title: Coumarins from Opopanax chironium. New dihydrofuranocoumarins and differential induction of apoptosis by imperatorin and heraclenin.
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.
authors.affiliation: Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Università del Piemonte Orientale, Via Bovio 6, 28100 Novara, Italy. appendino@pharm.unipmn.it
authors.forename: Giovanni
authors.initials: G
authors.lastname: Appendino
authors.forename: Federica
authors.initials: F
authors.lastname: Bianchi
authors.forename: Ammar
authors.initials: A
authors.lastname: Bader
authors.forename: Claudio
authors.initials: C
authors.lastname: Campagnuolo
authors.forename: Ernesto
authors.initials: E
authors.lastname: Fattorusso
authors.forename: Orazio
authors.initials: O
authors.lastname: Taglialatela-Scafati
authors.forename: Magdalena
authors.initials: M
authors.lastname: Blanco-Molina
authors.forename: Antonio
authors.initials: A
authors.lastname: Macho
authors.forename: Bernd L
authors.initials: BL
authors.lastname: Fiebich
authors.forename: Paul
authors.initials: P
authors.lastname: Bremner
authors.forename: Michael
authors.initials: M
authors.lastname: Heinrich
authors.forename: Mauro
authors.initials: M
authors.lastname: Ballero
authors.forename: Eduardo
authors.initials: E
authors.lastname: Muñoz
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019661:Apiaceae / Q000737:chemistry*; D017209:Apoptosis / Q000187:drug effects*; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007558:Italy; D019169:Jurkat Cells; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D012802:Sicily; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D003374:Coumarins