title: Antifungal amides from Piper arboreum and Piper tuberculatum.
abstract: In continuation of our study of the Piperaceae we have isolated several amides, mainly those bearing isobutyl, pyrrolidine, dihydropyridone and piperidine moieties. Bioactivity-guided fractionation of extracts from leaves of Piper arboreum yielded two new amides, N-[10-(13,14-methylenedioxyphenyl)-7(E),9(Z)-pentadienoyl]-pyrrolidine (1), arboreumine (2) together with the known compounds N-[10-(13,14-methylenedioxyphenyl)-7(E)-pentaenoyl]-pyrrolidine (3) and N-[10-(13,14-methylenedioxyphenyl)-7(E),9(E)-pentadienoyl]-pyrrolidine (4). Catalytic hydrogenation of 3 yielded the amide N-[10-(13,14-methylenedioxyphenyl)-pentanoyl]-pyrrolidine (5). We also have isolated six amides (6-11) and two antifungal cinnamoyl derivatives (12, 13) from seeds and leaves of Piper tuberculatum. Compounds 1-11 showed antifungal activity as determined by direct bioautography against Cladosporium sphaerospermum while compounds 3-4 and 6-13 also showed antifungal activity against C. cladosporioides.
authors.affiliation: Instituto de Química, Universidade Estadual Paulista, CP 355, 14800-900, Araraquara-SP, Brazil. maysaf@iq.unesp.br
authors.forename: Renata
authors.initials: R
authors.lastname: Vasques da Silva
authors.forename: Hosana M Debonsi
authors.initials: HM
authors.lastname: Navickiene
authors.forename: Massuo J
authors.initials: MJ
authors.lastname: Kato
authors.forename: Vanderlan da S
authors.initials: Vda S
authors.lastname: Bolzani
authors.forename: Christiane I
authors.initials: CI
authors.lastname: Méda
authors.forename: Maria Claudia M
authors.initials: MC
authors.lastname: Young
authors.forename: Maysa
authors.initials: M
authors.lastname: Furlan
mesh_terms: D000577:Amides / Q000737:chemistry / Q000302:isolation & purification*; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D026321:Piperaceae / Q000737:chemistry*
chemical_list: D000577:Amides; D000935:Antifungal Agents