A Distinctive Structural Twist in the Aminoimidazole Alkaloids from a Calcareous Marine Sponge:  Isolation and Characterization of Leucosolenamines A and B

Paul Ralifo,† Karen Tenney,† Frederick A. Valeriote,‡ and Phillip Crews*†
Department of Chemistry and Biochemistry and Institute of Marine Sciences, University of California, Santa Cruz, California 95064, and Division of Hematology and Oncology, Josephine Ford Cancer Center, Detroit, Michigan 48202
J. Nat. Prod., 2007, 70 (1), pp 33–38
DOI: 10.1021/np060462b
Publication Date (Web): December 22, 2006
Copyright © 2007 American Chemical Society and American Society of Pharmacognosy
†

 University of California, Santa Cruz.

,
‡

 Josephine Ford Cancer Center.

,
*

 Corresponding author. Tel:  831-459-2603. Fax:  831-459-2935. E-mail:  phil@chemistry.ucsc.edu.

Abstract

Abstract Image

Bioassay-guided fractionation of Papua New Guinea collections of Leucosolenia sp. resulted in the isolation of the novel compounds leucosolenamines A (5) and B (6) and the known compound thymidine (7). Compound 5 contains a 2-aminoimidazole core substituted at C-4 and C-5 by an N,N-dimethyl-5,6-diaminopyrimidine-2,4-dione and a benzyl group, respectively. Compound 6 retains the same core structure; however C-4 is substituted by a 5,6-diamino-1,3-dimethyl-4-(methylimino)-3,4-dihydropyrimidin-2(1H)-one moiety. This substitution pattern is unique and has never been observed in calcareous imidazole alkaloid chemistry. Leucosolenamine A (5) was mildly cytotoxic against the murine colon adenocarcinoma C-38 cell line.

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History

  • Published In Issue January 26, 2007
  • Received September 19, 2006

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