Novel Non-methylene-Interrupted Dienoic and Trienoic Fatty Acids with a Terminal Double Bond in Ovaries of the Limpet Cellana toreuma

Lipids. 2020 May;55(3):285-290. doi: 10.1002/lipd.12225. Epub 2020 Feb 23.

Abstract

In this study, to obtain further information on the structural diversity of non-methylene-interrupted (NMI) fatty acids (FA) in the gonads of the limpet Cellana toreuma, previously unreported minor NMI FA, fractionated by argentation thin-layer chromatography (TLC), in the ovaries were characterized by gas chromatography-mass spectrometry (GC-MS) analysis of their 3-pyridylcarbinol derivatives. As a result, five novel NMI FA were identified as 5,14-pentadecadienoic acid (15: 2Δ5,14), 5,9,18-nonadecatrienoic acid (19:3Δ5,9,18), 5,9,20-heneicosatrienoic acid (21:3Δ5,9,20), 7,13,20-heneicosatrienoic acid (21:3Δ7,13,20), and 5,9,22-tricosatrienoic acid (23:3Δ5,9,22). Possible biosynthetic pathways for these FA are also discussed in relation to structural variations of NMI FA regioisomers. This study clearly reinforces the findings of our previous works with structurally diverse NMI FA with a terminal double bond.

Keywords: Cellana toreuma; 3-Pyridylcarbinol derivatives; Limpet; Non-methylene-interrupted fatty acid; Odd-chain fatty acid; Terminal double bond.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chromatography, Thin Layer
  • Fatty Acids / analysis*
  • Fatty Acids / biosynthesis
  • Fatty Acids / chemistry
  • Female
  • Gas Chromatography-Mass Spectrometry
  • Gastropoda / chemistry*
  • Gastropoda / metabolism
  • Ovary / chemistry
  • Ovary / metabolism
  • Signal Transduction

Substances

  • Fatty Acids