• Title/Summary/Keyword: Flavonoid glycosides

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Comparative Phytochemical Profiling of Methanolic Extracts of Different Parts of White Dandelion (Taraxacum coreanum) using Hybrid Ion-mobility Q-TOF MS

  • Hyemi Jang;Mira Choi;Eunmi Lee;Kyoung-Soon Jang
    • Mass Spectrometry Letters
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    • v.15 no.2
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    • pp.95-106
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    • 2024
  • Taraxacum coreanum, known as the native Korean white dandelion, has been historically used in traditional medicine due to its various therapeutic properties. However, the specific benefits and mechanisms of white dandelion in alleviating particular symptoms or diseases remain uncertain due to the complexity of its phytochemical profile. In this study, we aimed to elucidate the phytochemical profiles of methanolic extracts of different parts of the white dandelion (flower, leaf, stem, and root) using hybrid ion-mobility Q-TOF MS. Using the trapped ion mobility-based PASEF technique, 3715 and 2114 molecular features with MS2 fragments were obtained in positive and negative ion modes, respectively, and then a total of 360 and 156 phytochemical compounds were annotated by matching with a reference spectral library in positive and negative ion modes, respectively. Subsequent feature-based molecular networking analysis revealed the phytochemical differences across the four different parts of the white dandelion. Our findings indicated that the methanolic extracts contained various bioactive compounds, including lipids, flavonoids, phenolic acids, and sesquiterpenes. In particular, lipids such as linoleic acids, lysophosphatidylcholines, and sesquiterpenoids were predominantly present in the leaf, while flavonoid glycosides and lysophosphoethanolamines were notably enriched in the flower. An assessment of the total phenolic content (TPC) and total flavonoid content (TFC) of the methanolic extracts revealed that the majority of phytochemicals were concentrated in the flower. Interestingly, despite the root extract displaying the lowest TPC and TFC values, it exhibited the highest radical scavenging rate when normalized to TPC and TFC, suggesting a potent antioxidant effect. These findings and further investigations into the biological activities and medicinal potential of the identified compounds, particularly those exclusive to specific plant parts, may contribute to the development of novel therapeutic agents derived from white dandelion.

Comparison of Flavonoid Characteristics between Blueberry (Vaccinium corymbosum) and Black Raspberry (Rubus coreanus) Cultivated in Korea using UPLC-DAD-QTOF/MS (UPLC-DAD-QTOF/MS를 이용한 국내 재배 블루베리(Vaccinium corymbosum)와 복분자(Rubus coreanus)의 플라보노이드 특성 비교)

  • Jin, Young;Kim, Heon-Woong;Lee, Min-Ki;Lee, Seon-Hye;Jang, Hwan-Hee;Hwang, Yu-Jin;Choe, Jeong-Sook;Lee, Sung-Hyun;Cha, Youn-Soo;Kim, Jung-Bon
    • Korean Journal of Environmental Agriculture
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    • v.36 no.2
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    • pp.87-96
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    • 2017
  • BACKGROUND: The objective of this study was to identify and compare the main phenolic compounds (anthocyanins, flavonoids, phenolic acids) in blueberry and black raspberry cultivated in Korea using ultra-performance liquid chromatography diode array detection-quadrupole time-of-flight mass spectrometry (UPLC-DAD-QTOF/MS). METHODS AND RESULTS: Twenty-nine flavonoids were identified by comparison of ultraviolet and mass spectra with data in a chemical library and published data. Blueberry contained flavonols including kaempferol, quercetin, isorhamnetin, myricetin, and syringetin aglycones. Isorhamnetin 3-O-robinobioside, kaempferol 3-O-(6"-O-acetyl)glucoside, quercetin, quercetin 3-O-arabinofuranoside (avicularin), quercetin 3-O-(6''-O-malonyl) glucoside, and quercetin 3-O-robinobioside were detected for the first time in blueberry. The flavonoids in raspberry consisted of quercetin aglycone and its glycosides. The mean total flavonoid content in blueberry [143.0 mg/100 g dry weight (DW)] was 1.5-times that in raspberry (95.4 mg/100 g DW). The most abundant flavonoid in blueberry was quercetin 3-O-galactoside (hyperoside, up to 76.1 mg/100 g DW) and that in raspberry was quercetin 3-O-glucuronide (miquelianin, up to 55.5 mg/100 g DW). Miquelianin was not detected in blueberry. CONCLUSION: Flavonol glycosides were the main flavonoids in blueberry and black raspberry cultivated in Korea. The composition and contents of flavonoids differed between blueberry and black raspberry, and may be affected by the cultivar and cultivation conditions.

Constituents of the Fruits and Leaves of Euodia daniellii

  • Yoo, Sang-Woo;Kim, Ju-Sun;Kang, Sam-Sik;Son, Kun-Ho;Chang, Hyeun-Wook;Kim, Hyun-Pyo;Bae, Ki-Hwan;Lee, Chong-Ock
    • Archives of Pharmacal Research
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    • v.25 no.6
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    • pp.824-830
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    • 2002
  • Four flavonoid glycosides, flavaprin (7), evodioside B (8), vitexin (11), and hesperidin (12), as well as the coumarins bergapten (1), xanthotoxin (2), and isopimpinellin (3), the lignan simplexoside (10), the steroids ${\beta}-sitosterol$ (4) and daucosterol (5), the limonoids isolimonexic acid (6) and limonin (9), and uracil (13) and myo-inositol (14) have been isolated from Euodia daniellii. The structures of these compounds were established from spectral data. Among the isolates, bergapten showed cyclooxygenase-2 inhibitory activity with an $IC_{50}$ value of $6.2{\;}{\mu\textrm{g}}/ml. Flavonoids isolated from this plant exhibited no cytotoxic activity against the human tumor cell lines, A549, SKOV-3, SKMEL-2, XF498, and HCT15.

Evaluation of Skin Sebosuppression by Components of Total Green Tea (Camellia sinensis) Extracts

  • Kim, Jeong-Kee;Shin, Hyun-Jung;Lee, Byeong-Gon;Lee, Sang-Jun
    • Food Science and Biotechnology
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    • v.17 no.3
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    • pp.464-469
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    • 2008
  • In human beings, it is known that there is a correlation between the occurrence of acne and the ability to suppress sebum. Sebosuppression may be related to the inhibition of sebocyte proliferation, differentiation, and lipogenesis in sebaceous glands. To investigate the skin sebosuppressive activity of green tea extract, the in vivo effects of its flavonoid compounds on the androgen-dependent stimulation of pigmented macules in hamsters and performed in vitro experiments with human primary sebocytes were examined. Our results imply a dual activity of skin sebosuppression by green tea flavonoids; some catechins including epigallocatechin-3-gallate (EGCG) and gallocatechin-3-gallate (GCG) may reduce the differentiation of sebocytes by inhibiting PPAR-${\gamma}1$ mRNA expression, whereas some flavonol glycosides including kaempferol may inhibit lipogenesis in sebaceous glands by decreasing levels of the mature form of sterol-sensitive response elements binding protein-1c (SREBP-1c). Therefore, green tea is a potentially effective material for use in the development of health foods or cosmetics for skin sebosuppression.

Antioxidant Activity of Flavonoids in Plant Origin Food (식물성 식품에 존재하는 Flavonoids의 항산화 활성)

  • 김건희;최미희
    • Food Science and Preservation
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    • v.6 no.1
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    • pp.121-135
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    • 1999
  • Effective synthetic antioxidants such as butylated hydroxyanisole(BHA) and butylated hydroxytoluene(BHT) have been widely used in the food industry, but they are suspected to be toxic and carcinogenic effects. Therefore, the development of safely available natural antioxidants such as ascorbic acid, ${\alpha}$-tocopherol, ${\beta}$-carotene, flavonoids and selenium is essential. In particular, flavonoids, 2-phenyl-benzo-${\alpha}$-pyrones, are polyphenolic compounds that occur ubiquitously in food of plant origin. flavonoids occur in foods generally as O-glycosides with sugars bound usually at the C\ulcorner position. And variations in their heterocyclic ring gibes rise to flavones, flavonols, flavanones, flavanols, catechins, anthocyanidins, chalcone and isoflavones. Vegetables, fruits, and beverages are the main dietary sources of the flavonols, primarily as quercetin, kaempferol, and myricetin and the corresponding flavones, apigenin and luteolin. These flavonoids have biological activity such as antioxidant, anti-inflammatory, antithrombotic, antimutagenic, anticarcimogenic antiallergic and antimicrobial activity effects in vitro and in vivo. Flavonoids posses strong antioxidant activities acting as oxygen radicals scavenger, metal chelators and enzyme inhibitor. The antioxidant activity of flavonoids is determined by their molecular structure and more specially, by the position and degree of hydroxylation of the ring structure. All flavonoids with the 3`, 4`-dihydroxy(ortho-dihydroxy) posses marked antioxidant activity. And antioxidant activity increases with the number of hydroxyl groups substituted on the A-and B-rings. There is as yet no certainty about the effect of the presence of a double bond between C\ulcorner and C\ulcorner on the antioxidant activity of flavonoids.

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Flavonoid Glycosides Inhibit Sortase A and Sortase A-Mediated Aggregation of Streptococcus mutans, an Oral Bacterium Responsible for Human Dental Caries

  • Yang, Woo-Young;Kim, Chang-Kwon;Ahn, Chan-Hong;Kim, Heegyu;Shin, Jongheon;Oh, Ki-Bong
    • Journal of Microbiology and Biotechnology
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    • v.26 no.9
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    • pp.1566-1569
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    • 2016
  • Three flavonoids were isolated from dried flowers of Sophora japonica using repetitive column chromatography and high-performance liquid chromatography. The flavonoids were identified as rutin (1), quercetin-3'-O-methyl-3-O-α-ʟ-rhamnopyranosyl(1 → 6)-β-ᴅ-glucopyranoside (2), and quercetin (3) on the basis of spectroscopic analysis and comparison of values reported in the literature. These compounds inhibited the action of sortase A (SrtA) from Streptococcus mutans, a primary etiologic agent of human dental caries. The onset and magnitude of inhibition of saliva-induced aggregation of S. mutans treated with compound 1 was comparable to that of untreated S. mutans with a deletion of the srtA gene.

Norisoprenoids and Hepatoprotective Flavone Glycosides from the Aerial Parts of Beta vulgaris var. cicla

  • Kim, In-Kyum;Chin, Young-Won;Lim, Song-Won;Kim, Young-Choong;Kim, Jin-Woong
    • Archives of Pharmacal Research
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    • v.27 no.6
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    • pp.600-603
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    • 2004
  • (+)-Dehydrovomifoliol (1). 3-hydroxy-5$\alpha$,6$\alpha$-epoxy-$\beta$-ionone (2), vitexin 7 -O-$\beta$-D-glucopyrano-side (3), and vitexin 2'-O-$\beta$-D-glucopyranoside (4) were isolated as new constituents from the aerial parts of Beta vulgaris var. cicla. Compounds 3 and 4 demonstrated hepatoprotective activity with values of 65.8 and 56.1%, respectively, in primary cultured rat hepatocytes with $CCl_4$-induced cell toxicity, compared to controls. This was comparable to that of silibinin (69.8%) which was used as a positive control.trol.

The Anti-oxidative Compounds of Smilax riparia Leaves (Smilax riparia 잎의 항산화 성분)

  • 조은선;김정일;김호현;전인주;함인혜;황완균
    • YAKHAK HOEJI
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    • v.47 no.5
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    • pp.300-306
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    • 2003
  • Rhizoma of Smilax china has been used as anti-inflammatory and analgesic, antiedemic agent in Korean folk medicine. In order to investigate the efficacy of anti-oxidative activity, the activity-guided fractionation and the isolation were performed. Each fractions ($H_2O$ fraction, 20%, 40%, 60%, 100% MeOH fractions and CHCl$_3$ fraction) was examined antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging potential. It was revealed that 40%, 20% MeOH fractions and $H_2O$ fractions have significant anti-oxidative activity. From 40% and 20% MeOH fractions two flavonoid glycosides and one procyanidin were isolated and elucidated apigenin-7-Ο-$\alpha$-L-rhamnopyranosyl(1\longrightarrow2)-$\beta$-D-glucopyranoside, apigenin-7-Ο-$\alpha$-L-rhamnopyranosyl(1\longrightarrow6)-$\beta$-D-glucopyranoside and catechin(4$\alpha$\longrightarrow6)epicatechin through their physicochemical data and IR, FAB-MS, $^{13}$ C-NMR, and $^1$H-NMR analysis with authentics, respectively. The isolated compounds were examined by DPPH method. Apigenin-7-Ο-$\alpha$-L-rhamnopyranosyl(1\longrightarrow2)-$\beta$-D-glucopyranoside and catechin (4$\alpha$\longrightarrow6) epicatechin showed powerful radical scavenging activities on DPPH radical among three compounds.

Bidirectional Interactions between Green Tea (GT) Polyphenols and Human Gut Bacteria

  • Se Rin Choi;Hyunji Lee;Digar Singh;Donghyun Cho;Jin-Oh Chung;Jong-Hwa Roh;Wan-Gi Kim;Choong Hwan Lee
    • Journal of Microbiology and Biotechnology
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    • v.33 no.10
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    • pp.1317-1328
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    • 2023
  • Green tea (GT) polyphenols undergo extensive metabolism within gastrointestinal tract (GIT), where their derivatives compounds potentially modulate the gut microbiome. This biotransformation process involves a cascade of exclusive gut microbial enzymes which chemically modify the GT polyphenols influencing both their bioactivity and bioavailability in host. Herein, we examined the in vitro interactions between 37 different human gut microbiota and the GT polyphenols. UHPLC-LTQ-Orbitrap-MS/MS analysis of the culture broth extracts unravel that genera Adlercreutzia, Eggerthella and Lactiplantibacillus plantarum KACC11451 promoted C-ring opening reaction in GT catechins. In addition, L. plantarum also hydrolyzed catechin galloyl esters to produce gallic acid and pyrogallol, and also converted flavonoid glycosides to their aglycone derivatives. Biotransformation of GT polyphenols into derivative compounds enhanced their antioxidant bioactivities in culture broth extracts. Considering the effects of GT polyphenols on specific growth rates of gut bacteria, we noted that GT polyphenols and their derivate compounds inhibited most species in phylum Actinobacteria, Bacteroides, and Firmicutes except genus Lactobacillus. The present study delineates the likely mechanisms involved in the metabolism and bioavailability of GT polyphenols upon exposure to gut microbiota. Further, widening this workflow to understand the metabolism of various other dietary polyphenols can unravel their biotransformation mechanisms and associated functions in human GIT.

Tissue Concentration of Quercetin, Isoquercitrin and Hyperoside, and Lipid Profile Changes Following 8-Week Feeding of Angelica keiskei Powder in Rats (백서에서 신선초 8주 투여에 의한 quercetin, isoquercitrin 및 hyperoside의 체내농도 및 혈중 지질함량 변화)

  • Choe, Kyu-Hong;Choe, Sun-Nam;Choo, Jong-Jae;Lee, Jeong-Yeol;Kim, Jong-Yeon;Kim, Ju-Wan;Choi, Ji-Sung;Park, Ki-Seok;Park, Kwan-Ha
    • Korean Journal of Food Science and Technology
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    • v.39 no.6
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    • pp.721-724
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    • 2007
  • In this study, we examined the effects of Angelica keiskei (AK) in rats, in order to evaluate tissue quercetin concentrations and serum lipid profile changes. Dried AK powder was added to a regular chow at a 5% level, and fed for 8 weeks to male rats. AK significantly lowered serum total cholesterol, low-density lipoprotein cholesterol, and very low-density lipoprotein cholesterol levels, while it increased high-density lipoprotein cholesterol levels. However, AK did not influence serum triglyceride levels. Two antioxidant flavonoids present in AK, quercetin and its glycoside isoquercitrin, were detected in the serum and liver of the rat. However, another quercetin glycoside, hyperoside, was not detected in either the serum or liver despite its presence in the diet. These results indicate that AK seems to alter serum lipid concentrations, possibly through the body's absorption of certain quercetin glycosides.