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Biologically Active Triterpenoids of Biogenetic Interest from the Fresh Fruit Coats of Azadirachta indica

2000; Elsevier BV; Volume: 56; Issue: 22 Linguagem: Inglês

10.1016/s0040-4020(00)00244-1

1464-5416

Bina S. Siddiqui, Munawwer Rasheed, Ghiasuddin, Shaheen Faizi, S. N. H. Naqvi, Rana Muhammad Sabir Tariq,

Insect Resistance and Genetics

Two new triterpenoids of biogenetic interest, namely, 26,27-dinor-17-oxa-1, 14,20(22)-trien-3, 16-dioxo-7α-acetoxy-17β-methoxy-4,4,8-trimethyl(5α, 13α)-cholane (meliacinin) 1 and 24,25,26,27-tetranor-apotirucalla(-apoeupha)-7α-acetoxy-1,14,20(22)-trien-3-oxo-23-oic acid (azadironic acid) 2 have been isolated from the fresh fruit coats of Azadirachta indica. Their structures were established through comparative spectral studies. 1 is the first dinorapoeuphane with seco ring D of deoxygedunin type and 2 is the first tetranorapoeuphane with an open side chain representing a biogenetic intermediate between the intact triterpenoids and meliacins. Both 1 and 2 showed toxicity against mosquito (Anopheles stephensi) with LC50 13 and 4.5 ppm, respectively.