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New ceramides from Rantherium suaveolens

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Lipids

Abstract

A mixture of five new ceramides was isolated from the aerial parts of Rantherium suaveolens and characterized by spectroscopic and chemical methods. Their structures were elucidated by spectroscopic and chemical methods as (2S, 3S, 4R, 2′R, 14E)-2-(2′-hydroxydocosanoylamino)-14-octadecene-1,3,4-triol (1), (2S,3S,4R,2′R, 14F)-2-(2′-hydroxytricosanoylamino)-14-octadecene-1,3,4-triol (2), (2S,3S,4R,2′R,14F)-2-(2′-hydroxytetracosanoylamino)-14-octadecene-1,3,4-triol (3), (2S,3S,4R,2′R,14E)-2-(2′-hydroxypentacosanoylamino)-14-octadecene-1,3,4-triol (4), and (2S,3S,4R,2′R,14E)-2-(2′-hydroxyhexacosanoylamino)-14-octadecene-1,3,4-triol (5).

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Abbreviations

CC:

column chromatography

HMBC:

heteronuclear multiple bond correlation

LCB:

long-chain base

MTPA:

α-methoxy-α-(trifluoromethyl)phenylacetyl acid

References

  1. Alapetite, G.P. (1981) Flora of Tunisia, Tunisian Scientific Publications, Official Press, Republic of Tunisia, Tunis, Tunisia.

    Google Scholar 

  2. le Floc’h, E. (1983) Contribution to an Ethnobotanical Study of the Tunisian Flora, pp. 82–83, Tunisian Scientific Publications, Official Press, Republic of Tunisia, Tunis, Tunisia.

    Google Scholar 

  3. Issaoui, A., Kallala, A., Naffeti, M., and Akrimi, N. (1996) Plants from South Tunisia, Ministry of the Environment and Territorial Management, p. 174, State Secretariat of Scientific Research and Technology, Tunisia.

    Google Scholar 

  4. Oueslati, M.H., Ben Jannet, H., Abreu, P.J.M., and Mighri, Z. (2004) Alcools tetrahydropyraniques polyacetyleniques antibacteriens de la plate Rantherium suaveolens poussant dans le sud Tunisien, J. Soc. Alger. Chim. 14, 245–258.

    CAS  Google Scholar 

  5. Braham, H., Mighri, Z., Ben Jannet, H., Matthew, S., and Abreu, P.M. (2005) Antioxidant Phenolic Glycosides from Moricandia arvensis, J. Nat. Prod. 68, 517–522.

    Article  PubMed  CAS  Google Scholar 

  6. Oueslati, M.H., Ben Jannet, H., Abreu, P.J.M., and Mighri, Z. (2006) A New C9 nor-Isoprenoid Glucoside from Rantherium suaveolens, Nat. Prod. Res., in press.

  7. Gaver, R.C., and Sweeley, C.C. (1965) Methods for Methanolysis of Sphingolipids and Direct Determination of Long-Chain Bases by Gas Chromatography, J. Am. Oil Chem. Soc. 42, 294–298.

    PubMed  CAS  Google Scholar 

  8. Vogel, A. (1978) Vogel’s Textbook of Practical Organic Chemistry, 4th edn., pp. 292, Longman, London.

    Google Scholar 

  9. McLaughlin, J.L. (1991) Crown Gall Tumours on Potato Discs and Brine Shrimp Lethality: Two Simple Bioassays for Higher Plant Screening and Fractionation, in Methods in Plant Biochemistry (Hostettman, K., eds.), Vol. 6, pp. 1–32, Academic, London.

    Google Scholar 

  10. Krishna, N., Muralidhar, P., Kumar, M.M., Rao, D.V., and Rao, C.B. (2004) New Sphingosines from a Gorgonian, Pseudopterogorgia australiensis Ridley, of the Indian Ocean, J. Nat. Prod. 67, 1423–1425.

    Article  PubMed  CAS  Google Scholar 

  11. Zhan, Z.-J., and Yue, J.-M. (2003) New Glyceroglycolipid and Ceramide from Premna microphylla, Lipids 38, 1299–1303.

    Article  PubMed  CAS  Google Scholar 

  12. Qi, S.-H., Wu, D.-G., Zhang, S., and Luo, X.-D. (2003) A New Tetranortriterpenoid from Dysoxylum lenticellatum, Z. Naturforsch. 58b, 1128–1132.

    Google Scholar 

  13. Gao, J.-M., Dong, Z.-J., and Liu, J.-K. (2001) A New Ceramide from the Basidiomycete Russula cyanoxantha, Lipids 36, 175–180.

    Article  PubMed  CAS  Google Scholar 

  14. Loukaci, A., Bultel-Poncé, V., Longeon, A., and Guyot, M. (2000) New Lipids from the Tunicate Cystodytes cf. dellechiajei, as PLA2 Inhibitors, J. Nat. Prod. 63, 799–802.

    Article  PubMed  CAS  Google Scholar 

  15. Asai, N., Fusetani, N., Matsunaga, S., and Sasaki, J. (2000) Sex Pheromones of the Hair Crab Erimacrus isenbeckii. Part 1: Isolation and Structures of Novel Ceramides, Tetrahedron 56, 9895–9899.

    Article  CAS  Google Scholar 

  16. Rubino, F.M., Zecca, L., and Sonnino, S. (1994) Characterization of Complex Mixture of Ceramides by Fast Atom Bombardment and Precursor and Tandem Mass Spectrometry, in Mass Spectrometry, Biol. Mass Spectrom. 23, 82–90.

    Article  CAS  Google Scholar 

  17. Rossi, R., and Veracini, C.A. (1982) Insect Pheromone Components. Use of 13C NMR Spectroscopy for Assigning the Configuration of C=C Double Bonds of Monoenic or Dienic Pheromone Components and for Quantitative Determination of Z/E Mixtures, Tetrahedron 38, 629–644.

    Google Scholar 

  18. Cateni, F., Zilic, J., Falsone, G., Scialino, G., and Banfi, E. (2003) New Cerebrosides from Euphorbia peplis, L.: Antimicrobial Activity Evaluation, Bioorg. Med. Chem. Lett. 15, 4345–4350.

    Article  Google Scholar 

  19. Dale, J.A., and Mosher, H.S. (1973) Nuclear Magnetic Resonance Enantiomer Reagents. Configurational Correlations via Nuclear Magnetic Resonance Chemical Shifts of Diastereomic Mandelate, O-Methylmandelate, and α-Methoxy-α-trifluoromethylphenylacetate (MTPA) Esters, J. Am. Chem. Soc. 95, 512–519.

    Article  CAS  Google Scholar 

  20. Rasmussen, H.B., Christensen, S.B., Kvist, L.P., Kharazmi, A., and Huansi, A.G. (2000) Absolute Configuration and Antiprotozoal Activity of Minquartynoic Acid, J. Nat. Prod. 63, 1295–1296.

    Article  PubMed  CAS  Google Scholar 

  21. Seco, J.M., Quiñoá, E., and Riguera, R. (2001) A Practical Guide for the Assignment of the Absolute Configuration of Alcohols, Amines and Carboxylic Acids by NMR, Tetrahedron: Asymmetry 12, 2915–2925.

    Article  CAS  Google Scholar 

  22. Su, B.-N., Misico, R., Park, E.J., Santarsiero, B.D., Mesecar, A.D., Fong, H.H.S., Pezzuto, J.M., and Kinghorn, A.D. (2002) Isolation and Characterization of Bioactive Principles of the Leaves and Stems of Physalis philadelphica, Tetrahedron 58, 3453–3466.

    Article  CAS  Google Scholar 

  23. Liu, J.-K., Hu, L., and Dong, Z.-J. (2003) A Glucosylceramide with a Novel Ceramide and Three Ceramides from the Basidiomycete Cortinarius umidicola, Lipids 38, 669–675.

    Article  PubMed  CAS  Google Scholar 

  24. De Vivar, M.E.D., Seldes, A.M., and Maier, M.S. (2002) Two Novel Glucosylceramides from Gonads and Body Walls of the Patagonian Starfish Allostichaster inaequalis, Lipids 37, 597–603.

    Article  Google Scholar 

  25. Costantino, V., Fattorusso, E., Mangoni, A., Di Rosa, M., Ianaro, A., and Maffia, A. (1996) Glycolipids from Sponges. IV. Immunomodulating Glycosyl Ceramides from the Marine Sponge Agelas dispar, Tetrahedron 52, 1573–1578.

    Article  CAS  Google Scholar 

  26. Li, H.-y., Matsunaga, S., and Fusetani, N. (1995) Halicylindrosides, Antifungal and Cytotoxic Cerebrosides from the Marine Sponge Halichondria cylindrata, Tetrahedron 51, 2273–2280.

    Article  CAS  Google Scholar 

  27. Jin, W., Rinehart, K.L., and Jares-Erijman, E. (1994) Ophidiacerebrosides: Cytotoxic Glycosphingolipids Containing a Novel Sphingosine from a Sea Star, J. Org. Chem. 59, 144–147.

    Article  CAS  Google Scholar 

  28. Iguchi, R., Natori, T., and Komori, T. (1990) Isolation and Characterization of Acanthacerebroside B and Structure Elucidation of Related, Nearly Homogenous Cerebrosides, Liebigs Ann. Chem., 51–55.

  29. Sugiyama, S., Honda, M., and Komori, T. (1988) Asymmetric Synthesis of Phytosphingosine and Phytosphingosine Anhydro Base: Assignment of the Absolute Stereochemistry. Liebigs Ann. Chem., 619–625.

  30. Sugiyama, S., Honda, M., Higuchi, R., and Komori, T. (1991) Stereochemistry of the Four Diastereomers of Ceramide and Ceramide Lactoside, Liebigs Ann. Chem. 349–356.

  31. Murakami, T., and Taguchi, K. (1999) Stereocontrolled Synthesis of Novel Phytosphingosine-type Glucosaminocerebrosides, Tetrahedron 55, 989–1004.

    Article  CAS  Google Scholar 

  32. Cremesti, A.E., and Fischi, A.S. (2000) Current Methods for the Identification and Quantitation of Ceramides: An Overview, Lipids 35, 937–945.

    Article  PubMed  CAS  Google Scholar 

  33. Kester, M., and Kolesnick, R. (2003) Sphingolipids as Therapeutics. Pharmacol. Res. 47, 365–371.

    Article  PubMed  CAS  Google Scholar 

  34. Sot, J., Goñi, F. M., and Alonso, A. (2005) Molecular Associations and Surface-Active Properties of Short- and Long-N-Acyl Chain Ceramides, Biochim. Biophys. Acta 1711, 12–19.

    Article  PubMed  CAS  Google Scholar 

  35. Stoica, B.A., Movsesyan, V.A., Knoblach, S.M., and Faden, A.I. (2005) Ceramide Induces Neuronal Apoptosis Through Mitogen-Activated Protein Kinases and Causes Release of Multiple Mitochondrial Proteins, Mol. Cell. Neurosci. 29, 355–371.

    Article  PubMed  CAS  Google Scholar 

  36. Azuma, H., Takao, R., Niiro, H., Shikata, K., Tamagaki, S., Tachibana, T., and Ogino, K. (2003) Total Synthesis of Symbioramide Derivatives from l-Serine and Their Antileukemic Activities, J. Org. Chem. 68, 2790–2797.

    Article  PubMed  CAS  Google Scholar 

  37. Aouali, N., Eddabra, L., Macadré, J., and Morjani, H. (2005) Immunosuppressors and Reversion of Multidrug-Resistance, Crit. Rev. Oncol. Hematol., 56, 61–70.

    PubMed  Google Scholar 

  38. Sperling, P., and Heinz, E. (2003) Plant Sphingolipids: Structural Diversity, Biosynthesis, First Genes and Functions, Biochim. Biophys. Acta 1632, 1–15.

    PubMed  CAS  Google Scholar 

  39. Jiang, H., Huang, X., Nakanishi, K., and Berova, N. (1999) Nanogram Scale Absolute Configurational Assigment of Ceramides by Circular Dichroism, Tetrahedron Lett. 40, 7645–7649.

    Article  CAS  Google Scholar 

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Author information

Authors and Affiliations

  1. Faculté des Sciences de Monastir, Laboratoire de Chimie des Substances Naturelles et de Synthèse Organique, Monastir, Tunisie

    M. Habib Oueslati, Zine Mighri & H. Ben Jannet

  2. REQUIMTF, Departmento de Química, Faculdade de Ciências e Tecnologia da Universidade, Nova de Lisboa, 2829-516, Caparica, Portugal

    Pedro M. Abreu

Authors
  1. M. Habib Oueslati
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  2. Zine Mighri
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  3. H. Ben Jannet
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  4. Pedro M. Abreu
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Corresponding author

Correspondence to Pedro M. Abreu.

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Oueslati, M.H., Mighri, Z., Jannet, H.B. et al. New ceramides from Rantherium suaveolens . Lipids 40, 1075–1079 (2005). https://doi.org/10.1007/s11745-005-1472-3

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  • DOI: https://doi.org/10.1007/s11745-005-1472-3

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