Summary
2-Amino-6-[(1'R,2'S)-1',2'-dihydroxypropyl]-3-methyl-pterin-4-one (1) has been isolated from the marine anthozoanAstroides calycularis; its structure was illustrated by spectral analyses including 2D-NMR and by partial synthesis.1 appears to possess cell-growth inhibiting activity.
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References
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1H-NMR of2 in CDCl3: δ 1.99 (3H, s, CH3COO−); 2.15 (3H, s, CH3COO−); 2.30 (3H, s, CH3CON−); 8.69 (1H, bs, H-7); 6.01 (1H, d, J=5.5 Hz, H−1'); 5.44 (1H, dq, J=5.5 and 6.5 Hz, H-2'); 3.61 (3H, s, CH3-N); 1.26 (3H, d, J=6.5 Hz, H3-3').
High-resolution mass spectra fragments of2: m/z 317.119 (2%), M+-AcOH; 302.0909 (4), M+−AcOH−CH3; 291.0953 (22), M+−CH2=CHOAc; 275.0999 (88), M+−AcOH−CH2=C=O; 260.0901 (20), M+−AcOH−CH3−N=C=O; 259.1066 (36), M+−2AcOH; 249.0851 (100), M+−CH2=CHOAc−CH2=C=O; 244.0846 (95), M+−2AcOH−CH3. Mass spectra were taken on AEI-902 instrument.
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Spectra were recorded on a Bruker WM-250 spectrometer in DMSO. The assignments of the protonated carbon atom were based on13C−1H shift correlation 2D-NMR spectroscopy via1J couplings which showed interrelation of all the protonated carbons with the pertinent proton(s); The shift correlation with polarization transfer via J-coupling experiments were performed using a Bruker microprogram adjusting the fixed delays D3 and D4 to give maximum polarization for JC−H=135 Hz. The assignments of the remaining carbon atoms were based on comparison with the 2-amino-4-pteridinones, whose13C-NMR data were previously reported13, and on the results of the gated decoupling experiment.
Ewers, U., Günther, H., and Jaenicke, L., Chem. Ber.106 (1973) 3951.
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29 December 1986
Work supported by C.N.R. (Progetto Finalizzato ‘Chimica Fine e Secondaria’) and by Ministero Pubblica Istruzione Italy. — Acknowledgments. Mass spectral data were provided by ‘Servizio di Spettrometria di massa del C.N.R. e dell'Università di Napoli’. The assistance of the staff is gratefully appreciated. Finally we would like to thank Prof. C. Pietropaolo for supplying chick embryo fibroblasts.
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Aiello, A., Fattorusso, E., Magno, S. et al. 2-Amino-6-[(1'R,2'S)-1',2'-dihydroxypropyl]-3-methyl-pterin-4-one, a biologically active metabolite from the anthozoanAstroides calycularis Pallas. Experientia 43, 950–952 (1987). https://doi.org/10.1007/BF01951683
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DOI: https://doi.org/10.1007/BF01951683