Coumarins from Opopanax chironium. New dihydrofuranocoumarins and differential induction of apoptosis by imperatorin and heraclenin

  • J Nat Prod. 2004 Apr;67(4):532-6. doi: 10.1021/np0340652.
Giovanni Appendino  1 ,  Federica Bianchi ,  Ammar Bader ,  Claudio Campagnuolo ,  Ernesto Fattorusso ,  Orazio Taglialatela-Scafati ,  Magdalena Blanco-Molina ,  Antonio Macho ,  Bernd L Fiebich ,  Paul Bremner ,  Michael Heinrich ,  Mauro Ballero ,  Eduardo Muñoz
Affiliations
  • 1. Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Università del Piemonte Orientale, Via Bovio 6, 28100 Novara, Italy. [email protected]
PMID: 15104479 DOI: 10.1021/np0340652
Abstract

Opopanax chironium is a rich source of furano- and dihydrofuranocoumarins, whose accumulation in all plant parts and especially the roots is presumably responsible for the poisonous properties of the species. The presence of two distinct chemotypes was evidenced, with the one from Sicily affording the new dihydrofuranocoumarins 5d and 5e, while extracts from the Sardinian chemotype showed powerful apoptotic activity, which was traced to the prenylated furanocoumarins heraclenin (2a) and imperatorin (2b). Despite a close structural similarity, compounds 2a and 2b induced Apoptosis in Jurkat leukemia cells in mechanistically different ways.

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