STIMULATION OF WITCHWEED GERMINATION BY SESQUITERPENE LACTONES - A STRUCTURE ACTIVITY STUDY

被引:57
作者
FISCHER, NH [1 ]
WEIDENHAMER, JD [1 ]
RIOPEL, JL [1 ]
QUIJANO, L [1 ]
MENELAOU, MA [1 ]
机构
[1] UNIV VIRGINIA,DEPT BIOL,CHARLOTTESVILLE,VA 22901
基金
美国国家科学基金会;
关键词
costunolide; dihydroparthenolide; eudesmanolides; germacranolides; germination stimulation; parthenolide; pseudoguaianolides; reynosin; santamarin; Scrophulariaceae; sesquiterpene lactones; Striga asiatica; witchweed;
D O I
10.1016/0031-9422(90)85170-K
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
Twenty-four natural and synthetic sesquiterpene lactones were tested as witchweed germination stimulants to determine the essential structural requirements for the stimulation of witchweed germination by dihydroparthenolide. All of the 10 germacranolides tested induced 40-65% germination of witchweed across a broad concentration range, from 10-5 to 10-9 M. The highest activity was observed with a mixture of the two eudesmanolides, santamarin and reynosin. These findings indicate that it is the spatial arrangement of the germacrane-eudesmane skeleton in conjunction with the five-membered lactone ring which is important in the promotion of witchweed germination, rather than the presence of any specific functional group on the molecule. The structure of these compounds is similar to portions of the active molecule (+)-strigol. © 1990.
引用
收藏
页码:2479 / 2483
页数:5
相关论文
共 11 条
[1]   ISOLATION AND CHARACTERIZATION OF SESQUITERPENE LACTONES COSTUNOLIDE, PARTHENOLIDE, COSTUNOLIDE DIEPOXIDE, SANTAMARINE, AND REYNOSIN FROM MAGNOLIA-GRANDIFLORA L [J].
ELFERALY, FS ;
CHAN, YM .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1978, 67 (03) :347-350
[2]   MOLECULAR-STRUCTURE OF A CIS-DECALIN-TYPE EUDESMANOLIDE AND ITS FORMATION FROM A GUAIANOLIDE-1(10)-EPOXIDE [J].
FISCHER, NH ;
WUSHIH, YF ;
CHIARI, G ;
FRONCZEK, FR ;
WATKINS, SF .
JOURNAL OF NATURAL PRODUCTS, 1981, 44 (01) :104-110
[3]   DIHYDROPARTHENOLIDE AND OTHER SESQUITERPENE LACTONES STIMULATE WITCHWEED GERMINATION [J].
FISCHER, NH ;
WEIDENHAMER, JD ;
BRADOW, JM .
PHYTOCHEMISTRY, 1989, 28 (09) :2315-2317
[4]   NEW MELAMPOLIDE SESQUITERPENE LACTONES FROM MELAMPODIUM-LEUCANTHUM [J].
FISCHER, NH ;
WILEY, RA ;
LIN, HN ;
KARIMIAN, K ;
POLITZ, SM .
PHYTOCHEMISTRY, 1975, 14 (10) :2241-2245
[5]   NEW PSEUDOGUAIANOLIDES FROM AMBROSIA CONFERTIFLORA DC (COMPOSITAE) [J].
FISCHER, NH ;
MABRY, TJ .
TETRAHEDRON, 1967, 23 (06) :2529-&
[7]   BIOLOGICAL-ACTIVITIES OF SESQUITERPENE LACTONES [J].
PICMAN, AK .
BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 1986, 14 (03) :255-281
[8]  
RAMAIAH KV, 1983, STRIGA BIOL CONTROL, P71
[9]   TERPENOIDS .11. THE STRUCTURE OF COSTUNOLIDE, A NEW SESQUITERPENE LACTONE FROM COSTUS ROOT OIL [J].
RAO, AS ;
KELKAR, GR ;
BHATTACHARYYA, SC .
TETRAHEDRON, 1960, 9 (3-4) :275-283
[10]  
RODRIGUES AAS, 1978, PHYTOCHEMISTRY, V17, P953