Allelochemicals from Stauranthus perforatus, a Rutaceous tree of the Yucatan Peninsula, Mexico.
Aqueous leachates and a CHCl3-MeOH (1:1) extract of roots of Stauranthus perforatus showed a significant phytotoxic effect on Amaranthus hypochondriacus and Echinochloa crus-galli. Bioassay-directed fractionation of the active organic extract led to the isolation and characterization of ten secondary metabolites, which included two pyranocoumarins [xanthyletin (1) and 3-(1',1'-dimethylallyl)-xanthyletin (2)], four furanocoumarins [chalepensin (3), ammirin (4), chalepin (5) and 2'-isopropyl-psoralene (6)], two lignans [asarinin (7) and fargesin (8)], one sesquiterpene [4,5-epoxi-beta-caryophyllene (9)], and one alkamide [pellitorine (10)]. From these compounds, 2'-isopropyl-psoralene (6) or anhydromarmesin, is reported for the first time as a natural product, whereas compounds 4-10 are now reported as being present in S. perforatus. Metabolites 1, 3-5 and 10 caused significant inhibition of radicle growth of A. hypochondriacus and E. crus-galli. Furthermore, in a greenhouse experiment the decomposition of the leaves and roots in the soil had a significant inhibitory effect on the growth of weeds. The allelopathic action of the decomposition of roots was evident up to the sixth week of the experiment. The effect of leaves was comparable to that of DPCA (dimethyl tetrachloroterephthalate), a commercial herbicide. Finally different concentrations of Stauranthus root powder were combined with maize kernels and used to feed corn weevil. The treatments resulted in high mortality of this insect.
Anaya
Ana Luisa
AL
Instituto de Ecología, UNAM. Circuito Exterior, Ciudad Universitaria, 04510, México, D.F. alanaya@miranda.ecologia.unam.mx
Macías-Rubalcava
Martha
M
Cruz-Ortega
Rocío
R
García-Santana
Clara
C
Sánchez-Monterrubio
Perla N
PN
Hernández-Bautista
Blanca E
BE
Mata
Rachel
R
D000818:Animals; D001681:Biological Assay; D008800:Mexico; D015394:Molecular Structure; D010675:Pheromones / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology / Q000633:toxicity; D018517:Plant Roots / Q000187:drug effects / Q000254:growth & development; D027821:Rutaceae / Q000737:chemistry* / Q000187:drug effects / Q000254:growth & development; D014197:Trees / Q000737:chemistry* / Q000187:drug effects / Q000254:growth & development
D010675:Pheromones