An Overview of Neolignans of the Genus Piper L.: Isolation Methods and Biological Activities

Macedo, Arthur Ladeira; Santos, Thais Carvalho Costa dos; Valverde, Alessandra L.; Moreira, Davyson de Lima; Vasconcelos, Thatyana R. A.

doi:10.2174/1389557516666161130094826

Cited by 17 publications

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“…The major constituent of the crude extract is formed through the selective oxidation of the allyl group of the phenolic ring. A variety of neolignans have been isolated from other Piper species, but this represents the first example that contains a hydroxylated propenyl side chain (Macedo et al, 2017). While the conversion of the alcohol to ketone 3 is anticipated to be facile, compound 3 was not always present in detectable concentrations in the crude extracts of the leaves.…”

Section: Discussionmentioning

confidence: 95%

Isolation of new neolignans and an unusual meroterpenoid from Piper cabagranum

de Oliveira,

Ledvina,

Leonard

et al. 2024

Front. Nat. Prod.

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A novel meroterpenoid cabagranin D was isolated with related neolignans cabagranins A–C from the leaves of Piper cabagranum (Costa Rica). Cabagranins A–C represent the first examples of 3,3′-neolignans isolated from the plant genus Piper, and the meroterpenoid cabagranin D displays an unprecedented Diels–Alder conjugate of an unsubstituted phenylpropenone and α-phellandrene. Details of the full structural elucidation of these compounds and a discussion of their potential biosynthetic relationships are presented.

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Section: Discussionmentioning

confidence: 95%

Isolation of new neolignans and an unusual meroterpenoid from Piper cabagranum

de Oliveira,

Ledvina,

Leonard

et al. 2024

Front. Nat. Prod.

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“…Nevertheless, some phenolic compounds have been found in the leaves of a few Piper species in La Selva, including two that are part of our experimental communities (Baldwin & Schultz, 1988; Conde‐Hernandez & Guerrero‐Beltran, 2014; Diaz et al, 2012; Maxwell et al, 1999). A very notable exception are the neolignans, a group of less common phenolic compounds that are abundant and diverse across the Piperaceae, and that cannot be detected via GC–MS (Chen et al, 2021; Jensen et al, 1994; Macedo et al, 2017; Maxwell et al, 1999). Contrastingly, terpenoids (from monoterpenes to sesquiterpenes), smaller phenylpropanoids, and alkaloids (imide and amide alkaloids for Piperaceae) can be easily detected using standard GC–MS equipment and have been shown to play key roles in Piper defense (Benevides et al, 1999; Dyer et al, 2001; Parmar et al, 1997, 1998; Whitehead & Bowers, 2014).…”

Section: Discussionmentioning

confidence: 99%

Testing the role of local plant chemical diversity on plant–herbivore interactions and plant species coexistence

Salazar

Marquis

2022

Ecology

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Accumulating evidence suggests that herbivorous insects influence the local composition and richness of Neotropical plant species, particularly in species‐rich genera. Species richness, phylogenetic diversity, and chemical diversity all influence the ability of insect herbivores to find and utilize their hosts. The relative impact of these components of diversity on species coexistence and plant–herbivore interactions is not well understood. We constructed 60 local communities of up to 13 species of Piper (Piperaceae) in native, mature forest at a lowland wet forest location in Costa Rica. The species composition of each community was chosen such that species richness, phylogenetic diversity, and GCMS‐based chemical diversity were varied independently among communities. We predicted that chemical diversity would most strongly affect the communities across time, with smaller effects of taxonomic and phylogenetic diversity. At 13 months after the experimental planting, we assessed survivorship of each cutting, measured total leaf area loss of the survivors, leaf area loss to generalist and specialist herbivorous insect species, and local extinction of species. Generalist and specialist herbivory decreased with increasing levels of species richness and phylogenetic diversity, respectively. Surprisingly, there was no independent effect of chemical diversity on any of the three measures of herbivore damage. Nevertheless, plots with a higher chemical and phylogenetic diversity showed decreased plant mortality and local species extinction. Overall, our results suggested that both chemical and phylogenetic similarity are important factors in the assembly and maintenance of tropical plant communities. The fact that chemical diversity influences plant mortality suggests that leaf herbivores, and possibly other plant natural enemies, could increase plant diversity via the selective mortality of similar chemotypes.

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“…A variety of neolignans have been isolated from other Piper species, however, this represents the first example containing an oxidized propenyl side chain. 10 While the conversion of the alcohol to ketone 3 is anticipated to be facile, the aryl vinyl ketone's high electrophilic reactivity, its exceptionally rare occurrence in natural products, and the observed transformation of the alcohol in cabagranin A to cabagranin C during storage, collectively suggest that the free enone might not always be present in detectable concentrations within the plant. [11][12][13] This could potentially result from the instability of the vinyl ketone and its presumed toxicity as a covalent modifier of biomolecules.…”

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confidence: 99%

Isolation and structure determination of new neolignans and cabagranin D, an unusual meroterpenoid from Piper cabagranum

de Oliveira Jr.,

Ledvina,

Leonard

et al. 2023

Preprint

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A novel meroterpenoid cabagranin D was isolated along with related neolignans cabagranins A-C from the leaves of Piper cabagranum (Costa Rica). Cabagranins A-C represent the first examples of 3,3’-neolignans isolated from the Piper genus of plant and the meroterpenoid cabagranin D, representing an unprecedented Diels-Alder conjugate of an unsubstituted phenylpropenone and alpha-phellandrene. Details of the full structural elucidation of these compounds and a discussion of the potential biosynthetic relationships are presented.

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An Overview of Neolignans of the Genus Piper L.: Isolation Methods and Biological Activities

Abstract: The present review aims to summarize extraction and isolation methods and biological activities of the different types of neolignans covering the period from 1968 to January 2016.

Cited by 17 publications

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Isolation of new neolignans and an unusual meroterpenoid from Piper cabagranum

Isolation of new neolignans and an unusual meroterpenoid from Piper cabagranum

Testing the role of local plant chemical diversity on plant–herbivore interactions and plant species coexistence

Isolation and structure determination of new neolignans and cabagranin D, an unusual meroterpenoid from Piper cabagranum

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