• Title/Summary/Keyword: chrysophanol

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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.

Antidiabetic Stilbene and Anthraquinone Derivatives from Rheum undulatum

  • Choi Sang Zin;Lee Sung Ok;Jang Ki Uk;Chung Sung Hyun;Park Sang Hyun;Kang Hee Chol;Yang Eun Young;Cho Hi Jae;Lee Kang Ro
    • Archives of Pharmacal Research
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    • v.28 no.9
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    • pp.1027-1030
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    • 2005
  • The antidiabetic-activity-guided fractionation and isolation of the $80\%$ EtOH extracts obtained from cultivated Korean Rhubarb rhizomes (Rheum undulatum, Polygonaceae) led to the isolation and characterization of one stilbene, desoxyrhapontigenin(1) and two anthraquinones, emodin (2) and chrysophanol (3). Their structures were established by chemical and spectroscopic methods. Compounds 1, 2, and 3 inhibited postprandial hyperglycemia by 35.8, 29.5, $42.3\%$, respectively.

Cytotoxic Compounds from the Flowers of Paulownia coreana (오동나무꽃의 항암성분)

  • Oh, Joa-Sub;Zee, Ok-Pyo;Moon, Hyung-In
    • Korean Journal of Pharmacognosy
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    • v.31 no.4
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    • pp.449-454
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    • 2000
  • In search for plant-derived cytotoxic compounds, it was found that the $CHCl_3$ and EtOAC extracts obtained from the flowers of Paulownia coreana Uyeki (Scrophulariaceae) exhibited significant cytotoxic activity against human tumor cell lines, A549, SK-OV-3, SK-MEL-2, XF498, and HCT15. Activity-guided fractionation on the basis of the inhibitory activity against the growth of human tumor cell lines, in vitro, and repeated column chromatography afforded several cytotoxic compounds from P. coreana. The structures and stereochemistry of these compounds were established, on the basis of analysis of spectra including IR, UV, EI-MS, $^{1}H-NMR,\;^{13}C-NMR$ and some chemical transformations, as Compound PCCl $(2-hydroxy-4(15),11(13)-eudesmadien-8{\beta},12-olide)$, Compound $PCC2(2,3-dihydro-4-hydroxy-1(15),11(13)-xanthadien-8{\beta},12-olide)$, Compound PCE1 (chrysophanol), Compound PCE2 (emodin), Compound PCE3 (physcion). Cytotoxic activity of compounds obtained from P. coreana. on five tumor cells lines was evaluated by procedure of SRB methods.

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Quantitative Analysis of Sennoside A and Anthraquinones for the Guideline for the Quality Control of Rhubarbs (유통 대황의 Sennoside A 및 Anthraquinone 함량분석을 통한 품질관리 기준에 관한 연구)

  • Choi, Hee-Kyoung;Kim, Kyung-Hee;Seo, Yong-Taek;Yook, Chang-Soo;Jang, Young-Pyo
    • Korean Journal of Pharmacognosy
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    • v.42 no.2
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    • pp.144-148
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    • 2011
  • Rhubarb (Rhei Rhizoma) has been used for the various clinical purposes such as purgative, stomach protective and pain relief for a long time. However, rhubarb in current market has a problem of quality control under which many of rhubarb fail to meet the standard specified in Korean Pharmacopoeia. This study was carried out to validate the method for the evaluation of the quality of five rhubarbs and Rumex species; Rheum palmatum, R. officinale, R. tanguticum, R. franzenbachii, R. undulatum, and Rumex species. The content of sennoside A with five anthraquinones (aloe-emodin, rhein, emodin, chrysophanol and physcion) in five rhubarbs and one Rumex has been performed by using HPLC quantitation analysis. In results, only four samples in Palmata sect. were qualified with sennoside A and those samples were R. officinale and R. tanguticum. Samples of R. palmatum did not meet the standard contents of sennoside A. The contents of anthraquinones in Palmata sect. were two times larger than those in Rhapontica sect. Moreover the content variations of anthraquinones were smaller than those of sennoside A. Thus, anthraquinones can be the key characterizing molecules to control quality of rhubarb.

A Study on the Antigastritic Effects of Rheum Species Extracts and Their Active Components (대황 추출물의 항위염 작용과 유효성분에 관한 연구)

  • Hwang, In Young;Jeong, Choon Sik
    • Journal of Food Hygiene and Safety
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    • v.28 no.4
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    • pp.330-336
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    • 2013
  • Rheum tanguticum has long been used in oriental medicine as antipyretics, analgesics, anti-inflammation, aperient, hypertension medicine and medicine for skin disease. This study has investigated the effectiveness of defense for gastritis making use of Rheum tanguticum and its similar plants, Rumex cripus, Rheum officinale, Rhem palmatum and Rheum undulatum. Chysophanol, chrysophanol-8-O-glc, Desoxyrhaponticin desoxyrhaponti-genin, emodin, isorhaponticin, 2-methoxy-4-hydroxyanthraquinone-5-O-glc, physcion, pirace-tannol-3'-O-glc, resveratrol, rhaponticin and rhapontigenin are used as the components of Rheum tanguticum. In HCl ethanol-induced gastritis in rat, the most effective extract was 70 percent ethanol which is of Rheum tanguticum, showing the inhibition of 91.8 percent to the gastric lesions. 70% ethanol extract of Rhem palmatum and Rumex cripus shown inhibition of 75.6 percent and 73.2 percent, respectively. This effectiveness is considered as acid-neutralizing capacity, anti-H.pylori and anti-oxidant activity. 70% ethanol extract of Rheum tanguticum and its component, piracetannol-3'-O-glc exhibited higher free radical scavenging activity than others. These results suggest that Rheum species extracts and their active components could be utilized for the treatment of gastritis. Furthermore, these results are expected to contribute the standardization with objectivity and reliability for Rheum species, medicinal herbs. In addition, it can contribute to the prevention of indiscriminate distribution of imitation, and the rising rate of dependence on imports of medicinal herbs, and mixing prevention of low-quality goods.

Free Radical Scavenging Effect and Oxidative Stress Protective Activity of Domestic Processed Polygoni Multiflori Radix (국내산 법제 하수오의 라디칼 소거능 및 산화적 스트레스 개선 효과)

  • Kim, Hyun Young;Kim, Jun Young;Cho, Eun Ju;Choi, Ji Myung;Hwang, Chung Eun;Lee, Hee Yul;Ahn, Min Ju;Lee, Jin Hwan;Kim, Yun-Geun;Ko, Keon Hee;Goo, Young-Min;Oh, Kyeong Yeol;Cho, Kye Man
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.44 no.6
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    • pp.809-815
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    • 2015
  • In this study, we confirmed biological compounds from methanol (MeOH) extract of processed Polygoni Multiflori Radix (PPMR), and the radical scavenging effect and oxidative stress protective activity of MeOH extract of PPMR were investigated under in vitro conditions using LLC-$PK_1$ renal epithelial cells. In HPLC analysis, MeOH extract of PPMR contained four species of biological compounds named 2,3,5,4'-tetrahydroxystilbene 2-O-${\beta}$-D-glucoside, emodin, chrysophanol, and rhein. 2,3,5,4'-Tetrahydroxystilbene 2-O-${\beta}$-D-glucoside was detected as the main compound in PPMR as 115.02 mg/kg. MeOH extract of PPMR showed 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis (3-ethylbenzthiazoline-6-sulphonic acid) diammonium salt (ABTS), and hydroxyl radical scavenging activities in a concentration- dependent manner. In particular, upon $50{\mu}g/mL$ of PPMR extract treatment, DPPH, ABTS, and hydroxyl radical scavenging activities were approximately 48.4%, 57.9%, and 81.2%, respectively. LLC-$PK_1$ cell viability declined in response to oxidative stress induced by pyrogallol, sodium nitroprusside (SNP), and morpholinosydnonimine (SIN-1) generators of NO, $O_2{^-}$, and $ONOO^-$, respectively. However, MeOH extract of PPMR significantly and dose-dependently inhibited oxidative-stressed LLC-$PK_1$ cell cytotoxicity. In fact, upon $50{\mu}g/mL$ of PPMR extract treatment, LLC-$PK_1$ cell viabilities were approximately 82.1%, 89.1%, and 77.6% compared to stress levels induced by pyrogallol, SNP, and SIN-1, respectively.

Antioxidative and Hepatoprotective Effects of Injinho-Tang and Osumogwa-Tang (인진호탕(茵蔯蒿湯)과 오수목과탕(吳茱木瓜湯)의 항산화(抗酸化) 및 간세포(肝細胞) 보호효과(保護效果))

  • Lee, Sang-Hyun;Kim, Young-Bok
    • Herbal Formula Science
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    • v.16 no.1
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    • pp.117-130
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    • 2008
  • Korean traditional medicine has been used for the treatment of the various diseases based on both oriental medicinal theory and clinical trials. Thus, the prescriptions of Korean traditional medicine would be useful for the development of new therapeutics. This research focuses on the fundamental study in Korean traditional prescriptions for the development of new hepatoprotective agents. We found two prescriptions. Injinho-Tang and Osumogwa-Tang, showed the significant DPPH free radical scavenging and hepatoprotective effect, respectively. It is well-known that free radical scavenging effect is related to the prevention of various pathological events including liver injury. This paper deals with hepatoprotective effects on tacrine-induced cytotoxicity in Hep G2 cells, free radicals scavenging on both DPPH and superoxide of above two prescriptions. Hot water extract of Injinho-Tang did not show the significant hepatoprotective effect on tacrine-induced cytotoxicity in Hep G2 cells, however, it shows the significant scavenging effects for both DPPH and superoxide radicals. On the other hand, all of the hot water extracts of constituent herbal drugs in Injinho-Tang exhibited the promising protective effect on tacrine-induced cytotoxicity in Hep G2 cells. Of these, water extract of Rhei Rhizoma showed the most prominent effect on tacrine-induced cytotoxicity in Hep G2 cells. Bioassay-guided fractionation of Rhei Rhizoma extract has furnished four compounds, and their chemical structures have been identified by comparison of their spectral data with those of literature as chrysophanol (1), emodin (2), 3,5-dihydroxy-4'- methoxystilbene (3), and rhapontigenin (4), respectively. Among the isolated compounds, compounds 2-4 revealed the significant hepatoprotective effect in vitro when their $EC_{50}$ values compare with that of silybin, as a positive control. It also exhibited that emodin possessed the most hepatoprotective effect among these active compounds. In case of Osumogwa-Tang, its hot water extract showed the moderate protective effect on tacrine-induced cytotoxicity in Hep G2 cells. Hot water extract of Chaenomelis Fructus, one of the constituent herbal drug of this prescription, exhibited the significant hepatoprotective effect with $EC_{50}$ value of $7.8{\pm}0.1\;{\mu}g/ml$, however, it showed strong cytotoxicity in Hep G2 cells above the concentration of $25\;{\mu}g/ml$. It was revealed that both hot water extract of Evodiae Fructus and its butanol soluble fraction showed the moderate hepatoprotective effect but concentration-dependent activity in Hep G2 assay system. Two quinolone alkaloids, evocarpine and dihydroevocarpine, also tested for their hepatoprotective effects on tacrine-induced cytotoxicity in Hep G2 cells, however, these two compounds derived from the Evodiae Fructus as the major constituents did not show in vitro hepatoprotective effect. From these results, it would be necessary to further isolation of its hepatoprotective compounds from the butanol soluble fraction of the hot water extract of Evodiae Fructus.

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Effect of Rheum undulatum Extract on Antioxidant Activity and Activity of Matrix Metalloproteinase-1 in Human Skin Fibroblasts (대황 추출물의 항산화 활성 및 MMP-1 저해 활성)

  • Park, Sung-Min;Lee, Gye-Won;Cho, Young-Ho
    • Journal of Life Science
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    • v.18 no.12
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    • pp.1700-1704
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    • 2008
  • Rheum undulatum L. has been commonly used as a cure for hematemesis, dropsy, and haematuria in the Oriental medicine for a long time. The main constituents of R. undulatum are chrysophanol and emodin, which are an antioxidative substance that has an anthraquinone structure. In the present study, to develop a new anti-aging agent, we examined the antioxidant activity and the inhibitory effect of the R. undulatum extract on the synthesis of MMP-1 in UVA-irradiated human dermal fibroblasts and MMP-1 activity. The R. undulatum extract was found to scavenge 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals and superoxide radicals in the xanthine/ xanthine oxidase system by a dose-dependent manner, respectively. UVA-induced MMP-1 expression was reduced about 79.5% by 1 ${\mu}g$/ml of the R. undulatum extract and also inhibited MMP-1 activity in a dose-dependent manner. In conclusion, it was observed that the R. undulatum extract has the antioxidant activity, regulation of UVA-induced MMP-1 production, and inhibition of MMP-1 activity. Therefore, these results suggest that the R. undulatum extract can be developed as a new anti-aging component of cosmetics.

Algicidal Characteristics of Cashew Nut Oil against Microalgae and Development of its Mixtures with Synergistic Effects (미세조류에 대한 캐슈넛 오일의 살조활성특징과 상승효과를 가지는 혼합처리제 탐색)

  • Kwak, Hwa Sook;Kim, Bo Gwan;Kim, Jin-Seog
    • Weed & Turfgrass Science
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    • v.5 no.3
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    • pp.136-143
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    • 2016
  • This study was conducted to investigate the algicidal characteristics of cashew nut oil (CNO) and to develop CNO mixtures with other compounds having synergistic effects on the growth inhibition against a blue-green alga, Microcystis aeruginosa. Among tested CNOs, CNO with higher anacardic acid contents (Ana-A) exhibited the best algicidal activity against M. aeruginosa. Ana-A showed broad algicidal spectrum with particular greater activity against blue-green algae than green algae. Ana-A showed the greatest activity against to Oscillatoria tenuis ($IC_{50}=0.19{\mu}g\;mL^{-1}$) among the tested blue-green algae and to Chlorella vulgaris ($IC_{50}=4.54{\mu}g\;mL^{-1}$) among the tested green algae, respectively. In a mixture experiment to evaluate a chemical interaction in M. aeruginosa control, Ana-A showed a strong synergistic effect with MSB and menadione, mild synergistic effect with citric acid, and additive effect with chryspophanol, copper sulfate and quinoclamine. Taken together, our results suggest that CNO containing higher anacardic acid can be used as an eco-friendly natural algicide for selective control of blue-green algae such as M. aeruginosa and O. tenuis through an optimization of application rate and in combination with synergists such as MSB and menadione.