Document Detail

Synthesis and insect antifeedant activity of plumbagin derivatives with the amino acid moiety.
MedLine Citation:
PMID:  19530696     Owner:  NLM     Status:  MEDLINE    
A series of plumbagin derivatives (4a-4k) containing an amino acid moiety were synthesized under mild esterification conditions in excellent yields (35%-80%) and screened for their antifeedant activities in tobacco caterpillar (Spodoptera litura) and castor semilooper (Achaea janata) using a no-choice laboratory bioassay. The parent compound plumbagin lacked significant activity, but the analogues were effective in reducing feeding by two insect species. The introduction of an N-acetyl-l-amino acid side chain to the Michael adduct of plumbagin at the third position of the quinone moiety significantly increased antifeedant activity. Several of the analogues were also toxic or caused developmental abnormalities following topical administration.
Thonthula Sreelatha; Atmakur Hymavathi; Katragadda Suresh Babu; Joish Madhusudana Murthy; Usha Rani Pathipati; Janaswamy Madhusudana Rao
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of agricultural and food chemistry     Volume:  57     ISSN:  1520-5118     ISO Abbreviation:  J. Agric. Food Chem.     Publication Date:  2009 Jul 
Date Detail:
Created Date:  2009-07-15     Completed Date:  2009-11-13     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0374755     Medline TA:  J Agric Food Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  6090-4     Citation Subset:  IM    
Division of Organic Chemistry- I, Natural Product Laboratory, Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 607, India.
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MeSH Terms
Benzoquinones / chemistry
Eating / drug effects
Insecticides / administration & dosage,  chemical synthesis*,  chemistry
Larva / physiology
Moths / physiology*
Naphthoquinones / administration & dosage,  chemistry*
Spodoptera / physiology*
Structure-Activity Relationship
Reg. No./Substance:
0/Benzoquinones; 0/Insecticides; 0/Naphthoquinones; 106-51-4/benzoquinone; 11062-77-4/Superoxides; 481-42-5/plumbagin

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

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