Identification of unprecedented purine-containing compounds, the zingerines, from ginger rhizomes (Zingiber officinale Roscoe) using a phase-trafficking approach

Phytochemistry

Volumn 72, Issue 9, 2011, Pages 935-941

  Araya, Juan J ^a   Zhang, Huaping ^a   Prisinzano, Thomas E ^a   Mitscher, Lester A ^a   Timmermann, Barbara N ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

Alkaloids; Fractionation; Ginger; Natural products; Phase trafficking; Zingerines

Indexed keywords

ZINGIBER OFFICINALE;

ADENINE; CATECHOL DERIVATIVE; FATTY ALCOHOL; GINGEROL; GUAIACOL; PURINE; PURINE DERIVATIVE;

ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; GINGER; ISOLATION AND PURIFICATION; RHIZOME;

ADENINE; CATECHOLS; FATTY ALCOHOLS; GINGER; GUAIACOL; MOLECULAR STRUCTURE; PURINES; RHIZOME;

EID: 79955783342     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2011.03.007     Document Type: Article

References (21)

1. M. Afzal, D. Al-Hadidi, M. Menon, J. Pesek, and M.S.I. Dhami Ginger: an ethomedical, chemical and pharmacological review Drug Metabol. Drug Interact. 18 2001 159 191
2. S.D. Alexandratos Ion-exchange resins: a retrospective from industrial and engineering chemistry research Ind. Eng. Chem. Res. 48 2009 388 398
3. B.H. Ali, G. Blunden, M.O. Tanira, and A. Nemmar Some phytochemical, pharmacological and toxicological properties of ginger (Zingiber officinale Roscoe): a review of recent research Food Chem. Toxicol. 46 2008 409 420 (Pubitemid 350297543)
4. J. Appenzeller, G. Mihci, M.T. Martin, J.F. Gallard, J.L. Menou, N. Boury-Esnalllt, J. Hooper, S. Petek, S. Chevalley, A. Valentin, A. Zaparucha, A. Al-Mourabit, and C. Debitus Agelasines J, K, and L from the Solomon Islands marine sponge Agelas cf Mauritiana J. Nat. Prod. 71 2008 1451 1454
5. J.J. Araya, G. Montenegro, L.A. Mitscher, and B.N. Timmermann Application of phase-trafficking methods to natural products research J. Nat. Prod. 73 2010 1568 1572
6. D.L. Flynn Phase-trafficking reagents and phase-switching strategies for parallel synthesis Med. Res. Rev. 19 1999 408 431 (Pubitemid 29416596)
7. J.L. Funk, J.B. Frye, J.N. Oyarzo, and B.N. Timmermann Comparative effects of two gingerol-containing Zingiber officinale extracts on experimental rheumatoid arthritis J. Nat. Prod. 72 2009 403 407
8. S.D. Jolad, R.C. Lantz, A.M. Solyom, G.J. Chen, R.B. Bates, and B.N. Timmermann Fresh organically grown ginger (Zingiber officinale): composition and effects on LPS-induced PGE(2) production Phytochemistry 65 2004 1937 1954 (Pubitemid 38981684)
9. S.D. Jolad, R.C. Lantz, G.J. Chen, R.B. Bates, and B.N. Timmermann Commercially processed dry ginger (Zingiber officinale): composition and effects on LPS-stimulated PGE(2) production Phytochemistry 66 2005 1614 1635 (Pubitemid 40950555)
10. J.S. Kim, S.I. Lee, H.W. Park, J.H. Yang, T.Y. Shin, Y.C. Kim, N.I. Baek, S.H. Kim, S.U. Choi, B.M. Kwon, K.H. Leem, M.Y. Jung, and D.K. Kim Cytotoxic components from the dried rhizomes of Zingiber officinale Roscoe Arch. Pharmacol. Res. 31 2008 415 418
11. R.C. Lantz, M. Sarihan, G.J. Chen, and B. Timmermann Sites of action of compounds isolated from ginger FASEB J. 18 2004 A99
12. H. Rosemeyer The chemodiversity of purine as a constituent of natural products Chem. Biodivers. 1 2004 361 401
13. S. Sang, J. Hong, H. Wu, J. Liu, C.S. Yang, M.-H. Pan, V. Badmaev, and C.-T. Ho Increased growth inhibitory effects on human cancer cells and anti-inflammatory potency of shogaols from Zingiber officinale relative to gingerols J. Agric. Food. Chem. 57 2009 10645 10650
14. A. Solinas, and M. Taddei Solid-supported reagents and catch-and-release techniques in organic synthesis Synthesis-Stuttgart 16 2007 2409 2453 (Pubitemid 47338891)
15. I. Vanrensen, and M. Veit Simultaneous determination of phenolics and alkaloids using ion exchange chromatography for sample preparation Phytochem. Anal. 6 1995 121 124
16. D.C. Wang, H. Xiang, D. Li, H.Y. Gao, H. Cai, L.J. Wu, and X.M. Deng Purine-containing cucurbitane triterpenoids from Cucurbita pepo cv dayangua Phytochemistry 69 2008 1434 1438
17. A.E. Wright, G.P. Roth, J.K. Hoffman, D.B. Divlianska, D. Pechter, S.H. Sennett, E.A. Guzman, P. Linley, P.J. McCarthy, T.P. Pitts, S.A. Pomponi, and J.K. Reed Isolation, synthesis, and biological activity of aphrocallistin, an adenine-substituted bromotyramine metabolite from the hexactinellida sponge Aphrocallistes beatrix J. Nat. Prod. 72 2009 1178 1183
18. T. Yosief, A. Rudi, and Y. Kashman Asmarines A-F, novel cytotoxic compounds from the marine sponge Raspailia species J. Nat. Prod. 63 2000 299 304 (Pubitemid 30173681)
19. Y.G. Zhang, R.R. Tian, S.C. Liu, X.L. Chen, X.Z. Liu, and Y.S. Che Alachalasins A-G, new cytochalasins from the fungus Stachybotrys charatum Biorg. Med. Chem. 16 2008 2627 2634
20. Y.G. Zhang, R.R. Tian, S.C. Liu, X.L. Chen, X.Z. Liu, and Y.S. Che Alachalasins A-G, new cytochalasins from the fungus Stachybotrys charatum Biorg. Med. Chem. 17 2009 428 (16, pp. 2627)
21. R.Y. Zhao, Y. Yan, M.X. Li, and H.S. Yan Selective adsorption of tea polyphenols from aqueous solution of the mixture with caffeine on macroporous crosslinked poly(N-vinyl-2-pyrrolidinone) Reac. Funct. Pol. 68 2008 768 774