STRUCTURAL ELUCIDATION AND ABSOLUTE-CONFIGURATION OF NOVEL BETA-AGAROFURAN (EPOXYEUDESMENE) SESQUITERPENES FROM MAYTENUS-MAGELLANICA (CELASTRACEAE)

被引:20
作者
GONZALEZ, AG [1 ]
NUNEZ, MP [1 ]
RAVELO, AG [1 ]
SAZATORNIL, JG [1 ]
VAZQUEZ, JT [1 ]
BAZZOCCHI, IL [1 ]
MORALES, EQ [1 ]
MUNOZ, OM [1 ]
机构
[1] UNIV SANTIAGO DE COMPOSTELA,FAC CIENCIAS,DEPT QUIM,SANTIAGO,SPAIN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 11期
关键词
D O I
10.1039/p19920001437
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Six dihydro-beta-agarofuran [5,11-epoxy-5-beta,10-alpha-eudesm-4(14)-ene] sesquiterpenes with a novel substitution pattern were isolated from Maytenus magellanica and their structures were elucidated by means of H-1 and C-13 NMR spectroscopic studies, including H-1-C-13 heteronuclear correlation (HETCOR), long range correlation spectra with inverse detection (HMBC) and NOE experiments. Their absolute configurations were determined by application of the CD exciton chirality method while hydrolysis and preparation of derivatives provided additional information. One of the sesquiterpenes exhibited significant antifeedant activity against Spodoptera littoralis.
引用
收藏
页码:1437 / 1441
页数:5
相关论文
共 20 条
[1]  
BAX A, 1986, J AM CHEM SOC, V108, P1093
[2]  
BRUNING R, 1978, PHYTOCHEMISTRY, V17, P1821, DOI 10.1016/S0031-9422(00)88719-1
[3]  
CROMBIE L, 1986, J CHEM SOC P61, P53
[4]  
DENHERTOG HJ, 1974, TETRAHEDRON LETT, V26, P2219
[5]  
Gonzalez A. G., 1988, REV LATINOAM QUIM, V19, P36
[6]  
GONZALEZ AG, 1983, IL FARMACO, V43, P501
[7]  
HARADA N, 1983, CIRCULAR DICHROIC SP
[8]  
HARADA N, 1969, J AM CHEM SOC, V91, P2989
[9]   MAYTOLINE, MAYTINE, AND MAYTOLIDINE, NOVEL NICOTINOYL SESQUITERPENE ALKALOIDS FROM MAYTENUS-SERRATA (HOCHST, EX A RICH) R WILCZEK [J].
KUPCHAN, SM ;
SMITH, RM .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (01) :115-118
[10]  
LOESENER T, 1978, NATURLICHEN PFLANZEF, V3, P189