A novel group of very long chain polyenoic fatty acids in dipolyunsaturated phosphatidylcholines from vertebrate retina

Aveldaño, M I

doi:10.1016/s0021-9258(19)75767-6

Cited by 142Fatty Acid Research and HealthLipid metabolism and biosynthesisLipid Membrane Structure and Behavior

A novel group of very long chain polyenoic fatty acids in dipolyunsaturated phosphatidylcholines from vertebrate retina

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Aveldaño, M I·1987·Journal of Biological Chemistry

DOI 10.1016/s0021-9258(19)75767-6

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Abstract

Dipolyunsaturated phosphatidylcholines from bovine retina contain a whole series of unusual fatty acids. Methyl esters from these acids are very strongly retained on polar and nonpolar gas-liquid chromatography stationary phases. On thin layers of silica-AgNO3, they separate as tetra-, penta-, and hexaenoic fatty acid methyl esters. After hydrogenation, the three polyunsaturated fractions give the same series of saturated methyl esters, having 20 (or 22)-36 carbon atoms. High pressure liquid chromatography, as well as gas-liquid chromatography, indicates that the new components of the three fractions are even-carbon homologs of well known polyenoic fatty acids of the n-6 and n-3 families, since they behave as series of 20-36-carbon tetraenoic (n-6), pentaenoic (n-3 and n-6), and hexaenoic (n-3) fatty acids. Their occurrence in phospholipid molecules also having docosahexaenoate (22:6) explains the separation of major dipolyunsaturated phosphatidylcholines from retina into dodecaenoic, undecaenoic, and decaenoic fractions after argentation thin layer chromatography. Using high pressure liquid chromatography, the latter are resolved into individual species having 10-12 double bonds and 42-58 carbon atoms. The unusual PCs are thus endowed not only with the highest degree of unsaturation, but with the longest hydrocarbon chains yet reported for vertebrate glycerophospholipids. It is shown that phosphatidylcholines containing the novel fatty acids are highly concentrated in photoreceptor membranes and that they occur in the retina of vertebrates so distant in evolution as fish, birds, and various mammals.

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After VLC-PUFAs are generated via ELOVL4, they are incorporated into phospholipids in the PRC inner segment, where they become part of PRC outer membrane biogenesis and tightly interact with rhodopsin.
“After VLC-PUFAs are generated via ELOVL4, they are incorporated into phospholipids in the PRC inner segment, where they become part of the PRC outer membrane biogenesis (Aveldaño, 1987) and tightly interact with rhodopsin (Aveldaño, 1988),”
From Docosanoids and elovanoids from omega-3 fatty acids are pro-homeostatic modulators of inflammatory responses, cell damage and neuroprotection (2018) · cites this paper as Aveldaño, 1987
ELOVL4 synthesizes VLC-PUFAs in the retina and testes, and it synthesizes very-long-chain saturated fatty acids (VLC-SFAs) in the skin and brain.
“ELOVL4 synthesizes VLC-PUFAs in the retina (Agbaga et al., 2010, 2008; Aveldaño, 1987) and testes (Oresti et al., 2010), and it synthesizes very-long-chain saturated fatty acids (VLC-SFAs) in the skin and brain (Cameron et al., 2007; Monroig et al., 2010).”
From Docosanoids and elovanoids from omega-3 fatty acids are pro-homeostatic modulators of inflammatory responses, cell damage and neuroprotection (2018) · cites this paper as Aveldaño, 1987

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Retracted
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Authors: Aveldaño, M. I.
Corresponding author: Aveldaño, M I
Venue: Journal of Biological Chemistry
Publisher: Elsevier BV
Published: 1987-01
Volume: 262
Issue: 3
Pages: 1172-1179
ISSN: 0021-9258 (ISSN-L)
DOI: 10.1016/s0021-9258(19)75767-6
OpenAlex: W1567065116
Cited by: 142
References: 19
Citations by year: 2026: 2 · 2025: 1 · 2024: 2 · 2023: 3 · 2022: 4 · 2021: 7 · 2020: 3 · 2019: 5 · 2018: 6 · 2017: 5 · 2016: 3 · 2015: 4 · 2014: 6 · 2013: 2 · 2012: 2
FWCI: 8.29
Type: journal article
Language: en
Open access: hybrid
doi.org
Licence: cc-by
www.elsevier.com/tdm/userlicense/1.0/ (tdm)
www.elsevier.com/legal/tdmrep-license (tdm)
creativecommons.org/licenses/by/4.0/ (vor, 12355 d)
Locations: Journal of Biological Chemistry (publishedVersion, cc-by)
PubMed (publishedVersion)
Topics: Health Sciences › Nursing › Nutrition and Dietetics › Fatty Acid Research and Health
Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Lipid metabolism and biosynthesis
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Lipid Membrane Structure and Behavior
Keywords: vertebrate retina, photoreceptor membranes, docosahexaenoic acid, omega-6 fatty acids, omega-3 fatty acids, fatty acid methyl esters, HPLC, gas-liquid chromatography, glycerophospholipids, fish retina, birds, mammals
MeSH terms: Animals, Cattle, Chromatography, Gas, Chromatography, High Pressure Liquid, Chromatography, Thin Layer, Fatty Acids, Unsaturated, Phosphatidylcholines, Photoreceptor Cells, Retina

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A novel group of very long chain polyenoic fatty acids in dipolyunsaturated phosphatidylcholines from vertebrate retina

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