Long-chain alkenes of the haptophytes Isochrysis galbana and Emiliania huxleyi

G Rieley, J W Leftley, M A Teece, T M Peakman, Christine Campbell, A M Raven

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Abstract

The major alkenes of the haptophytes Isochrysis galbana (strain CCAP 927/14) and Emiliania huxleyi (strains CCAP 920/2 and VAN 556) have been identified by nuclear magnetic resonance spectroscopy and by mass spectrometric analysis of their dimethyl disulfide adducts. The dominant alkene in I, galbana is (22Z)-1,22-hentriacontadiene, with 1,24-hentriacontadiene and 1,24-tritriacontadiene present in much lower abundance; (22Z)-1,22-hentriacontadiene also occurs in E. huxleyi (strain CCAP 920/2), together with (2Z,22Z)-2,22-hentriacontadiene (the major hydrocarbon) and (3Z,22Z)-3,22-hentriacontadiene. Minor abundances of 2,24-hentriacontadiene and 2,24-tritriacontadiene are also present in this strain. In contrast, the dominant alkene in E. huxleyi (strain VAN 556) is (15 E,22 E)-1,16,23-heptatriacontatriene with the related alkatriene 1,15,22-octatriacontatriene also present and (22Z)-1,22-hentriacontadiene occurring as a minor component. From structural relationships (15E,22 E)-1,15,22-heptatriacontatriene is proposed to derive from the same biosynthetic pathway as that of the characteristic C-37 alkenones which occur in both E. huxleyi and I. galbana. The C-31 and C-33 dienes likely derive from chain extension and decarboxylation of (Z)-9-octadecenoic acid or (Z)-7-hexadecenoic acid, using a pathway analogous to that elucidated previously in the chlorophyte Botryococcus braunii. Therefore, long-chain dienes and trienes, which can co-occur in haptophytes, may have distinct biosynthetic pathways.
Original languageEnglish
Pages (from-to)617-625
Number of pages9
JournalLIPIDS
Volume33
Issue number6
Publication statusPublished - 1998

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    Rieley, G., Leftley, J. W., Teece, M. A., Peakman, T. M., Campbell, C., & Raven, A. M. (1998). Long-chain alkenes of the haptophytes Isochrysis galbana and Emiliania huxleyi. LIPIDS, 33(6), 617-625.