Synthesis and insect antifeedant activity of plumbagin derivatives with the amino acid moiety.
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.
Sreelatha
Thonthula
T
Division of Organic Chemistry- I, Natural Product Laboratory, Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 607, India.
Hymavathi
Atmakur
A
Babu
Katragadda Suresh
KS
Murthy
Joish Madhusudana
JM
Pathipati
Usha Rani
UR
Rao
Janaswamy Madhusudana
JM
D000818:Animals; D016227:Benzoquinones / Q000737:chemistry; D004435:Eating / Q000187:drug effects; D007306:Insecticides / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000737:chemistry; D007814:Larva / Q000502:physiology; D009036:Moths / Q000502:physiology*; D009285:Naphthoquinones / Q000008:administration & dosage / Q000737:chemistry*; D018411:Spodoptera / Q000502:physiology*; D013329:Structure-Activity Relationship; D013481:Superoxides
D016227:Benzoquinones; D007306:Insecticides; D009285:Naphthoquinones; D013481:Superoxides; C004532:quinone; C014758:plumbagin