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Characterization of trans ‐monounsaturated alkenyl chains in total plasmalogens (1‐ O ‐alk‐1′‐enyl‐2‐acyl glycerophospholipids) from sheep heart
Author(s) -
Wolff Robert L.
Publication year - 2002
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-002-0965-4
Subject(s) - glycerophospholipids , chemistry , double bond , plasmalogen , cis–trans isomerism , stereochemistry , organic chemistry , biochemistry , phospholipid , membrane
In the present study, we investigated the alkenyl chains from sheep heart plasmalogens (1‐ O ‐alk‐1′‐enyl‐2‐acyl glycerophospholipids) after their conversion into trimethylene dioxyalkanyl (TMDOA) derivatives. Particular attention was given to monounsaturated alkenyl chains (C 18 mainly). For this purpose, a combination of silver ion TLC and GLC on highly polar, very long capillary columns was applied to TMDOA derivatives. Approximately 30 different alkenyl chains could be separated, and the main observation was that the component previously reported as a cis ‐9 18∶1 alkenyl chain in plasmalogens embraces in fact a wide range of trans and cis isomers, in amounts equal to 7.9 and 5.6%, respectively, of total alkenyl chains. Concerning the trans ‐monoenoate fraction, isomers with their ethylenic bond spanning from Δ6–Δ8 to Δ16 were tentatively identified on the basis of their distribution profile, which was similar to that of trans ‐18∶1 acids prepared and isolated from sheep adipose tissue. The main trans ‐monoenoic C 18 alkenyl chain in sheep heart plasmalogens would thus have its double bond in position 11, which seems logical, as alkenyl chains are derived from the corresponding alcohols, themselves issued from the corresponding FA, and in this particular case, vaccenic ( trans ‐11 18∶1) acid. cis ‐Monoenoic C 18 alkenyl chains also appear more complex than realized earlier, showing in particular isomers with their ethylenic bond farther than the Δ9 position, in addition to the main isomer derived from oleic acid. Several trans ‐16∶1 alkenyl chains could be observed (totaling ca . 1%), but cis ‐16∶1 isomers were present in trace amounts only.