Evaluation of Insecticidal Activity of Diterpenes and Lignans from Aristolochia malmeana against Anticarsia gemmatalis

Messiano, Gisele B.; Vieira, Leandro M.; Machado, Marcos B.; Lopes, Lucia Maria Xavier; Bortoli, Sérgio Antônio De; Zukerman-Schpector, Júlio

doi:10.1021/jf703594z

Cited by 56 publications

(35 citation statements)

References 35 publications

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“…For example, there are many formulas containing various species of the genus Aristolochia that are commonly used in traditional medicine in China, Japan, and Singapore [2] . Beside those used in East Asia, several species of the genus Aristolochia have been used to regulate menstruation, induce labor, expel parasites, relieve pain, and treat arthritis, cancer, diarrhea, and snake bites in India, West Africa, the Mediterranean, and South America [3][4][5] .…”

Section: Introductionmentioning

confidence: 99%

Microarray analysis reveals the inhibition of nuclear factor-kappa B signaling by aristolochic acid in normal human kidney (HK-2) cells

Chen

Chiang

et al. 2010

Acta Pharmacol Sin

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Aim: To study the molecular mechanism underlying the effect of aristolochic acid (AA), a major active component of plants from the Aristolochiaceae family using microarray analysis. Methods: Human kidney (HK-2) cells were treated with AA (0, 10, 30, and 90 μmol/L) for 24 h, and the cell viability was measured by a 3-(4,5-dimethylthiazol-2yl)-2,5-diphenyltetrazolium bromide assay. Complementary DNA microarrays were used to investigate the gene expression pattern of HK-2 cells exposed to AA in triplicate. A quantitative reverse transcriptase-polymerase chain reaction (qRT-PCR) assay was used to verify the microarray data for selected nuclear factor kappa B (NF-κB)-regulated genes. Furthermore, the subcellular localization of NF-κB p65 was visualized by immunofluorescence confocal microscopy in HK-2 cells. The NF-κB activity was examined by a luciferase reporter assay in HK-2/NF-κB transgenic cells. Results: AA exhibited a dose-dependent cytotoxic effect in HK-2 cells and induced alterations in the gene expression profiles related to the DNA damage response, DNA repair, macromolecule metabolic process, carbohydrate metabolic process, DNA metabolic process, apoptosis, cell cycle, and transcription. In addition, 9 biological pathways associated with immunomodulatory functions were downregulated in AA-treated HK-2 cells. A network analysis revealed that NF-κB played a central role in the network topology. Among NF-κB-regulated genes, 8 differentially expressed genes were verified by qRT-PCR. The inhibition of NF-κB activity by AA was further confirmed by immunofluorescence confocal microscopy and by NF-κB luciferase reporter assay. Conclusion: Our data revealed that AA could suppress NF-κB activity in normal human cells, perhaps partially accounting for the reported anti-inflammatory effects of some plants from the genus Aristolochia.Keywords: aristolochic acid; microarray analysis; nuclear factor-kappa B; human kidney HK-2 cells; confocal microscopy; luciferase reporter assay Acta Pharmacologica Sinica (2010) 31: 227-236; doi: 10.1038/aps.2009 Original Article # These authors contributed equally to this work. * To whom correspondence should be addressed. [7,8] . AA was found to possess anti-inflammation effects as demonstrated by its ability to inhibit phospholipase A 2 (PLA 2 ) when administered by intramuscular or intraperitoneal injection [9,10] . Furthermore, AA was also reported to inhibit Group I PLA 2 in humans with sepsis [11] . From in vitro studies, AA has been shown to suppress phospholipohydration of PLA 2 derived from human synovial fluid, cobra venom, porcine pancreas, and human platelets [12] . The anti-inflammatory activities of AA in different models of inflammation have promoted its use in many countries in herbal formulations for arthritis, rheumatism, gout and chronic inflammatory skin diseases [13,14] . Moreover, double-blind studies in healthy volunteers show that AA increased the phagocytic activity of peripheral granulocytes after treatment with AA 0.9 mg/d for three to ten consecutive days [...

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Section: Introductionmentioning

confidence: 99%

Microarray analysis reveals the inhibition of nuclear factor-kappa B signaling by aristolochic acid in normal human kidney (HK-2) cells

Chen

Chiang

et al. 2010

Acta Pharmacol Sin

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“…7,[13][14][15][16] Compounds 4 and 6-9 were also identified with reference to authentic samples obtained from Aristolochia malmeana. C NMR and by comparison of its spectroscopic data with those reported for trigonellinium chloride and monohydrate.…”

Section: Resultsmentioning

confidence: 99%

“…The chemical constituents of Brazilian Aristolochiaceae species, such as lignans, have shown antiplasmodial, 4 antimycobacterial, 5 insecticidal, 6,7 anti-inflammatory, and analgesic activities. 8 Despite the significant number of Brazilian Aristolochia species (around 100), the volatile compounds they contain are known for only a few species.…”

Section: Introductionmentioning

confidence: 99%

Chemical constituents of Aristolochia giberti

Marchesini¹,

Prado²,

Messiano³

et al. 2009

J. Braz. Chem. Soc.

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Foram isoladas quatorze substâncias de Aristolochia giberti, entre elas, um novo triterpeno, (-)-onocera-8,8'-diol. Além destas, 3-hidróxipropanoato, acetato e formato foram detectados por técnicas de RMN, o que sugere que estas substâncias sejam derivadas do 2-butinodioato, não detectável por RMN de 1 H. As análises dos óleos essenciais de caules e folhas, por CG-EM e quimiometria, mostraram grande similaridade entre as espécies cultivadas no Brasil e aquelas na Argentina, o que permitiu confirmar a identificação da espécie e diferenciar os óleos de acordo com as partes da planta.Fourteen compounds were isolated from Aristolochia giberti. These included a new triterperne, (-)-onocera-8,8'-diol. In addition, 3-hydroxypropanoate, acetate, and formate were detected by NMR techniques, which suggests that they are derivatives from 2-butynedioate, which is not detected by 1 H NMR. GC-MS and chemometric analyses of essential oils from stems and leaves showed great similarity between this cultivated species in Brazil and that in Argentina, which allowed us to confirm the species identity and to differentiate the oils according to the plant parts. IntroductionAristolochia species (Aristolochiaceae) are generally sold at Brazilian markets under their popular names, particularly as "One Thousand Man", and little distinction has been made among the species. They have been mainly used in Brazilian traditional medicine as abortifacients, stomachics, antiophidians, antiasthmatics, and expectorants, and recently in slimming therapies.1,2 Aristolochic acids constitute a class of compounds that are characteristic of the Aristolochia genus. These acids have been associated with Chinese herb nephropathy, which is a kind of severe kidney disease caused by the intake of excessive aristolochic acids.3 Therefore, it is essential, for health safety and quality control of related Brazilian herbal medicines, to know the chemical composition of these species, among them Aristolochia giberti Hook., and to develop efficient methods for species identification.The chemical constituents of Brazilian Aristolochiaceae species, such as lignans, have shown antiplasmodial, 4 antimycobacterial, 5 insecticidal, 6,7 anti-inflammatory, and analgesic activities. Despite the significant number of Brazilian Aristolochia species (around 100), the volatile compounds they contain are known for only a few species. 9 In our previous studies on essential oils from roots of 10 Aristolochia species, we investigated the oil composition and correlated them to morphological groups by GC-MS and chemometric analyses, which could also help in the identification of these species. 9A total of 64 compounds were identified in the analysed essential oils from stems and leaves of A. giberti collected in Argentina and Paraguay, which corresponded to around 77% to 92% of the constituents in the oils.10,11 Methanolic extracts of A. giberti protected against enzymatic and non-enzymatic lipid peroxidation in microsomal membranes of rat. 12The goals of the present study were to in...

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“…2) (Fig. 3) of copalic acid and/or kolavenic acid (Messiano et al, 2008;Marchesini et al, 2009). The A1 sample was selected to GC-MS analysis and presented β-bisabolene (29.95%), Z-α--bergamotene (25.65%) and β-cariophyllene (10.27%) as major compound (Table 2).…”

Section: Physicochemical Analysesmentioning

confidence: 99%

Physicochemical and antimicrobial properties of copaiba oil: implications on product quality control

Fonseca

Barros

Apel

et al. 2015

Acta Sci Pol Technol Aliment

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Background. The copaiba oil is a common natural product used in cosmetic industry and as a nutraceutical product. However, lack of quality control and scarce knowledge about its antimicrobial activity is a point of concern. The proposal of this study was to investigate the physicochemical properties and the antimicrobial activity of fi ve commercial brands of copaiba oil. Material and methods. Acidity and ester index, refractory index, solubility in alcohol, and thin layer chromatography were performed to verify the physicochemical properties of fi ve commercial copaiba oils sold in local pharmacies. Ultra performance liquid chromatography coupled with diode-array detection and electrospray ionization quadrupole time-of-flight mass spectrometry (UPLC-DAD/ESI-Q-TOF-MS) was used to investigate diterpene acids while the volatile compounds were analysed by gas chromatography-mass spectrometry (GC-MS). Antibacterial and antifungal activities were also evaluated by agar diffusion technique; and minimal inhibitory concentration and maximal bactericidal concentration were defi ned for each sample and bacteria. Results. The physical-chemical analysis revealed heterogeneity between all samples analysed. The A1 sample showed characteristics of copaiba oil and was mainly composed by hydrocarbon sesquiterpenes (29.95% β-bisabolene, 25.65% Z-α-bergamotene and 10.27% β-cariophyllene). Among diterpene acids, the UPLC-DAD/ESI-Q-TOF-MS data are compatible with presence of copalic and/or kolavenic acid (m/z 305 [M + H]

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Evaluation of Insecticidal Activity of Diterpenes and Lignans from Aristolochia malmeana against Anticarsia gemmatalis

Cited by 56 publications

References 35 publications

Microarray analysis reveals the inhibition of nuclear factor-kappa B signaling by aristolochic acid in normal human kidney (HK-2) cells

Microarray analysis reveals the inhibition of nuclear factor-kappa B signaling by aristolochic acid in normal human kidney (HK-2) cells

Chemical constituents of Aristolochia giberti

Physicochemical and antimicrobial properties of copaiba oil: implications on product quality control

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