Luteolin, a Compound with Adenosine A1 Receptor-Binding Activity, and Chromone and Dihydronaphthalenone Constituents from Senna siamea

Activity-guided fractionation led to the isolation of luteolin (1) from the leaves of Senna siamea (syn. Cassia siamea). This compound was found to be an antagonist at the adenosine A(1) receptor with a K(i) value in the low micromolar range. Four additional nonactive compounds (2-5) were also isolated, and their structures were elucidated. One compound was identified as cassia chromone (5-acetonyl-7-hydroxy-2-methylchromone) (2). Three other compounds are new, and they were identified as 5-acetonyl-7-hydroxy-2-hydroxymethyl-chromone (3), 4-(trans)-acetyl-3,6,8-trihydroxy-3-methyldihydronaphthalenone (4), and 4-(cis)-acetyl-3,6,8-trihydroxy-3-methyldihydronaphthalenone (5).