C(25) highly branched isoprenoid alkenes from the marine benthic diatom Pleurosigma strigosum.

Abstract:

:The hydrocarbon composition of the marine diatom Pleurosigma strigosum isolated from coastal Mediterranean sediments is described. A suite of five C(25) highly branched isoprenoid (HBI) alkenes with 2-5 double bonds were detected together with n-C(21:4) and n-C(21:5) alkenes and squalene. The analysis by (1)H and (13)C NMR spectroscopy of two isolated HBI alkenes allowed the structural identification of a novel C(25) HBI triene (2,6,10,14-tetramethyl-7-(3-methylpent-4-enyl)-pentadeca-5E,13-diene) and the first identification in diatom cells of 2,6,10,14-tetramethyl-7-(3-methylpent-4-enyl)-pentadec-5E-ene, an HBI previously detected in marine sediments and particulate matter. The other minor C(25) HBIs detected were a tetraene and a pentaene that have been previously identified in other diatoms from the genera Haslea and Rhizosolenia, and one other C(25) tetraene that could not be structurally identified. The structures of the HBI alkenes of P. strigosum were compared with those of C(25) homologues previously identified in three other Pleurosigma sp. (Pleurosigma intermedium, Pleurosigma planktonicum and Pleurosigma sp.). Unlike most structures previously reported, none of the HBI alkenes produced by P. strigosum showed an unsaturation at C7-C20, or E/Z isomerism of the trisubstituted double bond at C9-C10 (whenever present).

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Grossi V,Beker B,Geenevasen JA,Schouten S,Raphel D,Fontaine MF,Sinninghe Damsté JS

doi

10.1016/j.phytochem.2004.09.002

subject

Has Abstract

pub_date

2004-11-01 00:00:00

pages

3049-55

issue

22

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(04)00470-4

journal_volume

65

pub_type

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