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Biotransformation of linoleic acid by Clavibacter sp. ALA2: Heterocyclic and heterobicyclic fatty acids

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Lipids

Abstract

Clavibacter sp. ALA2 transformed linoleic acid into a variety of oxylipins. In previous work, three novel fatty acids were identified, (9Z)-12,13,17-trihydroxy-9-octadecenoic acid and two tetrahydrofuran-(di)hydroxy fatty acids. In this report, we confirm the structures of the tetrahydrofuran-(di)hydroxy fatty acids by nuclear magnetic resonance as (9Z)-12-hydroxy-13,16-epoxy-9-octadecenoic acid and (9Z)-7,12-dihydroxy-13,16-epoxy-9-octadecenoic acid. Three other products of the biotransformation were identified as novel heterobicyclic fatty acids, (9Z)-12,17;13,17-diepoxy-9-octadecenoic acid, (9Z)-7-hydroxy-12,17;13,17-diepoxy-9-octadecenoic acid, and (9Z)-12,17;13,17-diepoxy-16-hydroxy-9-octadecenoic acid. Thus, Clavibacter ALA2 effectively oxidized linoleic acid at C-7,-12,-13,-16, and/or-17.

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Abbreviations

ANS:

Na 8-anilino-1-napthalenesulfonate

CS:

chemical shift

EI-MS:

electron impact-mass spectrum

GC:

gas chromatography

GC-MS:

gas chromatography-mass spectrometry

HPLC:

high-performance liquid chromatography

NMR:

nuclear magnetic resonance

OTMSi:

trimethylsilyloxy ether

RT:

retention time

TLC:

thin-layer chromatography

UV:

ultraviolet

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Author information

Authors and Affiliations

  1. Bioactive Agents Research, ARS, USDA, 61604, Peoria, Illinois

    Harold W. Gardner

  2. Oil Chemical Research, ARS, USDA, 1815 N. University Street, 61604, Peoria, Illinois

    Ching T. Hou & Wanda Brown

  3. Analytical Chemical Services, National Center for Agricultural Utilization Research, ARS, USDA, 61604, Peoria, Illinois

    David Weisleder

Authors
  1. Harold W. Gardner
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  2. Ching T. Hou
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  3. David Weisleder
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  4. Wanda Brown
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Corresponding author

Correspondence to Ching T. Hou.

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Gardner, H.W., Hou, C.T., Weisleder, D. et al. Biotransformation of linoleic acid by Clavibacter sp. ALA2: Heterocyclic and heterobicyclic fatty acids. Lipids 35, 1055–1060 (2000). https://doi.org/10.1007/s11745-000-0618-7

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  • DOI: https://doi.org/10.1007/s11745-000-0618-7

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