Skip to main content
SpringerLink
Log in

Hydroxy long-chain fatty acids in fungi

  • Review
  • Published:
World Journal of Microbiology & Biotechnology Aims and scope Submit manuscript

Abstract

Hydroxy long-chain fatty acids occur widely in animals and plants and have important physiological activities in these eukaryotes. There are indications that these compounds are also common and important in fungi. The occurrence of hydroxy-polyunsaturated fatty acids (hydroxy-PUFAs) is of biotechnological importance, because these compounds are potentially high-value lipid products with medical applications. This review pays particular attention to the production of hydroxy-PUFAs by yeasts and other fungi. Hydroxy-PUFAs derived from lipoxygenase activity appear to be present in most fungi, while hydroxy-PUFAs from cyclooxygenase activity (i.e. prostaglandins) have mainly been implicated in the Oomycota and in yeasts from the genus Dipodascopsis. The occurrence of other hydroxy long-chain fatty acids in fungi is also discussed briefly; these include hydroxy fatty acids that are generally associated with cytochrome P-450 monooxygenase activity (i.e. terminal and sub-terminal hydroxy acids and diols derived from the corresponding epoxides) as well as 2-hydroxy-fatty acids and 3-hydroxy-fatty acids.

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

References

  • AlexopoulusC.J. 1962 Introductory Mycology. New York: John Wiley & Sons.

    Google Scholar 

  • AttrepK.A., BellmanW.P., AttrepJrM., LeeJ.B. & BraseltonJrW.E. 1980 Separation and identification of prostaglandin A1 in onion. Lipids 15, 292–297.

    Article  CAS  Google Scholar 

  • BiggsR. 1937 Dipodascus uninucleatus. Mycologia 29, 34–44.

    Article  Google Scholar 

  • BildG.S., BhatS.G., RamadossC.S. & AxelrodB. 1978 Biosynthesis of a prostaglandin by a plant enzyme. Journal of Biological Chemistry 253, 21–23.

    CAS  Google Scholar 

  • BothaA., KockJ.L.F., CoetzeeD.J., LindeN.A. & VanDykM.S. 1992a Yeast eicosanoids. II. The influence of non-steroidal anti-inflammatory drugs on the life cycle of Dipodascopsis. Systematic and Applied Microbiology 15, 155–160.

    Article  CAS  Google Scholar 

  • BothaA., KockJ.L.F., CoetzeeD.J., Van DerBergL. & BotesP.J. 1992b Yeast eicosanoids. I. The distribution and taxonomic value of cellular fatty acids and arach idonic acid metabolites in the Dipodascaceae and related taxa. Systematic and Applied Microbiology 15, 148–154.

    Article  CAS  Google Scholar 

  • BrodowskyI.D., HambergM. & OliwE.H. 1992 A linoleic acid (8R)-dioxygenase and hydroperoxide isomerase of the fungus Gaeumannomyces graminis. Journal of Biological Chemistry 267, 14738–14745.

    CAS  Google Scholar 

  • BrodowskyI.D. & OliwE.H. 1992 Metabolism of 18: 2(n-6), 18: 3(n-3), 20: 4(n-6) and 20: 5(n-3) by the fungus Gaeumannomyces graminis: identification of metabolites formed by 8-hydroxylation and ω2 and ω3 oxygenation. Biochimica et Biophysica Acta 1124, 59–65.

    Article  CAS  Google Scholar 

  • CapdevilaJ.H., JinY., KararaA. & FalckJ.R. 1993 Cytochrome P-450 epoxygenase dependent formation of novel endogenous epoxyeicosatrienoyl-phospholipids. In Eicosanoids and other Bioactive Lipids in Cancer, Inflammation and Radiation Injury — Proceedings of the 2nd International Conference, eds NigamS., HonnK.V., MarnettL.J. & WaldenT.L. pp. 11–15. Massachusetts: Kluwer Academic.

    Chapter  Google Scholar 

  • DayS. 1993 A shot in the arm for plants. New Scientist 137, 36–40.

    Google Scholar 

  • FinnertyW.R. 1989 Microbial lipid metabolism. In Microbial Lipids, Vol. 2, eds RatledgeC. & WilkinsonS.G. pp. 525–566. San Diego: Academic Press.

    Google Scholar 

  • FunkC.D. & PowellW.S. 1983 Metabolism of linoleic acid by prostaglandin endoperoxide synthase from adult and fetal blood vessels. Biochimica et Biophysica Acta 754, 57–71.

    Article  CAS  Google Scholar 

  • GregsonR.P., MarwoodJ.F. & QuinnR.J. 1979 The occurrence of prostaglandins PGE2 and PGF2 α in a plant — the red alga Gracilaria lichnoides. Tetrahedron Letters 46, 4505–4506.

    Article  Google Scholar 

  • HambergM. 1986 Isolation and structures of lipoxygenase products from Saprolegnia parasitica. Biochimica et Biophysica Acta 876, 688–692.

    Article  CAS  Google Scholar 

  • HambergM., HermanC.A. & HermanR.P. 1986 Novel biological transformations of 15Ls-hydroperoxy-5,8,11,13-eicosatetraenoic acid. Biochimica et Biophysica Acta 877, 447–457.

    Article  CAS  Google Scholar 

  • HermanR.P. & HermanC.A. 1985 Prostaglandins or prostaglandin-like substances are implicated in normal growth and development in Oomycetes. Prostaglandins 29, 819–830.

    Article  CAS  Google Scholar 

  • HermanR.P. & LuchiniM.M. 1989 Lipoxygenase activity in the oomycete Saprolegnia is dependent on environmental cues and reproductive competence. Experimental Mycology 13, 372–379.

    Article  CAS  Google Scholar 

  • HermanR.P., LuchiniM.M. & HermanC.A. 1989 Hormone-dependent lipoxygenase activity in Achlya ambisexualis. Experimental Mycology 13, 95–99.

    Article  CAS  Google Scholar 

  • JanistynB. 1982 Gas chromatographic-mass spectroscopic identification of prostaglandin F2α in flowering Kalanchoe blossfeldiana v. Poelln. Planta 154, 485–487.

    Article  CAS  Google Scholar 

  • JensenE.C., OggC. & NickersonK.W. 1992 Lipoxygenase inhibitors shift the yeast/mycelium dimorphism in Ceratocystis ulmi. Applied and Environmental Microbiology 58, 2505–2508.

    CAS  Google Scholar 

  • KemalC., Louis-FlambergP., Krupinski-OlsenR. & ShorterA.L. 1987 Reductive inactivation of soybean lipoxygenase 1 by catechols: a possible mechanism for regulation of lipoxygenase activity. Biochemistry 26, 7064–7072.

    Article  CAS  Google Scholar 

  • KendrickB. 1992 The Fifth Kingdom. Ontario: Mycologue Publications.

    Google Scholar 

  • KerwinJ.L., SimmonsC.A. & WashinoR.K. 1986 Eicosanoid regulation of oosporogenesis by Lagenidium giganteum. Prostaglandins, Leukotrienes and Medicine 23, 173–178.

    Article  CAS  Google Scholar 

  • KockJ.L.F., CoetzeeD.J., VanDykM.S., TruscottM., BothaA. & AugustynO.P.H. 1992 Evidence for, and taxonomic value of, an arachidonic acid cascade in the Lipomycetaceae. Antonie van Leeuwenhoek 62, 251–259.

    Article  CAS  Google Scholar 

  • KockJ.L.F., CoetzeeD.J., VanDykM.S., TruscottM., CloeteF.C., VanWykV. & AugustynO.P.H. 1991 Evidence for pharmacologically active prostaglandins in yeasts. South African Journal of Science 87, 73–76.

    CAS  Google Scholar 

  • Kreger-van RijN.J.W. 1974 The species Dipodascopsis uninucleata (Biggs) Batra et Millner. Persoonia 8, 105–109.

    Google Scholar 

  • KurtzmanC.P., VesonderR.F. & SmileyM.J. 1974 Formation of extracellular 3-D-hydroxypalmitic acid by Saccharomycopsis malanga. Mycologia 66, 582–587.

    Article  Google Scholar 

  • Laniado-SchwartzmanM., DavisK.L., McGiffJ.C., LevereR.D. & AbrahamN.G. 1988 Purification and characterization of cytochrome P-450-dependent arachidonic acid epoxygenase from human liver. Journal of Biological Chemsitry 263, 2536–2542.

    CAS  Google Scholar 

  • LöselD. M. 1988 Fungal lipids. In Microbial Lipids, Vol. 1, eds RatledgeC. & WilkinsonS.G. pp. 699–806. San Diego: Academic Press.

    Google Scholar 

  • LyudnikovaT.A., RodopulaA.K. & EgorovI.A. 1984 Lipoxygenase activity of the yeast Saccharomyces vini strain MSh-2. Applied Biochemistry and Microbiology 20, 142–144.

    Google Scholar 

  • MarcusA.J., SafierL.B., UllmanH.L., IslamN., BroekmanM.J., FalckJ.R., FischerS. & VonSchackyC. 1988 Platelet—neutrophil interactions. (12S)-Hydroxyeicosatetra-en-1,20-dioic acid: a new eicosanoid synthesized by unstimulated neutrophils from (12S)-20-dihydroxyeicosatetra-enoic acid. Journal of Biological Chemistry 263, 2223–2229.

    CAS  Google Scholar 

  • MathewsC.K. & VanHoldeK.E. 1990 Biochemistry. Redwood City, CA: Benjamin/Cummings.

    Google Scholar 

  • MatzudaY., BeppuT. & ArimaK. 1978 Crystallization and positional specificity of hydroperoxidation of Fusarium lipoxygenase. Biochimica et Biophysica Acta 530, 439–450.

    Article  Google Scholar 

  • MierschO., SchmidtJ., SembdnerG. & SchreiberK. 1989 Jasmonic acid-like substances from the culture filtrate of Botryodiplodia theobromae. Phytochemistry 28, 1303–1305.

    Article  CAS  Google Scholar 

  • Moore-LandeckerE. 1972 Fundamentals of Fungi. Engelwood Cliffs: Prentice-Hall.

    Google Scholar 

  • PanossianA.G. 1987 Search of prostaglandins and related compounds in plants. Prostaglandins 33, 363–381.

    Article  CAS  Google Scholar 

  • RatledgeC. 1993 Single cell oils — have they a biotechnological future? Trends in Biotechnology 11, 278–284.

    Article  CAS  Google Scholar 

  • RattrayJ.B.M. 1988 Yeasts. In Microbial Lipids, Vol. 1, eds RatledgeC. & WilkinsonS.G. pp. 555–697. San Diego: Academic Press.

    Google Scholar 

  • SamuelssonB., DahlénS.-E., LindgrenJ.A., RouzerC.A. & SerhanC.H. 1987 Leukotrienes and lipoxins: structures, biosynthesis, and biological effects. Science 237, 1171–1176.

    Article  CAS  Google Scholar 

  • SatohT., MatzudaY., TakashioM., SatohK., BeppuT. & ArimaK. 1976 Isolation of lipoxygenase-like enzyme from Fusarium oxysporum. Agricultural and Biological Chemsitry 40, 953–961.

    Article  CAS  Google Scholar 

  • ScheweT., KuhnH. & RapoportM. 1987 Lipoxygenases: measurement, characterization and properties. In Prostaglandins and Related Substances — a Practical Approach, eds BenedettoC., McDonald-GibsonR.G., NigamS. & SlaterT.F. pp. 229–242. Washington DC: IRL Press.

    Google Scholar 

  • SchweizerE. 1989 Biosynthesis of fatty acids and related compounds. In Microbial Lipids, Vol. 2, eds RatledgeC. & WilkinsonS.G. pp. 3–50. San Diego: Academic Press.

    Google Scholar 

  • ShechterG. & GrossmanS. 1983 Lipoxygenase from baker's yeast: purification and properties. International Journal of Biochemistry 15, 1295–1304.

    Article  CAS  Google Scholar 

  • SimmonsC.A., KerwinJ.L. & WashinoR.K. 1987 Preliminary characterization of lipoxygenase from the entomopathogenic fungus Lagenidium giganteum. In The Metabolism, Structure, and Function of Plant Lipids, eds StumpfP.K., MuddJ.B. & NesW.D. pp. 421–423. New York: Plenum.

    Chapter  Google Scholar 

  • Smit, M.S. 1993 The turnover of exogenous arachidonic acid by the yeast Dipodascopsis uninucleata. PhD Thesis. Department of Microbiology and Biochemistry, University of the Orange Free State, Bloemfontein, South Africa.

  • SmithW.L. 1989 The eicosanoids and their biochemical mechanism of action. Biochemical Journal 259, 315–324.

    CAS  Google Scholar 

  • SmithW.L. & BorgeatP. 1985 The eicosanoids: prostaglandins, thromboxanes, leukotrienes, and hydroxy-eicosaenoic acids. In Biochemistry of Lipids and Membranes, eds VanceD.E. & VanceJ.E. pp. 325–360. Redwood City, CA: Benjamin/Cummings.

    Google Scholar 

  • StodolaF.H., DeinemaM.H. & SpencerJ.F.T. 1967 Extracellular lipids of yeasts. Bacteriological Reviews 31, 194–213.

    CAS  Google Scholar 

  • Van Der Berg, L. 1993 Evidence for the production of arachidonic acid metabolites by Saccharomyces cerevisiae. M.Sc. Thesis. Department of Microbiology and Biochemistry, University of the Orange Free State, Bloemfontein, South Africa.

  • Van DerWaltJ.P., VonArxJ.A., FerreiraN.P. & RichardsP.D.G. 1987 Zygozyma gen. nov., a new genus of the Lipomycetaceae. Systematic and Applied Microbiology 9, 115–120.

    Article  Google Scholar 

  • VanDykM.S., KockJ.L.F., CoetzeeD.J., AugustynO.P.H. & NigamS. 1991 Isolation of a novel arachidonic acid metabolite 3-hydroxy-5,8,11,14-eicosatetraenoic acid (3-HETE) from the yeast Dipodascopsis uninucleata UOFS-Y128. FEBS letters 283, 195–198.

    Article  Google Scholar 

  • VesonderR.F., WickerhamL.J. & RohwedderW.K. 1968 3-D-Hydroxypalmitic acid: a metabolic product of the yeast NRRL Y-6954. Canadian Journal of Chemistry 46, 2628–2629.

    Article  CAS  Google Scholar 

  • VickB.A. & ZimmermannD.C. 1979 Distribution of a fatty acid cyclase enzyme in plants. Plant Physiology 64, 203–205.

    Article  CAS  Google Scholar 

  • WeissmannG. 1991 Aspirin. Scientific American 265, 58–64.

    Google Scholar 

  • WisemanA. 1980 Xenobiotic-metabolising cytochromes P-450 from micro-organisms. Trends in Biochemical Sciences 5, 102–104.

    Article  CAS  Google Scholar 

Download references

Authors
  1. M. S. Van Dyk
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. J. L. F. Kock
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. Botha
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

The authors are with the Department of Microbiology and Biochemistry, University of the Orange Free State, P.O. Box 339, Bloemfontein, 9300, South Africa

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Van Dyk, M.S., Kock, J.L.F. & Botha, A. Hydroxy long-chain fatty acids in fungi. World J Microbiol Biotechnol 10, 495–504 (1994). https://doi.org/10.1007/BF00367653

Download citation

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00367653

Key words

Search

Navigation