific isomers, RRO, ROR and ORR, was about 91%. The contents of other 1,3-diricinoleoyl-2-acyl-glycerols among the three stereospecific isomers were as follows: 1,3-diricinoleoyl-2-linoleoyl-sn-glycerol, 95%; 1,3-diricinoleoyl-2-linolenoyl-sn-glycerol, 96%; 1,3-diricinoleoyl-2-stearoyl- sn-glycerol, 96%; 1,3-diricinoleoyl-2-palmitoyl-sn-glycerol, 78%; and 1,3-diricinoleoyl-2-lesqueroloyl-sn-glycerol, 31%. These non-hydroxyl fatty acids were mostly at the sn-2 position of triacylglycerols in castor oil. These results suggest that phospholipase A2 hydrolysis of phosphatidylcholine (PC) containing non-hydroxyl fatty acid at the sn-2 position is either blocked or partially blocked in vivo. Phospholipase A2 hydrolysis of 2-lesqueroloyl-PC is not blocked and is similar to that of 2-ricinoleoyl-PC. Transgenic inhibition of phospholipase C hydrolysis of PC might be used to block the incorporation of non-hydroxyl fatty acids into triacylglycerols, thus increasing the content of ricinoleate in seed oil.

KW - Castor oil

KW - Diricinoleoylacylglycerols

KW - Diricinoleoyloleoylglycerol

KW - LC-MS

KW - Phospholipase A

KW - Phospholipase C

KW - Regiospecific analysis

KW - Ricinoleate

KW - Ricinus communis L.

KW - Triacylglycerols

UR - http://www.scopus.com/inward/record.url?scp=34147109362&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34147109362&partnerID=8YFLogxK

U2 - 10.1021/jf063105f

DO - 10.1021/jf063105f

M3 - Article

VL - 55

SP - 2209

EP - 2216

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

SN - 0021-8561

IS - 6

ER -