PAF-antagonistic bicyclo[3.2.1]octanoid neolignans from leaves of Ocotea macrophylla Kunth. (Lauraceae).
Di-nor-benzofuran neolignan aldehydes, Delta(7)-3,4-methylenedioxy-3'-methoxy-8',9'-dinor-4',7-epoxy-8,3'-neolignan-7'-aldehyde (ocophyllal A) 1, Delta(7)-3,4,5,3'-tetramethoxy-8',9'-dinor-4',7-epoxy-8,3'-neolignan-7'-aldehyde (ocophyllal B) 2, and macrophyllin-type bicyclo[3.2.1]octanoid neolignans (7R, 8R, 3'S, 4'S, 5'R)-Delta(8)'-4'-hydroxy-5'-methoxy-3,4-methylenedioxy-2',3',4',5'-tetrahydro-2'-oxo-7.3',8.5'-neolignan (ocophyllol A) 3, (7R, 8R, 3'S, 4'S, 5'R)-Delta(8)'-4'-hydroxy-3,4,5'-trimethoxy-2',3',4',5'-tetrahydro-2'-oxo-7.3',8.5'-neolignan (ocophyllol B) 4, (7R, 8R, 3'S, 4'S, 5'R)-Delta(8)'-4'-hydroxy-3,4,5,5'-tetramethoxy-2',3',4',5'-tetrahydro-2'-oxo-7.3',8.5'-neolignan (ocophyllol C) 5, as well as 2'-epi-guianin 6 and (+)-licarin B 7, were isolated and characterized from leaves of Ocotea macrophylla (Lauraceae). The structures and configuration of these compounds were determined by extensive spectroscopic analyses. Inhibition of platelet activating factor (PAF)-induced aggregation of rabbit platelets were tested with neolignans 1-7. Although compound 6 was the most potent PAF-antagonist, compounds 3-5 showed some activity.
Coy-Barrera
Ericsson D
ED
Universidad Nacional de Colombia, Facultad de Ciencias, Departamento de Química, Laboratorio de Investigación en Productos Naturales Vegetales, Ciudad Universitaria, Cra 30 45-03, AA 14490, Bogotá DC, Colombia. edcoyb@unal.edu.co
Cuca-Suárez
Luis E
LE
Sefkow
Michael
M
D000447:Aldehydes / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D017705:Lignans / Q000737:chemistry* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D027444:Ocotea / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry*; D010972:Platelet Activating Factor / Q000037:antagonists & inhibitors*; D010974:Platelet Aggregation / Q000187:drug effects; D011817:Rabbits
D000447:Aldehydes; D017705:Lignans; D010972:Platelet Activating Factor