Skip to main content
SpringerLink
Log in

Phospholipids of New Zealand Edible Brown Algae

  • Original Article
  • Published:
Lipids

Abstract

Edible brown algae have attracted interest as a source of beneficial allenic carotenoid fucoxanthin, and glyco- and phospholipids enriched in polyunsaturated fatty acids. Unlike green algae, brown algae contain no or little phosphatidylserine, possessing an unusual aminophospholipid, phosphatidyl-O-[N-(2-hydroxyethyl) glycine], PHEG, instead. When our routinely used technique of 31P-NMR analysis of phospholipids was applied to the samples of edible New Zealand brown algae, a number of signals corresponding to unidentified phosphorus-containing compounds were observed in total lipids. NI (negative ion) ESI QToF MS spectra confirmed the presence of more familiar phospholipids, and also suggested the presence of PHEG or its isomers. The structure of PHEG was confirmed by comparison with a synthetic standard. An unusual MS fragmentation pattern that was also observed prompted us to synthesise a number of possible candidates, and was found to follow that of phosphatidylhydroxyethyl methylcarbamate, likely an extraction artefact. An unexpected outcome was the finding of ceramidephosphoinositol that has not been reported previously as occurring in brown algae. An uncommon arsenic-containing phospholipid has also been observed and quantified, and its TLC behaviour studied, along with that of the newly synthesised lipids.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

Abbreviations

AsPL:

Arsenophospholipid, 3-((4-((dimethylarsoryl)methyl)-3,5-dihydroxytetrahydrofuran-2-yl)oxy) phosphatidylglycerol

CPI:

Ceramide phosphoinositol

DCL:

Deacylated cardiolipin

DGTA:

Diacylglyceryl hydroxymethyltrimethyl-β-alanine

DPNGE:

Diphosphatidyl N-glycolylethanolamine

GPA:

Glycerophosphate (deacylated PtdOH)

GPC:

Glycerophosphocholine (deacylated PtdCho)

GPE:

Glycerophosphoethanolamine (deacylated PtdEtn)

GPHEG:

Glycerophospho-O-[N-(2-hydroxyethyl) glycine], deacylated PHEG

GPI:

Glycerophosphoinositol (deacylated PtdIns)

HEG:

N-(2-Hydroxyethyl) glycine

N-CAPE:

N-(1-Carboxy-3-aminopropyl-3)-1,2-diacyl-sn-3-glycerophosphorylethanolamine

NI ESI QToF MS:

Negative ion electrospray ionisation quadrupole time-of-flight mass spectrometry

PECM:

PtdEtn-carboxymethyl (also known as phosphatidylhydroxyethyl methylcarbamate)

PHEG:

Phosphatidyl-O-[N-(2-hydroxyethyl) glycine]

PiNGE:

Phosphatidyl iso-N-glycolylethanolamine

PNGE:

Phosphatidyl N-glycolylethanolamine

Ptd2Gro:

Cardiolipin

PtdCho:

Phosphatidylcholine

PtdEtn:

Phosphatidylethanolamine

PtdGro:

Phosphatidylglycerol

PtdIns:

Phosphatidylinositol

PtdOH:

Phosphatidic acid

PtdSer:

Phosphatidylserine

References

  1. Khotimchenko SV (2003) Lipids of marine macrophytic algae and grasses: structure, distribution, analysis. Svetashev VI (ed) Vladivostok, Dalnauka, Russian Academy of Sciences. ISBN 5-8044-0347-8

  2. Kumar SR, Hosokawa M, Miyashita K (2013) Fucoxanthin: a marine carotenoid exerting anti-cancer effects by affecting multiple mechanisms. Mar Drugs 11:5130–5147. doi:10.3390/md11125130

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Schmid CE, Müller DG, Eichenberger W (1994) Isolation and characterization of a new phospholipid from brown algae. intracellular localization and site of biosynthesis. J Plant Physiol 143:570–574. doi:10.1016/S0176-1617(11)81826-24

    Article  CAS  Google Scholar 

  4. Eichenberger W, Bigler P, Gfeller H, Gribi C, Schmid CE (1995) Phosphatidyl-O-[N-(2-hydroxyethyl)glycine] (PHEG), a new glycerophospholipid from brown algae (Phaeophyceae). J Plant Physiol 146:398–404

    Article  CAS  Google Scholar 

  5. Bligh EG, Dyer WJ (1959) A rapid method of total lipid extraction and purification. Can J Biochem Physiol 37:911–917

    Article  CAS  PubMed  Google Scholar 

  6. Barsukov LI, Batrakov SG, Bergelson LD, Dyatlovitskaya EV, Molotkovsky JG, Prokazova NV (1980) In: Bergelson LD (ed) Lipid biochemical preparations. Elsevier/North-Holland Biomedical Press, Amsterdam-New York-Oxford

    Google Scholar 

  7. Vaskovsky VE, Terekhova TA (1979) HPTLC of phospholipid mixtures containing phosphatidylglycerol. J High Resolut Chromatogr Chromatogr Commun 2:671–672

    Article  Google Scholar 

  8. Tindall BJ, Sikorski J, Smibert RM, Kreig NR (2007) Phenotypic characterization and the principles of comparative systematics. In: Reddy CA, Beveridge TJ, Breznak JA, Marzluf G, Schmidt TM, Snyder LR (eds) Methods for general and molecular microbiology, 3rd edn. ASM Press, Washington

    Google Scholar 

  9. Vaskovsky VE, Kostetsky EY, Vasendin IM (1975) A universal reagent for phospholipid analysis. J Chromatogr 114:129–141

    Article  CAS  PubMed  Google Scholar 

  10. Vyssotski M, MacKenzie A, Scott D (2009) TLC and 31P-NMR analysis of low polarity phospholipids. Lipids 44:381–389

    Article  CAS  PubMed  Google Scholar 

  11. Clark NG, Dawson RMC (1981) Alkaline O → N-transacylation. a new method for the quantitative diacylation of phospholipids. Biochem J 195:301–306

    Article  Google Scholar 

  12. Xiong Y, Zhao Y-Y, Goruk S, Oilund K, Field CJ, Jacobs RL, Curtis JM (2012) Validation of an LC–MS/MS method for the quantification of choline-related compounds and phospholipids in foods and tissues. J Chromatogr B 911:170–179. doi:10.1016/j.jchromb.2012.10.038

    Article  CAS  Google Scholar 

  13. Lowe G, Vilaivan T (1997) Amino acids bearing nucleobases for the synthesis of novel peptide nucleic acids. J Chem Soc Perkin Trans 1:539–546

    Article  Google Scholar 

  14. Daryaee F, Kobarfard F, Khalaj A, Farnia P (2009) Synthesis and evaluation of in vitro anti-tuberculosis activity of N-substituted glycolamides. Eur J Med Chem 44:289–295

    Article  CAS  PubMed  Google Scholar 

  15. Kim J-G, Jang DO (2009) Indium-catalyzed reaction for the synthesis of carbamates and carbonates: selective protection of amino groups. Tetrahedron Lett 50:2688–2692

    Article  CAS  Google Scholar 

  16. Garrett TA, Raetz CRH, Son JD, Richardson TD, Bartling C, Guan Z (2011) Non-enzymatically derived minor lipids found in Escherichia coli lipid extracts. Biochim Biophys Acta Mol Cell Biol Lipids 1811:827–837

    Article  CAS  Google Scholar 

  17. Hsu F-F, Turk J, Zhang K, Beverly SM (2007) Characterization of inositol phosphorylceramides from Leishmania major by tandem mass spectrometry with electrospray ionization. J Am Soc Mass Spectrom 18:1591–1604

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Raab A, Newcombe C, Pitton D, Ebel R, Feldmann J (2013) Comprehensive analysis of lipophilic arsenic species in a brown alga (Saccharina latissima). Anal Chem 85:2817–2824. doi:10.1021/ac303340t

    Article  CAS  PubMed  Google Scholar 

  19. Noguchi T, Matsui T, Miyazawa K, Asakawa M, Iijima N, Shida Y, Fuse M, Hosaka Y, Kirigaya C, Watabe K, Usui S, Fukagawa A (1994) Poisoning by the red alga ‘ogonori’ (Gracilaria verrucosa) on the Nojima Coast, Yokohama, Kanagawa Prefecture, Japan. Toxicon 32:1533–1538

    Article  CAS  PubMed  Google Scholar 

  20. Hutchinson A Yum Yum.. Edible New Zealand Plants! http://www.campermate.co.nz/yum-yum-edible-new-zealand-plants. Accessed Dec 2015

  21. Smith JL, Summers G, Wong R (2010) Nutrient and heavy metal content of edible seaweeds in New Zealand. N Z J Crop Hortic Sci 38:19–28

    Article  CAS  Google Scholar 

  22. Taylor S (2011) Marine medicinal foods: implications and applications, macro and microalgae. Advances in food and nutrition research, vol 64. Academic Press, San Diego, USA (ISBN 0123877008)

    Google Scholar 

  23. Dominguez H (2013) Functional ingredients from algae for foods and nutraceuticals. Woodhead Publishing Series in Food Science, Technology and Nutrition, Elsevier, Burlington, USA (ISBN 0857098683)

    Book  Google Scholar 

  24. Kim S-K (2011) Marine cosmeceuticals: trends and prospects. CRC Press, Boca Raton, USA (ISBN 1439860297)

    Book  Google Scholar 

Download references

Acknowledgements

The authors are grateful to Callaghan Innovation for funding (SIF “Novel Bioactives”), to Dr. Peter Dyer for extracting egg yolk phospholipids and Dr. Yinrong Lu for help with QToF MS support, Alison Speakman for help in information retrieval (all-Callaghan Innovation), to Dr. Shigeyuki Imamura (Imamura Enzyme Technologies Corporation, Shizuoka, Japan) for a gift of Actinomadura PLD, and to anonymous reviewers for helping to make this article better.

Author information

Authors and Affiliations

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

    Mikhail Vyssotski, Kirill Lagutin, Andrew MacKenzie, Kevin Mitchell & Dawn Scott

Authors
  1. Mikhail Vyssotski
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kirill Lagutin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Andrew MacKenzie
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Kevin Mitchell
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Dawn Scott
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mikhail Vyssotski.

Ethics declarations

Conflict of interest

Authors declare that there is no conflict of interest.

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Vyssotski, M., Lagutin, K., MacKenzie, A. et al. Phospholipids of New Zealand Edible Brown Algae. Lipids 52, 629–639 (2017). https://doi.org/10.1007/s11745-017-4266-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11745-017-4266-x

Keywords

Search

Navigation