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Antifungal amides from Piper arboreum and Piper tuberculatum.
Phytochemistry. 2002 Mar; 59(5):521-7.P

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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Authors+Show Affiliations

Vasques da Silva R
Instituto de Química, Universidade Estadual Paulista, CP 355, 14800-900, Araraquara-SP, Brazil. maysaf@iq.unesp.br
Navickiene HM
No affiliation info available
Kato MJ
No affiliation info available
Bolzani Vda S
No affiliation info available
Méda CI
No affiliation info available
Young MC
No affiliation info available
Furlan M
No affiliation info available

MeSH

AmidesAntifungal AgentsMagnetic Resonance SpectroscopyMolecular StructurePiperaceae

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

11853747

Citation

Vasques da Silva, Renata, et al. "Antifungal Amides From Piper Arboreum and Piper Tuberculatum." Phytochemistry, vol. 59, no. 5, 2002, pp. 521-7.
Vasques da Silva R, Navickiene HM, Kato MJ, et al. Antifungal amides from Piper arboreum and Piper tuberculatum. Phytochemistry. 2002;59(5):521-7.
Vasques da Silva, R., Navickiene, H. M., Kato, M. J., Bolzani, V. d. a. . S., Méda, C. I., Young, M. C., & Furlan, M. (2002). Antifungal amides from Piper arboreum and Piper tuberculatum. Phytochemistry, 59(5), 521-7.
Vasques da Silva R, et al. Antifungal Amides From Piper Arboreum and Piper Tuberculatum. Phytochemistry. 2002;59(5):521-7. PubMed PMID: 11853747.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Antifungal amides from Piper arboreum and Piper tuberculatum. AU - Vasques da Silva,Renata, AU - Navickiene,Hosana M Debonsi, AU - Kato,Massuo J, AU - Bolzani,Vanderlan da S, AU - Méda,Christiane I, AU - Young,Maria Claudia M, AU - Furlan,Maysa, PY - 2002/2/21/pubmed PY - 2002/5/23/medline PY - 2002/2/21/entrez SP - 521 EP - 7 JF - Phytochemistry JO - Phytochemistry VL - 59 IS - 5 N2 - 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. SN - 0031-9422 UR - https://www.unboundmedicine.com/medline/citation/11853747/Antifungal_amides_from_Piper_arboreum_and_Piper_tuberculatum_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0031942201004319 DB - PRIME DP - Unbound Medicine ER -