Literature DB >> 11853747

Antifungal amides from Piper arboreum and Piper tuberculatum.

Renata Vasques da Silva1, Hosana M Debonsi Navickiene, Massuo J Kato, Vanderlan da S Bolzani, Christiane I Méda, Maria Claudia M Young, Maysa Furlan.   

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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Year:  2002        PMID: 11853747     DOI: 10.1016/s0031-9422(01)00431-9

Source DB:  PubMed          Journal:  Phytochemistry        ISSN: 0031-9422            Impact factor:   4.072


  16 in total

1.  A new hypoxia inducible factor-2 inhibitory pyrrolinone alkaloid from roots and stems of Piper sarmentosum.

Authors:  Heidi Rose Bokesch; Roberta Scott Gardella; Daniel Christopher Rabe; Donald Paul Bottaro; William Marston Linehan; James Brislin McMahon; Tawnya Carlene McKee
Journal:  Chem Pharm Bull (Tokyo)       Date:  2011       Impact factor: 1.645

2.  Fruit secondary compounds mediate the retention time of seeds in the guts of Neotropical fruit bats.

Authors:  Justin W Baldwin; Susan R Whitehead
Journal:  Oecologia       Date:  2014-09-28       Impact factor: 3.225

3.  Piperlongumine inhibits atherosclerotic plaque formation and vascular smooth muscle cell proliferation by suppressing PDGF receptor signaling.

Authors:  Dong Ju Son; Soo Yeon Kim; Seong Su Han; Chan Woo Kim; Sandeep Kumar; Byeoung Soo Park; Sung Eun Lee; Yeo Pyo Yun; Hanjoong Jo; Young Hyun Park
Journal:  Biochem Biophys Res Commun       Date:  2012-09-17       Impact factor: 3.575

4.  Ovicidal effect of Piperaceae species on Biomphalaria glabrata, Schistosoma mansoni host.

Authors:  Ludmila Nakamura Rapado; Priscila Orechio de Moraes Lopes; Lydia Fumiko Yamaguchi; Eliana Nakano
Journal:  Rev Inst Med Trop Sao Paulo       Date:  2013 Nov-Dec       Impact factor: 1.846

5.  Antifungal Compounds from Piper Species.

Authors:  Wen-Hui Xu; Xing-Cong Li
Journal:  Curr Bioact Compd       Date:  2011-12

6.  Shedding Light on Chemically Mediated Tri-Trophic Interactions: A 1H-NMR Network Approach to Identify Compound Structural Features and Associated Biological Activity.

Authors:  Lora A Richards; Celso Oliveira; Lee A Dyer; Arran Rumbaugh; Federico Urbano-Muñoz; Ian S Wallace; Craig D Dodson; Christopher S Jeffrey
Journal:  Front Plant Sci       Date:  2018-08-17       Impact factor: 5.753

Review 7.  Natural cinnamic acids, synthetic derivatives and hybrids with antimicrobial activity.

Authors:  Juan David Guzman
Journal:  Molecules       Date:  2014-11-25       Impact factor: 4.411

8.  Ontogenetic Changes in the Chemical Profiles of Piper Species.

Authors:  Anderson Melo Gaia; Lydia Fumiko Yamaguchi; Camilo Guerrero-Perilla; Massuo Jorge Kato
Journal:  Plants (Basel)       Date:  2021-05-28

9.  Schistosomiasis control using piplartine against Biomphalaria glabrata at different developmental stages.

Authors:  Ludmila Nakamura Rapado; Alessandro de Sá Pinheiro; Priscila Orechio de Moraes Victor Lopes; Harold Hilarion Fokoue; Marcus Tullius Scotti; Joaquim Vogt Marques; Fernanda Pires Ohlweiler; Sueli Ivone Borrely; Carlos Alberto de Bragança Pereira; Massuo Jorge Kato; Eliana Nakano; Lydia Fumiko Yamaguchi
Journal:  PLoS Negl Trop Dis       Date:  2013-06-06

10.  Secondary Metabolic Profiles of Two Cultivars of Piper nigrum (Black Pepper) Resulting from Infection by Fusarium solani f. sp. piperis.

Authors:  Shirlley F M da Luz; Lydia F Yamaguchi; Massuo J Kato; Oriel F de Lemos; Luciana P Xavier; José Guilherme S Maia; Alessandra de R Ramos; William N Setzer; Joyce Kelly do R da Silva
Journal:  Int J Mol Sci       Date:  2017-12-07       Impact factor: 5.923

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