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Fatty Acids from a Glass Sponge Aulosaccus sp. Occurrence of New Cyclopropane-Containing and Methyl-Branched Acids

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Lipids

Abstract

In order to identify new structures, the free fatty acids from an extract of a glass sponge Aulosaccus sp. (from the north-west Pacific) belonging to one of the least chemically investigated classes (Hexactinellida), were fractionated by RP-HPLC and analyzed by NMR spectroscopy and GC–MS of their pyrrolidine derivatives, methyl(ethyl) esters and their dimethyl disulfide adducts. One hundred and twenty-three C12–C31 acids (including nine new compounds) were detected, one hundred and ten of these compounds have not been found previously in glass sponges. The levels of common methylene-interrupted polyenes, monoenes of the (n–7) family and less common branched-chain components proved to be high. New acids were shown to be 5,13-dimethyl-tetradec-4-enoic, cis-10,11-methylene-heptadecanoic, 10,12-dimethyl-octadecanoic, cis-12,13-methylene-nonadecanoic, (14E)-13-methyl-eicos-14-enoic, 19-methyl-eicos-13-enoic, cis-20,21-methylene-heptacosanoic, 27-methyl-octacos-21-enoic and (22Z)-nonacos-22-enoic. Some important mass spectrometric characteristics of pyrrolidides of homologous cyclopropane fatty acids are reported and discussed.

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Abbreviations

FA:

Fatty acid(s)

GC–MS:

Gas chromatography–mass spectrometry

RP-HPLC:

High-performance liquid chromatography in the reversed-phase mode

NMR:

Nuclear magnetic resonance

DMDS:

Dimethyl disulfide

MS:

Mass spectrum(spectra)

RT:

Retention time

ECL:

Equivalent chain length

PUFA:

Polyunsaturated fatty acid(s)

References

  1. Santalova EA, Denisenko VA, Dmitrenok PS, Drozdov AL, Stonik VA (2015) Cerebrosides from a Far-Eastern glass sponge Aulosaccus sp. Lipids 50:57–69

    Article  CAS  Google Scholar 

  2. Santalova EA, Denisenko VA, Dmitrenok PS (2015) Structural analysis of the minor cerebrosides from a glass sponge Aulosaccus sp. Lipids 50:1209–1218

    Article  CAS  PubMed  Google Scholar 

  3. Lawson MP, Bergquist PR, Cambie RC (1984) Fatty acid composition and classification of the Porifera. Boichem Syst Ecol 12:375–393

    Article  CAS  Google Scholar 

  4. Thiel V, Blumenberg M, Hefter J, Pape Th, Pomponi Sh, Reed J, Reitner J, Wörheide G, Michaelis W (2002) A chemical view of the most ancient metazoa—biomarker chemotaxonomy of hexactinellid sponges. Naturwissenschaften 89:60–66

    Article  CAS  PubMed  Google Scholar 

  5. Vetter W, Walther W (1990) Preparation of pyrrolidides from fatty acids via trimethylsilyl esters for gas chromatographic-mass spectrometric analysis. J Chromatogr 513:405–407

    Article  CAS  Google Scholar 

  6. AOCS Lipid Library (updated June 2012) N-Acyl pyrrolidine derivatives of fatty acids—archive of mass spectra. http://lipidlibrary.aocs.org/Analysis/content.cfm?ItemNumber=39471. Accessed May–August 2016

  7. Frost DJ, Gunstone FD (1975) The PMR analysis of non-conjugated alkenoic and alkynoic acids and esters. Chem Phys Lipids 15:53–85

    Article  CAS  PubMed  Google Scholar 

  8. Gunston FD, Pollard MR, Scrimgeour CM, Vedanayagam HS (1977) 13C-Nuclear magnetic resonance studies of olefinic fatty acids and esters. Chem Phys Lipids 18:115–129

    Article  Google Scholar 

  9. Gunstone FD (1990) 1H- and 13C-NMR spectra of six n–3 polyene esters. Chem Phys Lipids 56:227–229

    Article  CAS  Google Scholar 

  10. Knothe G (2006) NMR Characterization of dihydrosterculic acid and its methyl ester. Lipids 41:393–396

    Article  CAS  PubMed  Google Scholar 

  11. Andersson BA (1978) Mass spectrometry of fatty acid pyrrolidides. Prog Chem Fats other Lipids 16:279–308

    Article  CAS  PubMed  Google Scholar 

  12. AOCS Lipid Library (updated March 2014) Cyclopropyl and cyclopropenyl fatty acids. http://lipidlibrary.aocs.org/content.cfm?ItemNumber=39505. Accessed August 2016

  13. Carballeira NM, Sostre A, Restituyo JA (1999) Synthesis of racemic 9-methyl-10-hexadecenoic acid. Chem Phys Lipids 97:87–91

    Article  CAS  PubMed  Google Scholar 

  14. Rodkina SA, Imbs AB, Krasokhin VB (2008) Fatty acids of sponges from the Sea of Okhotsk. Russ J Mar Biol 34:384–390

    Article  CAS  Google Scholar 

  15. Berge JP, Barnathan G (2005) Fatty acids from lipids of marine organisms: molecular biodiversity, roles as biomarkers, biologically active compounds, and economical aspects. Adv Biochem Engin Biotechnol 96:49–125

    CAS  Google Scholar 

  16. Kornprobst JM, Barnathan G (2010) Demospongic acids revisited. Mar Drugs 8:2569–2577

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Carballeira NM, Shalabi F (1994) Unusual lipids in the Caribbean sponges Amphimedon viridis and Desmapsamma anchorata. J Nat Prod 57:1152–1159

    Article  CAS  PubMed  Google Scholar 

  18. Christie WW, Brechany EY, Stefanov K, Popov S (1992) The fatty acids of the sponge Dysidea fragilis from the Black Sea. Lipids 27:640–644

    Article  CAS  Google Scholar 

  19. Wayne Moss C, Holzer G, Wallace PL, Hollis DG (1990) Cellular fatty acid compositions of an unidentified organism and a bacterium associated with cat scratch disease. J Clin Microbiol 28:1071–1074

    Google Scholar 

  20. Couderc F (1995) Gas chromatography/tandem mass spectrometry as an analytical tool for the identification of fatty acids. Lipids 30:691–699

    Article  CAS  PubMed  Google Scholar 

  21. Carballeira NM, Sostre A, Stefanov K, Popov S, Kujumgiev A, Dimitrova-Konaklieva S, Tosteson CG, Tosteson TR (1997) The fatty acid composition of a Vibrio alginolyticus associated with the alga Cladophora coelothrix. Identification of the novel 9-methyl-10-hexadecenoic acid. Lipids 32:1271–1275

    Article  CAS  PubMed  Google Scholar 

  22. Rontani JF, Christodoulou S, Koblizek M (2005) GC–MS structural characterization of fatty acids from marine aerobic anoxygenic phototrophic bacteria. Lipids 40:97–108

    Article  CAS  PubMed  Google Scholar 

  23. AOCS Lipid Library (updated June 2012) Branched-chain fatty acids. Saturated mid-chain methyl-branched fatty acids. Isoprenoid fatty acids. http://lipidlibrary.aocs.org/content.cfm?ItemNumber=39321. Accessed August 2016

  24. Nechev J, Christie WW, Robaina R, de Diego FM, Ivanova A, Popov S, Stefanov K (2002) Chemical composition of the sponge Chondrosia reniformis from the Canary Islands. Hydrobiologia 489:91–98

    Article  CAS  Google Scholar 

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Acknowledgements

The authors express their gratitude to Drs O.P. Moiseenko, L.P. Ponomarenko for their kind help in GC–MS analyses and Prof. V.A. Stonik for reading the manuscript and discussion.

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Authors and Affiliations

  1. G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of Russian Academy of Sciences, Pr. 100 let Vladivostoku, 159, Vladivostok, 690022, Russia

    Elena A. Santalova & Vladimir A. Denisenko

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  1. Elena A. Santalova
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  2. Vladimir A. Denisenko
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Correspondence to Elena A. Santalova.

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Santalova, E.A., Denisenko, V.A. Fatty Acids from a Glass Sponge Aulosaccus sp. Occurrence of New Cyclopropane-Containing and Methyl-Branched Acids. Lipids 52, 73–82 (2017). https://doi.org/10.1007/s11745-016-4214-1

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  • DOI: https://doi.org/10.1007/s11745-016-4214-1

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