NDLI: Novel Di-, Tri-, and tetraenoic fatty acids with bis-methylene-interrupted double-bond systems from the sponge Haliclona cinerea

Content Provider	Springer Nature Link
Author	Joh, Yong Goe Elenkov, Ivaylo J. Stefav, Kamen L. Popov, Simeon S. Dobson, Gary Christie, William W.
Copyright Year	1997
Abstract	Unusual fatty acids, with up to 34 carbon atoms and containing one or two bis-methylene-interrupted doublebond systems, have been identified in the sponge Haliclona cinerea from the Black Sea. These include the dienes—5,9–16∶2, 7,11–18∶2, 9,13–20∶2, 13,17–24∶2, 15,19–26∶2, 17,21–28∶2, 19,23–30∶2 and 21,25–32∶2; trienes—5,9,23–30∶3, 5,9,24–31∶3, 5,9,25–32∶3, and 5,9,27–34∶3; and the tetraenes—5,9,19,23–30∶4, 5,9,21,25–32∶4, and 5,9,23,27–34∶4. In addition, 5,9,13-eicosatrienoic acid was present. Many of these do not appear to have been described before, and only 5,9–16∶2 and 5,9,23–30∶3 are found often in sponges. They were identified by using silver-ion high-performance liquid chromatography to simplify the complex mixture of fatty acids for subsequent analysis by gas chromatography-mass spectrometry as picolinyl ester derivatives. Deuteration with Wilkinson’s catalyst in homogeneous solution confirmed the structures. We speculate that the di- and tetraenoic fatty acids arise by chain elongation of 5,9-hexadecadienoic acid, also a major component of the lipids, followed by further insertion of double bonds in the 5 and 9 positions. The trienes may be formed from 9-hexadecenoic acid by similar mechanisms.
Starting Page	13
Ending Page	17
Page Count	5
File Format	PDF
ISSN	00244201
Journal	Lipids
Volume Number	32
Issue Number	1
e-ISSN	15589307
Language	English
Publisher	Springer Berlin Heidelberg
Publisher Date	1997-01-01
Publisher Place	Berlin, Heidelberg
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Lipidology Neurochemistry Medical Biochemistry Nutrition Medicinal Chemistry Microbial Genetics and Genomics
Content Type	Text
Resource Type	Article
Subject	Cell Biology Organic Chemistry Biochemistry

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