Alvaradoins E-N, antitumor and cytotoxic anthracenone C-glycosides from the leaves of Alvaradoa haitiensis.

Abstract

Bioactivity-directed fractionation of an extract of the leaves of Alvaradoa haitiensis, using the KB (human oral epidermoid carcinoma) cell line, led to the isolation and identification of 10 new anthracenone C-glycosides, alvaradoins E-N (1-10), along with the known compound chrysophanol (11). The cytotoxicity of all compounds was evaluated, and preliminary structure-activity relationships are suggested. The most potent compounds in the in vitro assays (1 and 2) were evaluated in vivo versus the P388 (murine lymphocytic leukemia) model, and alvaradoin E (1) showed antileukemic activity (125% T/C) at a dose of 0.2 mg kg-1 per injection when administered intraperitoneally.

• Authors: Sharnelle S Phifer, Dongho Lee, Eun-Kyoung Seo, Nam-Cheol Kim, Tyler N Graf, David J Kroll, Hernan A Navarro, Robert A Izydore, Francisco Jiménez, Ricardo Garcia, William C Rose, Craig R Fairchild, Robert Wild, Djaja D Soejarto, Norman R Farnsworth, A Douglas Kinghorn, Nicholas H Oberlies, Monroe E Wall, Mansukh C Wani
• Journal: Journal of natural products (J Nat Prod) Vol. 70 Issue 6 Pg. 954-61 (Jun 2007) ISSN: 0163-3864 [Print] United States
• PMID: 17552563 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't)

Chemical References

• Anthracenes
• Antineoplastic Agents, Phytogenic
• Monosaccharides
• alvaradoin E

Topics

• Animals
• Anthracenes (chemistry, isolation & purification, pharmacology)
• Antineoplastic Agents, Phytogenic (chemistry, isolation & purification, pharmacology)
• Dominican Republic
• Drug Screening Assays, Antitumor
• Humans
• KB Cells
• Leukemia P388
• Models, Biological
• Molecular Structure
• Monosaccharides (chemistry, isolation & purification, pharmacology)
• Plant Leaves (chemistry)
• Plants, Medicinal (chemistry)
• Simaroubaceae (chemistry)
• Structure-Activity Relationship