Antioxidant Activity of Anthraquinones and Flavonoids from Flower ofReynoutria sachalinensis

Zhang, Xinfeng; Thương, Phương Thiện; Jin, Wen; Su, Nguyen Duy; Sok, Dai‐Eun; Bae, KiHwan; Kang, Sam Sik

doi:10.1007/bf02975130

Cited by 64 publications

(37 citation statements)

References 20 publications

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“…Repeated column chromatography of soluble fractions obtained fifteen compounds (1-15) including 1-2 from hexane-soluble fraction, 3-13 from EtOAc-soluble fraction and 14-15 from BuOHsoluble fraction. On the basis of their physicochemical data, and by comparing with those published in the literature, isolated compounds (1-15) were identified as chyrsophanol (1) (Sang et al, 2005), physcion (2) (Carmo et al, 1981), desoxyrhaponticin (3) (Kashiwada et al, 1984), rhapontincin (4) (Yoshiki et al, 1984), resveratrol (5) (Jin et al, 2002), desoxyrhapontigenin (6) (Kashiwada et al, 1984), emodin (7) (Choi et al, 2005), rhapontigenin (8) (Kashiwada et al, 1984), chrysophanol-8-O-E-D-glucopyranoside (9) (Kashiwada et al, 1984), piracetannol-3'-E-D-glucopyranoside (10) (Kashiwada et al, 1984), piceid (11) (Kashiwada et al, 1984), H-viniferin (12) (Ito et al, 1999;Kim et al, 1999), isorhapontin (14) (Artemnika et al, 2004), and emodin-8-O-E-glucopyranoside (15) (Zhang et al, 2005).…”

Section: Resultsmentioning

confidence: 96%

Lipoxygenase inhibitory constituents from rhubarb

et al. 2008

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Phytochemical study on the ethanol extract of rhubarb led to the isolation of fifteen compounds, including five anthraquinones: chrysophanol (1), physcion (2), emodin (7), chrysophanol-8-O-beta-D: -glucopyranoside (9) and emodin-8-O-beta-D: -glucopyranoside (15), and ten stilbenes: desoxyrhaponticin (3), rhaponticin (4), resveratrol (5), desoxyrhapotigenin (6), rhapontigenin (8), piceatannol-3'-O-beta-D: -glucopyranoside (10), piceid (11), epsilon-viniferin (12), ampelopsin B (13) and isorhaponticin (14). Their structures were identified by comparing the physicochemical data with those of published papers. Among the isolated compounds, stilbene derivatives (3-6, 8 and 10-14) showed remarkable inhibitory effect on lipoxygenase with IC(50) values ranging from 6.7 to 74.1 microM. The inhibition kinetics analyzed by Lineweaver-Burk plots found that they were competitive inhibitors with the linoleic acid at the active site of lipoxygenase. In addition, stilbenes exhibited significantly free radical scavenging activity against ABTS(.+) with trolox equivalent activity capacity (TEAC) values ranging from 1.16 to 4.64. Whereas, anthraquinone derivatives (1-2, 7, 9 and 15) neither inhibited lipoxygenase nor scavenged free radical ABTS(.+). These results indicated that stilbene derivatives were considerate to be mainly lipoxygenase inhibitor and free radical scavenger constituents of rhubarb.

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Section: Resultsmentioning

confidence: 96%

Lipoxygenase inhibitory constituents from rhubarb

et al. 2008

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“…Many others biological activities for these flavonoid glycosides have been described, including antioxidant (compounds 1 and [66,67] amoebicidal, spasmogenic and giardicidal (compound 1), [68] antilipoxygenase (compound 2), [69] analgesic (compound 2), [70] antiviral (compounds 1 [71] and 4 [59] ), anti-inflamatory (compounds 1, 2 and 4), [72] and tissue thromboplastin inhibitory (compounds 1, 3 and 4). [73] DOSY NMR has found many uses in chemical research as can be seen in numerous reports in the literature.…”

Section: Resultsmentioning

confidence: 99%

DOSY NMR applied to analysis of flavonoid glycosides from Bidens sulphurea

Rodrigues¹,

Silva²,

Oliveira³

et al. 2009

Magnetic Reson in Chemistry

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2D DOSY 1H NMR has proved to be a useful technique in the identification of the molecular skeleton of the four major compounds of ethyl acetate extract of aerial parts of Bidens sulphurea (Asteraceae). The combination of this technique with HPLC, mass spectrometry and other NMR techniques enabled the identification of four flavonoid glycosides: quercetin-3-O-beta-D-galactopyranoside, quercetin-3-O-beta-D-glycopyranoside, quercetin-3-O-alpha-L-arabinofuranoside and quercetin-3-O-beta-D-rhamnopyranoside.

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“…The 1 H NMR signals for these compounds were found in the aromatic region (6-8ppm) and sugar region (3-4.2 ppm). The configuration of the sugars were determined by the coupling constant of the anomeric hydrogen, where compound 3 showed the anomeric hydrogen at δ5.58 with J=1.00 Hz, indicating that arabinofuranoside is α (Zhang et al, 2005), compound 4 was δ5.17 with J=7.2 Hz, showing a β configuration for xyloside (Yan et al, 2002), and compound 5 was δ5.39 with J=7.8 Hz, a β configuration for galactoside (Santos, Schripsema, Kuster, 2005).…”

Section: Resultsmentioning

confidence: 99%

Phytochemical constituents and preliminary toxicity evaluation of leaves from Rourea induta Planch. (Connaraceae)

Kalegari

Miguel

Dias

et al. 2011

Braz. J. Pharm. Sci.

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Most active plants are toxic at high doses and it is therefore important to investigate the preliminary toxicity of plant extracts. The Rourea induta species is a potential drug with no phytochemical or biological studies registered in the literature. Thus, a phytochemical study and a toxicity analysis of the ethanolic extract obtained from the leaves of Rourea induta Planch., Connaraceae, was run. A long chain hydrocarbon, n-tetracosane, and four flavonoids were identified: quercetin, and three glycosylated derivates, quercetin-3-O-α-arabinofuranoside, quercetin-3-O-β-xyloside and quercetin-3-O-β-galactoside. This is the first time these have been isolated in this species. The structures were elucidated by 13 C NMR, 1 H NMR, UV and IR spectroscopy. The toxicity evaluation of extracts was performed by the brine shrimp method and determination of hemolytic activity. The samples demonstrated no toxic potential by the analyzed methods. A maioria das plantas ativas é tóxica em doses elevadas, portanto, é importante a investigação da toxicidade preliminar dos extratos das plantas. A espécie Rourea induta é uma droga potencial que não apresenta estudo fitoquímico ou biológico descrito na literatura. Assim, um estudo fitoquímico e análises toxicológicas foram realizados com o extrato etanólico obtido das folhas de Rourea induta Planch., Connaraceae. Foram obtidos um hidrocarboneto de cadeia longa, n-tetracosano, e quatro flavonóides, quercetina e três derivados glicosilados, quercetina-3-O-α-arabinofuranosideo, quercetina-3-O-β-xilosideo e quercetina-3-O-β-galactosideo. Esta é a primeira vez que estes compostos são isolados nesta espécie. As estruturas foram elucidadas por espectroscopia de RMN-13 C, RMN-1 H, ultravioleta e infravermelho. A avaliação da toxicidade dos extratos foi analisada pelo método da Artemia salina e atividade hemolítica. Nenhuma das amostras testadas apresentou um potencial tóxico pelos métodos analisados.Unitermos: Rourea induta/fitoquímica. Connaraceae/fitoquímica. Flavonóides. N-tetracosano. Extrato de plantas/toxicidade.

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Antioxidant Activity of Anthraquinones and Flavonoids from Flower ofReynoutria sachalinensis

Cited by 64 publications

References 20 publications

Lipoxygenase inhibitory constituents from rhubarb

Lipoxygenase inhibitory constituents from rhubarb

DOSY NMR applied to analysis of flavonoid glycosides from Bidens sulphurea

Phytochemical constituents and preliminary toxicity evaluation of leaves from Rourea induta Planch. (Connaraceae)

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