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Metabolism in porifera-V, biosynthesis of 19-Nor-Stanols: Conversion of cholesterol into 19-nor-cholestanols by the spongeAxinella polypoides

  • Specialia Chimica, Biochimica
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Riassunto

La spugnaAxinella polypoides transforma il [26-14C]-colesterolo nel 19-nor-colestanolo (1), mentre non utilizza 1′[1-14C]-acetato per la sintesi dei 19-nor-stanoli (1–8). Si suggerisce che questi unici stanoli si originano da steroli dietarici per rimozione del metile in 10.

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Literatur

  1. P. De Luca, M. De Rosa, L. Minale andG. Sodano, J. chem. Soc. PerkinI, 2132 (1972). —P. De Luca, M. De Rosa, L. Minale, R. Puliti, G. Sodano, F. Giordano andL. Mazzarella, J. chem. Soc. Chem. Commun.1973, 825.

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  6. 19-Nor-stanols have the same TLC Rf on silica gel as cholesterol.

  7. Portion of the labelled phenyl acetates from 19-nor-stanols deriving from 48 h incubation with [26-14C]-cholesterol was added to a mixture of carrier phenyl acetates to obtain a specific radioactivity of 4×102 dpm/mg and subjected to preparative GLC. A Carlo Erba gaschromatograph, model G-V, equipped with a flame ionization detector was used and the separation was performed using a 2-m glass column (i.d. 6 mm) packed with 1% 0V-1 Gas-Chrom 80–100 mesh and operated at 260° with N2 at 120 ml/min. The first peak corresponding to 19-norcholesta-1,3,5(10)-trien-3-yl acetate (9) (31.6% of the total mixture) has a specific radioactivity of 1.2×102 dpm/mg.

  8. Acknowledgments. We thank the Zoological Station (Naples) for provision of the sponges and use of Laboratory facilities. The technical assistance of Mr.A. Crispino is also acknowledged.

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Authors and Affiliations

  1. Laboratorio per la Chimica di Molecode di Interesse Biologico del C.N.R., Via Toiano 2, Arco Felice, Napoli, Italy

    M. De Rosa, L. Minale & G. Sodano

Authors
  1. M. De Rosa
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  2. L. Minale
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  3. G. Sodano
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Additional information

Experimental details are given in reference. In a typical experiment 200 mg of labelled 19-nor-steran-3-ones were added to 25 mg of carrier 5α-cholestan-3-one.

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De Rosa, M., Minale, L. & Sodano, G. Metabolism in porifera-V, biosynthesis of 19-Nor-Stanols: Conversion of cholesterol into 19-nor-cholestanols by the spongeAxinella polypoides. Experientia 31, 758–759 (1975). https://doi.org/10.1007/BF01938445

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  • DOI: https://doi.org/10.1007/BF01938445

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