Instituto de Ecología, UNAM. Circuito Exterior, Ciudad Universitaria, 04510, México, D.F.
Published: February 2005
AI Article Synopsis
Article Abstract
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.
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.
A combination of HPLC-MS and HPLC-NMR techniques has been used to analyse the cytotoxic fractions of the dichloromethane extract of bark of Stauranthus perforatus. Six furanocoumarins (byakangelicol, heraclenin, heraclenol, imperatorin, isopimpinellin and xanthotoxin) and nine quinoline alkaloids (two known compounds, veprisine and 5-hydroxy-1-methyl-2-phenyl-4-quinolone, along with seven novel compounds, stauranthine, 3',4'-dihydroxy-3',4'-dihydroveprisine, 3',4'-dihydroxy-3',4'-dihydrostauranthine, 3',6'-dihydroxy-3',6'-dihydroveprisine, 3',6'-dihydroxy-3',6'-dihydrostauranthine, 6'-hydroxy-3'-ketoveprisine and 6'-hydroxy-3'-ketostauranthine) have been identified in the fractions.
Xanthyletin (1), 3-(1',1'-dimethylallyl)xanthyletin (2), and chalepensin (3), the major coumarins isolated from Stauranthus perforatus, inhibit ATP synthesis from water to methylviologen in spinach thylakoids in a concentration-dependent manner. At low concentration chalepensin (3) inhibits basal and phosphorylating electron flow from water to K(3)[Fe(CN)(6)] without affecting uncoupled electron flow but accelerating Mg(2+)-ATPase activity. Thus, at low concentration the compound behaves as an energy transfer inhibitor.
