Skip to main content
SpringerLink
Log in

Novel oxylipins from the temperate red alga polyneura latissima: Evidence for an arachidonate 9(S)-lipoxygenase

  • Article
  • Published:
Lipids

Abstract

The oxylipin chemistry of the temperate red alga Polyneura latissima has been investigated. The structures of three novel oxylipins, 8-[1′(Z),3′(Z),6′(Z)-dodecatriene-1′-oxyl-5(Z),7(E)-octadienoic acid, 7(S *)-hydroxy-8(S *),9(S *)-epoxy-5(Z), 11(Z),14(Z)-eicosatrienoic acid, 7(R *)-hydroxy-8(S *), 9(S *)-epoxy-5(Z), 11(Z),14(Z)-eicosatrienoic acid, together with two known eicosanoids, 9(S)-hydroxy-5(Z), 7(E), 11(Z), 14(Z)-eicosatetraenoic acid, and 9, 15-dihydroxy-5(Z),7(E),11(Z),13(E)-eicosatetraenoic acid, were elucidated by spectroscopic methods and chemical degradation. The oxygenation pattern of these oxylipins suggests that P. latissima metabolizes polyunsaturated fatty acids via a 9(S)-lipoxygenase.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

COSY:

correlation spectroscopy

diHETE:

dihydroxyeicosatetraenoic acid

GC-MS:

gas chromatography-mass spectrometry

HETCOR:

heteronuclear correlation

HETE:

hydroxyeicosatetraenoic acid

HpETE:

hydroperoxyeicosatetraenoic acid

HPLC:

high-performance liquid chromatography

HR EIMS:

high-resolution electron impact mass spectrometry

IR:

infrared

LR:

Iow resolution

MS:

mass spectral

NMR:

nuclear magnetic resonance

TLC:

thin-layer chromatography

TMS:

trimethylsilyl

UV:

ultraviolet

References

  1. Gregson, R.P., Marwood, J.F., and Quinn, R.J. (1979) The Occurrence of Prostaglandins PGE2 and PGF2α in a Plant-The Red Alga Gracilaria lichenoides, Tetrahedron Lett. 46, 4505–4506.

    Article  Google Scholar 

  2. Bernart, M., and Gerwick, W.H. (1988) Isolation of 12-(S)-HEPE from the Red Marine Alga Murrayella periclados and Revision of Structure of an Acyclic Icosanoid from Laurencia hybrida. Implication to the Biosynthesis of the Marine Prostanoid Hybridalactone, Tetrahedron Lett. 29, 2015–2018.

    Article  CAS  Google Scholar 

  3. Moghaddam, M., Gerwick, W.H., and Ballantine, D.L. (1990) Discovery of the Mammalian Insulin Release Modulator Hepoxilin B3 from the Tropical Red Algae Platysiphonia miniata and Cottoniella filamentosa, J. Biol. Chem. 265, 6126–6130.

    PubMed  CAS  Google Scholar 

  4. Gerwick, W.H., and Bernart, M. (1993) Eicosanoids and Related Compounds from Marine Algae, in Advances in Marine Biotechnology: Pharmaceutical and Bioactive Natural Products (Attaway, D.H., and Zaborsky, O.R., eds.), Vol. 1, pp. 101–152, Plenum Press, New York.

    Google Scholar 

  5. Gerwick, W.H. (1994) Structure and Biosynthesis of Marine Algal Oxylipins, Biochim. Biophys. Acta 1311, 243–255.

    Google Scholar 

  6. Nagle, D.G., and Gerwick, W.H. (1990) Constanolactones A and B, Novel Cyclopropyl Hydroxy Eicosanoids from the Temperate Red Alga Constantinea simplex, Tetrahedron Lett. 31, 2995–2998.

    Article  CAS  Google Scholar 

  7. Camp, R.D., Mallet, A.I., Woollard, P.M., Brain, S.D., Black, A.K., and Greaves, M.W. (1983) The Identification of Hydroxy Fatty Acids in Psoriatic Skin, Prostaglandins 26, 431–447.

    Article  PubMed  CAS  Google Scholar 

  8. Just, G., and Wang, Z.Y. (1986) Total Synthesis of 8(S)-,9(S)-, and 12(S)-HETE Methyl Esters, J. Org. Chem. 51, 4796–4802.

    Article  CAS  Google Scholar 

  9. Saniere, M., Merre, Y.L., Barbe, B., Koscielniak, T., Dumas, J., Micas-Languin, D., and Depezay, J. (1989) Total Enantiospecific Synthesis of (9S)-and (9R)-9-Hydroxyeicosatetraenoic Acid (9-HETE) Methyl Ester Angew. Chem. Int. Ed. Engl. 28, 614–615.

    Article  Google Scholar 

  10. The Sadtler Standard Spectra, Vol. 12, Sadtler Research Laboratories, Philadelphia, PA, 1969, Spectrum #7448.

  11. Galliard, T., Phillips, D.R., and Frost, D.J. (1973) Novel Divinyl Ether Fatty Acids in Extracts of Solanum tuberosum, Chem. Phys. Lipids 11, 173–180.

    Article  CAS  Google Scholar 

  12. Galliard, T., and Phillips, D.R. (1972) The Enzymic Conversion of Linoleic Acid into 9-(Nona-1′, 3′-dienoxy)non-8-enoic Acid, A Novel Unsaturated Ether Derivative Isolated from Homogenates of Solarium tuberosum, Biochem. J. 129, 743–753.

    PubMed  CAS  Google Scholar 

  13. Galliard, T., and Matthew, J.A. (1975) Enzymatic Reactions of Fatty Acid Hydroperoxides in Extracts of Potato Tuber, Biochim. Biophys. Acta 398, 1–9.

    PubMed  CAS  Google Scholar 

  14. Corey, E.J., Nagata, R., and Wright, S.W. (1987) Biomimetic Total Synthesis of Colneleic Acid and Its Function as a Lipoxygenase Inhibitor, Tetradedron Lett. 28, 4917–4920.

    Article  CAS  Google Scholar 

  15. Fahlstadius, P., and Hamberg, M. (1990) Stereospecific Removal of the pro-R Hydrogen at C-8 of (9S)-Hydroperoxy-octadecadienoic Acid in the Biosynthesis of Colneleic Acid, J. Chem. Soc. Perkin Trans. 1, 2027–2030.

    Article  Google Scholar 

  16. Pace-Asciak, C.R., Mizuno, K., and Yamamoto, S. (1983) Resolution by DEAE-Cellulose Chromatography of the Enzymatic Steps in the Transformation of Arachidonic Acid into 8,11,12-and 10,11,12-Trihydroxy-eicosatrienoic Acid by the Rat Lung, Prostaglandins 25, 79–84.

    Article  PubMed  CAS  Google Scholar 

  17. Mihelich, E.D. (1979) Vanadium-Catalyzed Epoxidation. I.A. New Selectivity Pattern of Acyclic Allylic Alcohols, Tetrahedron Lett. 20, 4729–4732.

    Article  Google Scholar 

  18. Bernart, M.W., Whatley, G., and Gerwick, W.H. (1993) Unprecedented Oxylipins from the Marine Green Alga Acrosiphonia coalita, J. Nat. Prod. 56, 245–259.

    Article  PubMed  CAS  Google Scholar 

  19. Lopez, A., and Gerwick, W.H. (1987) Two New Icosapentaenoic Acids from the Oregon Red Seaweed Ptilota filicina, Lipids 22, 190–194.

    PubMed  CAS  Google Scholar 

  20. Lopez, A., and Gerwick, W.H. (1988) Ptilodene, A Novel Icosanoid Inhibitor of 5-Lipoxygenase and Na+/K+ATPase from the Marine Alga Ptilota filicina, Tetrahedron Lett. 29, 1505–1506.

    Article  CAS  Google Scholar 

  21. Breitmaier, E., and Voelter, W. (1987) Carbon-13 NMR Spectroscopy, 3rd edn., 197 pp., VCH Publishers, Weinheim, Germany.

    Google Scholar 

  22. Reddy, C.C., Whelan, J., Rao, K.K., and Reddanna, P. (1989) Mechanism of Formation of Leukotrienes and Lipoxins from Arachidonic Acid Catalyzed by Homogeneous Lipoxygenase from Potato Tubers, in Advances in Prostaglandin, Thromboxane, and Leukotriene Research (Samuelsson, B., Wong, P.Y.K., and Sun, F.F., eds.), pp. 132–136, Raven Press, Ltd., New York.

    Google Scholar 

  23. Gardner, H.W. (1991) Recent Investigations into the Lipoxygenase Pathway of Plants, Biochim. Biophys. Acta 1084, 221–239.

    PubMed  CAS  Google Scholar 

  24. Gerwick, W.H. (1996) Epoxy Allylic Carbocations as Conceptual Intermediates in the Biogenesis of Diverse Marine Oxylipins, Lipids 31, 1215–1231.

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. College of Pharmacy, Oregon State University, 97331, Corvallis, Oregon

    Zhi-Dong Jiang & William H. Gerwick

Authors
  1. Zhi-Dong Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. William H. Gerwick
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Jiang, ZD., Gerwick, W.H. Novel oxylipins from the temperate red alga polyneura latissima: Evidence for an arachidonate 9(S)-lipoxygenase. Lipids 32, 231–235 (1997). https://doi.org/10.1007/s11745-997-0029-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11745-997-0029-9

Keywords

Search

Navigation