• Title/Summary/Keyword: 9-dihydroxy-2

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Novel Withanolides from the Flowers of Datura tatula

  • Srivastava, Anjani;Manickam, M.;Sinha-Bagchia, A.;Sinhaa, S.C.;Ray, A.B.
    • Natural Product Sciences
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    • 제2권1호
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    • pp.9-13
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    • 1996
  • Three new withanolides, designated as withatatulins B, C, and D, were isolated from the fresh flowers of Datura tatula Linn. Detailed spectral analysis of these compounds permitted advancement of their structures respectively, as $5{\beta},6{\beta}-epoxy-12{\beta}$,21-dihydroxy-1-oxo-witha-2,24-dienolide (2), $6{\beta},12{\beta},21-trihydroxy-1-oxowitha$ 2, 4,24-trienolide (3) and $5{\beta},6{\beta},12{\beta}$,21-tetrahydroxy-1-oxo-witha-2,24-dienolide (4a). Withanolides with oxygen functions both at 12 and 21-positions are rare and first reported from Datura species.

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A New Indolinepeptide from Paecilomyces sp. J300

  • Kwon, Hak-Cheol;Kim, Kyung-Ran;Zee, Sang-Deuk;Cho, Sae-Yun;Lee, Kang-Ro
    • Archives of Pharmacal Research
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    • 제27권6호
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    • pp.604-609
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    • 2004
  • A new indolinepeptide (3) was isolated, together with two known compounds, a cerebroside (1) and an alloxazine (2), from silkworm larvae infected with Paecilomyces sp. J300. On the basis of spectroscopic data, their structures were elucidated as (4E, 8E, 25, 2'R, 3R )-N-2'-hydroxy-hexadecanoyl-1-O-$\beta$-D-glucopyranosyl-9-methyl-4, 8-sphingadienine (1), 7,8-dimethylalloxazine (2) and 3$\beta$,5-dihydroxy-1-N-methyl-indoline-2$\beta$-carbonyl amino-D-alanyl-erythro-$\beta$-hydoxyiso-leucinyl-glycine (3).

Isolation and Structure Determination of Coumarin Derivatives from the Roots of Angelica dahurica

  • Kim, Ji-Yeon;Son, Jong-Keun;Song, Dong-Keun
    • Journal of Evidence-Based Herbal Medicine
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    • 제3권1호
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    • pp.35-41
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    • 2010
  • From the roots of Angelica dahurica Bentham et Hooker (Umbelliferae), three known coumarin derivatives have been isolated and identified as 8-(2-hydroxy-3-methoxy-3-methylbutyloxy) psoralen, 5,8-di(2,3-dihydroxy-3-methylbutyloxy) psoralen, 9-[3-($\beta$-D-glucopyranosyloxy)-2-hydroxy-3-methylbutoxy]-7H-furo[3,2-g][1]benzopyran-7-one. This is the first report of the occurrence of these compounds in this plant. These three compounds were tested for activity in septic shock model. Among these compounds, 2 showed relatively strong preventive activity against septic shock.

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Induction of apoptosis and $\G_1$ arrest by LJ-331, a novel nucleoside analog,in human leukemia HL-60 cells

  • Lee, Eun-Jin;Shin, Dae-Hong;Jeong, Nak-Shin;Lee, Sang-Kook
    • 대한약학회:학술대회논문집
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    • 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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    • pp.90.2-90.2
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    • 2003
  • In a continuous effort to develop novel anticancer agents we newly synthesized and evaluated the antitumor activity of nucleoside analogues. One analogue, 4-[2-Chlor-6-(3-iodo-benzylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentanecarboxylic acid methylamide (LJ-331), has been shown to exert a potent inhibition of human cancer cell growth in vitro including human lung (A549), stomach (SNU-638) and leukemia (HL-60) cancer cells. Following mechanism of action study revealed that LJ-331 induces cell cycle arrest at the G$_1$ phase in HL-60 cells and evokes apoptotic phenomena such as an increase in DNA ladder intensity and chromatin condensation by a dose-and time-dependent manner. (omitted)

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Protective agents against sepsis from the root bark of Paeonia suffruticosa

  • Li-Gao;Xu , Ming-Lu;Seo, Chang-Seob;Kim, Hyo-Jin;Lee, You-Jeong;Lee, Yeun-Koung;Son, Jong-Keun;Song, Dong-Keun
    • 대한약학회:학술대회논문집
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    • 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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    • pp.199.2-199.2
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    • 2003
  • The bioassay-guided fractionation of protective agents against sepsis-induced lethality from the root bark of Paeonia suffruticosa led to the isolation of ten known compounds: paeonol (1), 2,5-dihydroxy-4-methoxyacetophenone (2) methyl 3-hydroxy-4- methoxybenzoate (3), acetovanillone (4), benzoic acid (5), benzoylpaeoniflorin (6), paeonoside (7), paeoniflorin (8), oxypaeoniflorin (9) and apiopaeonoside (10). Among them, 4 exhibited the highest survival rate in a dose-dependent manner (100% with a dose of 30 mg/kg versus 16.7% for the control experiment) and showed reduction of plasma alanine aminotransferase (ALT) value on the in vivo assay model of sepsis induced by LPS/GalN.

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Fluoxymesterone, $C_{20}H_{29}FO_3$의 결정구조 (The Crystal Structure of Fluoxymesterone, $C_{20}H_{29}FO_3$)

  • 김의성;박권일;조성일
    • 한국결정학회지
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    • 제4권1호
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    • pp.6-10
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    • 1993
  • 11 β ,17 β -dihydroxy-9a-fluoro-l7a-methyl androst-4-en-3-one (Fluoxymesterone), CgoH29 FO,, orthorhombic, P2,2,2,, a=13.468(5) A, b= 19.554 (2)A, c=6.578(9)A, a=b=r=90˚, A (CuKa)=1.5406 A , Dm=1.289cm-3, Dc=1.299cm-3 and Z=4 at T=298k. The structure was solved by direct method using seminvariants of ggg Parity group and refined by the full-matrix least-square method, resulting model with reliability factor R=0.069 for 1098 unique reflection over 3σ . Ring A is an 1β-2a-half chair, 5 ring has a highly symmetrical chair conformation, C ring is in a distorted chair conformation and D ring is a 13aenveLope conformation. In the crystal structure, the molecules are packed with a hydrogen bond of 011-H23‥‥03(0.5+x, 1.5-y, 1.0-z) [1.94(9) A of H‥‥0.2.786(9)A of 0‥‥0 and 165(8) ˚ of

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Involvement of Akt in mitochondria-dependent apoptosis induced by a naphthoquinone analog

  • Kang, Seung-Koo;Kim, Hae-Jong;Chun, Young-Jin;Kim, Mie-Young
    • 대한약학회:학술대회논문집
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    • 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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    • pp.158.2-158.2
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    • 2003
  • Vitamin K-related analogs induce growth inhibition in various cancer cell lines. We report that 2,3-dichloro-5,8-dihydroxy-1, 4-naphthoquinone (DDN), a naphthoquinone analog, induces mitochondria-dependent apoptosis in human promyeloid leukemic HL-60 cells. DDN induced cytochrome c release, cleavage of Bid, and activation of caspases -8, -9 and -3. Cleavage of Bid, the caspase-8 substrate, was inhibited by the broad caspase inhibitor zVAD-fmk, whereas cytochrome c release was not affected by zVAD-fmk. (omitted)

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In vitro Metabolism of Methallylescaline in Human Hepatocytes Using Liquid Chromatography-High Resolution Mass Spectrometry

  • Kim, Sunjoo;Kim, Ju-Hyun;Kim, Dong Kyun;Lee, Jaesin;In, Sangwhan;Lee, Hye Suk
    • Mass Spectrometry Letters
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    • 제9권3호
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    • pp.86-90
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    • 2018
  • Methallylescaline, 2-(3,5-dimethoxy-4-[(2-methylprop-2-en-1-yl)oxy]phenyl)ethanamine, is a new psychoactive substance with potent agonist of 5-HT receptor, but there is little information on its pharmacological effect, metabolism, and toxicity. It is necessary to characterize the metabolic profiling of methallylescaline in human hepatocytes using liquid chromatography-high resolution mass spectrometry. Methallylescaline was metabolized to three hydroxy-methallylescaline (M1-M3) and dihydroxy-methallylescaline (M4) via hydroxylation in human hepatocytes. CYP2D6, CYP2J2, CYP1A2, and CYP3A4 enzymes were responsible for the metabolism of methallylescaline. The metabolites as well as methallylescaline would be used for monitoring the abuse of methallylescaline.

Phytochemical Constituents of Salsola komarovii and Their Effects on NGF Induction

  • Cho, Hyeon Kyung;Suh, Won Se;Kim, Ki Hyun;Kim, Sun Yeou;Lee, Kang Ro
    • Natural Product Sciences
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    • 제20권2호
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    • pp.95-101
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    • 2014
  • Five lignan glycosides, seven megastigmane glycosides, and seven phenolic compounds were isolated by repeated column chromatography from the MeOH extract of Salsola komarovii. Their structures were determined to be lariciresinol-9-O-${\beta}$-$\small{D}$-glucopyranoside (1), alangilignoside C (2), conicaoside (3), (+)-lyoniresinol 9'-O-${\beta}$-$\small{D}$-glucopyranoside (4), (8S,8'R,7'R)-9'-[(${\beta}$-glucopyranosyl)oxy]lyoniresinol (5), blumenyl B ${\beta}$-$\small{D}$-glucopyranoside (6), blumenyl A ${\beta}$-$\small{D}$-glucopyranoside (7), staphylionoside D (8), icariside $B_2$ (9), (6R,9S)-3-oxo-${\alpha}$-ionol ${\beta}$-$\small{D}$-glucopyranoside (10), 3-oxo-${\alpha}$-ionol 9-O-${\beta}$-$\small{D}$-apiofuranosyl-($1{\rightarrow}6$)-${\beta}$-$\small{D}$-glucopyranoside (11), blumenol B 9-O-${\beta}$-$\small{D}$-apiofuranosyl-($1{\rightarrow}6$)-${\beta}$-$\small{D}$-glucopyranoside (12), benzyl 6-O-${\beta}$-$\small{D}$-apiofuranosyl-${\beta}$-$\small{D}$-glucopyranoside (13), canthoside C (14), tachioside (15), isotachioside (16), biophenol 2 (17), 2-(3,4-dihydroxy)-phenyl-ethyl-${\beta}$-$\small{D}$-glucopyranoside (18), and cuneataside C (19) by spectroscopic methods. All the isolated compounds 1 - 19 were reported from this source for the first time. Compounds 2, 3 and 6 upregulated NGF secretion to $118.8{\pm}3.6%$, $128.2{\pm}9.3%$ and $111.1{\pm}7.1%$ without significant cell toxicity.

Constituents of the Herb of Isodon excisus var. coreanus

  • Kim, Ho-Kyoung;Whang, Wan-Kyunn;Kim, Il-Hyuk
    • Archives of Pharmacal Research
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    • 제20권3호
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    • pp.291-296
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    • 1997
  • The studies were carried out to evaluate the constituents in the aerial part of Isodon excisus var. coreanus (Labiatae). From the aqueous fraction of methanol extract, compound I (${\alpha}$-[[3-(3, 4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-benzenepropanoic acid), compound II (9-methyl-dihydroferulic acid-4-O-.betha.-D-glucopyranosyl $(1{\rightarrow}2)$-${\alpha}$-L- rhamnopyranosyl (1.rarw.4)-.betha.-D-glucopyranoside), compound III (ent-7.alpha., 11${\alpha}$,15.betha.-trihydroxy-kaur-16-en-1-O-.betha.-D-glucopyranoside) and compound IV ($2{\alpha}$,3${\beta}$,$7{\alpha}$,23-tetrahydroxy-olean-12 -en-28-oic acid 28-O-${\beta}$-D-glucopyranoside) were isolated and identified on the basis of their physicochemical and spectroscopic evidences[IR, FAB(-)MS,$^{1}H-NMR,$$^{13}C-NMR,$$ HMQC$$^{1}H-^{1}H $COSY and HMBC (Heteronuclear Multiple Bond Connectivity)]. Especially, New compounds II and III were named Isodonin A and Isodonin B respectively.

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