Document Detail


Total synthesis of Calebin-A, preparation of its analogues, and their neuronal cell protectivity against beta-amyloid insult.
MedLine Citation:
PMID:  11549465     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A total synthesis of Calebin-A (1), a novel curcuminoid isolated from turmeric (Curcuma longa, Zingiberaceae) that has been demonstrated to protect neuronal cells from beta-amyloid insult, was successfully achieved in four steps. Elaborating on this synthetic route, 13 analogues were prepared for a structure-activity relationship (SAR) study. It was found that the parent compound 1 and derivatives 21, 28, and 30 protect PC12 rat pheocromocytoma and IMR-32 human neuroblastoma cells from beta-amyloid(25-35) insult. These results suggest that hydroxy group at para-position is most critical for the expression of biological activity.
Authors:
D S Kim; J Y Kim
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Bioorganic & medicinal chemistry letters     Volume:  11     ISSN:  0960-894X     ISO Abbreviation:  Bioorg. Med. Chem. Lett.     Publication Date:  2001 Sep 
Date Detail:
Created Date:  2001-09-10     Completed Date:  2002-03-12     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  9107377     Medline TA:  Bioorg Med Chem Lett     Country:  England    
Other Details:
Languages:  eng     Pagination:  2541-3     Citation Subset:  IM    
Affiliation:
The Program for Collaborative Research in Pharmaceutical Science and the Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, IL 60612, USA. dshlkim@uic.edu
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MeSH Terms
Descriptor/Qualifier:
Amyloid beta-Protein / toxicity*
Animals
Biochemistry / methods
Cinnamates
Curcumin / analogs & derivatives,  pharmacology*
Dose-Response Relationship, Drug
Humans
Magnetic Resonance Spectroscopy
Monoterpenes
Neuroprotective Agents / chemistry*,  pharmacology*
Peptide Fragments / toxicity*
Rats
Structure-Activity Relationship
Tumor Cells, Cultured
Chemical
Reg. No./Substance:
0/Amyloid beta-Protein; 0/Cinnamates; 0/Monoterpenes; 0/Neuroprotective Agents; 0/Peptide Fragments; 0/amyloid beta-protein (25-35); 0/calebin-A; 458-37-7/Curcumin

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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