Insecticidal Properties of Some Metabolites of JamaicanPiperspp., and the Amides Synthesized from 5,6-ZandE-Butenolides ofPiper fadyenii

Nair, Muraleedharan G.; Mansingh, Ajay P.; Burke, Basil A.

doi:10.1080/00021369.1986.10867898

Cited by 4 publications

(5 citation statements)

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“…Therefore, the compound 1 was identified as 4,6-dimethoxy-5-E-phenylbutenolide (5,6-E-fadyenolide), previously isolated from roots of Piper fadyenii. 6,7 The LREIMS spectrum of 1 and 2 showed the same molecular ion-peak and fragment ions, suggesting similar structures. The IR spectrum with bands at 1745, 1592, 1493, and 1443 cm -1 confirming the presence of conjugated lactone group and aromatic ring in the structure of compound 2.…”

Section: Resultsmentioning

confidence: 82%

“…Therefore, the compound 2 was identified as 4,6-dimethoxy-5-Z-phenylbutenolide, as previously defined to 5,6-Z-fadyenolide, also isolated from roots and aerial parts of Piper fadyenii. 6,7 There are only few report of piperolides in Piperaceae species and to date they have been described from Piper fadyenii 6,7 and P. sanctum 8,9 which occur from Jamaica and Mexico, respectively. In such reports 8 the NMR data of compounds 1 and 2 were assigned only to the butenolide moiety.…”

Section: Resultsmentioning

confidence: 99%

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Antifungal piperolides from Piper malacophyllum (Prels) C. DC.

Lago¹,

Tanizaki²,

Young³

et al. 2005

J. Braz. Chem. Soc.

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O estudo fitoquímico biomonitorado do extrato em CH 2 Cl 2 das folhas de Piper malacophyllum através da técnica de bioautografia frente a fungos, resultou no isolamento de dois piperolidos bioativos: 4,6-dimetóxi-5-E-fenilbutenolido (1) e 4,6-dimetóxi-5-Z-fenilbutenolido (2). Essas substâncias foram identificadas com base na análise dos espectros de IV, EM e RMN, incluindo técnicas bidimensionais, e comparação com dados descritos na literatura. A configuração E da ligação dupla confere maior atividade para 1 considerando-se que as quantidades mínimas de 1 e 2 necessária para inibir o crescimento dos fungos Cladosporium cladosporioides e C. sphaerospermum foram de 1,0/1,0 µg (1) e de 5,0/10,0 µg (2), respectivamente.Bioactivity-guided fractionation of the CH 2 Cl 2 extract from leaves of Piper malacophyllum using bioautography assay against fungi, led to the isolation of two known bioactive piperolides: 4,6-dimethoxy-5-E-phenylbutenolide (1) and 4,6-dimethoxy-5-Z-phenylbutenolide (2). IR, MS and NMR spectroscopic data were used for the identification of these compounds including comparison with previously reported data. The E configuration is associated to higher activity for compound 1, since the minimum amount required for the growth inhibition of Cladosporium cladosporioides and C. sphaerospermum were 1.0/1.0 µg (1) and 5.0/10.0 µg (2), respectively.

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Section: Resultsmentioning

confidence: 82%

Section: Resultsmentioning

confidence: 99%

Antifungal piperolides from Piper malacophyllum (Prels) C. DC.

Lago¹,

Tanizaki²,

Young³

et al. 2005

J. Braz. Chem. Soc.

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“…Downloaded Much has been written about the effects of black pepper (Piper nigrum L.) extracts on house flies (52,53,54) especially the compounds piperine, pellitorine, and pipericide. In a particularly imaginative piece of work, Nair et al, (55) isolated Z and E-fadyenolide ( Figure 19) from Piper fadyenii with a view to accomplishing two goals. To open the fadyenolide ring at the oxygen bridge, and to replace the exocyclic carbonyl with a nitrogen thereby making a piperine analog.…”

Section: In a Series Of Short-stepmentioning

confidence: 98%

Natural Products and Their Potential in Agriculture

Cutler¹

1988

ACS Symposium Series

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Biologically active natural products are derived from three major sources: the fermentation of microorganisms, higher plants, and insects. However, compounds derived from these sources may act within each or all of these domains. That is, compounds derived from microorganisms and higher plants may affect insects and vice versa. Often, natural products are obtained in limited quantities and small yields do not lend themselves to extensive testing. During the past three years there has been increased synthesis of natural product templates and their analogs for evaluation in biological systems. Relative to these approaches, assorted natural products from microorganisms, including oligopeptides, acyclic polyketols and some relatively simple molecules are examined. The brassinosteroids and photodynamic herbicides, from higher plants, are discussed. Finally, compounds that are produced by insects, or which affect insects, are reviewed.In common with my primal ancestors, whose life began in a garden, my first recollections were not so much of people but of trees, flowers, the sun, rain, clouds, blue sky, and the sound of the cuckoo. Especially imprinted on my senses was the peppery smell of lupin at the early age of two, and there followed the scent of roses and English lavender: dire warnings about foxglove and deadly nightshade were issued as I wandered about gardens. An introduction to the world of secondary metabolites had started early in life and subsequently led to my first scientific job, in the mid

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“…24,25 Despite the high distribution of flavanones 26 , the presence of dihydrochalcones in the genus Piper has been restricted to P. aduncum, 10,18-20,27-29 P. fadyenii, 20 and P. hispidum. [18][19][20] All of the isolated chromenes, dihydrochalcone, and flavanones are being reported here for the first time in P. mollicomum, since no phytochemical studies have previously been conducted with this species. Otherwise, although chromenes and flavonoids have previously been reported in P. lhotzkyanum, 3,4 the occurrence of 4 and 7 has been described at first time in this species.…”

Section: -13mentioning

confidence: 99%

Antifungal derivatives from Piper mollicomum and P. lhotzkyanum (Piperaceae)

Lago¹,

Young²,

Reigada³

et al. 2007

Quím. Nova

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Recebido em 28/7/06; aceito em 9/3/07; publicado na web em 24/7/07Bioguided fractionation of the extracts from leaves of Piper mollicomum and Piper lhotzkyanum against the fungi Cladosporium cladosporioides and C. sphaerospermum afforded seven bioactive compounds, four being chromenes: methyl 2,2-dimethyl-2H-chromene-6-carboxylate, methyl 8-hydroxy-2,2-dimethyl-2H-chromene-6-carboxylate, 2-methyl-2-[4'-methyl-3'-pentenyl]-2H-1-benzopyran-6-carboxylic acid, 2,2-dimethyl-2H-chromene-6-carboxylic acid, one a dihydrochalcone: 2',6'-dihydroxy-4'-methoxydihydrochalcone, and two flavanones: 7-methoxy-5,4'-dihydroxy-flavanone and 7,4'-dimethoxy-5-hydroxy-flavanone. The structures of the bioactive isolated derivatives were elucidated by interpretation of their NMR data [ 1 H and 13 C (BBD, DEPT 135°)], and mass spectral data as well as by comparison with data described in the literature.

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Insecticidal Properties of Some Metabolites of JamaicanPiperspp., and the Amides Synthesized from 5,6-ZandE-Butenolides ofPiper fadyenii

Cited by 4 publications

References 3 publications

Antifungal piperolides from Piper malacophyllum (Prels) C. DC.

Antifungal piperolides from Piper malacophyllum (Prels) C. DC.

Natural Products and Their Potential in Agriculture

Antifungal derivatives from Piper mollicomum and P. lhotzkyanum (Piperaceae)

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