Antimycobacterial coumarins from the sardinian giant fennel (Ferula communis).
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.
Appendino
Giovanni
G
Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Università del Piemonte Orientale, Viale Ferrucci 33, 28100 Novara, Italy. appendino@pharm.unipmn.it
Mercalli
Enrico
E
Fuzzati
Nicola
N
Arnoldi
Lolita
L
Stavri
Michael
M
Gibbons
Simon
S
Ballero
Mauro
M
Maxia
Andrea
A
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
D000900:Anti-Bacterial Agents; D003374:Coumarins; C497313:E-omega-benzoyloxyferulenol; C092340:ferulenol