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Novel Long-Chain Diol Phospholipids from Some Bacteria Belonging to the Class Thermomicrobia

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Lipids

Abstract

Polar lipids of bacteria from the class Thermomicrobia are known to contain long-chain 1,2-diols instead of glycerol, although the nature of polar head groups has not been investigated. We have studied phospholipid classes of two species from the class Thermomicrobia—Sphaerobacter thermophilus and Thermomicrobia sp. WKT50.2. TLC and 31P-NMR analysis of polar lipids revealed that both S. thermophilus and Thermomicrobia sp. WKT50.2 contain the same set of four major phospholipid classes. Structures of the novel phospholipids in S. thermophilus were established as 2-acylalkyldiol-1-O-phosphoinositol, 2-acylalkyldiol-1-O-phosphoinositol mannoside, 2-acylalkyldiol-1-O-phospho-acylmannoside, and 2-acylalkyldiol-1-O-phosphoinositol acylmannoside. To our knowledge, this is the first report of a phospholipid with a mannose directly bound to the phosphate. We also analyzed fatty acids and long-chain 1,2-diols of S. thermophilus and Thermomicrobia sp. WKT50.2 and compared our data with available information for T. roseum. All species share a similar set of fatty acids, with 12-Me 18:0 being the major fatty acid. The major diol in S. thermophilus was identified as 13-Me 19:0 (66.2 %). The 21:0 diol was the major component both in Thermomicrobia sp. WKT50.2 (50.6 %) and in T. roseum (56.6 %).

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Abbreviations

diolPIns:

2-Acylalkyldiol-1-O-phosphoinositol

diolPInsMan:

2-Acylalkyldiol-1-O-phosphoinositol mannoside

diolP-acylMan:

2-Acylalkyldiol-1-O-phospho-acylmannoside

diolPIns-acylMan:

2-Acylalkyldiol-1-O-phosphoinositol acylmannoside

NMR:

Nuclear magnetic resonance

TLC:

Thin-layer chromatography

ESI:

Electrospray ionisation

GCMS:

Gas chromatography–mass spectrometry

MS:

Mass spectrometry

HMBC:

Heteronuclear multiple bond coherence

HSQC:

Heteronuclear single quantum coherence

COSY:

Correlation spectroscopy

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Acknowledgments

This work was supported by Callaghan Innovation, Capability Fund project “Bioactives from New Zealand extremophiles” and the GNS Science Geothermal Resources of New Zealand (GRN) programme. We are grateful to Dr. Herbert Wong for NMR spectra recording and Dr. Yinrong Lu for MS recording (both from Callaghan Innovation).

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Authors and Affiliations

  1. Callaghan Innovation, 69 Gracefield Road, P. O. Box 31310, Lower Hutt, 5040, New Zealand

    Kirill Lagutin, Andrew MacKenzie & Mikhail Vyssotski

  2. Extremophile Research Group, GNS Science, Private Bag 2000, Taupo, 3352, New Zealand

    Karen M. Houghton & Matthew B. Stott

Authors
  1. Kirill Lagutin
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  2. Andrew MacKenzie
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  3. Karen M. Houghton
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  4. Matthew B. Stott
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  5. Mikhail Vyssotski
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Corresponding author

Correspondence to Kirill Lagutin.

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Lagutin, K., MacKenzie, A., Houghton, K.M. et al. Novel Long-Chain Diol Phospholipids from Some Bacteria Belonging to the Class Thermomicrobia . Lipids 50, 303–311 (2015). https://doi.org/10.1007/s11745-014-3979-3

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