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Metabolism of 1-acyl-2-oleoyl-sn-glycero-3-phosphoethanolamine in castor oil biosynthesis

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Lipids

Abstract

We have examined the role of 2-oleoyl-PE (phosphatidylethanolamine) in the biosynthesis of triacylglycerols (TAG) by castor microsomes. In castor microsomal incubation, the label from 14C-oleate of 1-palmitoyl-2-[1-14C]oleoyl-sn-glycero-3-phosphoethanolamine is incorporated into TAG containing ricinoleate. The enzyme characteristics, such as optimal pH, and the effect of incubation components of the oleoyl-12-hydroxylase using 2-oleoyl-PE as incubation substrate are similar to those for 2-oleoyl-PC (phosphatidylcholine). However, compared to 2-oleoyl-PC, 2-oleoyl-PE is a less efficient incubation substrate of oleoyl-12-hydroxylase in castor microsomes. Unlike 2-oleoyl-PC, 2-oleoyl-PE is not hydroxylated to 2-ricinoleoyl-PE by oleoyl-12-hydroxylase and is not desaturated to 2-linoleoyl-PE by oleoyl-12-desaturase. We have demonstrated the conversion of 2-oleoyl-PE to 2-oleoyl-PC and vice versa. The incorporation of label from 2-[14C]oleoyl-PE into TAG occurs after its conversion to 2-oleoyl-PC, which can then be hydroxylated or desaturated. We detected neither PE-N-monomethyl nor PE-N,N-dimethyl, the intermediates from PE to PC by N-methylation. The conversion of 2-oleoyl-PE to 2-oleoyl-PC likely occurs via hydrolysis to 1,2-diacyl-sn-glycerol by phospholipase C and then by cholinephosphotransferase. This conversion does not appear to play a key role in driving ricinoleate into TAG.

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Abbreviations

DAG:

diacylglycerol

FA:

fatty acid

FAME:

fatty acid methyl ester

FFA:

free fatty acid

HPLC:

high-performance liquid chromatography

2-linoleoyl-PC:

1-acyl-2-linoleoyl-sn-glycero-3-phosphocholine

2-oleoyl-PC:

1-acyl-2-oleoyl-sn-glycero-3-phosphocholine

2-oleoyl-PE:

1-acyl-2-oleoyl-sn-glycero-3-phosphoethanolamine

PC:

phosphatidylcholine

PE:

phosphatidylethanolamine

2-ricinoleoyl-PC:

1-acyl-2-ricinoleoyl-sn-glycero-3-phosphocholine

2-ricinoleoyl-PE:

1-acyl-2-ricinoleoyl-sn-glycero-3-phosphoethanolamine

TAG:

triacylglycerol

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Authors and Affiliations

  1. Agricultural Research Service, Western Regional Research Center, U.S. Department of Agriculture, 94710, Albany, California

    Jiann-Tsyh Lin, Karen M. Lew, Jennifer M. Chen & Thomas A. McKeon

  2. Department of Biological Mechanisms and Functions, Nagoya University, 464-8601, Nagoya, Japan

    Yugo Iwasaki

Authors
  1. Jiann-Tsyh Lin
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  2. Karen M. Lew
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  3. Jennifer M. Chen
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  4. Yugo Iwasaki
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  5. Thomas A. McKeon
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Correspondence to Jiann-Tsyh Lin.

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Lin, JT., Lew, K.M., Chen, J.M. et al. Metabolism of 1-acyl-2-oleoyl-sn-glycero-3-phosphoethanolamine in castor oil biosynthesis. Lipids 35, 481–486 (2000). https://doi.org/10.1007/s11745-000-547-5

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  • DOI: https://doi.org/10.1007/s11745-000-547-5

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