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Electro-oxidation of hispanolone and anti-inflammatory properties of the obtained derivatives
Elizabeth Nieto-Mendoza1, Juan A Guevara-Salazar, María Teresa Ramírez-Apan
1Instituto de Química de la Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán C.P. 04510, Mexico.
Abstract:
The electrochemical oxidation ((+)Pt-Ni(-)/NH(4)Br/MeOH) of the natural product hispanolone (1a) produced, in high yield (>95%), spiro-tetracyclic compounds 7a-7d as a result of the intramolecular addition of the C-9 hydroxyl group into the C-16 position with the simultaneous addition of a CH(3)O group at the C-15 position of the hispanolone furan moiety. After the electrochemical oxidation, an acid-catalyzed slow secondary reaction occurred producing the previously undescribed alpha-butenolide derivative, iso-Leopersin G (9). An anti-inflammatory study with the electro-synthesized compounds showed that 1a has higher anti-inflammatory properties with very low cytotoxicity (e.g., the inhibition of TPA-induced ear edema assay IC(50) = 1.05 microM/ear, positive control indomethacin IC(50) = 0.27 microM/ear).
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