Document Detail

The phytotoxic lichen metabolite, usnic acid, is a potent inhibitor of plant p-hydroxyphenylpyruvate dioxygenase.
MedLine Citation:
PMID:  11034349     Owner:  NLM     Status:  MEDLINE    
The lichen secondary metabolite usnic acid exists as a (-) and a (+) enantiomer, indicating a alpha or beta projection of the methyl group at position 9b, respectively. (-)-Usnic caused a dose-dependent bleaching of the cotyledonary tissues associated with a decrease of both chlorophylls and carotenoids in treated plants whereas no bleaching was observed with the (+) enantiomer. (-)-Usnic acid inhibited protophorphyrinogen oxidase activity (I50 = 3 microM), but did not lead to protoporphyrin IX accumulation. Bleaching appears to be caused by irreversible inhibition of the enzyme 4-hydroxyphenylpyruvate dioxygenase by (-)-usnic acid (apparent IC50 = 50 nM).
J G Romagni; G Meazza; N P Nanayakkara; F E Dayan
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  FEBS letters     Volume:  480     ISSN:  0014-5793     ISO Abbreviation:  FEBS Lett.     Publication Date:  2000 Sep 
Date Detail:
Created Date:  2000-11-07     Completed Date:  2000-11-07     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0155157     Medline TA:  FEBS Lett     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  301-5     Citation Subset:  IM    
USDA/ARS, Natural Products Utilization Research Unit, University of Mississippi, Lafayette Co 38677, USA.
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MeSH Terms
4-Hydroxyphenylpyruvate Dioxygenase / antagonists & inhibitors*
Benzofurans / chemistry,  pharmacology*
Carotenoids / biosynthesis
Chlorophyll / metabolism
Cotyledon / drug effects
Enzyme Inhibitors / chemistry,  pharmacology*
Molecular Structure
Reg. No./Substance:
0/Benzofurans; 0/Enzyme Inhibitors; 125-46-2/usnic acid; 1406-65-1/Chlorophyll; 36-88-4/Carotenoids; EC Dioxygenase

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