Two insecticidal tetranortriterpenoids from Azadirachta indica.
Two new triterpenoids, 6 alpha-O-acetyl-7-deacetylnimocinol [24,25,26,27-tetra-norapotirucalla-(apoeupha)-6 alpha-acetoxy-7 alpha-hydroxy-1,14,20,22-tetraen-21,23-epoxy-3-one] (1) and meliacinol [24,25,26,27-tetranorapotirucalla-(apoeupha)-1 alpha-trimethylacryloxy-21,23-6 alpha,28-diepoxy-16-oxo-17-oxa-14,20,22-trien-3 alpha,7 alpha-diol] (2) were isolated from the methanolic extract of the fresh leaves of Azadirachta indica (neem). Their structures have been elucidated through spectral studies, including 2D-NMR (COSY-45, NOESY, HMQC and HMBC). The bioactivity of these as well as of nimocinol, reported earlier from the same source, is reported. The first compound and nimocinol showed toxicity on fourth instar larvae of mosquitoes (Aedes aegypti) with LC50 values of 21 and 83 ppm, respectively. The second compound had no effect upto 100 ppm.
Siddiqui
B S
BS
H.E.J. Research Institute of Chemistry, University of Karachi, Pakistan. bina@khi.comsats.net.pk
Afshan
F
F
Ghiasuddin
Faizi
S
S
Naqvi
S N
SN
Tariq
R M
RM
D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification*
D007306:Insecticides; D014315:Triterpenes