Antifungal amides from Piper arboreum and Piper tuberculatum.
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.
Vasques da Silva
Renata
R
Instituto de Química, Universidade Estadual Paulista, CP 355, 14800-900, Araraquara-SP, Brazil. maysaf@iq.unesp.br
Navickiene
Hosana M Debonsi
HM
Kato
Massuo J
MJ
Bolzani
Vanderlan da S
Vda S
Méda
Christiane I
CI
Young
Maria Claudia M
MC
Furlan
Maysa
M
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*
D000577:Amides; D000935:Antifungal Agents