Antifeedant rings B and D opened limonoids from Khaya senegalensis

被引:54
作者
Nakatani, M
Abdelgaleil, SAM
Kurawaki, J
Okamura, H
Iwagawa, T
Doe, M
机构
[1] Kagoshima Univ, Fac Sci, Dept Chem & Biosci, Kagoshima 8900065, Japan
[2] Univ Alexandria, Fac Agr, Dept Pesticide Chem, Alexandria, Egypt
[3] Osaka City Univ, Grad Sch Sci, Dept Chem, Sumiyoshi Ku, Osaka 5588585, Japan
来源
JOURNAL OF NATURAL PRODUCTS | 2001年 / 64卷 / 10期
关键词
D O I
10.1021/np010082k
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Three new rings B and D opened limonoids, two mexicanolides named khayanone (1) and 2-hydroxy-seneganolide (2) and one rearranged phragmalin limonoid of 1-O-acetylkhayanolide A (3), were isolated together with six known B,D-seco compounds from the acetone extract of the stem bark of Khaya senegalensis. Structures of new compounds were elucidated by spectroscopic means, and the absolute stereochemistry of 1 was established by CD study of the dibenzoate derivative. The insect antifeedant and antiviral activities of the new compounds were also determined.
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收藏
页码:1261 / 1265
页数:5
相关论文
共 20 条
[1]  
Abdelgaleil SAM, 2000, HETEROCYCLES, V53, P2233
[2]   Khayanolides, rearranged phragmalin limonoid antifeedants from Khaya senegalensis [J].
Abdelgaleil, SAM ;
Okamura, H ;
Iwagawa, T ;
Sato, A ;
Miyahara, I ;
Doe, M ;
Nakatani, M .
TETRAHEDRON, 2001, 57 (01) :119-126
[3]   LIMONOID CHEMISTRY OF GENUS KHAYA (MELIACEAE) [J].
ADESIDA, GA ;
STYLES, BT .
PHYTOCHEMISTRY, 1971, 10 (08) :1845-&
[4]  
Dalziel J. M., 1937, USEFUL PLANTS W TROP, P325
[5]   EXCITON CHIRALITY METHOD AND ITS APPLICATION TO CONFIGURATIONAL AND CONFORMATIONAL STUDIES OF NATURAL-PRODUCTS [J].
HARADA, N ;
NAKANISHI, K .
ACCOUNTS OF CHEMICAL RESEARCH, 1972, 5 (08) :257-+
[6]  
LEY SV, 1993, NAT PROD REP, P109
[7]   TRICHILININ, A NEW HEXACYCLIC LIMONOID FROM TRICHILIA-ROKA [J].
NAKATANI, M ;
IWASHITA, T ;
MIZUKAWA, K ;
HASE, T .
HETEROCYCLES, 1987, 26 (01) :43-46
[8]   3 NEW ANTIFEEDING MELIACARPININS FROM CHINESE MELIA-AZEDARACH LINN [J].
NAKATANI, M ;
HUANG, RC ;
OKAMURA, H ;
IWAGAWA, T ;
TADERA, K ;
NAOKI, H .
TETRAHEDRON, 1995, 51 (43) :11731-11736
[9]   Seneganolide, a novel antifeeding mexicanolide from Khaya senegalensis [J].
Nakatani, M ;
Abdelgaleil, SAM ;
Okamura, K ;
Iwagawa, T ;
Doe, M .
CHEMISTRY LETTERS, 2000, (08) :876-877
[10]   Khayanolides A and B, new rearranged phragmalin limonoid antifeedants from Khaya senegalensis [J].
Nakatani, M ;
Abdelgaleil, SAM ;
Okamura, H ;
Iwagawa, T ;
Sato, A ;
Doe, M .
TETRAHEDRON LETTERS, 2000, 41 (33) :6473-6477