• 제목/요약/키워드: New and known compounds

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A New Phenylbutanone Glucoside from Salvia plebeia

  • Jin, Qiang-Hao;Han, Xiang-Hua;Hwang, Ji-Hye;Hong, Seong-Su;Park, Mie-On;Lee, Chul;Lee, Chang-Hee;Lee, Dong-Ho;Lee, Mi-Kyeong;Hwang, Bang-Yeon
    • Natural Product Sciences
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    • 제15권2호
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    • pp.106-109
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    • 2009
  • Phytochemical investigations of the EtOAc-soluble fraction of the whole plants of Salvia plebeia using repeated column chromatography with preparative HPLC led to the isolation of a new phenylbutanone glucoside, 4-{4-0-[6-(4-hydroxybenzoyl)-0-${\beta}$-D-glucopyranosyl]-3-hydroxyphenyl}-butan-2-one (salviaplebeiaside, 1) along with two known phenolic compounds, rosmarinic acid methyl ester (2) and luteolin-7-0-${\beta}$-D-glucoside (3). The structures of these compounds were determined on the basis of spectroscopic methods including 1D-, 2D-NMR and MS spectrometry and comparison of spectroscopic data with those of values reported in the literatures.

Poria cocos 균핵에서 분리한 성분들과 DNA Topoisomerase I의 반응양상 및 효소저해 활성 (Binding Mode and Inhibitory Activity of Constituents Isolated from Sclerotium of Poria cocos with DNA Topoisomerase I)

  • 최인희;김지현;김춘미
    • 약학회지
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    • 제49권5호
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    • pp.428-436
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    • 2005
  • DNA topoisomerase I(TOP1) helps the control of DNA replication, transcription and recombination by assist­ing breaking and rejoining of DNA double strand. Camptothecin (CPT) and its derivative, topotecan, are known to inhibit TOP1 by intercalating into TOP1-DNA complex. Recently various non-CPT intercalators are synthesized for a new class of TOP1 inhibitors. In this study, six compounds isolated from Poria cocos were investigated for their interaction with TOP1­DNA complex using the flexible docking program, FlexiDock. The binding modes were analyzed and compared with the TOP1 inhibition activities. The compounds that showed potent activity were intercalated between the + 1/-1 base pairs of DNA, located near the active site phosphotyrosine723 and formed hydrogen bonds with active site residues. On the other hand, compounds with no activity were not docked at all. The binding modes were well correlated with the inhibition activity, suggesting the possibility that potent inhibitors can be designed from the information presented by the docking study.

Antimicrobial Constituents from Fruits of Ailanthus Altissima SWINGLE

  • Zhao Chun-Chao;Shao Jian-Hua;Li Xian;Xu Jing;Zhang Peng
    • Archives of Pharmacal Research
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    • 제28권10호
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    • pp.1147-1151
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    • 2005
  • A new naturally occurring sterol, compound 5, and six known stigmasterols were isolated from fruits of Ailanthus altissima Swingle by repeated column chromatography and RP-HPLC. Their structures were identified as, 5${\alpha}$-stigmastane-3,6-dione (1), 3${\beta}$-hydroxystigmast-5-en-7-one (2), stigmast-5-ene-3${\beta}$, 7${\alpha}$-diol (3), 6${\alpha}$-hydroxystigmast-4-en-3-one (4), 5${\alpha}$-stigmastane-3${\beta}$, 6${\beta}$-diol (5), stigmast-4-ene-3${\beta}$, 6${\alpha}$-diol (6), stigmast-5-ene-3${\beta}$, 7${\alpha}$, 20$\xi$-triol (7) by spectral analysis and comparison with the published data. These compounds have not been reported from genus Ailanthus, whereas compound 7 was identified by NMR for the first time. In addition, the $95\%$ ethanol extract and compounds from the fruits of Ailanthus altissima SWINGLE were assayed for in vitro antimicrobial activity. The extract was potent active against the assayed bacteria while compounds 3 and 7 exhibited moderate activity.

Chemical Constituents from Acer mandshuricum and Their Effects on the Function of Osteoblastic MC3T3-E1 Cells

  • Ding, Yan;Liang, Chun;Nguyen, Huu Tung;Choi, Eun-Mi;Kim, Jeong-Ah;Kim, Young-Ho
    • Bulletin of the Korean Chemical Society
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    • 제31권4호
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    • pp.929-933
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    • 2010
  • A new compound, 4-methoxyl 5-hydroxymethyl benzoic 3-O-$\beta$-D-glucopyranoside (1), has been isolated from the leaves and stems of Acer mandshuricum, along with nine known compounds (2-10). Their structures were determined by a variety of spectroscopic analyses. The effect of compounds 1-10 on the function of osteoblastic MC3T3-E1 cells was examined by determining alkaline phosphatase (ALP) activity, collagen synthesis, and mineralization. Compound 1 significantly increased the function of osteoblastic MC3T3-E1 cells; $5.0\;{\mu}M$ of 1 increased ALP activity, collagen synthesis, and mineralization of MC3T3-E1 cells to 114.7, 119.5, and 108.2% (P < 0.05) of the basal value, respectively. In addition, compounds 2-10 also potently increased the function of osteoblastic MC3T3-E1 cells.

Asimina triloba 씨앗으로부터 세포독성 Annonaceous Acetogenin으로서의 2,4-cis- 및 trans-isoannonacin (2,4-cis- and trans-isoannonacin: Cytotoxic Ketolactone Annonaceous Acetogenins from the Seeds of Asimina triloba)

  • 김달환;정순자;김종원;우미희
    • 생약학회지
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    • 제29권4호
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    • pp.331-337
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    • 1998
  • Most Annonaceous acetogenins are potently bioactive and offer exciting potential as new antitumor, pesticidal and other bioactivites. The major mode of action of the acetogenin is inhibition of electron transport in the mitochodria. Two known cytotoxic ketolactone Annonaceous acetogenins, (2,4-cis)-isoannonacin (compound 1) and (2,4-trans)-isoannonacin (compound 2), have been isolated from Asimina triloba (Annonaceae) by bioactivity directed fractionation. The structures were characterized on the basis of chemical and spectral data. Compounds 1 and 2, which are known but are first isolated from the seeds of this species, were ob-tained. In brine shrimp lethality test (BST), 1 and 2 exhibited cytotoxicity.

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Inhibitory Effects of Total Extract and Flavonols from Hardy Rubber Tree (Eucommia ulmoides Oliver) Leaves on the Glycation of Hemoglobin

  • Kim, Hye-Young;Kim, Kyong;Lee, Myung-Ki
    • Food Science and Biotechnology
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    • 제15권4호
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    • pp.603-605
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    • 2006
  • Our previous study demonstrated that aqueous ethanolic extract of hardy rubber tree (HRT; Eucommia ulmoides Oliver) leaves potently inhibited glycation, and that two known flavonols and one new flavonol were the active compounds in protein glycation in vitro using the model system of bovine serum albumin and fructose. The aim of this study was to examine the effectiveness of HRT extract and its flavonols against the glycation of hemoglobin (Hb) in primary cultured rat erythrocytes. The extract at $40-400\;{\mu}g/mL$ and the flavonols at $0.2-20\;{\mu}g/mL$ significantly inhibited Hb glycation in a concentration-dependent manner. They were more effective than aminoguanidine, a well-known inhibitor of glycation. Three flavonols seemed to be responsible for the inhibitory activity of the extract, furthermore, the extract of HRT leaves showed advantages over single isolated flavonols in the inhibition of Hb glycation.

열대 해면동물 Lipastrotethya sp.에서 분리된 사포닌 화합물 (A New Triterpenoid Saponin from the Tropical Marine Sponge Lipastrotethya sp.)

  • 엄태양;이연주;이희승
    • Ocean and Polar Research
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    • 제38권4호
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    • pp.287-294
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    • 2016
  • Marine sponges have been a remarkably rich source of pharmacologically active and structurally diverse natural products. As a part of our continuing search for novel secondary metabolites of biomedical importance from marine invertebrate, we encountered the sponge Lipastrotethya sp. from Chuuk, Micronesia. The crude organic extract of this animal exhibited considerable cytotoxicity against the K562 cell line. Guided by the $^1H$ NMR analysis, flash chromatography of the crude extract followed by HPLC yielded a new triterpene glycoside, along with ten known saponins of the sarasinoside class. The structure of this new compound was determined by combined spectroscopic methods such as COSY, HSQC and HMBC experiment. Among these metabolites, six compounds exhibited moderate cytotoxicity against ACHN, MDA-MB-231, NCI-H23 and NUGC-3 cell lines.

Scalaran-type sesterterpenes from a Marine Sponge Smenospongia species showing the AMPK activation

  • Hwang, Buyng-Su;Rho, Jung-Rae
    • 한국자기공명학회논문지
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    • 제16권1호
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    • pp.1-10
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    • 2012
  • A new scalaran class sesterterpenoid with five known ones was isolated from a marine sponge Smenospongia species collected from the Gageo island, Korea. Chemical structure of all of compounds was determined on the basis of a combination of extensive 1D and 2D NMR experiments and MS data. The new compound exhibited a new functional group on a common scalaran sesterterpene skeleton, identified as 12-deacetoxy-23-deacetoxyscalarin. The compound 1 moderately showed the effect of the activation of AMP-activated protein kinase (AMPK) in L6 myoblast cell.

New Flavonol Glycosides from Leaves of Symplocarpus renifolius

  • Whang, Wan-Kyunn;Lee, Moo-Taek
    • Archives of Pharmacal Research
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    • 제22권4호
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    • pp.423-427
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    • 1999
  • A study was carried out to evaluate flavonol glycosides in leaves of Symplocarpus renifolius (Araceae). From the water fraction of the MeOH extract, three new flavonol glycosides were isolated along with three known compounds, Kaempferol-3-O-$\beta$-glucopyranosyl-($1{\rightarrow}2$)-$\beta$-D-glucopyranosyl-7-O-$\beta$-D-glucopyranoside, quercetin-3-O-$\beta$-D-glucopyranosy-1-($1{\rightarrow}2$)-$\beta$-D-glucopyranoside, and caffeic acid. The structures of the new flavonol glycosides were elucidated by chemical and spectral analyses a quercetin-3-O-$\beta$-D-glucopyranosyl-($1{\rightarrow}2$)-$\beta$-D-glucopyranosyl-7-O-$\beta$-D-glucopyranoside, isorhamnetin-3-O-$\beta$-D-glucopyranosyl-(1 2)-$\beta$-D-glucopyranosyl-7-O-$\beta$-D-glucopyranosdie, and quercetin-3-O$\beta$-D-glucopyranosyl-($1{\rightarrow}2$)-$\beta$-D-glycopyranosyl-7-O-($6^{IIII}$-trans-caffeoyl)-$\beta$-D-glucopyranoside.

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A New Megastigmane Glucoside from the Aerial Parts of Erythronium japonicum

  • Lee, Seung-Young;Lee, Il-Kyun;Choi, Sang-Un;Lee, Kang-Ro
    • Natural Product Sciences
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    • 제18권3호
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    • pp.166-170
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    • 2012
  • The purification of the MeOH extract from the aerial parts of Erythronium japonicum using column chromatography furnished a new megastigmane glucoside, erthrojaponiside (1), together with six known megastigmane derivatives (2 - 7). The structure of the new compound (1) was determined through 1D and 2D NMR spectral data analysis and chemical means. The isolated compounds (1 - 7) were tested for cytotoxicity against four human tumor cells in vitro using a Sulforhodamin B (SRB) bioassay.