Document Detail

Structure-activity relationship of seco-tanapartholides isolated from Achillea falcata for inhibition of HaCaT cell growth.
MedLine Citation:
PMID:  19464086     Owner:  NLM     Status:  MEDLINE    
Four sesquiterpene lactones were isolated from Achillea falcata, through bioassay-guided fractionation, based on their differential ability to affect HaCaT cell growth. Identified seco-tanapartholides: 3-beta-methoxy-iso-seco-tanapartholide (1), tanaphillin (2), iso-seco-tanapartholide (3), and 8-hydroxy-3-methoxy-iso-seco-tanaparatholide (4) were found to differentially decrease keratinocyte cell viability. In addition, the stereoselectivity, lipophilicity, and number and position of hydroxyl groups present in these compounds were correlated with their biological activities for HaCaT cell growth inhibition. Statistical analyses confirmed an enhanced potency of the beta-OH iso-seco-tanapartholide over the alpha:beta-OH diastereoisomeric mixture. The highest potency, however, was mainly the function of the enhanced lipophilicity of the molecule.
Akram Ghantous; Niveen Nasser; Ihab Saab; Nadine Darwiche; Najat A Saliba
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2009-05-04
Journal Detail:
Title:  European journal of medicinal chemistry     Volume:  44     ISSN:  1768-3254     ISO Abbreviation:  Eur J Med Chem     Publication Date:  2009 Sep 
Date Detail:
Created Date:  2009-07-20     Completed Date:  2009-10-14     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0420510     Medline TA:  Eur J Med Chem     Country:  France    
Other Details:
Languages:  eng     Pagination:  3794-7     Citation Subset:  IM    
American University of Beirut, Department of Biology, Beirut, Lebanon.
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MeSH Terms
Achillea / chemistry*
Cell Line, Tumor
Cell Proliferation / drug effects
Cell Survival / drug effects
Growth Inhibitors / chemistry*,  isolation & purification,  pharmacology*
Keratinocytes / cytology
Lactones / chemistry,  isolation & purification,  pharmacology
Plant Components, Aerial / chemistry*
Sesquiterpenes, Guaiane / chemistry*,  isolation & purification,  pharmacology*
Structure-Activity Relationship
Reg. No./Substance:
0/Growth Inhibitors; 0/Lactones; 0/Sesquiterpenes, Guaiane

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