Sequestration of prenylated benzoic acid and chromenes by Naupactus bipes (Coleoptera: Curculionidae) feeding on Piper gaudichaudianum (Piperaceae)

Ramos, Clécio S.; Vanin, Sérgio Antonio; Kato, Massuo Jorge

doi:10.1007/s00049-009-0011-0

Cited by 20 publications

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“…Whereas larvae sequester prenylated benzoic acid derivatives from the roots, adults sequester chromenes from the leaves. The latter are also incorporated in the eggs (Ramos et al 2009). …”

Section: Prenylated Aromatic Compounds In Coleopteramentioning

confidence: 99%

Plant chemistry and insect sequestration

2009

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Most plant families are distinguished by characteristic secondary metabolites, which can function as putative defence against herbivores. However, many herbivorous insects of different orders can make use of these plant-synthesised compounds by ingesting and storing them in their body tissue or integument. Such sequestration of putatively unpalatable or toxic metabolites can enhance the insects' own defence against enemies and may also be involved in reproductive behaviour. This review gives a comprehensive overview of all groups of secondary plant metabolites for which sequestration by insect herbivores belonging to different orders has been demonstrated. Sequestered compounds include various aromatic compounds, nitrogen-containing metabolites such as alkaloids, cyanogenic glycosides, glucosinolates and other sulphurcontaining metabolites, and isoprenoids such as cardiac glycosides, cucurbitacins, iridoid glycosides and others. Sequestration of plant compounds has been investigated most in insects feeding or gathering on Apocynaceae s.l. (Apocynoideae, Asclepiaoideae), Aristolochiaceae, Asteraceae, Boraginaceae, Fabaceae and Plantaginaceae, but it also occurs for some gymnosperms and even lichens. In total, more than 250 insect species have been shown to sequester plant metabolites from at least 40 plant families. Sequestration predominates in the Coleoptera and Lepidoptera, but also occurs frequently in the orders Heteroptera, Hymenoptera, Orthoptera and Sternorrhyncha. Patterns of sequestration mechanisms for various compound classes and common or individual features occurring in different insect orders are highlighted. More research is needed to elucidate the specific transport mechanisms and the physiological processes of sequestration in various insect species.

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“…Whereas larvae sequester prenylated benzoic acid derivatives from the roots, adults sequester chromenes from the leaves. The latter are also incorporated in the eggs (Ramos et al 2009). …”

Section: Prenylated Aromatic Compounds In Coleopteramentioning

confidence: 99%

Plant chemistry and insect sequestration

2009

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“…The phytochemistry of the Piperaceae species, mainly of the Piper genus (Parmar et al ., ), has been studied extensively due to the variety of biological activities displayed by their secondary metabolites (Alécio et al ., ; Navickiene et al ., ; Martins et al ., ; Lago et al ., ). Phytochemical studies of Brazilian species of Piperaceae have revealed the presence of amides (Silva et al ., ; Navickiene et al ., ), neolignans (Benevides et al ., ), lignans (Martins et al ., , ; Ramos et al ., ) and prenylated benzoic acid and chromene (Baldoqui et al ., ; Ramos and Kato, ; Ramos et al ., ).…”

Section: Introductionmentioning

confidence: 97%

Secondary Metabolites from the Phloem of Piper solmsianum (Piperaceae) in the Honeydew of Edessa meditabunda

Ramos

Kato

2012

Phytochemical Analysis

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ABSTRACT:Introduction -The phytochemistry of species of the genus Piper has been studied extensively, including Piper solmsianum. However, no studies have addressed the phytochemistry of the sap content of Piper species. Objective -To evaluate the transferring of secondary compounds from the saps of P. solmsianum to the honeydew of Edessa meditabunda. Methodology -The honeydew of E. meditabunda and saps of P. solmsianum were analysed by GC-MS, 1 H-NMR and LC-MS. Results -The lignan (À)-grandisin and the phenylpropanoid (E)-isoelemicin were detected in both saps of P. solmsianum and honeydew of E. meditabunda. Conclusion -Analysis of honeydew secreted by the sap-sucking insect E. meditabunda indicated that (À)-grandisin and (E)-isoelemicin are absorbed from the phloem of Piper solmsianum.

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Section: Introductionmentioning

confidence: 99%

“…In terms of ecological importance, Piper species have been considered as model due to the richness of species and diversity of interactions with herbivores. [16][17][18][19][20][21] In general, Piperaceae species can be easily propagated and the availability of data on taxonomy, molecular phylogeny, ecology and chemical composition provides the basis for multidisciplinary studies.Most of the phytochemical investigation has been addressed to determine major bioactive secondary metabolites and thus, Piperaceae species have shown to produce amides, pyrones, chromenes and lignoids. [22][23][24][25][26][27][28] Several Piper species are pioneer, and can be found in forest borders and for such reason they are also under risk of depletion by anthropic activities.…”

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Chemometric analysis of ESIMS and NMR data from Piper species

Yamaguchi

Freitas

Yoshida

et al. 2011

J. Braz. Chem. Soc.

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O perfil metabólito baseado na aplicação de análises multivariadas (análise de componentes principais, PCA) dos dados de espectrometria de massas com ionização electrospray (ESIMS) no modo positivo e de ressonância magnética nuclear (RMN) do 1 H de extratos brutos de espécies de Piper destacou algumas espécies caracterizadas pela produção de lignanas (P. solmsianum, P. truncatum e P. cernuum), neolignanas (P. regnellii) e cromenos (P. gaudichaudianum). Análises específicas em conjunto de espécies caracterizadas morfologicamente por apresentarem inflorescências pêndulas e globosas (P. caldense, P. carniconnectivum, P. bowiei e P. permucronatum) ou em espécies que produzem amidas indicaram o potencial mais significativo para tais análises como critério para estudos fitoquímicos posteriores. Análises intraespecíficas de plântulas das espécies P. solmsianum, P. regnellii e P. gaudichaudianum indicaram uma composição química nas folhas baseada na presença dos fenilpropanóides dilapiol e apiol, diferentemente do que produzem as plantas adultas. No caso das espécies que produzem amidas, a composição apresentou-se relativamente constante independentemente do estágio de desenvolvimento.The metabolomic profiling based on the application of multivariate analysis (principal component analysis, PCA) of positive mode electrospray ionization mass spectrometric (ESIMS) and 1 H nuclear magnetic resonance (NMR) data of crude extracts highlighted some species characterized by lignans (P. solmsianum, P. truncatum and P. cernuum), neolignans (P. regnellii) and chromenes (P. gaudichaudianum). A specific analysis focusing on species having pendant and globular inflorescences (P. caldense, P. carniconnectivum, P. bowiei and P. permucronatum) or amides-producing species indicated higher potential of the methodology in determining similarities and establishing priorities for further phytochemical investigation. Such intraspecific analysis applied to analyzed seedling leaves of the P. solmsianum, P. regnellii and P. gaudichaudianum species revealed the production of dillapiole and apiole instead of lignans, neolignans or prenylated benzoic acid, produced by the adult leaves, respectively. In case of amides-producing species, a similar profile was observed regardless the developmental stage.Keywords: Piperaceae, principal component analysis, secondary metabolites, fingerprinting Chemometric Analysis of ESIMS and NMR Data from Piper Species J. Braz. Chem. Soc. 2372 IntroductionThe knowledge on secondary chemistry of tropical plant species is limited to approximately 5-10% of the total species described so far. In fact, this limited study indicates the potential for finding novel lead compounds from tropical biodiversity. Despite the availability of high throughput technology platforms to detect bioactive compounds, the process of cataloguing their composition possesses a significant challenge since it still involves largely the isolation and spectroscopic characterization of individual components. Additionally, the determination of a m...

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Sequestration of prenylated benzoic acid and chromenes by Naupactus bipes (Coleoptera: Curculionidae) feeding on Piper gaudichaudianum (Piperaceae)

Cited by 20 publications

References 50 publications

Plant chemistry and insect sequestration

Plant chemistry and insect sequestration

Secondary Metabolites from the Phloem of Piper solmsianum (Piperaceae) in the Honeydew of Edessa meditabunda

Chemometric analysis of ESIMS and NMR data from Piper species

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