Xanthine Oxidase Inhibitors from the Flowers of<i>Chrysanthemum sinense</i>

Nguyen, Manh Duc; Awale, Suresh; Tezuka, Yasuhiro; Ueda, Junichi; Tran, Quan Hung; Kadota, Shigetoshi

doi:10.1055/s-2005-873181

Cited by 94 publications

(73 citation statements)

References 15 publications

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“…9) Our results suggested that flavonoids and caffeoylquinic acid derivatives are the active XO inhibitory constituents in the flowers of C. sinense. Flavonoids and caffeoylquinic acid derivatives are groups of natural products with varied biological and pharmacological activities.…”

Section: Resultsmentioning

confidence: 88%

“…7) In a previous study, we reported that the methanolic extract of the flowers of this plant and its constituents showed potent inhibitory activity against XO in vitro. 8,9) The results suggested that flavonoids and caffeoylquinic acid derivatives may play an important role in the XO inhibitory activity of this plant. Therefore, in this study we investigated the in vivo hypouricemic effect of acacetin (1) and 4,5-O-dicaffeoylquinic acid methyl ester (2) (Fig.…”

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confidence: 94%

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Hypouricemic Effects of Acacetin and 4,5-O-Dicaffeoylquinic Acid Methyl Ester on Serum Uric Acid Levels in Potassium Oxonate-Pretreated Rats

Nguyen

Awale

Tezuka

et al. 2005

Biological & Pharmaceutical Bulletin

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Gout is a common disease with a worldwide distribution and is mainly caused by deposition of monosodium urate crystals in joints and other tissues as a result of extracellular urate supersaturation.1) This diseases has been associated with hyperuricemia which results from the overproduction and/or underexcretion of uric acid and is greatly influenced by a high dietary intake of nucleic acids. [1][2][3] In the purine metabolism, xanthine and hypoxanthine are oxidized into uric acid by the activity of xanthine oxidase (XO).4) The compounds with ability to enhance the urinary excretion of uric acid or to inhibit uric acid biosynthesis have been generally employed for the treatment of gout.5) Allopurinol, a XO inhibitor which is used in clinically in the treatment of gout, but this drug suffers from many side effects such as hepatitis, nephropathy, and allergic reactions. 6)Chrysanthemum sinense SABINE (Asteraceae) is a medicinal plant which has been used in Vietnamese traditional medicine for the treatment of fever, rheumatism, inflammation, headache, and eyesight disorder. 7) In a previous study, we reported that the methanolic extract of the flowers of this plant and its constituents showed potent inhibitory activity against XO in vitro. 8,9) The results suggested that flavonoids and caffeoylquinic acid derivatives may play an important role in the XO inhibitory activity of this plant. Therefore, in this study we investigated the in vivo hypouricemic effect of acacetin (1) and 4,5-O-dicaffeoylquinic acid methyl ester (2) (Fig. 1), a flavonoid and a caffeoylquinic acid derivative, respectively, included in the flowers of C. sinense, using a rat model of hyperuricemia. MATERIALS AND METHODSChemicals 4,5-O-Dicaffeoylquinic acid methyl ester was isolated from the flowers of C. sinense, and its purity was confirmed by TLC and 1 H-NMR spectral observation as reported previously.10) Acacetin, allopurinol, and uric acid were obtained from Wako Pure Chemicals Industry (Osaka, Japan), and potassium oxonic acid was from Acros Organics (Geel, Belgium). Animals Male Sprague-Dawley rats (6 weeks old, nϭ8) obtained from Sankyo Labo Sevice (Tokyo, Japan) were maintained on a 12-h light/dark cycle in a temperature-and humidity-controlled room for 1 week prior to the experiment. The animals were fed with a laboratory pellet chow (CE-2; CLEA Japan Inc., Tokyo, Japan) and water ad libitum during the experiment. This study was conducted in accordance with the standards established by the Guide for the care and use of Laboratory Animals of Toyama Medical and Pharmaceutical University.Hypouricemic Effect in Potassium Oxonate-Treated Rats An animal model of hyperuricemia induced by the uricase inhibitor potassium oxonate has been used to study in vivo anti-hyperuricemia effects of drugs. 5,6) Briefly, rats were treated with the uricase inhibitor potassium oxonate (PO) (250 mg/kg, i.p.) 1 h before oral (p.o) or intraperitoneal (i.p) administration of test compounds. Blood was taken by cutting the tail tip 2 h after the test drug administ...

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Section: Resultsmentioning

confidence: 88%

mentioning

confidence: 94%

Hypouricemic Effects of Acacetin and 4,5-O-Dicaffeoylquinic Acid Methyl Ester on Serum Uric Acid Levels in Potassium Oxonate-Pretreated Rats

Nguyen

Awale

Tezuka

et al. 2005

Biological & Pharmaceutical Bulletin

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“…The main purpose of the present study was to determine the inhibitory effect of CYN on XOD activity since it is a target enzyme for the treatment of gout and related symptoms. [36], and the types of inhibition were determined as competitive. The competitive type of XOD inhibition with apigenin was also confirmed by Lin et al [34].…”

Section: Discussionmentioning

confidence: 99%

Inhibition of xanthine oxidase by Caulerpenyne from Caulerpa prolifera

Cengiz¹,

Çavaş²,

Yurdakoç³

et al. 2012

Turk J Bioch

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“…The isolation and structural analysis of the active compounds 13 and 14 clarified them to be luteolin and apigenin, respectively [13, . In previous studies, luteolin and apigenin was found to be XO inhibitors in the flowers and buds of Daphne genkwa (10), and the IC50 values for luteolin were reported to be between 0.6 and 11.6 mmol L 21 and between 0.36 and 0.7 mmol L 21 for apigenin (11)(12)(13)(14)(15). The IC50 value of the isolated luteolin and apigenin evaluated in this study were 2.3 and 3.0 mmol L…”

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confidence: 95%

Chemical Evidence for Potent Xanthine Oxidase Inhibitory Activity of Glechoma hederacea var. grandis Leaves (Kakidoushi-Cha)

Masuda

Takahashi

Inai

et al. 2013

J Nutr Sci Vitaminol

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Throughout Asia, people have utilized various indigenous plants for good health. Such plants, which are referred to as traditional folk teas, are now available in local farmers' markets and can be easily obtained and used. The results of a survey of local traditional teas for health promotion conducted in the Shikoku area of Japan indicated that three types of the teas, "shiso-cha," "seisou-cha," and "kakidoushi-cha" prepared from the leaves of plants of the Labiatae family, had xanthine oxidase (XO) inhibitory activity (1). XO is a key enzyme that catalyzes the oxidative conversion of hypoxanthine and xanthine to uric acid in the purine catabolism pathway. Inhibition of XO activity can reduce the risk of hyperuricemia and gout, which have been recognized as life-style related diseases (2). It is well known that most Labiatae plants contain rosmarinic acid as a major phenolic (3, 4). Our previously reported high-performance liquid chromatography (HPLC) analysis of the three tea extracts revealed similar profiles; this study also reveals that rosmarinic acid is a common major constituent (1). Rosmarinic acid has various biological activities, including the inhibition of XO. However, the half maximal inhibitory concentration (IC 50) of rosmarinic acid for its XO inhibitory activity has varied from 2.06 to more than 200 mmol L 21 (5-7). Our preliminary investigation of XO inhibition of rosmarinic acid revealed weak activity (below 30% inhibition at 300 mmol L 21). Therefore, other inhibitors are expected to contribute to the XO inhibitory activity of these teas. Nakanishi et al. (8) have clarified that two powerful XO inhibitory phenolics, whose structures were similar to that of rosmarinic acid, existed in the leaves of Perilla frutescens. The strong XO inhibitory activity of "shiso-cha" and "seisou-cha" is attributed to the inhibitory properties of the compounds because the teas are prepared from the same plant species. However, the active XO inhibitory constituents of "kakidoushi-cha" have not been reported; therefore, we investigated the active constituents of "kakidoushi-cha" (dry leaves of Glechoma hederacea var. grandis) to uncover chemical evidence for the activity of the tea. Materials and MethodsChemicals and instruments. Xanthine oxidase (purified from buttermilk) and vanillic acid were purchased from Wako Pure Chemical Industries, Ltd. (Osaka, Japan). Xanthine, uric acid, p-hydroxybenzoic acid, and protocatechuic acid were obtained from Nacalai Tesque, Inc. (Kyoto, Japan). Allopurinol, rosmarinic acid, and syringic acid were obtained from Sigma-Aldrich (St. Louis, MO). Caffeic acid, coumaric acid, ferulic acid, and luteolin were purchased from Tokyo Kasei (Tokyo, Japan). Rosmarinic acid methyl ester was synthesized from rosmarinic acid by Fisher esterification. Solvents for HPLC were purchased from Kishida Chemicals (Osake, Japan) as HPLC grade. All other solvents were obtained from Nacalai Tesque. Analytical HPLC was performed with a PU-2989plus low-pressure gradient system (JASCO, Tokyo, Japan) equipp...

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Xanthine Oxidase Inhibitors from the Flowers ofChrysanthemum sinense

Cited by 94 publications

References 15 publications

Hypouricemic Effects of Acacetin and 4,5-O-Dicaffeoylquinic Acid Methyl Ester on Serum Uric Acid Levels in Potassium Oxonate-Pretreated Rats

Hypouricemic Effects of Acacetin and 4,5-O-Dicaffeoylquinic Acid Methyl Ester on Serum Uric Acid Levels in Potassium Oxonate-Pretreated Rats

Inhibition of xanthine oxidase by Caulerpenyne from Caulerpa prolifera

Chemical Evidence for Potent Xanthine Oxidase Inhibitory Activity of Glechoma hederacea var. grandis Leaves (Kakidoushi-Cha)

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