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An Unprecedented Occurrence of Δ5,9- and Δ9,15-Dienoic Fatty Acids in Ovaries of the Archaeogastropod Limpet Cellana toreuma

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Lipids

Abstract

A detailed structural diversity of dienoic fatty acids (FA), including non-methylene-interrupted dienoic FA, of triacylglycerols and polar lipids in ovaries of Cellana toreuma was clarified for the first time by using capillary gas chromatography–mass spectrometry of their 3-pyridylcarbinol esters and argentation thin-layer chromatography. Interestingly, in addition to 5,9-octadecadienoic (18:2Δ5,9), 5,9-eicosadienoic (20:2Δ5,9), 5,9-heneicosadienoic (21:2Δ5,9), 5,9-docosadienoic (22:2Δ5,9), 5,9-tricosadienoic (23:2Δ5,9), and 5,9-tetracosadienoic (24:2Δ5,9) acids, previously identified in ovaries of C. grata, rare FA 5,9-hexadecadienoic (16:2Δ5,9), 5,9-nonadecadienoic (19:2Δ5,9), and 21-methyl-5,9-docosadienoic (iso 23:2Δ5,9) were newly recognized in ovaries of C. toreuma. Detectable amounts of four Δ9,15-dienoic FA were present in the ovary lipids. The FA identified were one novel 9,15-heneicosadienoic (21:2Δ9,15) acid and known 9,15-docosadienoic (22:2Δ9,15), 9,15-tricosadienoic (23:2Δ9,15), and 9,15-tetracosadienoic (24:2Δ9,15) acids. The findings help to explain the broad evidence of the structural diversity in marine gastropods and suggest biomarkers to evaluate marine food web relations.

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Fig. 1
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Abbreviations

EI:

Electron impact

FA:

Fatty acid(s)

FID:

Flame ionization detector

GLC:

Gas–liquid chromatography

GC–MS:

Gas chromatography–mass spectrometry

MS:

Mass spectrum

NMI:

Non-methylene-interrupted

TAG:

Triacylglycerols

TLC:

Thin-layer chromatography

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Acknowledgments

This study was supported by the Cooperative Program (No. 120, 2014) of the Atmosphere and Ocean Research Institute, The University of Tokyo.

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Authors and Affiliations

  1. Bioscience Laboratory, Miyako College, Iwate Prefectural University, Miyako, 027-0039, Japan

    Hideki Kawashima

  2. Department of Food Science and Human Nutrition, Faculty of Human Life Sciences, Fuji Women’s University, Ishikari, 061-3204, Japan

    Masao Ohnishi

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  1. Hideki Kawashima
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  2. Masao Ohnishi
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Correspondence to Hideki Kawashima.

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The authors declare no conflict of interest.

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Kawashima, H., Ohnishi, M. An Unprecedented Occurrence of Δ5,9- and Δ9,15-Dienoic Fatty Acids in Ovaries of the Archaeogastropod Limpet Cellana toreuma . Lipids 51, 257–262 (2016). https://doi.org/10.1007/s11745-015-4107-8

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  • DOI: https://doi.org/10.1007/s11745-015-4107-8

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