• Title/Summary/Keyword: Chrysophanol

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Anti-obesity and hypolipidemic effects of Rheum undulatum in high-fat diet-fed C57BL/6 mice through protein tyrosine phosphatase 1B inhibition

  • Lee, Woo-Jung;Yoon, Goo;Hwang, Ye-Ran;Kim, Yong-Kee;Kim, Su-Nam
    • BMB Reports
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    • v.45 no.3
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    • pp.141-146
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    • 2012
  • Protein tyrosine phosphatase 1B (PTP1B) is important in the regulation of metabolic diseases and has emerged as a promising signaling target. Previously, we reported the PTP1B inhibitory activity of Rheum undulatum (RU). In the present study, we investigated the metabolic regulatory effects of RU in a high-fat diet (HFD) model. RU treatment significantly blocked body weight gain, which was accompanied by a reduction of feed efficiency. In addition, it led to a reduction of liver weight mediated by overexpression of PPAR${\alpha}$ and CPT1 in the liver, and an increase in the expression of adiponectin, aP2, and UCP3 in adipose tissue responsible for the reduction of total and LDL-cholesterol levels. Chrysophanol and physcion from RU significantly inhibited PTP1B activity and strongly enhanced insulin sensitivity. Altogether, our findings strongly suggest that 2 compounds are novel PTP1B inhibitors and might be considered as anti-obesity agents that are effective for suppressing body weight gain and improving lipid homeostasis.

Anthraquinones and Sterols from the Korean Marine Echiura Urechis unicintus (한국산 해양 의충동물 개불에서 Anthraquinone 및 Sterol 성분연구)

  • Chang, Sung-keun;Park, Yong-Hyun;Chai, Seuk;Kim, In-Kyu;Seo, Young-Wan;Cho, Ki-woong;Shin, Jong-Heon
    • Journal of the Korean Chemical Society
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    • v.42 no.1
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    • pp.64-68
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    • 1998
  • Three anthraquinones, chrysophanol, physcion and 1-o-methyl-2-methoxychrysophanol which have $Na^+,K^+-ATPase$ and cyclic AMP phosphodiesterase lowering activities related to cardiotonic action were isolated from the Korean marine echiura, Urechis unicintus. Spectroscopic methods, including HMQC, HMBC and NOE studies, were used to establish the structures.

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Extracts of Rheum undulatum L. Inhibits COX-2 Activities in Lipopolysaccharide-stimulated Raw 264.7 Cells (종대황 추출물의 COX-2 활성 억제 효과)

  • 하혜경;이제현;김정숙
    • Biomolecules & Therapeutics
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    • v.8 no.1
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    • pp.73-77
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    • 2000
  • Rheum undulatum L. has been used as Rhei Radix in Korean Pharmacopea although their pharmacological effects were not studied much. In this studym, we tested anti-inflammatory effect as a representative activity of Rheum undulatum L. extracts using cyclooxygenase (COX)-2 inhibition. Murine macrophage, Raw 264.7 cells were incubated with lipopolysaccharide (1 $\mu\textrm{g}$/ml) to induce COX-2. The prostagladin $E_2$ ($PGE_2$) levels as an indicator of COX-2 activity were determined in the culture medium using ELISA. Inhibition of acetylsalicylic acid (ASA) as a standard, aloe-emodin, chrysophanol, rhein, 80% ethanol extract of Rheum undulatum L. (Ex) and ether fraction (Fr) after acid hydrolysis of Rheum undulatum L. were tested in induced COX-2 described above. $IC_{50}$ values were 0.082 $\mu\textrm{g}$/ml for ASA. 181 $\mu\textrm{g}$/ml for aloe-emodin, 3.65 $\mu\textrm{g}$/ml for emodin, 144 $\mu\textrm{g}$/ml for chrysophanol, 39.8 $\mu\textrm{g}$/ml for rhein, 141 $\mu\textrm{g}$ of herb/ml for Ex, and 95.7 $\mu\textrm{g}$ of herb/ml for Fr. We found that Ex and Fr of Rheum undulatum L. were more effective than other anthraquinones, since their $IC_{50}$ are lower than others.

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Chemical Components of Rumex acetosella L. (애기수영의 화학적 성분)

  • Choe, Sang-Gil;Hwang, Bang-Yeon;Kim, Min-Su;Oh, Gap-Jin;Lee, Kyong-Soon;Ro, Jai-Seop
    • Korean Journal of Pharmacognosy
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    • v.29 no.3
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    • pp.209-216
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    • 1998
  • In the course of phytochemical studies of Rumex acetosella L. (Polygonaceae), the MeOH extract of the whole plants was fractionated with $CH_2Cl_2$ and $H_2O$, and the $CH_2Cl_2$ layer was fractionated again with 90% MeOH and hexane. Whereas $H_2O$ layer was fractionated with EtOAc and then with n-BuOH again. By repeated column chromatography, compound 1 was isolated from the 90% MeOH fraction, compounds 1, 2, 3, 4 and 5 were from the ethylacetate fraction, and compound 5 was from the n--BuOH fraction. On the basis of physico-chemical, spectroscopic evidences and in comparison with authentic samples, the structures of them were confirmed to emodin, citreorosein, $chrysophanol-8-O-{\beta}-D-glucopyranoside$, luteolin and $luteolin-7-O {\beta}-D-glucopyranoside$.

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Simultaneous Analysis of Four Standards of The Herbal Formula, DF-02, of Ephedra intermedia and Rheum palmatum, using by High Performance Liquid Chromatography-Ultraviolet Detector (HPLC-UVD)

  • Choi, Seong Yeon;Jeong, Birang;Jang, Hyeon Seok;Lee, Jiho;Kwon, Yong Soo;Yoon, Yoosik;Shin, Soon Shik;Yang, Heejung
    • Natural Product Sciences
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    • v.25 no.2
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    • pp.111-114
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    • 2019
  • The herbal formula, DF-02, consisting of Ephedra intermedia and Rheum palmatum are used for the treatment of the metabolic diseases such as obesity and liver fibrosis in Korean local clinics. We aimed to develop the simultaneous analytical conditions for four standards, (+)-pseudoephedrine (PSEP) and (-)-ephedrine (EP) for E. intermedia, and aloe-emodin (AE) and chrysophanol (CP) for R. palmatum using HPLC-UV techniques. The validated conditions yielded the high precision (relative standard deviation (RSD) < 3.65%) and the recoveries (94 - 106%) using the calibration curves with high linearity ($R^2$ > 0.9994). As a result, four standards of DF-02 were simultaneously determined under the developed method, which will be utilized for the quality control or evaluation of DF-02 and many herbal preparations containing E. intermedia and R. palmatum.

Constituents from the Roots of Hemerocallis fulva (원추리 지하부의 성분 연구)

  • Kim, Ju-Sun;Son, Kun-Ho;Chang, Hyeun-Wook;Kim, Hyun-Pyo;Bae, Ki-Hwan;Kang, Sam-Sik
    • Korean Journal of Pharmacognosy
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    • v.33 no.2 s.129
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    • pp.105-109
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    • 2002
  • Besides chrysophanol and friedelin, mixtures of n-hydrocarbons [pentacosane (72.6%), heptacosane (14.6%), tetracosane (5.8%), nonacosane (4.1 %) and hexacosane (2.9%)], n-hydrocarbon alcohols [octacosanol (70.5%) and hexacosanol (29.5%)], l-monoacyl glycerols [acyl part; behenic acid (43.5%), lignoceric acid (32.4%), cerotic acid (9.3%), tricosanoic acid (8.9%), pentacosanoic acid (2.6%), octacosanoic acid (2.3%), heneicosanoic acid (1.0%)], wax esters [behenic acid (56.3%), lignoceric acid (23.0%), cerotic acid (19.8%), tricosanoic acid (4.6%), octacosanoic acid (4.0%), pentacosanoic acid (1.7%), triacontanoic acid (0.6%)/ octacosanol (33.7%), hexacosanol (21.0%), tetracosanol (15.6%), triacontanol (10.5%), docosanol (6.0%), tricosanol (6.0%), heptacosanol (4.2%), nonacosanol (3.0%)] and sterols [${\beta}-sitosterol$ (73.2%), stigmasterol (14.6%), campesterol (12.2%)] were isolated from the roots of Hemerocallis fulva. The acid : alcohol combinations of the major wax esters were $C_{48}$: 22 : 26, 24 : 24, $C_{46}$: 22 : 24, and $C_{44}$: 22 : 22. This is the first report of l-monoacyl glycerols and friedelin from this plant. All isolates were identified on the basis of spectral data and chemical reactions.

Isolation of Anthraquinone Derivatives from the Root of Rumex japonicus H. (참소리쟁이 뿌리에서 안트라퀴논계 화합물의 분리 및 생리활성)

  • Hwang, Seon-Woo;Ha, Tae-Joung;Lee, Jong-Rok;Lee, Jun;Nam, Sang-Hae;Park, Ki-Hun;Yang, Min-Suk
    • Applied Biological Chemistry
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    • v.47 no.2
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    • pp.274-278
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    • 2004
  • Four anthraquinone derivatives were isolated from the root of Rumex japonicus Houtt. These compounds were identified as physcion, emodin, chrysophanol-10,10'-bianthrone and $physcion-10,10'-bianthrone^(a)$, respectively. The last compound (a), especially, showed strong activity against A549, PC-3, UO-31 and HCT-15 human cancer cell lines with $IC_{50}$ values, ranging from 0.45 to $1.33\;{\mu}g/ml^{-1})$.

Cytotoxic Constituents of Rumex japonicus (참소리쟁이의 세포독성 성분)

  • Kim, Dae-Keun;Choi, Sang-Un;Ryu, Si-Yong;Lee, Kang-Ro
    • YAKHAK HOEJI
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    • v.42 no.3
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    • pp.233-237
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    • 1998
  • Activity-guided fractionation and repeated column chromatography afforded two cytotoxic compounds R-3 and R-4 from the root of Rumex japonicus HOUTT. Compou nds were identified as musizin and emodin, respectively, by the physicochemical and spectral data. Besides R-3 and R-4, two compounds R-1 and R-2, chrysophanol and physcion, respectively, were also isolated. The compound R-3 and R-4 exhibited cytotoxicity against cultured human tumor cell lines, A-549, SK-OV-3, SK-MEL-2, XF498 and HCT15 with $ED_{50}$ values ranging from 2.68 to $10.06{\mu}g/ml$.

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Anthraquinones with Immunostimulating Activity from Cassia tora L.

  • Chung, Ha-Sook
    • Preventive Nutrition and Food Science
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    • v.10 no.3
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    • pp.267-271
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    • 2005
  • Many of plants had been reported having immunostimulating activity. This study reports the immunostimulating activity of Cassia tora L. (Leguminosae) seed, by means of solvent extraction method. Ethanol extract and solvent fractions, n-hexane, chloroform, ethylacetate, n-butanol and aqueous layer of Cassia tora L. seed were tested for immunostimulating activity in vitro. The ethylacetate-soluble fraction caused significant inhibition on the production of nitric oxide by murine macrophages (RAW 264.7), and mouse splenocytes were also stimulated at the concentration of 10 pgfmL. Three anthraquinones, chrysophanol (1), isochrysophanol (2) and aloe-emodin (3) with immunostimulating activity were isolated from the ethylacetate-soluble fraction of Cassia tora L. seed through activity-monitored fractionation and isolation method. These results permit Cassia tora L. to be useful as one the of natural immunostimulating crops.

Constituents of the Fruits of Rumex japonicus with Inhibitory Activity on Aldose Reductase

  • Kim, Jong-Min;Jang, Dae-Sik;Lee, Yun-Mi;Lee, Ga-Young;Kim, Jin-Sook
    • Journal of Applied Biological Chemistry
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    • v.51 no.1
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    • pp.13-16
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    • 2008
  • Five anthraquinones, emodin (1), ${\omega}$-hydroxyemodin (2), chrysophanol-8-O-${\beta}$-D-glucoside (3), emodin-8-O-${\beta}$-D-glucoside (4), and physcion-8-O-${\beta}$-D-glucoside (5), and five flavonoids, kaempferol-3-O-${\beta}$-D-glucoside (6), quercetin (7), quercitrin (8), isoquercitrin (9), and (+)-catechin (10), were isolated from the EtOAc-soluble extract of the fruits of Rumex japonicus. The structures of 1-10 were identified by spectroscopic methods including NMR studies. This is the first report on the isolation of compounds 3-5 from this plant. The isolates were subjected to in vitro bioassays to evaluate their inhibitory activities on the rat lens aldose reductase (RLAR), among which two anthraquinones (1 and 4), and five flavonols (5-9) showed significant activities on RLAR.