• Title/Summary/Keyword: Dihydroxy Compound

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Structural Characterization of a Flavonoid Compound Scavenging Superoxide Anion Radical Isolated from Capsella bursa-pastoris

  • Kweon, Mee-Hyang;Kwak, Jae-Hyock;Ra, Kyung-Soo;Sung, Ha-Chin;Yang, Han-Chul
    • BMB Reports
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    • v.29 no.5
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    • pp.423-428
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    • 1996
  • A superoxide anion radical scavenger isolated from Capsella bursa-pastoris was characterized by infrared (IR) spectroscopy, sugar analysis, ultraviolet (UV) spectroscopy, $^{1}H$ and $^{13}C$ nuclear magnetic resonance (NMR) spectroscopies, and fast atom bombardment (FAB) mass analysis. The compound was assumed to be a flavonoid-O-glycoside from IR spectrum and UV absorption maxima. When the sugar composition of the compound was examined by thin layer chromatography (TLC) and gas chromatography (GC) of the acid hydrolysate, only glucose was detected. According to the results of UV spectrotroscopy by using shift reagents, the compound was supposed to be luteolin (5,7,3',4'-tetrahydroxy flavone) or chrysoeriol (5,7,4'-trihydroxy-3'-methoxy flavone) with glucose. Based on $^{1}H$- and $^{13}C-NMR$ spectroscopies, the compound was deduced as 7,4'-dihydroxy-5,3'-dimethoxy-${\alpha}$-6-c-glucosyl-${\beta}$-2"-o-glucosyl flavone. In FAB mass analysis the compound was finally characterized as 7,4'-dihydroxy-5,3'-dimethoxy-${\alpha}$-6-c-glucosyl-${\beta}$-2"-o-glucosyl flavone ($C_{29}H_{34}O_{16}$, M.W.=638).

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Anthraquinone and Stibene Derivatives from the Cultivated Korean Rubbarb Rhizomes

  • Ko, Sung-Kwon;Whang, Wan-Kyunn;Kim, Il-Hyuk
    • Archives of Pharmacal Research
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    • v.18 no.4
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    • pp.282-288
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    • 1995
  • The sutdies were carried out to evaluate the consituents in the rihzomes of the cultivated Korean Rhubarb (Polygonaceae). From the acetone fraction ofl methanol extract Compound I (1, 8-dihydroxy-3-methyl anthraquinone, chrysophanic acid), Compound II($chrysophanol-8-O-{\beta}-D-glucopyranoside$), Compound III ($emodin-8-O-{\beta}-D-glucopyranoside$) and Compound IV ($aloe-emodin-8-O-{\beta}-D-glucopyranoside$), and from the ether fraction Compound V(1, 8-dihydorxy-3-emthyl-6-methoxy anthraquinone, physcion) and Compound VI (1, 6, 8-thitydroxy-3-emthyl anthrauinone, emodin), and also from the n-buthanol fraction Compound VII ($rhapontigenin-3-O-{\beta}-D-glucopyranoside, rhaponticin$) and Compound VIII ($piceatannol-3'-O-{\beta}-D-glucopyranoside$), were isolated and identified on the basis of their physico-chemical and spectroscopic evidences (UV, IR, H-NMR, C-NMR, EI-MS), respectively.

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Antimycobacterial Activity and Cytotoxicity of Flavonoids from the Flowers of Chromolaena odorata

  • Suksamrarn, Apichart;Chotipong, Apinya;Suavansri, Tananit;Boongird, Somnuk;Timsuksai, Puntip;Vimuttipong, Saovaluk;Chuaynugul, Aporn
    • Archives of Pharmacal Research
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    • v.27 no.5
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    • pp.507-511
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    • 2004
  • From the flowers of Chromolaena odorata (Eupatorium odoratum) four flavanones, isosakuranetin (5,7-dihydroxy-4'-methoxyflavanone) (1), persicogenin (5,3'-dihydroxy-7,4'-dimethoxyflavanone) (2), 5,6,7,4'-tetramethoxyflavanone (3) and 4'-hydroxy-5,6,7-trimethoxyfla-vanone (4), two chalcones, 2'-hydroxy-4,4',5',6'-tetramethoxychalcone (5) and 4,2'-dihydroxy-4',5',6'-trimethoxychalcone (6), and two flavones, acacetin (5,7-dihydroxy-4'-methoxyflavone) (7) and luteolin (5,7,3',4'-tetrahydroxyflavone) (8) were isolated and identified. Compound 1 exhibited moderate antimycobacterial activity against Mycobacterium tuberculosis with the MIC value of 174.8 $\mu$M, whereas compounds 4,7, and 8 exhibited weak activity with the MIC values of 606.0, 704.2 and 699.3 $\mu$M respectively. Compound 7 showed moderate cytotoxicity against human small cell lung cancer (NCI-H187) cells with the MIC value of 24.6 $\mu$M, whereas compound 8 exhibited moderate toxicity against NCI-H187 cells and week toxicity against human breast cancer (BC) cells with the MIC values of 19.2 and 38.4 $\mu$M respectively.

A Novel Cycloartane Glycoside from Thalictrum uchiyamai

  • Choi, Young-Hee;Kim, Nan-Gyeong;Lee, Ihn-Ran
    • Archives of Pharmacal Research
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    • v.19 no.5
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    • pp.429-431
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    • 1996
  • A new cycloartane glycoside (1) was isolated from the aerial part of Thalictrum uchiyamai Nakai (Ranunculaceae). On the basis of chemical and physicochemical evidence, the aglycone structure of this compound was characterized as 116, 25-dihydroxy-3, 24-diacetoxy-9, 19-cycloartane-29-oic acid, a new derivative of cycloartane triterpene. Also the oli-gosaccharide moiety of this glycoside were determined as 29-O-${alpha}$-L-rhanmnopyranosyl- ($1rightarrow2$)-[${beta}$-D-xylofuranosyl-($1rightarrow6$)-${beta}$-D-glucopyranose by application of HMBC technoque. Consequently, the structure of compound 1 was elucidated as 29-O-${alpha}$-L-rhanmnopyranosy-($1rightarrow2$)-[${beta}$-D-xylofuranosyl-($1rightarrow6$)-${beta}$-D-glucopyranosyl-16, 25-dihydroxy-3, 24-diacetoxy-9, 19-cycloartane-29-oic acid ester.

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A New Phenolic Compound from Lespedeza tomentosa

  • Jang, Hyeon Seok;Choi, Seong Yeon;Yang, Heejung;Kim, Myong Jo;Chun, Wanjoo;Kwon, Yongsoo
    • Natural Product Sciences
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    • v.27 no.3
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    • pp.169-171
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    • 2021
  • A new phenolic compound and three known flavonoids isolated from the MeOH extracts of Lespedeza tomentosa. Based on spectral data, the isolated compounds were identified as methyl 4,5-dihydroxy-3-methoxy-2-(3-methylbut-2-en-1-yl)benzoate (1), 1-methoxylespeflorin G11 (2), farrerol (3) and 1-methoxylespeflorin I2 (4). Methyl 4,5-dihydroxy-3-methoxy-2-(3-methylbut-2-en-1-yl)benzoate (1) is newly isolated from plant source.

Phenolic and Furan Type Compounds Isolated from Gastrodia elata and their Anti-Platelet Effects

  • Pyo Mi Kyung;Jin Jing Ling;Koo Yean Kyoung;Yun-Choi Hye Sook
    • Archives of Pharmacal Research
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    • v.27 no.4
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    • pp.381-385
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    • 2004
  • Nine phenolic ($1\~9$) and two furan type (10, 11) compounds, were isolated from the methanolic extract of the tuber of Gastrodia elata Blume (Orchidaceae) in the course of continuing search for platelet anit-aggregating plant components. Compound 1 was identified as 4,4'-dihy-droxybenzyl sulfone, a novel compound for the best of our knowledge. Compound 10, 5-hydroxymethyl-2-furancarboxaldehyde, was isolated for the first time from this plant. Compound 1 ($IC_{50};\;83{\mu}M$) was about four times more inhibitory to U46619 induced aggregation than ASA ($IC_{50};\340{\mu}M$). Compound 9, 4,4'-dihydroxy-dibenzylether, ($IC_{50};\;5{\mu}M$, $3{\mu}M\;and\;33{\mu}M$, respectively) was $10\~}80$ fold more potent than ASA ($IC_{50};\;420\;{\mu}M,\;53\;{\mu}M\;and\;340\;{\mu}M$ respectively) to collagen, epinephrine and U46619 induced aggregation, although it is less active than ASA to AA induced aggregation.

Isolation and Structural Elucidation of Antimicrobial Compounds from Buckwheat Hull

  • Cho Jeong-Yong;Moon Jae-Hak;Kim Hye-Kyung;Ma Seung-Jin;Kim Seon-Jae;Jang Mi-Young;Kawazoe Kazuyoshi;Takaishi Yoshihisa;Park Keun-Hyung
    • Journal of Microbiology and Biotechnology
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    • v.16 no.4
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    • pp.538-542
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    • 2006
  • Three new compounds were isolated from the methanol extracts of buckwheat (Fagopyrum esculentum) hull, and their structures were determined to be 6,7-dihydroxy-3,7-dimethyl-octa-2(Z),4(E)-dienoic acid (1), 6,7-dihydroxy-3,7-dimethyl-octa-2(E),4(E)-dienoic acid (2), and 4,7-dihydroxy-3,7-dimethyl-octa-2(E),5(E)-dienoic acid (3) by NMR and MS spectroscopic analyses. These compounds at $500{\mu}g$ concentration showed antimicrobial activity against Staphylococcus aureus, demonstrated by the paper disc method.

A New coumarin from the seeds of Jute (Corchorus olitorius L.)

  • Mukherjee, K.K.;Mitra, S.K.;Ganguly, S.N.
    • Natural Product Sciences
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    • v.4 no.1
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    • pp.51-52
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    • 1998
  • From the chloroform extract of the defatted seeds of jute a new coumarin $C_9H_6O_4$, $m.p.\;178-179^{\circ}C$, was isolated. The structure of the compound was established as 4,7-dihydroxy coumarin on the basis of physical methods viz. $^1H\;NMR,\;^{13}C\;NMR$ and Ms.

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Antihypertensive Activities of Diterpenoid (16,17-dihydroxy-16-${\beta}-(-)$-kaurane-19-oic acid) in Siegesbeckiae pubescens Against Okamoto-Spontaneously Hypertensive Rats (희첨 성분중 디터핀 물질이 오까모토 고혈압 모델 쥐에 미치는 혈압 강하작용)

  • Kim, Jae-Hoon;Yu, Jae-Chun;Chang, Il-Moo;Lee, Jong-Heun;Kim, Joong-Soo
    • Korean Journal of Pharmacognosy
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    • v.11 no.2
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    • pp.61-65
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    • 1980
  • As a folkloric medicine, Siegesbeckia pubescens has been used for treatment of brain stroke and hypertension. Diterpene compound, 16,17-dihydroxy 16-${\beta}-(-)$ kaurane-19-oic acid, was isolated from the plant. Its potential antihypertensive activity was evaluated againstan animal model of hypertension, Okamoto-SHR. When diterpene compound with dose of 50mg/kg/day was orally administered, it exhibited mild antihypertensive activity comparable with propranolol administration dose of 75mg/kg/day.

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Phenolic Constituents from the Aerial Parts of Artemisia stolonifera

  • Lee, Kang-Ro;Hong, Seung-Woo;Kwak, Jong-Hwan;Pyo, Suhkneung;Jee, Ok-Pyo
    • Archives of Pharmacal Research
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    • v.19 no.3
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    • pp.231-234
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    • 1996
  • Two acetophenone glycosides, 2, 4-dihydroxy-6-methoxy acetophenone $4-O-\beta-D-glucopyranoside(I)$, 2, 4, 6-trihydroxy acetophenone $2-O-\beta-D-glucopyranoside(II)$, together with coniferin(III) were isolated from the aerial parts of Artemisia stolonifera (Max.) Kom. The structures of the compounds were elucidated on the basis of spectroscopic evidence. Compound IIwas also confirmed as a new phenolic glycoside from natural sources. In addition, compound I induced cytostatic activity of macrophasges, while compounds II and III did not.

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