• Title/Summary/Keyword: New and known compounds

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Two New Bibenzyl Glucosides from Dendrobium chrysotoxum

  • Dong, Fa-Wu;Luo, Huai-Rong;Wan, Qin-Li;Xu, Feng-Qing;Fan, Wei-Wei;Wang, Kai-Jin;Li, Ning;Hu, Jiang-Miao
    • Bulletin of the Korean Chemical Society
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    • v.33 no.7
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    • pp.2247-2250
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    • 2012
  • Two new bibenzyl glucosides, 3,3',4',5-tetramethoxybibenzyl-4-O-${\beta}$-D-glucopyranoside (1) and 3,4,4',5-tetramethoxybibenzyl-3'-O-${\beta}$-D-glucopyranoside (2), together with five known ones, chrysotobibenzyl (3), erianin (4), chrysotoxine (5), gigantol (6) and tristin (7) were isolated from the stems of Dendrobium chrysotoxum. The structures of those compounds were elucidated by extensive spectroscopic analysis. Moreover, compounds 1-7 were assessed for inhibitory activity of two enzymes-AChE (acetylcholine esterase) and BChE (butyrylcholine esterase).

Review of Functional Volatile Component in Essential Oil of Medicinal and Aromatic Plants (자원식물의 기능성 정유성분 이용 고찰)

  • 정해곤;방진기;성낙술;김성민
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.48
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    • pp.41-48
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    • 2003
  • The number of natural products obtained from plants has now reached over 100,000 and new chemical compounds are being discovered ever year. Medicinal and Aromatic plants and their extracts have been used for centuries to relieve pain, aid healing, kill bacteria and insects are important as the antifungal and anti-herbivore agents with further compounds being involved in the symbiotic associations. Although their functions in plants have not been fully established, it is Known that some substances have growth regulatory properties while others are involved in pollination and seed dispersal. The complex nature of these chemicals are usually produced in various types of secretory structures which is an important character of a plant family and also influenced and controlled by genetic and ecological factors. Detailed anatomical description of these structures ave relevant to the market value of the plants, the verification of authenticity of a given species and for the detection of substitution or adulteration. Volatile oils are used for their therapeutic action for flavoring of lemon, in perfumery of rose or as starting materials for the synthesis of other compounds of turpentine. For therapeutic purposes they are administered as inhalations of eucalyptus oil, peppermint oil, as gargles and mouthwashes of thymol and transdermally many essential oils including those of lavender, etc. With these current trend for using volatile components in essential oil will be increasing in the future in Korea and in the world as well.

Bioprospecting of Novel and Bioactive Metabolites from Endophytic Fungi Isolated from Rubber Tree Ficus elastica Leaves

  • Ding, Zhuang;Tao, Tao;Wang, Lili;Zhao, Yanna;Huang, Huiming;Zhang, Demeng;Liu, Min;Wang, Zhengping;Han, Jun
    • Journal of Microbiology and Biotechnology
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    • v.29 no.5
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    • pp.731-738
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    • 2019
  • Endophytic fungi are an important component of plant microbiota, and have the excellent capacity for producing a broad variety of bioactive metabolites. These bioactive metabolites not only affect the survival of the host plant, but also provide valuable lead compounds for novel drug discovery. In this study, forty-two endophytic filamentous fungi were isolated from Ficus elastica leaves, and further identified as seven individual taxa by ITS-rDNA sequencing. The antimicrobial activity of these endophytic fungi was evaluated against five pathogenic microorganisms. Two strains, Fes1711 (Penicillium funiculosum) and Fes1712 (Trichoderma harzianum), displayed broad-spectrum bioactivities. Our following study emphasizes the isolation, identification and bioactivity testing of chemical metabolites produced by T. harzianum Fes1712. Two new isocoumarin derivatives (1 and 2), together with three known compounds (3-5) were isolated, and their structures were elucidated using NMR and MS. Compounds 1 and 2 exhibited inhibitory activity against Escherichia coli. Our findings reveal that endophytic fungi from the rubber tree F. elastica leaves exhibit unique characteristics and are potential producers of novel natural bioactive products.

NF-κB Inhibition and PPAR Activation by Phenolic Compounds from Hypericum perforatum L. Adventitious Root

  • Li, Wei;Ding, Yan;Quang, Tran Hong;Nguyen, Thi Thanh Ngan;Sun, Ya Nan;Yan, Xi Tao;Yang, Seo Young;Choi, Chun Whan;Lee, Eun Jung;Paek, Kee Yoeup;Kim, Young Ho
    • Bulletin of the Korean Chemical Society
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    • v.34 no.5
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    • pp.1407-1413
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    • 2013
  • A new compound, perforaphenonoside A (1), along with 11 known compounds (2-12) were isolated from a methanol extract of adventitious roots of Hypericum perforatum. Their chemical structures were elucidated using chemical and physical methods as well as comparison of NMR and mass spectral data with previously reported data. Their inhibition of NF-${\kappa}B$ and activation of PPAR was measured in HepG2 cells using a luciferase reporter system. Among the compounds 3, 6, 7 and 12 inhibited NF-${\kappa}B$ activation stimulated by TNF${\alpha}$ in a dose-dependent manner, with $IC_{50}$ values ranging from 0.85 to $8.10{\mu}M$. Moreover, compounds 1-3, 7, 11 and 12 activated the transcriptional activity of PPARs in a dose-dependent manner, with $EC_{50}$ values ranging from 7.3 to $58.7{\mu}M$. The transactivational effects of compounds 1-3, 7, 11 and 12 were evaluated on three individual PPAR subtypes. Among them, compound 2 activated $PPAR{\alpha}$ transcriptional activity, with 153.97% stimulation at $10{\mu}M$, while compounds 1, 2 and 11 exhibited transcriptional activity of $PPAR{\gamma}$, with stimulation from 124.76% to 126.91% at $10{\mu}M$.

Cytotoxic Effect of Aromatic and Aliphatic Compounds Produced by Streptomyces sp. Isolated in Korea (한국 Streptomyces SP.로부터 분리한 방향족 화합물과 지질 화합물의 세포독성 연구)

  • Shin, Suck-Woo;Ryeom, Kon
    • Biomolecules & Therapeutics
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    • v.5 no.2
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    • pp.215-221
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    • 1997
  • In an effort to screen new selective antitumor agents from the broth of soil microorganism, cytotoxicity oriented screening was performed against tumor cells and 3 compounds (Compound 1, 2 and 3) were isolated from Sreptomyces parvullus ISP 5048 and their chemical structures were determined. Among these compounds, Compound 2 showed the highest cytotoxicity against P388Dl and L1210. While the $IC_{50}$/ values of compound 2 against P388Dl and L1210 were 0.073$\mu$g/ml and 0.07$\mu$g/ml, respectively, and the $IC_{50}$/ value of Compound 3 was 0.17$\mu$g/ml against human lung cancer cells, A549, the cytotoxicity of Compound 2 and 3 against normal cell line, Vero E6 cell was about 4- and 8-fold lower than that of adriamycin. Based on the chemical analysis data, Compound 3 was octacosamicine A, a known antibiotic, which was reported by Dobasih et al. (1988). Taken together the results demonstrated that Compound 2 and Compound 3 has the possibility to be developed as antitumor agent because of its potent cytotoxicity as well as high selectivity against various cancer cell lines.

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New Production of 5-Bromotoluhydroquinone and 4-O-Methyltoluhydroquinone from the Marine-Derived Fungus Dothideomycete sp.

  • Leutou, Alain S.;Yun, Keum-Ja;Choi, Hong-Dae;Kang, Jung-Sook;Son, Byeng-Wha
    • Journal of Microbiology and Biotechnology
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    • v.22 no.1
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    • pp.80-83
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    • 2012
  • The addition of NaBr to the fermentation medium of a marine isolate of the fungus Dothideomycete sp. resulted in induced production of two toluhydroquinone derivatives, 5-bromotoluhydroquinone (1) and 4-O-methyltoluhydroquinone (2), and two known compounds, toluhydroquinone (3) and gentisyl alcohol (4). The structures of 1 and 2 were assigned through the spectroscopic data analyses. Compounds 1-4 showed a potent antibacterial activity against the methicillin-resistant and multidrug-resistant Staphylococcus aureus (MRSA and MDRSA) with MIC (minimum inhibitory concentration) values of 6.2, 12.5, 6.2, and 12.5 ${\mu}g/ml$, respectively. Compounds 1-4 also exhibited a moderate radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) with $IC_{50}$ values of 11.0, 17.0, 12.0, and 7.0 ${\mu}M$, respectively, which were more active than the positive control, L-ascorbic acid ($IC_{50}$, 20.0 ${\mu}M$).

Lipoxygenase Inhibitory and Antioxidant Activities of Isolated Compounds from Moutan Cortex

  • Ha, Do-Thi;Trung, Trinh-Nam;Thuan, Nguyen-Duy;Yim, Nam-Hui;Min, Byung-Sun;Bae, Ki-Hwan
    • Natural Product Sciences
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    • v.16 no.2
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    • pp.68-74
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    • 2010
  • Phytochemical investigation on the ethyl acetate and n-butanol fractions of Moutan Cortex resulted in the isolation and characterization of a new monoterpene glycoside (3) and twenty known monoterpene glycosides (1, 2, 4-21). The structure of 3 was determined by spectroscopic data interpretation and physico-chemical properties. Compounds 1 and 8 presented a remarkable inhibitory activity against lipoxygenase-1 (LOX-1) with $IC_{50}$ values of 45.2 and $37.5\;{\mu}M$, respectively. Compounds 9, 10, 13, 18, 19, and 21 showed significant 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging effect with $IC_{50}$ values of 9.8, 25.5, 6.4, 15.2, 18.7, and $23.7\;{\mu}M$, respectively. Benzoylpaeoniflorin (8), which exhibited the highest inhibitory effect with an $IC_{50}$ value of $37.5{\pm}0.7{\mu}M$, was further analyzed the inhibition kinetics by Lineweaver-Burk plots. Results indicated that 8 is a non-competitive inhibitor, and the kinetic parameter values were estimated to be ($31.04\;{\mu}M$, Ki), ($0.29\;{\mu}M/min$, $V_m$), and ($48.50\;{\mu}M$, $K_m$).

Development of Near-Critical Water Reaction System for Utilization of Lignin as Chemical Resources

  • Eom, Hee-Jun;Hong, Yoon-Ki;Park, Young-Moo;Chung, Sang-Ho;Lee, Kwan-Young
    • 한국신재생에너지학회:학술대회논문집
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    • 2010.06a
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    • pp.251.2-251.2
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    • 2010
  • Plant biomass has been proposed to be an alternative source for petroleum-based chemical compounds. Especially, phenolic chemical compounds can be obtained from lignin by chemical depolymerization processes because lignin consists of complex aromatic polymer such as trans-p-coumaryl, coniferyl and sinapyl alcohols, etc. Phenolic chemical compounds from lignin were usually produced in super critical water. However, we applied Near-critical water (NCW) system because NCW is known as a good solvent for lignin depolymerization. Organic matter like lignin can be solved in NCW system and the system has a unique acid-base property without conventional non-eco-friendly chemicals such as sulfuric acid and sodium hydroxide. In this work, we tried to optimize the NCW depolymerization system by adjusting the processing variables such as reaction time, temperature and pressure. Moreover, the amount of additional phenol was optimized by changing the molar ratio between water and phenol. Phenol was used as capping agent to prevent re-polymerization of active fragment such as formaldehyde. Alkali-lignin was used as a starting material and characterized by a Solid State 13C-NMR, FT-IR and EA (Elemental Analysis). GC-MS analysis confirmed that o-cresol, p-cresol, anisole and 4-hydroxyphathalic acid were the main product and they were quantitatively analyzed by HPLC.

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New Geldanamycin Analogs from Streptomyces hygroscopicus

  • Wu, Cheng-Zhu;Jang, Jae-Hyuk;Ahn, Jong Seog;Hong, Young-Soo
    • Journal of Microbiology and Biotechnology
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    • v.22 no.11
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    • pp.1478-1481
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    • 2012
  • Geldanamycin (GM) and its analogs are important anticancer agents that inhibit heat shock protein (Hsp) 90, which is a major chaperone protein in cancer cells. Accordingly, based on interest in obtaining novel natural GM derivatives, the potential of Streptomyces hygroscopicus JCM4427, a GM producer, was explored for novel natural GM derivative(s), resulting in the discovery of new GM analogs as a biosynthetic shunt product and intermediates from its fermentation broth. In this study, the fermentation, isolation, structure determination, and biological activity of the compounds, two new tetracyclic thiazinogeldanamycin (1) and 19-hydroxy-4,5-dihydrogeldanamycin (3), together with the three known 4,5-dihydrothiazinogeldanamycin (2), reblastatin (4), and 17-demethoxy-reblastatin (5), are described.

A New Flavonol Glycoside from Tristemma hirtum (Melastomataceae)

  • Kenfack, Joseph Nandjou;Ponou, Beaudelaire Kemvoufo;Kuhlborn, Jonas;Teponno, Remy Bertrand;Nono, Raymond Ngansop;Fouedjou, Romuald Tematio;Opatz, Till;Park, Hee Juhn;Tapondjou, Leon Azefack
    • Natural Product Sciences
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    • v.24 no.3
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    • pp.213-218
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    • 2018
  • Chemical investigation of the plant Tristemma hirtum P. Beauv (Melastomataceae) resulted to the isolation of a new flavonol glycoside named quercetin-7-O-${\alpha}$-D-arabinofuranoside (1), together with nine known compounds including 3'-hexadecanoyl-2'-(9aZ)-tetradecanoyl-glycerol 1'-O-[${\beta}$-D-galactopyranosyl-(1'' ${\rightarrow}$ 6'')-${\alpha}$-D-galactopyranoside] (2), arjunolic acid (3), ${\beta}$-sitosterol-3-O-${\beta}$-D-glucopyranoside (4), terminolic acid (5), quercetin (6), asiatic acid (7), maslinic acid (8), $1{\beta}$-O-galloylpedunculagin (9) and 6-hydroxyapigenin 7-O-${\beta}$-D-glucopyranoside (10) from the methanol extract using normal and reversed phase column chromatography. The structures of these compounds were determined by comprehensive interpretation of their spectral data mainly including 1D- 2D-NMR ($^1H-^1H$ COSY, HSQC, and HMBC) spectroscopic and ESI-TOF-MS mass spectrometric analysis.