KNAW Repository

Distribution of heterocyst glycolipids in cyanobacteria

Bauersachs, T. and Compaore, J. and Hopmans, E.C. and Stal, L.J. and Schouten, S. and Damsté Sinninghe, J.S. (2009) Distribution of heterocyst glycolipids in cyanobacteria. Phytochemistry, 70, 2034-2039. ISSN 0031-9422.

[img]PDF - Published Version
Restricted to KNAW only


Official URL:


Thirty-four axenic strains of cyanobacteria were analysed for their glycolipid content using high performance liquid chromatography coupled to electrospray ionisation tandem mass spectrometry (HPLC/ESI-MS2). Species of the families Nostocaceae and Rivulariaceae, capable of biosynthesising heterocysts, contained a suite of glycolipids consisting of sugar moieties glycosidically bound to long-chain diols, triols, keto-ols and keto-diols. The aglycone moiety consisted of C26 or C28 carbon-chains with hydroxyl groups at the C-3, ω-1 or ω-3 positions. Keto-ols and keto-diols contained their carbonyl functionalities likely at the C-3 position. These compounds were absent in all analysed unicellular and filamentous non-heterocystous cyanobacteria and in the heterocyst-forming cyanobacterium Anabaena CCY9922 grown in the presence of combined nitrogen, supporting the idea that the long-chain glycolipids are an important and unique structural component of the heterocyst cell envelope. The glycolipids 1-(O-hexose)-3,25-hexacosanediol and 1-(O-hexose)-3-keto-25-hexacosanol were ubiquitously distributed in species of the family Nostocaceae. 1-(O-hexose)-3,25,27-octacosanetriol and 1-(O-hexose)-3-keto-25,27-octacosanediol were dominant in members of the Calothrix genus, while traces of those compounds were detected only in one species of the Nostocaceae family. Their distribution in heterocystous cyanobacteria suggests a chemotaxonomic relevance that might allow distinguishing between species of different genera. Culture experiments indicate that the amount of keto-ols and keto-diols decreases relatively to their corresponding diols and triols counterparts with increasing temperature. Possibly, this is an adaptation to optimise the cell wall gas permeability, preventing inactivation of the oxygen-sensitive nitrogenase while allowing the highest diffusion of atmospheric dinitrogen into the heterocyst.

Item Type:Article
Institutes:Nederlands Instituut voor Ecologie (NIOO)
ID Code:6197
Deposited On:23 Mar 2010 01:00
Last Modified:04 Sep 2014 09:32

Repository Staff Only: item control page