Characterization of flavone and flavonol aglycones by collision‐induced dissociation tandem mass spectrometry

L., Y.; Li, Q. M.; Heuvel, H. van den; Claeys, M.

doi:10.1002/(sici)1097-0231(199708)11:12<1357::aid-rcm983>3.3.co;2-0

Cited by 38 publications

(48 citation statements)

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“…The identified metabolites and their information in dog feces or/and urine was summarized in Table 2. To interpret the MS/MS fragmentation information of metabolites, the nomenclature of product ion employed was described by Ma et al [19] and Fabre et al [20] with minor modification. In brief, the bonds and aromatic rings of flavonone were labeled with numbers and capital letters, respectively, which is shown in M7 of Figure 3.…”

Section: Metabolism Studymentioning

confidence: 99%

“…The fragmentation pattern and retention time (19.7 min) were the same as that of the naringin standard, identifying this component as the parent drug naringin. MS/MS fragmentation showed the major fragment ions at m/z 459 ( 1,3 A À ion, the product of a retro Diels-Alder (RDA) reaction on naringin [19]), m/z 271 (À308 Da, loss of rhamnose and glucose group) and m/z 151 ( 1,3 A À ion, the product of a RDA reaction on the product ion at m/z 271).…”

Section: Metabolism Studymentioning

confidence: 99%

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Metabolism and excretion studies of oral administered naringin, a putative antitussive, in rats and dogs

Liu

Zou

Yang

et al. 2012

Biopharm & Drug Disp

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Naringin, a major active flavonone glycoside from a traditional Chinese medicine Huajuhong, has been demonstrated to have activities such as peripheral antitussive, mucoregulator and anti-inflammatory. The purpose of this study was to elucidate the metabolism and mass balance of orally administered naringin in rats and dogs. After oral administration of naringin to rats and dogs at doses of 42 mg/kg and 12.4 mg/kg, respectively, metabolites in excreta were identified using a LC-Q-TOF system. The major metabolites including naringin, total naringenin (including free naringenin and its conjugates) and 4-hydroxyphenylpropionic acid in excreta were quantified by a LC-MS/MS system. Twenty-two metabolites were identified in dogs and 17 metabolites were detected in rats. The observed routes of naringin metabolism were hydroxylation, methylation, acetylation, hydrogenation, deglycosylation, dehydrogenation, glucuronidation, sulfation, glucosylation, ring-fission, oxidation, glycine conjugation and dehydroxylation. On the basis of these identified metabolites, a comprehensive metabolic pathway of naringin was proposed. About 21% of administered naringin was recovered in rat excreta in the form of naringin, total naringenin and 4-hydroxyphenylpropionic acid, and about 60% was recovered in dog excreta. The levels of 4-hydroxyphenylpropionic acid in excreta were higher than those of naringin and total naringenin, and the quantified metabolites were excreted more through feces, rather than urine. Most of these metabolites were excreted within 36 h post dose. The results of metabolism and excretion studies provide an explanation for future pharmacological and toxicological findings and are the groundwork for clinical studies.

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Section: Metabolism Studymentioning

confidence: 99%

Section: Metabolism Studymentioning

confidence: 99%

Metabolism and excretion studies of oral administered naringin, a putative antitussive, in rats and dogs

Liu

Zou

Yang

et al. 2012

Biopharm & Drug Disp

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“…In the present study, the focus was given to characterizing the newly detected polyphenols based on their molecular ion peaks and mass fragmentation patterns obtained from LC/MS/MS. The product ions produced by aglycone fragmentation of the polyphenols are denoted according to the nomenclature proposed by Ma et al (1997). i,j A À and i,j B À refer to product ions containing A-and B-rings, respectively, and the superscript i and j represent the broken C-ring bond positions (Fig.…”

Section: Resultsmentioning

confidence: 99%

Polyphenolic profile and antioxidant effects of various parts of Artemisia annua L.

Song

Desta

Kim

et al. 2015

Biomedical Chromatography

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An annual Korean weed, Artemisia annua L., has been used as a folk medicine for the treatment of a number of diseases. Remarkably, among the 32 polyphenols characterized in various parts of plant tissue, including flowers, leafs, stems and roots, 10 compounds were detected for the first time using liquid chromatography-tandem mass spectrometry (LC/MS/MS). The quantification method was validated using structurally related external standards with determination coefficients (R(2) ) ≥0.9995. The limits of detection and quantitation were 0.068-3.932 and 0.226-13.108 mg/L, respectively. The recoveries estimated at 50 and 100 mg/L ranged between 60.6-92.2 and 61.3-111%, respectively, with relative standard deviations <12%. The roots contained the largest concentration of identified components, while the flowers contained the least. The antioxidant capacity evaluated in terms of 1,1-diphenyl-2-picrylhydrazyl and 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation-scavenging activities and reducing power was highest in the roots and lowest in the flowers. The findings are well correlated and suggest that the antioxidant capacities principally depend upon the polyphenol concentrations in each part of the plant.

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“…2 and Table 1. The ions produced by the aglycone fragmentation of the flavanones and flavones were denoted in terms of the nomenclature proposed by Ma et al (1997). The notations i,j A + and i,j B + represent fragment ions containing intact A-and B-rings, respectively, where the superscripts i and j indicate the broken bonds of the C-ring.…”

Section: Separation and Characterizationmentioning

confidence: 99%

Flavonoid profiles of immature and mature fruit tissues of Citrus grandis Osbeck (Dangyuja) and overall contribution to the antioxidant effect

Kim

Lee

et al. 2014

Biomedical Chromatography

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Citrus fruits are a valuable functional food and their peel is used in East Asian folk medicine. In this study, the polar components of the fruit tissues of Citrus grandis Osbeck were analyzed using high-performance liquid chromatography-tandem mass spectrometry and compared with reported data. Among the 13 characterized compounds, eight flavonoids and one coumarin were identified for the first time in fruit tissues. The total amount of the identified components was the largest for the immature fruit peel, followed by mature fruit peel, mature fruit flesh, and immature fruit flesh. Naringin (2) and neohesperidin (3) were particularly rich in all samples. The antioxidant activity of the flavonoids extracted from fruit tissues increased in a dose-dependent manner. The activity of the fruit peels was significantly higher than that of the fruit flesh. Copyright © 2014 John Wiley & Sons, Ltd.

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Characterization of flavone and flavonol aglycones by collision‐induced dissociation tandem mass spectrometry

Cited by 38 publications

References 0 publications

Metabolism and excretion studies of oral administered naringin, a putative antitussive, in rats and dogs

Metabolism and excretion studies of oral administered naringin, a putative antitussive, in rats and dogs

Polyphenolic profile and antioxidant effects of various parts of Artemisia annua L.

Flavonoid profiles of immature and mature fruit tissues of Citrus grandis Osbeck (Dangyuja) and overall contribution to the antioxidant effect

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