Isolation, Structure Elucidation, and Biological Activity of Flavone 6-C-Glycosides from Alliaria petiolata

Kumarasamy, Yashodharan; Byres, Maureen; Cox, Philip; Delazar, Abbas; Jaspars, Marcel; Nahar, Lutfun; Shoeb, Mohammad; Sarker, Satyajit D.

doi:10.1023/b:conc.0000033926.72396.41

Cited by 61 publications

(36 citation statements)

References 21 publications

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“…6, by comparing the LC-MS and NMR data with the reported data. 15,16,18,19) In this study, it is demonstrated that these four compounds play a significant role in GRLH probing behavior. This is because each of these four compounds individually showed weak activities, but the combination of all of them showed high activity toward the GRLH.…”

Section: Resultsmentioning

confidence: 73%

Studies on probing stimulants for the green rice leafhopper, Nephotettix nigropictus (Stål) (Hemiptera: Cicadellidae), in the rice plant (Oryza sativa L.)

2016

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A crude rice extract caused a higher probing response than did the control in the green rice leafhopper, Nephotettix nigropictus. Bioassay-guided separation led to the isolation of four active compounds, isoscoparin and isovitexin 2″-O-(6‴-(E)-feruloyl)glucoside from ODS 40% methanol in water faction. Each of the compounds, or any combination without one of the four compounds, caused weaker probing responses than the crude rice extract. The activity was recovered only when all the compounds were combined.

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Section: Resultsmentioning

confidence: 73%

Studies on probing stimulants for the green rice leafhopper, Nephotettix nigropictus (Stål) (Hemiptera: Cicadellidae), in the rice plant (Oryza sativa L.)

2016

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“…Some aspects of plant defence were consistently decreased in introduced populations (Bossdorf et al 2004b;Hull-Sanders et al 2007), but overall evidence was rather ambiguous and did not support the EICA hypothesis (Bossdorf et al 2004a, b;Cipollini et al 2005;Hull-Sanders et al 2007;Cipollini and Lieurance 2012). Alliaria petiolata contains a broad array of secondary metabolites that putatively affect soil microbial communities (Cipollini 2002;Cipollini et al 2005;Callaway et al 2008;Bressan et al 2009;Lankau 2011) and likely play a role in defence against herbivores and pathogens Renwick 1998, 2001;Haribal et al 1999;Renwick et al 2001;Kumarasamy et al 2004;Cipollini and Gruner 2007). In connection with field surveys and further genetic studies, this body of research provides an excellent basis for characterizing individual-level variation in secondary chemicals, and potentially for linking this variation to ecosystem-level processes.…”

Section: Implicated In Several Key Hypotheses Of Invasion Successmentioning

confidence: 99%

The Global Garlic Mustard Field Survey (GGMFS): challenges and opportunities of a unique, large-scale collaboration for invasion biology

Colautti

Franks²,

Hufbauer³

et al. 2014

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To understand what makes some species successful invaders, it is critical to quantify performance differences between native and introduced regions, and among populations occupying a broad range of environmental conditions within each region. However, these data are not available even for the world's most notorious invasive species. Here we introduce the Global Garlic Mustard Field Survey, a coordinated distributed field survey to collect performance data and germplasm from a single invasive species: garlic mustard (Alliaria petiolata) across its entire distribution using minimal resources. We chose this species for its ecological impacts, prominence in ecological studies of invasion success, simple life history, and several genetic and life history attributes that make it amenable to experimental study. We developed a standardised field survey protocol to estimate population size (area) and density, age structure, plant size and Colautti et al. / NeoBiota 21: 29-47 (2014) 30 fecundity, as well as damage by herbivores and pathogens in each population, and to collect representative seed samples. Across four years and with contributions from 164 academic and non-academic participants from 16 countries in North America and Europe thus far, we have collected 45,788 measurements and counts of 137,811 plants from 383 populations and seeds from over 5,000 plants. All field data and seed resources will be curated for release to the scientific community. Our goal is to establish A. petiolata as a model species for plant invasion biology and to encourage large collaborative studies of other invasive species.

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“…These pure compounds were developed after spraying the TLC chromatogram (stationary phase: silica gel; mobile phase: ethyl acetate/methanol/ water/acetic acid 80:10:5:5 v/v) with NP/PEG, a characteristic reagent for flavonoid identification: isovitexin (Rf value of 0.80), iso orientin (Rf value of 0.50), swertisin (Rf value of 0.90) and swertiajaponin (Rf value of 0.65). Thus, the compounds were analyzed by 1 H, 13 C-NMR, HMQC and HMBC techniques and the data were compared with literature (Cheng et al 2000, Kumarasamy et al 2004). The thin layer chromatography on silica gel 60 F254 (Merck) with authentic standards (SigmaAldrich) was run for identification of aminoacids and sugars.…”

Section: Purificationmentioning

confidence: 99%

Genotoxic Maillard byproducts in current phytopharmaceutical preparations of Echinodorus grandiflorus

Lima

Waldhelm

Alves

et al. 2014

An. Acad. Bras. Ciênc.

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Extracts of Echinodorus grandiflorus obtained from dried leaves by three different techniques were evaluated by bacterial lysogenic induction assay (Inductest) in relation to their genotoxic properties. Before being added to test cultures, extracts were sterilized either by steam sterilization or ultraviolet light. Only the extracts prepared by infusion and steam sterilized have shown genotoxic activity. The phytochemical analysis revealed the presence of the flavonoids isovitexin, isoorientin, swertisin and swertiajaponin, isolated from a genotoxic fraction. They were assayed separately and tested negative in the Inductest protocol. The development of browning color and sweet smell in extracts submitted to heat, prompted further chemical analysis in search for Maillard´s reaction precursors. Several aminoacids and reducing sugars were cast in the extract. The presence of characteristic Maillard´s melanoidins products was determined by spectrophotometry in the visible region and the inhibition of this reaction was observed when its characteristic inhibitor, sodium bisulfite, was added prior to heating. Remarkably, this is the first paper reporting on the appearance of such compounds in a phytomedicine preparation under a current phytopharmaceutical procedure. The genotoxic activity of such heat-prepared infusions imply in some risk of developing degenerative diseases for patients in long-term, uncontrolled use of such phytomedicines.

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Isolation, Structure Elucidation, and Biological Activity of Flavone 6-C-Glycosides from Alliaria petiolata

Cited by 61 publications

References 21 publications

Studies on probing stimulants for the green rice leafhopper, <i>Nephotettix nigropictus</i> (Stål) (Hemiptera: Cicadellidae), in the rice plant (<i>Oryza sativa</i> L.)

Studies on probing stimulants for the green rice leafhopper, <i>Nephotettix nigropictus</i> (Stål) (Hemiptera: Cicadellidae), in the rice plant (<i>Oryza sativa</i> L.)

The Global Garlic Mustard Field Survey (GGMFS): challenges and opportunities of a unique, large-scale collaboration for invasion biology

Genotoxic Maillard byproducts in current phytopharmaceutical preparations of Echinodorus grandiflorus

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