Formation of 8,11,14-octadecatrienoic acid (18:3 n-4) from naturally occurring unique fatty acid, 9,12-hexadecadienoic acid (16:2 n-4), in animal cell cultures.
9,12-Hexadecadienoic acid (16:2 n-4), present in small amounts in fish oils as a naturally occurring unique fatty acid, was incorporated into the phospholipids in rat liver BRL-3A cells to a similar extent as linoleic acid (18:2 n-6). 11,14-Octadecadienoic acid (18:2 n-4) and 8,11,14-octadecatrienoic acid (18:3 n-4) were detected in the cellular lipids of BRL-3A cells when incubated in a medium supplemented with 16:2 n-4 methyl ester. The cellular levels of these acids increased in parallel with 16:2 n-4 methyl ester added to the medium. These compounds were probably formed through conversion from 16:2 n-4 to 16:3 n-4 by delta 6 desaturation, and then 18:3 n-4 was produced by elongation, and part of the surplus 16:2 n-4, not desaturated to 16:3 n-4, elongated to 18:2 n-4. These results suggested that 16:2 n-4 was desaturated by delta 6 desaturase in vitro. It was also shown that 16:2 n-4 inhibited arachidonic acid synthesis from exogenous linoleic acid in BRL-3A cells as efficiently as alpha-linolenic acid (18:3 n-3).
Nakano
N
N
Department of Food Science and Nutrition, Faculty of Agriculture, Kinki University, Nara, Japan.
Shirasaka
N
N
Murakami
T
T
Shimizu
S
S
Yoshizumi
H
H
D000818:Animals; D016718:Arachidonic Acid / Q000096:biosynthesis; D002478:Cells, Cultured; D002850:Chromatography, Gel; D002851:Chromatography, High Pressure Liquid; D005230:Fatty Acids, Nonesterified / Q000032:analysis; D005231:Fatty Acids, Unsaturated / Q000378:metabolism*; D005395:Fish Oils / Q000378:metabolism; D019787:Linoleic Acid / Q000378:metabolism; D008042:Linolenic Acids / Q000378:metabolism*; D008099:Liver / Q000166:cytology / Q000378:metabolism*; D010713:Phosphatidylcholines / Q000032:analysis; D010714:Phosphatidylethanolamines / Q000032:analysis; D010718:Phosphatidylserines / Q000032:analysis; D010743:Phospholipids / Q000032:analysis / Q000378:metabolism; D051381:Rats; D014242:Trichoderma / Q000737:chemistry; D014280:Triglycerides / Q000032:analysis
C121850:8,11,14-octadecatrienoic acid; D005230:Fatty Acids, Nonesterified; D005231:Fatty Acids, Unsaturated; D005395:Fish Oils; D008042:Linolenic Acids; D010713:Phosphatidylcholines; D010714:Phosphatidylethanolamines; D010718:Phosphatidylserines; D010743:Phospholipids; D014280:Triglycerides; C080021:9,12-hexadecadienoic acid; D016718:Arachidonic Acid; D019787:Linoleic Acid