Phytotoxins from Hofmeisteria schaffneri: isolation and synthesis of 2'-(2' '-hydroxy-4' '-methylphenyl)-2'-oxoethyl acetate1.
Activity-directed fractionation of a CH(2)Cl(2)-MeOH (1:1) extract of Hofmeisteria schaffneri led to the isolation of a new phytotoxin characterized as 2'-(2' '-hydroxy-4' '-methylphenyl)-2'-oxoethyl acetate and designated the trivial name of hofmeisterin (1). In addition, the known compounds beta-carotene, euparin, and 3',4',4a',9a'-tetrahydro-6,7'-dimethylspiro[benzofuran-3(2H),2'-pyrano[2,3-b]benzofuran]-2,4a'-diol (2) were obtained. The identification of the isolates was accomplished by spectroscopic methods. The structure of 1 was unequivocally confirmed by synthesis. The methyl derivative 1a was also synthesized following the same strategy. Compounds 1 and 2 inhibited radicle growth of Amaranthus hypochondriacus (IC(50) = 3.2 x 10(-4) and 1.2 x 10(-5) M, respectively) and significantly inhibited activation of the calmodulin (CaM)-dependent enzyme cAMP phosphodiesterase (PDE) with IC(50) values of 4.4 and 4.22 microM, respectively.
Pérez-Vásquez
Araceli
A
Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México.
Reyes
Adelfo
A
Linares
Edelmira
E
Bye
Robert
R
Mata
Rachel
R
D015105:3',5'-Cyclic-AMP Phosphodiesterases / Q000037:antagonists & inhibitors*; D027721:Amaranthus / Q000187:drug effects / Q000254:growth & development; D019659:Asteraceae / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D008800:Mexico; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*
C502718:2'-(2' '-hydroxy-4' '-methylphenyl)-2'-oxoethyl acetate; D004791:Enzyme Inhibitors; D010636:Phenols; D015105:3',5'-Cyclic-AMP Phosphodiesterases