Tetratriacontanonaenoic acid, first natural acid with nine double bonds isolated from a crustacean Bathynella natans

The very-long-chain polyunsaturated fatty acid-allZ-4,7,10,13,16,19,22,25,28-tetratriacontanonaenoic acid was determined and identified in the freshwater crustacean species Bathynella natans living in caves of central Europe by means of liquid chromatography-mass spectrometry with atmospheric pressure chemical ionization. The full structure was elucidated by using extensive spectroscopic analysis (H-1 and C-13 NMR, MS, IR and UV) including a chemical method. This acid was described in nature for the first time. A hypothesis is suggested for its origin and biosynthesis. (C) 2004 Elsevier Ltd. All rights reserved.