Document Detail

Rosmarinic acid, a new snake venom phospholipase A2 inhibitor from Cordia verbenacea (Boraginaceae): antiserum action potentiation and molecular interaction.
MedLine Citation:
PMID:  15992846     Owner:  NLM     Status:  MEDLINE    
Many plants are used in traditional medicine as active agents against various effects induced by snakebite. The methanolic extract from Cordia verbenacea (Cv) significantly inhibited paw edema induced by Bothrops jararacussu snake venom and by its main basic phospholipase A2 homologs, namely bothropstoxins I and II (BthTXs). The active component was isolated by chromatography on Sephadex LH-20 and by RP-HPLC on a C18 column and identified as rosmarinic acid (Cv-RA). Rosmarinic acid is an ester of caffeic acid and 3,4-dihydroxyphenyllactic acid [2-O-cafeoil-3-(3,4-di-hydroxy-phenyl)-R-lactic acid]. This is the first report of RA in the species C. verbenacea ('baleeira', 'whaler') and of its anti-inflammatory and antimyotoxic properties against snake venoms and isolated toxins. RA inhibited the edema and myotoxic activity induced by the basic PLA2s BthTX-I and BthTX-II. It was, however, less efficient to inhibit the PLA2 activity of BthTX-II and, still less, the PLA2 and edema-inducing activities of the acidic isoform BthA-I-PLA2 from the same venom, showing therefore a higher inhibitory activity upon basic PLA2s. RA also inhibited most of the myotoxic and partially the edema-inducing effects of both basic PLA2s, thus reinforcing the idea of dissociation between the catalytic and pharmacological domains. The pure compound potentiated the ability of the commercial equine polyvalent antivenom in neutralizing lethal and myotoxic effects of the crude venom and of isolated PLA2s in experimental models. CD data presented here suggest that, after binding, no significant conformation changes occur either in the Cv-RA or in the target PLA2. A possible model for the interaction of rosmarinic acid with Lys49-PLA2 BthTX-I is proposed.
Fábio K Ticli; Lorane I S Hage; Rafael S Cambraia; Paulo S Pereira; Angelo J Magro; Marcos R M Fontes; Rodrigo G Stábeli; José R Giglio; Suzelei C França; Andreimar M Soares; Suely V Sampaio
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Toxicon : official journal of the International Society on Toxinology     Volume:  46     ISSN:  0041-0101     ISO Abbreviation:  Toxicon     Publication Date:  2005 Sep 
Date Detail:
Created Date:  2005-08-01     Completed Date:  2005-10-19     Revised Date:  2007-11-15    
Medline Journal Info:
Nlm Unique ID:  1307333     Medline TA:  Toxicon     Country:  England    
Other Details:
Languages:  eng     Pagination:  318-27     Citation Subset:  IM    
Departamento de Análises Clínicas, Toxicológicas e Bromatológicas, FCFRP, Universidade de São Paulo, USP, Ribeirão Preto-SP, Brazil.
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MeSH Terms
Anti-Inflammatory Agents / pharmacology
Binding Sites
Caffeic Acids / isolation & purification
Cinnamates / isolation & purification,  pharmacology*
Cordia / chemistry*
Edema / metabolism
Enzyme Inhibitors / isolation & purification,  pharmacology*
Lactates / isolation & purification
Neurotoxins / antagonists & inhibitors,  toxicity
Phospholipases A / antagonists & inhibitors*,  chemistry,  metabolism
Phospholipases A2
Snake Venoms / enzymology
Time Factors
Reg. No./Substance:
0/Anti-Inflammatory Agents; 0/Caffeic Acids; 0/Cinnamates; 0/Depsides; 0/Enzyme Inhibitors; 0/Lactates; 0/Neurotoxins; 0/Snake Venoms; 23028-17-3/3,4-dihydroxyphenyllactic acid; 331-39-5/caffeic acid; 537-15-5/rosmarinic acid; EC 3.1.1.-/Phospholipases A; EC A2

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