Isoflavonoids of the Leguminosae

Veitch, Nigel C.

doi:10.1039/b616809b

Cited by 72 publications

(52 citation statements)

References 148 publications

(589 reference statements)

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“…The metabolite profiling revealed a large number of detected peaks to have PDA spectra corresponding to polyphenols with molecular weights ranging from 250 to 450 Da. Most of the PDA spectra were characteristic for either flavones or isoflavones, both known to be present in the Fabaceae family [27]. The high-resolution MS data gained from the UHPLC-PDA-TOFMS analysis provided molecular formula information for all detected LC peaks giving a first overview of the extract composition.…”

Section: Resultsmentioning

confidence: 99%

Integration of Microfractionation, qNMR and Zebrafish Screening for the In Vivo Bioassay-Guided Isolation and Quantitative Bioactivity Analysis of Natural Products

et al. 2013

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Natural products (NPs) are an attractive source of chemical diversity for small-molecule drug discovery. Several challenges nevertheless persist with respect to NP discovery, including the time and effort required for bioassay-guided isolation of bioactive NPs, and the limited biomedical relevance to date of in vitro bioassays used in this context. With regard to bioassays, zebrafish have recently emerged as an effective model system for chemical biology, allowing in vivo high-content screens that are compatible with microgram amounts of compound. For the deconvolution of the complex extracts into their individual constituents, recent progress has been achieved on several fronts as analytical techniques now enable the rapid microfractionation of extracts, and microflow NMR methods have developed to the point of allowing the identification of microgram amounts of NPs. Here we combine advanced analytical methods with high-content screening in zebrafish to create an integrated platform for microgram-scale, in vivo NP discovery. We use this platform for the bioassay-guided fractionation of an East African medicinal plant, Rhynchosia viscosa, resulting in the identification of both known and novel isoflavone derivatives with anti-angiogenic and anti-inflammatory activity. Quantitative microflow NMR is used both to determine the structure of bioactive compounds and to quantify them for direct dose-response experiments at the microgram scale. The key advantages of this approach are (1) the microgram scale at which both biological and analytical experiments can be performed, (2) the speed and the rationality of the bioassay-guided fractionation – generic for NP extracts of diverse origin – that requires only limited sample-specific optimization and (3) the use of microflow NMR for quantification, enabling the identification and dose-response experiments with only tens of micrograms of each compound. This study demonstrates that a complete in vivo bioassay-guided fractionation can be performed with only 20 mg of NP extract within a few days.

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Section: Resultsmentioning

confidence: 99%

Integration of Microfractionation, qNMR and Zebrafish Screening for the In Vivo Bioassay-Guided Isolation and Quantitative Bioactivity Analysis of Natural Products

et al. 2013

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“…Consequently, there is a need for the development of more comprehensive quantitative methods. 2,4,13 In this study, MRRF values were computed for 11 isoflavonoid standards, both aglycones and glycosides, at 260 nm using genistein as the group reference standard (Table 3). When possible, standards were obtained from two suppliers and, when sufficient standard was available, dried to provide MRRF D values.…”

Section: Resultsmentioning

confidence: 99%

“…6,14 They are found mainly in plants from the Leguminosae family, especially soybean and soybean products. 4,13 Flavanones exist primarily in citrus fruits, juices, and peels. 4,15 Dihydrochalcones, such as phloretin and phloridzin from apples, have similar UV absorbance profiles to the flavanones.…”

Section: Introductionmentioning

confidence: 99%

Quantitation of Flavanols, Proanthocyanidins, Isoflavones, Flavanones, Dihydrochalcones, Stilbenes, Benzoic Acid Derivatives Using Ultraviolet Absorbance after Identification by Liquid Chromatography–Mass Spectrometry

Lin

Harnly

2012

J. Agric. Food Chem.

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A general method was developed for the systematic quantitation of flavanols, proanthocyanidins, isoflavones, flavanones, dihydrochalcones, stilbenes, and hydroxybenzoic acid derivatives (mainly hydrolyzable tannins) based on UV band II absorbance arising from the benzoyl structure. The compound structures and the wavelength maximum were well correlated and were divided into four groups: the flavanols and proanthocyanidins at 278 nm, hydrolyzable tannins at 274 nm, flavanones at 288 nm, and isoflavones at 260 nm. Within each group, molar relative response factors (MRRFs) were computed for each compound based on the absorbance ratio of the compound and the group reference standard. Response factors were computed for the compounds as purchased (MRRF), after drying (MRRFD), and as the best predicted value (MRRFP). Concentrations for each compound were computed based on calibration with the group reference standard and the MRRFP. The quantitation of catechins, proanthocyanidins, and gallic acid derivatives in white tea was used as an example.

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“…This is due to a wide spectra of biological activities of these compounds and also participation in many physiological and biochemical processes (Schijlen et al 2004; Lepiniec et al 2006; Bovy et al 2007; Veitch and Grayer 2008; Veitch 2009; Paredes-Lopez et al 2010). Flavonoids represent numerous structures as a consequence of the phenolic ring B position as well as various substitutions of hydroxyl groups (Fig.…”

Section: Introductionmentioning

confidence: 99%

LC/MS profiling of flavonoid glycoconjugates isolated from hairy roots, suspension root cell cultures and seedling roots of Medicago truncatula

et al. 2011

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Hairy roots and suspension cell cultures are commonly used in deciphering different problems related to the biochemistry and physiology of plant secondary metabolites. Here, we address about the issue of possible differences in the profiles of flavonoid compounds and their glycoconjugates derived from various plant materials grown in a standard culture media. We compared profiles of flavonoids isolated from seedling roots, hairy roots, and suspension root cell cultures of a model legume plant, Medicago truncatula. The analyses were conducted with plant isolates as well as the media. The LC/MS profiles of target natural products obtained from M. truncatula seedling roots, hairy roots, and suspension root cell cultures differed substantially. The most abundant compounds in seedlings roots were mono- and diglucuronides of isoflavones and/or flavones. This type of glycosylation was not observed in hairy roots or suspension root cell cultures. The only recognized glycoconjugates in the latter samples were glucose derivatives of isoflavones. Application of a high-resolution mass spectrometer helped evaluate the elemental composition of protonated molecules, such as [M + H]+. Comparison of collision-induced dissociation MS/MS spectra registered with a quadrupole time-of-flight analyzer for tissue extracts and standards allowed us to estimate the aglycone structure on the basis of the pseudo-MS3 experiment. Structures of these natural products were described according to the registered mass spectra and literature data. The analyses conducted represent an overview of flavonoids and their conjugates in different types of plant material representing the model legume, M. truncatula.Electronic supplementary materialThe online version of this article (doi:10.1007/s11306-011-0287-2) contains supplementary material, which is available to authorized users.

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Isoflavonoids of the Leguminosae

Cited by 72 publications

References 148 publications

Integration of Microfractionation, qNMR and Zebrafish Screening for the In Vivo Bioassay-Guided Isolation and Quantitative Bioactivity Analysis of Natural Products

Integration of Microfractionation, qNMR and Zebrafish Screening for the In Vivo Bioassay-Guided Isolation and Quantitative Bioactivity Analysis of Natural Products

Quantitation of Flavanols, Proanthocyanidins, Isoflavones, Flavanones, Dihydrochalcones, Stilbenes, Benzoic Acid Derivatives Using Ultraviolet Absorbance after Identification by Liquid Chromatography–Mass Spectrometry

LC/MS profiling of flavonoid glycoconjugates isolated from hairy roots, suspension root cell cultures and seedling roots of Medicago truncatula

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