Planta Med 2008; 74 - PB16
DOI: 10.1055/s-0028-1084362

Structure and biological activity of coumaquinoline A from Toddalia asiatica. First isolation of a naturally-occurring quinolone-coumarin dimer

H Furukawa 1, M Kato 1, C Ito 1, M Ju-ichi 2
  • 1Faculty of Pharmacy, Meijo University, Tempaku, Nagoya 468–8503, Japan
  • 2Faculty of Pharmaceutical Sciences, Mukogawa Women's University, Nishinomiya, Hyogo 663–8179, Japan

In a search for novel bioactive natural products from plant sources, we isolated a novel quinolone-coumarin dimer named coumaquinoline A from leaves of Toddalia asiatica (L.) Lam. (Rutaceae). Structure 1 was established on the basis of spectroscopic (HMBC, NOE, and MS) and synthetic methods. In a biological test of cytotoxicity against HL-60 cells, natural product 1 showed no activity. However, synthetic regio-isomer 2 showed significant cytotoxicity induced by apoptosis through the activation of the caspase-9 and caspase-3 pathways triggered by mitochondrial dysfunction.