Antifungal amides from Piper arboreum and Piper tuberculatum.

Phytochemistry

Instituto de Química, Universidade Estadual Paulista, CP 355, 14800-900, Araraquara-SP, Brazil.

Published: March 2002

AI Article Synopsis

  • The study focuses on isolating various amides from the Piperaceae family, specifically from the leaves of Piper arboreum and Piper tuberculatum.
  • Two new amides were discovered, along with several known compounds, and additional amides were synthesized through catalytic hydrogenation.
  • The isolated compounds exhibited antifungal properties, particularly against the fungi Cladosporium sphaerospermum and C. cladosporioides.

Article 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.

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http://dx.doi.org/10.1016/s0031-9422(01)00431-9DOI Listing

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