NATURAL PRODUCT MODELS AS ALLELOCHEMICALS .1. POTENTIAL ALLELOPATHIC ACTIVITY OF SEVERAL SESQUITERPENE LACTONE MODELS

被引:102
作者
MACIAS, FA
GALINDO, JCG
MASSANET, GM
机构
[1] Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Apdo. 40, 11510 Puerto Real, Cádiz
关键词
SESQUITERPENE LACTONES; MELAMPOLIDES; CIS; CIS-GERMACRANOLIDES; GUAIANOLIDES; EUDESMANOLIDES; ALLELOPATHY; LACTUCA-SATIVA;
D O I
10.1016/0031-9422(92)80343-D
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A collection of 12 natural and synthetic sesquiterpene lactones with eudesmanolide, melampolide, cis,cis-germacranolide, and guaianolide skeletons have been prepared and tested as allelochemicals. The effect of a series of aqueous solutions at 10(-4)-10(-9) M of this collection is evaluated. The specific structural requirements related to their activity is discussed. The natural sesquiterpene lactones soulangianolide A, melampomagnolide A and B, zaluzanin C and isozaluzanin C have been synthesized from costunolide, parthenolide and dehydrocostuslactone using SeO2 and tert-butylhydroperoxide. The structures of the synthetic compounds were established by NMR spectroscopy.
引用
收藏
页码:1969 / 1977
页数:9
相关论文
共 21 条
[1]   MODE OF ACTION OF THE SESQUITERPENE LACTONE, TENULIN, FROM HELENIUM-AMARUM AGAINST HERBIVOROUS INSECTS [J].
ARNASON, JT ;
ISMAN, MB ;
PHILOGENE, BJR ;
WADDELL, TG .
JOURNAL OF NATURAL PRODUCTS, 1987, 50 (04) :690-695
[2]   NATURALLY OCCURRING TERPENE DERIVATIVES .133. NEW TYPE OF GERMACRANOLIDE FROM VERNONIA SPECIES [J].
BOHLMANN, F ;
BRINDOPKE, G ;
RASTOGI, RC .
PHYTOCHEMISTRY, 1978, 17 (03) :475-482
[3]  
DUKE S O, 1986, Reviews of Weed Science, V2, P15
[4]  
ELFERALY FS, 1984, PHYTOCHEMISTRY, V23, P2372
[5]  
ELFERALY FS, 1983, PHYTOCHEMISTRY, V22, P2239
[6]  
FISCHER N, 1986, SCI ALLELOPATHY, pCH12
[7]   STIMULATION OF WITCHWEED GERMINATION BY SESQUITERPENE LACTONES - A STRUCTURE ACTIVITY STUDY [J].
FISCHER, NH ;
WEIDENHAMER, JD ;
RIOPEL, JL ;
QUIJANO, L ;
MENELAOU, MA .
PHYTOCHEMISTRY, 1990, 29 (08) :2479-2483
[8]   INHIBITION AND PROMOTION OF GERMINATION BY SEVERAL SESQUITERPENES [J].
FISCHER, NH ;
WEIDENHAMER, JD ;
BRADOW, JM .
JOURNAL OF CHEMICAL ECOLOGY, 1989, 15 (06) :1785-1793
[9]  
FRAGA BM, 1991, NAT PROD REP, V8, P515
[10]   SESQUITERPENE LACTONES WITH ANTIBACTERIAL ACTIVITY FROM TANACETUM-ARGYROPHYLLUM VAR ARGYROPHYLLUM [J].
GOREN, N ;
JAKUPOVIC, J ;
TOPAL, S .
PHYTOCHEMISTRY, 1990, 29 (05) :1467-1469