Ring A-seco mosquito larvicidal limonoids from Turraea wakefieldii.
Five novel limonoids, 1-5, were isolated from the root bark of Turraea wakefieldii and were characterized as tecleaninoid derivatives. This is the first report of the natural occurrence of tecleanin-type limonoids with a five-membered-ring A-seco structure for which we propose the name neotecleanins. The relative stereochemical structures of compounds 1-5 were established on the basis of NMR spectroscopy. The absolute stereochemical structure of 5 was confirmed by X-ray diffraction methods. In mosquito larvicidal assays, compounds 1, 2 and 4 showed dose-dependent larvicidal activity against larvae of Anopheles gambiae s.s.
Ndung'u
Mary
M
International Centre of Insect Physiology and Ecology (ICIPE), PO Box 30772, Nairobi, Kenya
Hassanali
Ahmed
A
Hooper
Antony M
AM
Chhabra
Sumesh
S
Miller
Thomas A
TA
Paul
Rowena L
RL
Torto
Baldwyn
B
D000818:Animals; D000852:Anopheles; D001681:Biological Assay / Q000379:methods; D018360:Crystallography, X-Ray; D007306:Insecticides / Q000737:chemistry* / Q000302:isolation & purification; D007814:Larva; D036701:Limonins / Q000737:chemistry* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D029582:Meliaceae / Q000737:chemistry*; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry; D013237:Stereoisomerism
D007306:Insecticides; D036701:Limonins