Biosynthesis of Novel Divinyl Ether Oxylipins by Enzyme From Garlic (Allium sativum L.) Bulbs

  • Alexander N. Grechkin
  • Mats Hamberg
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 433)


First fatty acid divinyl ethers colneleic and colnelenic acids were detected by Galliard et al.1, 2 in in vitro experiments with potato tubers. Formation of these oxylipins, is controlled by 9-lipoxygenase activity and an enzyme, controlling dehydration of 9-hydroperoxide. Such a pathway, being not found in any other plant or animal species, was considered to be the unique property of potato tubers. Our recent in vitro studies of lipoxygenase pathway in garlic bulbs led to detection of novel divinyl ethers 12-[1′(E)-hexenyloxy]-9(Z),11(E)-dodecadienoic (etheroleic) and 12-[1′(E),3′(Z)-hexadienyloxy]-9(Z),11(E)-dodecadienoic (etherolenic) acids3, products of 13-hydroperoxides of linoleic and linolenic acids (13-HPOD and 13-HPOT) conversion, respectively.


Potato Tuber Allene Oxide Allium Sativum Lipoxygenase Pathway Normal Phase HPLC 
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  1. 1.
    T. Galliard and D.R. Phillips, Enzymic conversion of linoleic acid into 9-(1,3-nonadienoxy)-8-nonenoic acid, a novel unsaturated ether derivative isolated from homogenates of Solanum tuberosum tubers, Biochem. J. 129: 743 (1972).PubMedGoogle Scholar
  2. 2.
    T. Galliard and D.R. Phillips, Novel divinyl ether fatty acid in the extract of Solanum tuberosum, Chem. Phys. Lipids. 129: 743 (1972).Google Scholar
  3. 3.
    A.N. Grechkin, F.N. Fazliev and L.S. Mukhtarova, The lipoxygenase pathway in garlic (Allium sativum L.) bulbs: Detection of the novel divinyl ether oxylipins, FEBS Lett. 371: 159 (1995).PubMedCrossRefGoogle Scholar
  4. 4.
    A.N. Grechkin, R.A. Kuramshin, S.K. Latypov, E.Y. Safonova, T.E. Gafarova, and A.V. Ilyasov, Hydroperoxides of α-ketols. Novel products of the plant lipoxygenase pathway, Eur. J. Biochem. 199: 451 (1991).PubMedCrossRefGoogle Scholar
  5. 5.
    L.-Y. Zhang and M. Hamberg, A gas-liquid chromatographic method for steric analysis of 2-hydroxy, 3-hydroxy, and 2,3-dihydroxy acids, Chem. Phys. Lipids 74: 151 (1994).CrossRefGoogle Scholar
  6. 6.
    H.W. Gardner, Recent investigations into the lipoxygenase pathway of plants, Biochim. Biophys. Acta. 1084: 221 (1991).PubMedCrossRefGoogle Scholar
  7. 7.
    P. Fahlstadius and M. Hamberg, Stereospecific removal of the pro-R hydrogen at C-8 of (9S)-hydroperoxyoctadecadienoic acid in the biosynthesis of colneleic acid, J. Chem. Soc. Perkin Trans 1: 2027 (1990).CrossRefGoogle Scholar
  8. 8.
    L. Crombie, D.O. Morgan and E.H. Smith, An isotopic study (2H and 18O) of the enzymic conversion of linoleic acid into colneleic acid with carbon chain fracture: the origin of shorter chain aldehydes, J. Chem. Soc. Perkin Trans. 1: 567 (1991).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1997

Authors and Affiliations

  • Alexander N. Grechkin
    • 1
  • Mats Hamberg
    • 2
  1. 1.Institute of BiologyRussian Academy of SciencesKazanRussia
  2. 2.Department of Physiological Chemistry IIKarolinska InstitutetStockholmSweden

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