title: Antimycobacterial coumarins from the sardinian giant fennel (Ferula communis).
abstract: The structure of a new prenylated coumarin (E-omega-benzoyloxyferulenol, 1b) from the Sardinian giant fennel (Ferula communis) has been confirmed by synthesis. The parent compound ferulenol (1a) showed sub-micromolar antimycobacterial activity, which was partly retained in 1b and in the simplified synthetic analogue 3, but diminished in its omega-hydroxy and omega-acetoxy derivatives (1c and 1d, respectively). The outstanding activity of 1a, its low toxicity, and the evidence for definite structure-activity relationships make this prenylated 4-hydroxycoumarin an interesting antibacterial chemotype worth further investigation.
authors.affiliation: Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Università del Piemonte Orientale, Viale Ferrucci 33, 28100 Novara, Italy. appendino@pharm.unipmn.it
authors.forename: Giovanni
authors.initials: G
authors.lastname: Appendino
authors.forename: Enrico
authors.initials: E
authors.lastname: Mercalli
authors.forename: Nicola
authors.initials: N
authors.lastname: Fuzzati
authors.forename: Lolita
authors.initials: L
authors.lastname: Arnoldi
authors.forename: Michael
authors.initials: M
authors.lastname: Stavri
authors.forename: Simon
authors.initials: S
authors.lastname: Gibbons
authors.forename: Mauro
authors.initials: M
authors.lastname: Ballero
authors.forename: Andrea
authors.initials: A
authors.lastname: Maxia
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005309:Ferula / Q000737:chemistry*; D007558:Italy; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D003374:Coumarins; C497313:E-omega-benzoyloxyferulenol; C092340:ferulenol