Two insecticidal tetranortriterpenoids from Azadirachta indica

被引:76
作者
Siddiqui, BS [1 ]
Afshan, F
Ghiasuddin
Faizi, S
Naqvi, SNH
Tariq, RM
机构
[1] Univ Karachi, HEJ Res Inst Chem, Karachi 75270, Pakistan
[2] Baqai Med Univ, Dept Pharmacol, Karachi, Pakistan
[3] Univ Karachi, Dept Zool, Karachi 75270, Pakistan
关键词
Azadirachta indica; Meliaceae; fresh leaves; bioactivity; tetranortriterpenoids; meliacinol; 6 alpha-O-acetyl-7-deacetyl nimocinol;
D O I
10.1016/S0031-9422(99)00548-8
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 [生物化学与分子生物学]; 081704 [应用化学];
摘要
Two new triterpenoids, 6 alpha-O-acetyr-7-deacelplnimocinol [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-)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 sourer, 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. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:371 / 376
页数:6
相关论文
共 14 条
[1]
Chopra R. N., 1956, GLOSSARY INDIAN MED, P31
[2]
KRAUS W, 1981, LIEBIGS ANN CHEM, P181
[3]
KRAUS W, 1981, NATURAL PESTICIDES N, P53
[4]
LIMONOIDS OF BIOGENETIC INTEREST FROM MELIA-AZADIRACHTA L [J].
LAVIE, D ;
LEVY, EC ;
JAIN, MK .
TETRAHEDRON, 1971, 27 (16) :3927-&
[5]
Nadkarni K. M., 1976, INDIAN MATERIA MED, V1, P776
[6]
NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY . A CORRELATION OF SPECTRA OF SOME MELIACINS AND THEIR DERIVATIVES [J].
POWELL, JW .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (20) :1794-&
[7]
Raymond M, 1993, PROBIT ANAL MORTALIT
[8]
Schmutterer H., 1995, The neem tree: Azadirachta indica A. Juss. and other meliaceous plants: sources of unique natural products for integrated pest management, medicine, industry
[9]
TRITERPENOIDS FROM THE FRESH FRUIT COATS OF AZADIRACHTA-INDICA [J].
SIDDIQUI, BS ;
GHIASUDDIN ;
FAIZI, S ;
SIDDIQUI, S .
PHYTOCHEMISTRY, 1992, 31 (12) :4275-4278
[10]
Tetracyclic triterpenoids of the fruit coats of Azadirachta indica [J].
Siddiqui, BS ;
Ghiasuddin ;
Faizi, S .
PHYTOCHEMISTRY, 1998, 47 (08) :1631-1636