Marine Biology

, Volume 150, Issue 6, pp 1153–1160 | Cite as

High occurrences of brominated lipid fatty acids in boreal sponges of the order Halichondrida

  • Martin BlumenbergEmail author
  • Walter Michaelis
Research Article


Sponges of warm- and temperate- but also cold-waters are known to synthesize structurally diverse primary and secondary metabolites. These compounds fulfill a variety of functions including adaptations of the cell membranes to environmental conditions. We show here that boreal sponges of the order Halichondrida are rich sources of brominated lipid fatty acids. The comparison of lipid compositions of halichondrid Demospongiae from boreal and warmer waters indicates an accumulation of brominated fatty acids in sponges from colder settings. Moreover, the spatial distribution of brominated fatty acids in the sponge tissue of one widely distributed sponge of the North-East Atlantic (Phakellia ventilabrum) hints to a function related to membrane fluidity and permeability rather than to defense against predation. However, brominated fatty acids are diagnostic for the presence of bromoperoxidases in sponges and may therefore be potentially useful as markers in a chemical screening for secondary metabolites of pharmacological interest.


Sponge DMDS Double Bond Position Lipid Fatty Acid Sodium Thiosulfate Solution 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.



We acknowledge the crews of the RVs ‘Poseidon’ and ‘Hans Brattström’, and the research submersible ‘JAGO’ for excellent collaboration during the field work. Dr. Sven Possner, and Prof. Dr. Wittko Francke (Universität Hamburg) are thanked for helpful analytical support with the GC-IR. We thank Dr. Friederike Hoffmann (Universität Göttingen) for sponge taxonomy. Access to installations from the Institute of Marine Research has been funded by the Improving Human Potential Programme from the European Union through Contract No. HPRI-CT-1999-00056. The Norwegian Government is acknowledged for permission to carry out the field work. Financial support was provided by the Bundesministerium für Bildung und Forschung (BMBF). This paper represents publication No. 58 of the research program BOSMAN (03F0256A).


  1. Ayanoglu E, Popov S, Kornprobst JM, Aboud-Bichara A, Djerassi C (1983) Phospholipid studies of marine organisms: V. New alpha-methoxy acids from Higginsia tethyoides. Lipids 18:830–836CrossRefGoogle Scholar
  2. Barnathan G, Doumenq P, Njinkoue J-M, Miralles J, Debitus C, Levi C, Kornprobst J-M (1994) Sponge fatty acids. 3. Occurrence of series of n-7 monoenoic and iso-5,9 dienoic long-chain fatty acids in the phospholipids of the marine sponge Cinachyrella aff. schulzei Keller1. Lipids 29:297–303CrossRefGoogle Scholar
  3. Barnathan G, Kornprobst J-M, Doumenq P, Miralles J (1996) New unsaturated long-chain fatty acids in the phospholipids from the axinellida sponges Trikentrion loeve and Pseudaxinella cf. lunaecharta. Lipids 31:193–200CrossRefGoogle Scholar
  4. Barnathan G, Genin E, Velosaotsy NE, Kornprobst J-M, Al-Lihaibi S, Al-Sofyani A, Nongonierma R (2003) Phospholipid fatty acids and sterols of two Cinachyrella sponges from the Saudi Arabian Red Sea: comparison with Cinachyrella species from other origins. Comp Biochem Physiol B 135:297–308CrossRefGoogle Scholar
  5. Brantley SE, Molinski TF, Preston CM, DeLong EF (1995) Brominated acetylenic fatty acids from Xestospongia sp., a marine sponge-bacteria association. Tetrahedron 51:7667–7672CrossRefGoogle Scholar
  6. Buser HR, Arn H, Guerin P, Rauscher S (1983) Determination of double bond position in mono-unsaturated acetates by mass spectrometry of dimethyl disulfides adducts. Anal Chem 55:818–822CrossRefGoogle Scholar
  7. Carballeira NM, Maldonado L, Porras B (1987) Isoprenoid fatty acids from marine sponges. Are sponges selective? Lipids 22:767–769CrossRefGoogle Scholar
  8. Carballeira NM, Emiliano A (1993) Novel brominated phospholipid fatty acids from the Carribbean sponge Agelas sp. Lipids 28:763–766CrossRefGoogle Scholar
  9. Carballeira NM, Shalabi F (1993) Novel brominated phospholipid fatty acids from the Caribbean sponge Petrosia sp. J Nat Prod 56:739–746CrossRefGoogle Scholar
  10. Carreau JP, Dubacq JP (1978) Adaptation of a macro-scale method to the micro-scale for fatty acid methyl transesterification of biological lipid extracts. J Chromatogr 151:384–390CrossRefGoogle Scholar
  11. Christie WW, Brechany EY, Marekov IN, Stefanov KL, Andreev SN (1994) The fatty acids of the sponge Hymeniacidon sanguinea from the Black Sea. Comp Biochem Physiol B 109:245–252CrossRefGoogle Scholar
  12. Dembitsky VM, Srebnik M (2002) Natural halogenated fatty acids: their analogues and derivatives. Progr Lipid Res 41:315–367CrossRefGoogle Scholar
  13. Djerassi C, Lam W-K (1991) Sponge phospholipids. Acc Chem Res 24:69–75CrossRefGoogle Scholar
  14. Duque C, Cepeda N, Martinez A (1993) The steryl ester and phospholipid fatty acids of the sponge Agelas conifera from the Colombian Caribbean. Lipids 28:767–769CrossRefGoogle Scholar
  15. Garson MJ, Zimmermann MP, Battershill CN, Holden JL, Murphy PT (1994) The distribution of brominated long-chain fatty acids in sponge and symbiont cell types from the tropical marine sponge Amphimedon terpenensis. Lipids 29:509–516CrossRefGoogle Scholar
  16. Hahn S, Stoilov IL, Tam Ha TB, Raederstorff D, Doss GA, Li H-T, Djerassi C (1988) Biosynthetic studies of marine lipids. 17. The course of chain elongation and desaturation in long-chain fatty acids of marine sponges. J Am Chem Soc 110:8117–8124CrossRefGoogle Scholar
  17. Jefferts E, Morales RW, Litchfield C (1974) Occurrence of cis-5,cis-9-hexacosadienoic and cis-5,cis-9,cis-19-hexacosatrienoic acids in the marine sponge Microciona prolifera. Lipids 9:244–247CrossRefGoogle Scholar
  18. Lam W-K, Hahn S, Ayanoglu E, Djerassi C (1989) Phospholipid studies of marine organisms. 22. Structure and biosynthesis of a novel brominated fatty acid from a Hymeniacidonid sponge. J Org Chem 54:3428–3432CrossRefGoogle Scholar
  19. Lankelma J, Ayanoglu E, Djerassi C (1983) Double-bond location in long chain polyunsaturated fatty acids by chemical ionization-mass spectrometry. Lipids 18:853–858CrossRefGoogle Scholar
  20. Li Y, Ishibashi M, Sasaki T, Kobayashi J (1995) New bromine-containing unsaturated fatty acid derivatives from the Okinawan marine sponge Xestospongia sp. J Chem Res (S): 126–127Google Scholar
  21. Litchfield C, Morales RW (1976) Are demospongiae membranes unique among living organisms? In: Harrison FW, Cowden RR (Eds) Aspects of sponge biology. Academic, New York, pp 183–200CrossRefGoogle Scholar
  22. Mansoor TA, Baea BH, Hongb J, Leec CO, Sik Ima K, Jung JH (2005) New fatty acid derivatives from Homaxinella sp., a marine sponge. Lipids 40:981–985CrossRefGoogle Scholar
  23. Morales RW, Litchfield C (1976) Unusual C24, C25, C26 and C27 polyunsaturated fatty acids of the marine sponge Microciona prolifera. Biochim Biophys Acta 431:206–216CrossRefGoogle Scholar
  24. Pettit GR, McNulty J, Herald DL, Doubek DL, Chapuis J-C, Schmidt JM, Tackett LP, Boyd MR (1997) Antineoplastic agents. 362. Isolation and x-ray crystal structure of Dibromophakellistatin from the Indian Ocean sponge Phakellia mauritiana. J Nat Prod 60:180–183CrossRefGoogle Scholar
  25. Raederstorff D, Shu AYL, Thompson JE, Djerassi C (1987) Biosynthetic studies of marine lipids. 11. Synthesis, biosynthesis, and absolute configuration of the internally branched demospongic acid, 22-methyl-5,9-octacosadienoic acid. J Org Chem 52:2337–2346CrossRefGoogle Scholar
  26. Russell NJ (1990) Cold adaptation of microorganisms. Philos Trans R Soc Lond B 326:595–611CrossRefGoogle Scholar
  27. Russell NJ, Fukunaga N (1990) A comparison of thermal adaptation of membrane lipids in psychrophilic and thermophilic bacteria. FEMS Microbiol Rev 75:171–182CrossRefGoogle Scholar
  28. Schupp P, Eder C, Paul V, Proksch P (1999) Distribution of secondary metabolites in the sponge Oceanapia sp. and its ecological implications. Mar Biol 135:573–580CrossRefGoogle Scholar
  29. Thiel V, Jenisch A, Wörheide G, Löwenberg A, Reitner J, Michaelis W (1999) Mid-chain branched alkanoic acids from “living fossil” demosponges: A link to ancient sedimentary lipids? Org Geochem 30:1–14CrossRefGoogle Scholar
  30. Thiel V, Blumenberg M, Hefter J, Pape T, Pomponi SA, Reed J, Reitner J, Wörheide G, Michaelis W (2002) A chemical view of the most ancient metazoa - biomarker chemotaxonomy of hexactinellid sponges. Naturwissenschaften 89:60–66CrossRefGoogle Scholar
  31. Thompson JE, Walker RP, Faulkner DJ (1985) Screening and bioassays for biologically-active substances from forty marine sponge species from San Diego, California, USA. Mar Biol 88:11–21CrossRefGoogle Scholar
  32. van Peè KH, Unversucht S (2003) Biological dehalogenation and halogenation reactions. Chemosphere 52:299–312CrossRefGoogle Scholar
  33. van Soest RWM (1994) Demosponge distribution patterns. In: Van Soest RWM, van Kempen TMG, Braekman J-C (Eds) Sponges in time and space. A.A. Balkema, Rotterdam, pp 213–223Google Scholar
  34. Walkup RD, Jamieson GC, Ratcliff MR, Djerassi C (1981) Phospholipid studies of marine organisms: 2. Phospholipids, phospholipid-bound fatty acids and free sterols of the sponge Aplysina fistularis (Pallas) forma fulva (Pallas) (=Verongia thiona). Isolation and structure elucidation of unprecedented branched fatty acids. Lipids 16:631–646CrossRefGoogle Scholar
  35. Wijekoon WMD, Ayanoglu E, Djerassi C (1984) Phospholipid studies of marine organisms 9. New brominated demospongic acids from the phospholipids of two Petrosia species. Tetrahedron Lett 25:3285–3288CrossRefGoogle Scholar
  36. Willenz P, Hartmann WD (1989) Micromorphology and ultrastructure of Caribbean sclerosponges. I. Ceratoporella nicholsoni and Stromatospongia norae (Ceratoporellidae: Porifera). Mar Biol 103:387–401CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2006

Authors and Affiliations

  1. 1.Institute of Biogeochemistry and Marine ChemistryUniversity of HamburgHamburgGermany

Personalised recommendations