Pyrroloacridine Alkaloids from Plakortis quasiamphiaster:  Structures and Bioactivity

Paul Ralifo,† Laura Sanchez,† Nadine C. Gassner,† Karen Tenney,† R. Scott Lokey,† Theodore R. Holman,† 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 95–99
DOI: 10.1021/np060585w
Publication Date (Web): January 10, 2007
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

A re-collection of Plakortis quasiamphiaster from Vanuatu in 2003 resulted in the isolation of three known compounds, plakinidine A (1) and amphiasterins B1 (6) and B2 (7). Also isolated was a new bis-oxygenated pyrroloacridine alkaloid, plakinidine E (8), with a unique O-substitution versus N-substitution at position C-12 in 1. The biological evaluation of the active compounds in two assays provided complementary data. Plakinidine A (1) exhibited cytotoxicity against human colon H-116 cells with an IC50 of 0.23 μg/mL, but there were no effects against the yeast Saccharomyces cerevisiae diploid homozygous deletion strain of topoisomerase I (top1Δ). By contrast, 8 was inactive against H-116 cells but was potent in the yeast halo screen.

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History

  • Published In Issue January 26, 2007
  • Received November 21, 2006

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