A study of isomeric diglycosyl flavonoids by SORI CID of fourier transform ion cyclotron mass spectrometry in negative ion mode

Yan, Cunyu; Liu, Shuying; Zhou, Yihan; Song, Fengrui; Cui, Meng; Liu, Zhiqiang

doi:10.1016/j.jasms.2007.09.012

Cited by 12 publications

(9 citation statements)

References 23 publications

(32 reference statements)

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“…Upon CID fragmentation, the aglycone fragment was the base peak for all of the glycosides. For apigetrin and naringin, the [1,3 A] − fragment ion, with the sugar groups intact, was detected at approximately 20% abundance, that has been reported previously for flavonoid glycones 40 ; however, in the case of naringin, this ion could also correspond to fragmentation along the glycoside directly connected to the aglycone 38 . The neutral loss of m/z 132 from apiin corresponds to the loss of its pentose substituent.…”

Section: Resultssupporting

confidence: 75%

A capillary electrophoresis electrospray ionization-mass spectrometry method using a borate background electrolyte for the fingerprinting analysis of flavonoids in Ginkgo biloba herbal supplements

Johnson

Lunte

2016

Anal. Methods

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A laboratory-built sheath liquid capillary electrophoresis-mass spectrometry interface was used to develop a qualitative method for fingerprinting analysis of 14 structurally similar flavones, flavonols, flavonones, and several representative glycosides in plant samples. The migration order of the flavonoids was dependent on a the number of hydroxyl groups present on the flavonoid B-ring, extent of conjugation, number of glycosidic functionalities, and ability of the flavonoid to form stable borate complexes with the background electrolyte. Parent ion scans of the flavonoids yielded [M-H]−, except for catechol containing flavonoids, which were detected as borate adducts. These adducts can be used diagnostically to determine the presence or absence of catechol groups on unknown polyphenolic compounds. Product ion scans of the flavonoid glycosides and borate adducts typically yielded the deprotonated aglycone fragment as the base peak, which could be used to confirm the base structure of the flavonoid. This method’s utility was demonstrated by analyzing flavonoids present in ethanolic extracts of Ginkgo biloba herbal supplements.

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Section: Resultssupporting

confidence: 75%

A capillary electrophoresis electrospray ionization-mass spectrometry method using a borate background electrolyte for the fingerprinting analysis of flavonoids in Ginkgo biloba herbal supplements

Johnson

Lunte

2016

Anal. Methods

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“…In this case, compound 2 would be neoeriocitin (eriodictyol‐7‐ O ‐neohesperidiside) and compound 3 eriocitrin (eriodictyol‐7‐ O ‐rutinoside). According to the literature, compound 4 is probably a hesperidin or a neohesperidin . Compounds 5 and 6 present similar molecular weights and fragments ( m / z 595, 433, 287) and are probably didymin, poncirin or saponarin, while compounds 7, 8 and 9 were identified by their molecular weights and respective fragments.…”

Section: Resultsmentioning

confidence: 95%

Insights into the development of grapefruit nutraceutical powder by spray drying: physical characterization, chemical composition and 3D intestinal permeability

et al. 2019

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BACKGROUND The development of functional and nutraceutical foods comes from a greater awareness of the relationship between food and health by consumers. In recent years, the idea of purifying and encapsulating bioactive compounds through techniques such as spray drying has been well received by the food industry. The development and characterization of a grapefruit (Citrus paradisi) nutraceutical powder obtained by spray drying is of great interest owing to the different bioactive compounds and the potential health effects. RESULTS The grapefruit powder was characterized by a low water amount (1.5 g water per 100 g powder) and a high porosity (75%). The color parameters were L* = 80.0 ± 1.8, hab* = 61.7 ± 0.4 and Cab* = 11.4 ± 0.6. The IC50 values determined for the freeze‐dried oxalic acid extract (FDOA) and the freeze‐dried methanol–water extract (FDMW) were 0.48 and 0.72 mg mL−1 respectively, while the total phenolic content (TPC) ranged between 1274 and 1294 mg gallic acid equivalent (GAE) per 100 g dry basis (d.b.). Regarding total flavonoid content (TFC), FDOA presented the highest amount (6592 mg quercetin equivalent (QE) per 100 g d.b.). For both extracts, the cell viability in Caco‐2 and HT29‐MTX was above 90% at 100 μg mL−1. The bioavailability of the bioactive compounds was analyzed through a 3D intestinal model. Delphenidin‐3‐glucoside and hesperitin‐7‐O‐glucoside presented a permeation higher than 50%, followed by hesperidin which was close to 30%. CONCLUSION This work allows to establish that the formulation of grapefruit powder has great potential as a nutraceutical food, with spray drying being a good alternative technique in the food industry. © 2019 Society of Chemical Industry

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“…In contrast, the steric hindrance is greatly reduced in the flavone and flavanone with ring B conjugated on the C2 position. In addition, the double bond between C2 and C3 of the flavone skeleton allows extended conjugation among the three rings and forms an integrated -conjugated plane that may facilitate its binding to DNA [17,19,46,47]. In the case of flavanone, the single bond between C2 and C3 of the skeleton allows free rotation of ring B relative to the plane defined by ring A and ring C [47,48], which may result in more favorable conformations for its interaction with DNA.…”

Section: Relative Binding Affinities Of the Flavonoids To Dna Duplexesmentioning

confidence: 99%

Evaluation of flavonoids binding to DNA duplexes by electrospray ionization mass spectrometry

Zhaofu

Cui

Song

et al. 2008

J. Am. Soc. Mass Spectrom.

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In this study, electrospray ionization mass spectrometry (ESI·I\tIS) was Llsed to investigate the binding interactions of ten flavonoid aglycones and ten flavonoid glycosides with DNA duplexes. Relative binding affinities of the flavonoids toward DNA duplexes were estimated based on the fraction of bound DNA. The results revealed that the 4'-OH group of flavonoid aglycones was essential for their DNA-binding properties. Flavonoid glycosides with sugar chain linked on ring A or ring B showed enhanced binding toward the duplexes over their aglycone counterparts, whereas glycosylation of the flavonol quercetin on ring C exhibited a less pronounced effect. The aglycone skeletons and other hydroxyl substitutions on the aglycone also have an effect on the fractions of bound DNA. Upon collision-induced dissociation, the complexes containing flavonoid aglycones underwent the predominant ejection of a neutral ligand molecule, suggesting an intercalative DNA-binding mode. . These drugs may bind to certain DNA sequences, prevent the specific recognition of these sequences with their trans-acting factors, and interfere with the replication or transcription of certain genes, and thus exert their pharmacological activities [2]. Among the various organic molecules, natural products have attracted considerable interest given that many clinical anticancer drugs are natural products (or their derivatives) and most of them exert their effects by acting on DNA [1]. In this context, studies of the binding of natural products with DNA are helpful for better understanding the molecular basis of their bioac· tivities as well as providing useful guidance for further deSign of more efficient anticancer drugs [1, 3-7J.As an important class of natural products, flavonoids have received considerable attention because of their health benefits and chemopreventive properties [8]. Flavonoids consist of a diverse group of compounds derived from 2-phenolchromotome and can be categorized into several subgroups according to the structure (Table 1). Flavonoid aglycones and their modified forms are widely found in the roots, stalks, and fruits of many natural plants and act as the major functional components in many herb medicines [8,9]. Many studies have demonstrated that flavonoids possess a wide range of biological activities, such as anticancer, antiviral, antibacterial, antiOXidants, and anti~inflammatory effects [8J. These biological activities are considered to be related to their interaction with several enzymes in the human body as well as their notable antioxidant activity [8, 1OJ. Meanwhile, the binding of flavonoids to nucleic acid structures has also been recognized as one important mechanism of their actions [11-19[. The noncovalent interactions between flavonoids and DNA have been elucidated using several solution-phase techniques including absorption [20,21], fluorescence [21], linear dichroism [22], and nuclear magnetic resonance [23J spectroscopies, as well as electrochemical [24] and surface plasmon resonance [25] techniques. Ho...

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A study of isomeric diglycosyl flavonoids by SORI CID of fourier transform ion cyclotron mass spectrometry in negative ion mode

Cited by 12 publications

References 23 publications

A capillary electrophoresis electrospray ionization-mass spectrometry method using a borate background electrolyte for the fingerprinting analysis of flavonoids in Ginkgo biloba herbal supplements

A capillary electrophoresis electrospray ionization-mass spectrometry method using a borate background electrolyte for the fingerprinting analysis of flavonoids in Ginkgo biloba herbal supplements

Insights into the development of grapefruit nutraceutical powder by spray drying: physical characterization, chemical composition and 3D intestinal permeability

Evaluation of flavonoids binding to DNA duplexes by electrospray ionization mass spectrometry

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