Antifeedant properties and chemotaxonomic implications of sesquiterpene lactones and syringin from Rhaponticum pulchrum

Cis, Joanna; Nowak, Gerard; Kisiel, Wanda

doi:10.1016/j.bse.2006.05.019

Cited by 54 publications

(37 citation statements)

References 22 publications

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“…Growth inhibition was due not only to reduced food intake but also to decreased absorption of digested food constituents and metabolic disorders (Rosinski et al, 1988). Also stizolin (27), 9a-hydroxypartenolide (28), stizolicin (32), aguerin B (160) and chlorojanerin (219) showed good antifeedant properties against Sitophilus granaries, Trogoderma granarium and Tribolium confusum, while janerin (208) and cynaropicrin (162) inhibited feeding of the latter species only (Cis et al, 2006;Bloszyk, 1988).…”

Section: Effects On Insectsmentioning

confidence: 99%

Sesquiterpenoids in subtribe Centaureinae (Cass.) Dumort (tribe Cardueae, Asteraceae): Distribution, 13C NMR spectral data and biological properties

et al. 2013

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Section: Effects On Insectsmentioning

confidence: 99%

Sesquiterpenoids in subtribe Centaureinae (Cass.) Dumort (tribe Cardueae, Asteraceae): Distribution, 13C NMR spectral data and biological properties

et al. 2013

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“…12 There is some evidence for an ecological role for STL in plants, like their effectiveness as insect antifeedants, due to their bitter taste and cytotoxicity [13][14][15] and potential allelopathic activities.…”

Section: Introductionmentioning

confidence: 99%

“…1 Previous phytochemical investigation of L. ericoides leaves yielded mainly sesquiterpene lactones (STL), caffeoylquinic acids, di-C-glucosylflavones and flavonoid aglycones [3][4][5][6][7] (Figure 1). In vivo experiments indicated that vicenin-2 was the main anti-inflammatory compound in leaves 3 and that lignans 8 and caffeoylquinic acid derivatives, the latter isolated from both leaves and roots, 4,6 were the main analgesic compounds.Several biological activities have been attributed to STL.9-11 Anti-inflammatory and cytotoxic activities, among others, have been shown to be related to the a,b-unsaturated g-lactone moiety which can behave as Michael -acceptor for example, with cystein amino acid residues.12 There is some evidence for an ecological role for STL in plants, like their effectiveness as insect antifeedants, due to their bitter taste and cytotoxicity [13][14][15] and potential allelopathic activities. …”

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confidence: 99%

Differential metabolic and biological profiles of Lychnophora ericoides mart. (Asteraceae) from different localities in the Brazilian "campos rupestres"

Gobbo‐Neto

Guaratini

Pessoa

et al. 2010

J. Braz. Chem. Soc.

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Este artigo descreve a caracterização por CLAE-DAD-EM/EM e CLAE-DEC dos perfis de metabólitos secundários de extratos das folhas de Lychnophora ericoides Mart. de diferentes procedências e suas propriedades citotóxicas e antioxidantes. Extratos foliares de populações representando sete diferentes localidades foram avaliados quanto à atividade antioxidante pelo sistema DPPH e à atividade citotóxica em três linhagens tumorais. Os extratos foram eletroquimicamente caracterizados por CLAE-DEC e seus metabólitos secundários majoritários foram identificados por CLAE-DAD-EM e CLAE-DAD-EM/EM. Um metabolismo secundário defensivo amplificado, juntamente com as mais altas bioatividades antioxidantes e citotóxicas, foi encontrado para as plantas coletadas na interface entre dois tipos de vegetação. Estes resultados fornecem apoio adicional para a hipótese de que plantas ocorrendo na interface entre dois ecossistemas podem ser estimuladas a amplificar sua produção e armazenamento de metabólitos secundários defensivos, devido ao maior número de influências ambientais. This paper reports HPLC-DAD-MS/MS and HPLC-ECD characterisation of secondary metabolite profiles of Lychnophora ericoides Mart. leaf extracts from different provenances and their cytotoxic and antioxidant properties. Leaf extracts from populations representing seven different locations were evaluated for antioxidant activity by the DPPH radical scavenging system and activity towards cellular growth in three tumor cell lines. The extracts were electrochemically analysed by HPLC-ECD and their main secondary metabolites were identified by HPLC-DAD-MS and HPLC-DAD-MS/MS. An amplified defensive secondary chemistry, together with maximal cytotoxic and antioxidant bioactivities, were found for plants collected at the interface between two types of forest. These findings furnish additional support for the hypothesis that plants occurring at the interface between two forests ecosystems might be stimulated to amplify their own production and storage of defensive secondary metabolites due to the greater number of environmental influences.Keywords: Lychnophora ericoides, secondary metabolite infra-specific variation, hyphenated techniques, cytotoxic activity, antioxidant activity IntroductionThe genus Lychnophora (Asteraceae, Vernonieae) is restricted to the Brazilian "cerrado", the Brazilian savannas.1,2 Traditional medicine employs alcohol and water-alcohol preparations of leaves and root powder from several Lychnophora species for the treatment of wounds, inflammation and pain. 3,4 Among Lychnophora species, L. ericoides Mart. is the most widely used in traditional medicine. 3,4 This species occurs in small and well delimited Gobbo-Neto et al. 751 Vol. 21, No. 4, 2010 microendemic populations, usually containing between 20-50 adult individuals in a 100-200 m 2 area, and occurring in a particular type of high altitude, rocky field found in the Brazilian "cerrado". These fields are known as "campos rupestres". 1 Previous phytochemical investigation of L. ericoides le...

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“…364 Known guaianolides have been obtained from Centaurea helenioides, 375 Centaurea ptosimopappa, 376 Centaurea scabiosa, 377 Chondrilla juncea, 378 Ixeris dentata, 379 Rhaponticum pulchrum 380 and Taraxacum bessarabicum 381 The structures of a guaianolide 382 458 and of a tetrabromoderivative of cyclopropyldihydroargablin 383 have been determined by X-ray analysis. A conformational analysis of several 11,13-oxetane lactones has been carried out.…”

confidence: 99%

Natural Sesquiterpenoids

Fraga

2007

ChemInform

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Antifeedant properties and chemotaxonomic implications of sesquiterpene lactones and syringin from Rhaponticum pulchrum

Cited by 54 publications

References 22 publications

Sesquiterpenoids in subtribe Centaureinae (Cass.) Dumort (tribe Cardueae, Asteraceae): Distribution, 13C NMR spectral data and biological properties

Sesquiterpenoids in subtribe Centaureinae (Cass.) Dumort (tribe Cardueae, Asteraceae): Distribution, 13C NMR spectral data and biological properties

Differential metabolic and biological profiles of Lychnophora ericoides mart. (Asteraceae) from different localities in the Brazilian "campos rupestres"

Natural Sesquiterpenoids

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