Elucidation of phenolic metabolites in wheat seedlings (Triticum aestivum L.) by NMR and HPLC-Q-Orbitrap-MS/MS: Changes in isolated phenolics and antioxidant effects through diverse growth times

Lee, Han-Gyeol; Yang, Ji Yeong; Ji, Eun; Ahn, Hyung-Jae; Lee, Mi Ja; Kim, Ho; Song, Seung-Yeob; Kim, Du Hyun; Lee, Jin Hwan; Seo, Woo Duck

doi:10.1016/j.fochx.2022.100557

Cited by 9 publications

(6 citation statements)

References 41 publications

(182 reference statements)

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“…This O -glycosylation was mainly positioned at C-2″. Based on these observations and comparison of its MS data with pieces of literature ( 66 ), peak 3 was tentatively assigned as apigenin-8- C -glucoside-2"- O -glucoside (isovitexin-2"- O -glucoside), which has been found in wheat seedlings ( T. aestivum ) ( 39 ).…”

Section: Resultsmentioning

confidence: 70%

“…The relatively higher intensity of the ions [M − H − 90] − than the ion [M − H − 120] − suggested the 6- C -pentosyl-8- C -hexosyl substitution. Based on these observations and comparison of its MS data with reported pieces of literature ( 39 , 65 ), it was tentatively assigned as luteolin-6- C -arabinoside-8- C -glucoside (isocarlinoside), which has been found in wheat seedlings ( T. aestivum ) ( 39 ).…”

Section: Resultsmentioning

confidence: 78%

“…Therefore, peaks 7, 9, and 11 were tentatively identified as tricin-5- O -glucoside, tricin-7- O -glucoside, and tricin-4'- O -glucoside, respectively, and these are interchangeable. Tricin-7- O -glucoside and tricin-5- O -glucoside have been reported in wheat seedlings ( T. aestivum ) ( 39 , 45 ), whereas tricin-4'- O -glucoside has not been described previously.…”

Section: Resultsmentioning

confidence: 93%

“…Therefore, peaks 7, 9, and 11 were tentatively identified as tricin-5-O-glucoside, tricin-7-Oglucoside, and tricin-4'-O-glucoside, respectively, and these are interchangeable. Tricin-7-O-glucoside and tricin-5-O-glucoside have been reported in wheat seedlings (T. aestivum)(39,45), whereas tricin-4'-O-glucoside has not been described previously.Peak 30 (t R = 7.36 min, mass error 0.2 ppm) exhibited a deprotonated ion at m/z 475.1241 [M − H] − , and the MS/MS profile was observed with a high intensity of fragment ion at m/z 313.0708 [M − H − 162] − for tetrahydroxyflavone-dimethyl ether moiety without a hexose. Further comparison of its MS data with the literature (55) confirmed the tentative identification of this peak as luteolin 3′,4′-dimethylether-7-O-glucoside.…”

mentioning

confidence: 92%

“…Our research group has developed wheat mutant lines generated by γ-irradiated mutagenesis, which exhibited diverse phenotypes with different plant heights and colors ( 36 ). Although the metabolite composition of several parts of wheat, including grain (or wholegrain), bran, and sprout, has been extensively reported ( 2 , 3 , 37 – 39 ), the chemical profile of the hull part is still not fully characterized. Therefore, the hulls of γ-irradiated wheat mutant lines were collected for untargeted metabolite analysis using the LC–MS/MS method.…”

Section: Introductionmentioning

confidence: 99%

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Phytochemical profile and anti-inflammatory activity of the hull of γ-irradiated wheat mutant lines (Triticum aestivum L.)

Park,

Kil,

Ryoo

et al. 2023

Front. Nutr.

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Wheat (Triticum aestivum Linn.; Poaceae) is the second most cultivated food crop among all global cereal crop production. The high carbohydrate content of its grains provides energy, multiple nutrients, and dietary fiber. After threshing, a substantial amount of wheat hull is produced, which serves as the non-food component of wheat. For the valorization of these by-products as a new resource from which functional components can be extracted, the hull from the seeds of cultivated wheat mutant lines bred after γ-irradiation were collected. Untargeted metabolite analysis of the hull of the original cultivar (a crossbreeding cultivar., Woori-mil × D-7) and its 983 mutant lines were conducted using ultra-performance liquid chromatography–electrospray ionization quadrupole time-of-flight mass spectrometry technique. A total of 55 molecules were tentatively identified, including 21 compounds found in the Triticum species for the first time and 13 compounds not previously described. Among them, seven flavonolignans with a diastereomeric structure, isolated as a single compound from the hull of T. aestivum in our previous study, were used as the standards in the metabolite analysis. The differences in their collision cross-section values were shown to contribute to the clear distinction between tricine-lignan stereoisomers. To select functionally active agents with anti-inflammatory activity among the identified compounds, the wheat hull samples were evaluated for their inhibitory effect on nitric oxide production in lipopolysaccharide-stimulated RAW 264.7 cells. As a result of multivariate analysis based on the results of chemical and biological profiles of the wheat hull samples, 10 metabolites were identified as key markers, contributing to the distinction between active and inactive mutant lines. Considering that one of the four key markers attributed to anti-inflammatory activity has been identified to be a flavonolignan, the wheat hull could be a valuable source of diverse tricin-lignan type compounds and used as a natural health-promoting product in food supplements.

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Section: Resultsmentioning

confidence: 70%

Section: Resultsmentioning

confidence: 78%

Section: Resultsmentioning

confidence: 93%

mentioning

confidence: 92%

Section: Introductionmentioning

confidence: 99%

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Phytochemical profile and anti-inflammatory activity of the hull of γ-irradiated wheat mutant lines (Triticum aestivum L.)

Park,

Kil,

Ryoo

et al. 2023

Front. Nutr.

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Exploring anti‐inflammatory and antioxidant‐related quality markers of Artemisia absinthium L. based on spectrum–effect relationship

Wubuli,

Abdulla,

Zhao

et al. 2024

Phytochemical Analysis

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IntroductionArtemisia absinthium L. is a well‐known medicinal, aromatic, and edible plant with important medicinal and economic properties and a long history of use in treating liver inflammation and other diseases; however, there has been insufficient progress in quality control.ObjectiveThis study aimed to investigate the quality markers for the anti‐inflammatory and antioxidant activities of A. absinthium based on spectrum–effect relationship analysis.Materials and methodsEighteen batches of A. absinthium from different origins were used. Chemical fingerprints were obtained by ultra‐performance liquid chromatography (UPLC). The chemical compositions were identified by quadrupole‐Orbitrap high‐resolution mass spectrometry. Anti‐inflammatory activity was assessed by inhibition of cyclooxygenase‐2 and 15‐lipoxygenase in vitro and inhibition of nitric oxide release in lipopolysaccharide‐induced BV‐2 cells. Antioxidant activity was assessed by DPPH and ABTS radical scavenging assays. The relationship between bioactivity and chemical fingerprints was then analyzed using chemometrics including gray relational analysis, bivariate correlation analysis, and orthogonal partial least squares analysis.ResultsDifferent batches of A. absinthium extracts possessed significant anti‐inflammatory and antioxidant activities to varying degrees. Eighty compounds were identified from A. absinthium, and 12 main common peaks were obtained from the UPLC fingerprints. P3 (chlorogenic acid), P5 (isochlorogenic acid A), and P6 (isochlorogenic acid C) were screened as the most promising active compounds by correlation analysis and further validated for their remarkable anti‐inflammatory effects.ConclusionThis is the first study to screen the quality markers of A. absinthium by establishing the spectrum–effect relationship, which can provide a reference for the development of quality standards and further research on A. absinthium.

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Comparative metabolomic analysis of mouse plasma in response to different dietary conditions

Yang,

Kim,

Lee

et al. 2023

Food Sci Biotechnol

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Elucidation of phenolic metabolites in wheat seedlings (Triticum aestivum L.) by NMR and HPLC-Q-Orbitrap-MS/MS: Changes in isolated phenolics and antioxidant effects through diverse growth times

Cited by 9 publications

References 41 publications

Phytochemical profile and anti-inflammatory activity of the hull of γ-irradiated wheat mutant lines (Triticum aestivum L.)

Phytochemical profile and anti-inflammatory activity of the hull of γ-irradiated wheat mutant lines (Triticum aestivum L.)

Exploring anti‐inflammatory and antioxidant‐related quality markers of Artemisia absinthium L. based on spectrum–effect relationship

Comparative metabolomic analysis of mouse plasma in response to different dietary conditions

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