• Title/Summary/Keyword: anthraquinone derivatives

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Effects of Aloe-emodin and Emodin on Proliferation of the MKN45 Human Gastric Cancer Cell Line

  • Chihara, Takeshi;Shimpo, Kan;Beppu, Hidehiko;Yamamoto, Naoki;Kaneko, Takaaki;Wakamatsu, Kazumasa;Sonoda, Shigeru
    • Asian Pacific Journal of Cancer Prevention
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    • v.16 no.9
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    • pp.3887-3891
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    • 2015
  • Aloe-emodin (1, 8-dihydroxy-3-hydroxyl-methylanthraquinone; AE) and emodin (1,3,8-trihydroxy-6-methylanthraquinone; EM) are anthraquinone derivatives that have been detected in some medical plants and share similar anthraquinone structures. AE and EM have been shown to exhibit anticancer activities in various cancer cell lines; however, the inhibitory effects of these derivatives on the growth of cancer cells were previously reported to be different. Gastric cancer is the second most common cause of cancer cell death worldwide. In the present study, we examined the inhibitory effects of 0.05 mM AE and 0.05 mM EM on the proliferation of the MKN45 human gastric cancer cell line. The proliferation of MKN45 cells was significantly inhibited in AE- and EM-treated groups 24 h and 48 h after treatment. Furthermore, the inhibitory effects of EM were stronger than those of AE. The cell cycle of MKN45 cells were arrested in G0/G1 phase or G0/G1 and G2/M phases by AE and EM, respectively. However, an analysis of intracellular polyamine levels and DNA fragmentation revealed that the mechanisms underlying cell death following cell arrest induced by AE and EM differed.

A 26-Week Repeated Oral Dose Toxicity Test and a 4-Week Recovery Test of Cassia tora L. Water Extract in Sprague-Dawley Rats (Sprague-Dawley Rats을 이용한 결명자 물 추출물의 26주 반복 경구투여 독성시험 및 4주 회복시험)

  • Nho, Jong Hyun;Lee, Mu Jin;Jung, Ho Kyung;Jang, Ji Hun;Sim, Mi Ok;Jang, Min Cheol;Yong, Ju Hyun;Seo, Heung Sik;An, Byeong Kwan;Kim, Jong Choon;Cho, Hyun Woo
    • Korean Journal of Medicinal Crop Science
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    • v.26 no.2
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    • pp.157-169
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    • 2018
  • Background: Cassia tora L., an annual or perennial plant of the Fabaceae family, is traditional medicine with various biological activities, including anti-constipation and, anti-inflammation. Chemical compounds such as anthraquinone glycoside and naphthalene derivatives have been isolated from this plant. Cassia tora L. is a common contaminant of agricultural commodities, but is toxic to cattle and poultry. Methods and Results: To investigate the potential toxicity, Cassia tora L. aqueous extract (CO) was administered orally to rats for 26 weeks at 0 (control), 300, 1,500 and 3,000 mg/kg/day (n = 10 for male rats for each dose). The positive control comprised animals orally administered anthraquinone 100 mg/kg/day. There was no treatment-related mortality. An increase in the kidney weight was observed at 3,000 mg/kg/day of CO and anthraquinone 100 mg/kg/day. Macrophage infiltration in the colon was observed at CO 1,500 and 3,000 mg/kg/day and anthraquinone 100 mg/kg/day, but there were no significant toxicological changes in the incidence and severity of the finding. Conclusions: The oral no-observed-adverse-effect level (NOAEL) of CO was 3,000 mg/kg/day in male rats and no target organs were identified. In addition, 300 mg/kg was found to be the no-observed-effect level (NOEL) for systemic toxicity under the conditions of the study.

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.

Antimicrobial Effect of Emodin Isolated from Cassia tora Linn. Seeds against Food-Borne Bacteria

  • Lee, Na-Hyun;Lee, Sang-Min;Song, Da-Hyun;Yang, Ji-Yeon;Lee, Hoi-Seon
    • Journal of Applied Biological Chemistry
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    • v.56 no.3
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    • pp.187-189
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    • 2013
  • The antimicrobial activities of emodin and its derivatives (anthraquinone, alizarin, and alizarin-3-methyliminodiacetic acid) were evaluated using a paper disc diffusion method against foodborne bacteria (Bacillus cereus, Listeria monocytogenes, Staphylococcus intermedius, Salmonella typhimurium and Shigella sonnei). Emodin isolated from C. tora seeds has an antimicrobial activity against Bacillus cereus, followed by alizarin-3-methyliminodiacetic acid ($13.0{\pm}2.5mm$) and alizarin ($11.5{\pm}1.2mm$). Furthermore, emodin showed the antimicrobial activity against S. sonnei and S. typhimurium. In conclusion, C. tora seed and its active component derivatives are useful for the development of natural products on food supplemental agents and pharmaceuticals.

Synthesis and Cytotoxicity of 3-Carbamoyloxymethyl-1-azaanthraquinones (3-카바모일옥시메틸-1-아자안트라퀴논 유도체들의 합성 및 세포독성)

  • Lee, Hee-Soon;Choi, Jae-Young;Hong, Seoung-Soo;Cho, Jung-Sook;Kim, Young-Ho
    • YAKHAK HOEJI
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    • v.41 no.6
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    • pp.718-723
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    • 1997
  • In the course of developing novel antitumor intercalating agents, we synthesized 3- carbamoyloxymethyl-azaanthraquinones 6-12, incorporating the latent alkylating functionality. These compounds were designed to explore the effect of heteroatom incorporation into anthraquinone chromophore and the effect of the incorporation of the latent alkylating functionality. The derivatives were prepared by hetero Diels-Alder reaction as a key step followed by functionality of allylic methyl to the desired substituents. Growth inhibitory studies of the azaanthraquinones were conducted in vitro against human cancer cell lines (SNU-354: liver and MCF7: breast) and human epidermoid carcinoma cells that are sensitive (KB-3-1) and multidrug-resistant (KB-V-1). The derivatives were 10 to 100-fold less potent than doxorubicin against sensitive cell lines. However, they were marginally cross-resistant with doxorubicin against KB-V-1.

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Studies on the Anthraquinones of the Roots of Polygonum ciliinerve Owi (한국산(韓國産) 생약자원개발연구(生藥資源開發硏究) (제1보)(第1報) -나도하수오근(根)의 성분연구(成分硏究)-)

  • Han, Dae-Suk;Cho, Hi-Jae
    • Korean Journal of Pharmacognosy
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    • v.12 no.4
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    • pp.221-226
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    • 1981
  • Besides the emodin, three anthraquinone derivatives were isolated from the roots of Polygonum ciliinerve (Nakai) Owi which is indigenous exclusively to Korea. Two of them were identified as physcion and emodin-8-O-${\beta}$-D-glucoside by mp, uv, ir and nmr spectra. And the third was converted to physcion and sugar by hydrolysis. The quantitative analysis of free and combined form of emodin and physcion was done by the spectrophotometry.

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Printing of Polyester and Cotton Blends using Diaminoanthraquinone Disperse Dye and Monochlorotriazinyl Reactive Dye Mixtures (디아미노안트라퀴논계 분산염료/모노클로로트리진형 반응염료에 의한 폴리에스테르/면 혼방 직물의 날염)

  • 강숙녀
    • Textile Coloration and Finishing
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    • v.6 no.2
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    • pp.30-39
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    • 1994
  • To study the printing behaviors of Polyester and cotton(P/C) fabrics printed with disperse and reactive dyes, the effects of alkalis on the fixation of reactive dyes and the alkali-stability of disperse dyes in various methods of fixation were examined. The anthraquinone disperse dyes which have diamino derivatives as substituents without hydroxy group, such as C.I. Disperse Violet 1(D.V.1), C.I. Disperse Violet 28(D.V.28) and C.I.Disperse Blue 60(D.B.60) showed good results of fixation without regard to the concentration of NaHCO$_3$. In case of high temperature steaming(HTS) and unsaturated steaming(US)/HTS, D.V. 1 was alkali-stable and effective for P/C printing. A good result was obtained with D.V.1 and C.I.Reactive Orange 13(R.O.13) paste of 4% $K_{2}CO_{3}$. It was found that the unfixed D.V.28 bearing chloro group can hinder the fixation of monochlorotriaxinyl reactive dyes, and D.B.60 made little stain on 100% cotton. In thermosol(Tm), the dye uptake of D.V.1 was not decreased so much, but those of D.V.28 and D.B.60 were greatly decreased.

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Pharmacognostical Studies on ‘Ho-Jang’ (III) -Phytochemical Study of the Rhizome of Polygonum ellipticum Migo- (호장(虎杖)의 생약학적(生藥學的) 연구(硏究) (III) -둥근잎호장근경의 성분연구-)

  • Chi, Hyung-Joon;Choi, Jung-Rim;Yu, Seung-Cho
    • Korean Journal of Pharmacognosy
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    • v.13 no.4
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    • pp.145-152
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    • 1982
  • Three species of genus Polygonum, namely P. cuspidatum, P. sachalinense and P. ellipticum are distributed in Korea. Polygonum ellipticum Migo is a perennial herb in Polygonaceous plants. The root of the plant (Polygoni Rhizoma, 'Ho-jang') have been used as laxative, diuretic and for the treatment suppurative dermatitis in the oriental medicine. As the part of the study for the comparison of the three species in their components, the authors attempted to isolate the anthraquinones and stilbene derivative from the rhizome of P. ellipticum. The methanolic extract of dried rhizome of this plant was fractionated into ether soluble and insoluble fraction and each fraction was applied to column chromatography to isolate above mentioned components. Anthraquinone derivatives were isolated first; comp. I, mp $204{\sim}205^{\circ}$ (physcion), comp. II, mp $254{\sim}255^{\circ}$ (emodin), comp. IV, mp $191{\sim}192^{\circ}$ $(emodin-8-O-{\beta}-D-glucoside)$ and comp. III, mp $280{\sim}282^{\circ}$ $({\beta}-sitosterol-glucoside)$. They were identified by chemical properties and UV, IR and NMR spectra and by the direct comparison with authentic samples. Stilbene derivative was isolated secondly; comp. V, mp $255{\sim}256^{\circ}$ which was reported to possess antibacterial and antifungal activities.

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Phytochemical Study on Aloe vera

  • Choi, Jae-Sue;Lee, Seung-Ki;Sung, Chung-Ki;Jung, Jee-Hyung
    • Archives of Pharmacal Research
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    • v.19 no.2
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    • pp.163-167
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    • 1996
  • Aloe plants have been used as herbal medicine for centuries and the name aloe means the dried exudate from the cut leaves of Aloe ferox Mill. (Cape aloe, Liliaceae), Aloe ferryi Baker. (Socotrine aloe), A. bainesii Th. Dyer. (Natal aloe) and Aloe vera L. (Curacao aloe) (Namba, 1986). Among them, Aloe vera has not only been one of the most used natural drug well known for its cathartic properties, but also has been widely used as raw materials of cosmetics and health foods (Leung, 1978, Hoffenberg, 1979). Although previous investigations showed that the leaves of A. vera contain a number of anthracene and chromone derivatives such as aloin A, aloin B, 1, 3, 6, 8-tetra-nitro-4,5-dihydroxy-2-hydroxymethyl anthraquinone and 7-hydroxy-aloin, its chemical composition is far from being completely investigated (Hoffenberg, 1979, Rauwald and Voetig, 1982). As a part of our chemical investigations on the constituents of aloe, we report chemical investigation of the freeze dried ground leaves of A. vera which is led to the isolation of five compounds from the ethyl acetate soluble fraction of the methanolic extract.

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The dyeability and light fastness of amino azobenzene derivatives disperse dye( I ) (아미노 아조벤젠계 분산염료의 염색성 및 내광성(I))

  • Choi, Chang Nam;Lim, Seung Hee;Ryu, Hee Seok;Park, Hyung In;Hong, Sung Hak
    • Textile Coloration and Finishing
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    • v.8 no.3
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    • pp.24-30
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    • 1996
  • In order to investigate the light fastness of amino azo disperse dyes, some kinds of disperse dyes were prepared and dyed to polyester fabric under the different conditions, such as single or mixture state. After the dyed fabric was irradiated with carbon arc light for several hours, the color differences and K/S values of fabric were measured. The light fastness of amino azo disperse dye was decreased by the introduction of OH group to the dye molecule. But when the amino azo dye was mixed with the anthraquinone disperse dye, the light fastness was increased. It was considered that the dye molecules were aggregated on account of hydrogen bonding via OH groups, resulting the decrease of surface area of dye molecule which might be irradiated by the light.

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