Abstract
N6-methyl mucronatine (C8H12N5O) has been isolated from a dictyoceratid sponge collected in South East Queensland. The solid state structure of the new metabolite (I) was confirmed by X-ray crystallography, while an NMR study in d 4-MeOH reveals the presence of a minor tautomer identified as (II).
Graphical Abstract
The crystal structure of the purine N10-methyl mucronatine (C8H12N5O) is reported, isolated from a dictyoceratid sponge collected in South East Queensland, Australia
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Sakurada T, Gill MB, Frausto S, Copits B, Noguchi K, Shimamoto K, Swanson GT, Sakai R (2010) J Med Chem 53:6089–6099
Perry NB, Blunt JW, Munro MHG (1987) J Nat Prod 50:307–308
Yagi H, Matsunaga S, Fusetani N (1994) J Nat Prod 57:837–838
Mitchell SS, Whitehill AB, Trapido-Rosenthal HG, Ireland CM (1997) J Nat Prod 60:727–728
Chehade CC, Dias RLA, Berlinck RGS, Ferreira AG, Costa LV, Rangel M, Malpezzi ELA, De Freitas JC, Hajdu E (1997) J Nat Prod 60:729–731
Moon B, Baker BJ, McClintock JB (1998) J Nat Prod 61:116–118
Do Prado Gambardella MT, Dias RLA, Chehade CC, Berlinck RGS (1999) Acta Cryst C55:1585–1587
Bourguet-Kondracki ML, Martin MT, Vacelet J, Guyot M (2001) Tetrahedron Lett 42:7257–7259
Tasdemir D, Mangalindan GC, Concepción GP, Harper MK, Ireland CM (2001) Chem Pharm Bull 49:1628–1630
Jeong SJ, Inagaki M, Higuchi R, Miyamoto T, Ono M, Kuwano M, Van Soest RWM (2003) Chem Pharm Bull 51:731–733
Killday KB, Yarwood D, Sills MA, Murphy PT, Hooper JNA, Wright AE (2001) J Nat Prod 64:525–526
Panthong K, Garson MJ, Bernhardt PV (2006) Acta Cryst C62:o193–o195
Zelnik R, Haraguchi M, Matida AK, Lavie D, Frolow F, Weis AL (1986) J Chem Soc Perkin Trans 1:2051–2053
Cooper RA, De Freitas JC, Porreca F, Eisenhour CM, Lukas R, Huxtable RJ (1995) Toxicon 33:1025–1031
Pearce AN, Babcock RC, Lambert G, Copp BR (2001) Nat Prod Lett 15:237–241
Appleton DR, Page MJ, Lambert G, Copp BR (2004) Nat Prod Res 18:39–42
Berry Y, Bremner JB, Davis A, Samosorn S (2006) Nat Prod Res 20:479–483
Sheldrick GM (2008) Acta Crystallogr S A Found Crystallogr A64:112–122
Farrugia LJ (1999) J Appl Crystallogr 32:837–838
Farrugia LJ (1997) J Appl Crystallogr 30:565
Spek AL (2009) Acta Crystallogr S D D65:148–155
Acknowledgments
We thank the University of Queensland and the Australia Research Council for financial support. The assistance of Sharna K. Graham and Daniel Holdsworth with sample collection, and Mr Graham McFarlane for mass spectrometry is gratefully acknowledged. Permission to collect sponge samples was provided by the Queensland Department of Primary Industries and Fisheries.
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Suciati, Garson, M.J., Bernhardt, P.V. et al. A New N,N-Dimethyl Purine from an Australian Dictyoceratid Sponge . J Chem Crystallogr 41, 1669–1672 (2011). https://doi.org/10.1007/s10870-011-0155-y
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DOI: https://doi.org/10.1007/s10870-011-0155-y