• Title/Summary/Keyword: $^1H$-$^1H$ COSY

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곰팡이 분리주 MT60109가 생산하는 Phospholipase C 저해물질의 분리

  • Oh, Won-Keun;Lee, Hyun-Sun;Park, Chan-Sun;Ahn, Soon-Cheol;Ko, Hack-Ryong;Mheen, Tae-Ick;Ahn, Jong-Seog
    • Microbiology and Biotechnology Letters
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    • v.25 no.6
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    • pp.592-597
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    • 1997
  • During the screening of inhibitors against phospholipase C (PLC) and the formation of inositol phosphates (IP$_{t}$) at NIH3T3${\gamma}$1 cells from microbial secondary metabolites, we selected a fungal strain MT60109 which was capable of producing an inhibitor. By the taxonomic studies, this fungus was identified as Pseudallescheria sp. MT60109 and an inhibitor of PLC was purified by BuOH extraction and chromatographic techniques from the culture broth of Pseudallescheria sp. MT60109. The inhibitor was identified as thielavin B by the physico-chemical properties and spectroscopic analysis of UV, FAB-MS, $^{1}$H, $^{13}$C-NMR, $^{1}$H-$^{1}$H COSY and HMBC. Thielavin B showed potent inhibitory activity against PLC purified from bovine brain with an IC$_{50}$ of 20 $\mu$M. And it also inhibited the formation of inositol phosphates in platelet-derived growth factor (PDGF) -stimulated NIH3T3${\gamma}$1 cells with an IC$_{50}$ of 20 $\mu$M.

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Isolation and Structural Determination of Antifungal Antibiotic from Streptomyces hygroscopicus MJM1004 (Streptomyces hygroscopicus MJM1004가 생산하는 항진균성 항생 물질의 분리 및 구조 결정)

  • Bae, Ju-Yun;Kwon, Hyong-Jin;Suh, Joo-Won
    • Applied Biological Chemistry
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    • v.42 no.4
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    • pp.271-276
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    • 1999
  • Several Streptomyces strains were tested for potent antifungal agents active against phytopathogenic fungi. Among the tested, S. hygroscopicus MJM1004 showed a potent antifungal activity when assayed using Candida albicans as indicator organism. With the strain of MJM1004, fermentation medium for the production of an antifungal agent was developed with varying carbon sources, nitrogen sources, and mineral elements, which resulted in the highest productivity in the medium containing 2% soybean meal, 1% glucose, 2% starch, 0.3% $CaCO_3$, 0.05% $MgSO_4{\cdot}7H_2O$, 0.05% $K_2HPO_4$. The active compound showed a broad spectrum of antifungal activity against several plant pathogenic fungi. The antifungal compound was purified and showed the physicochemical characteristics similar to azalomycin F complex in NMR and MS analysis.

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A New Pyranoxanthone Inophyllin B from Calophyllum inophyllum

  • Ee, G.C.L.;Kua, A.S.M.;Cheow, Y.L.;Lim, C.K.;Jong, V.;Rahmani, M.
    • Natural Product Sciences
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    • v.10 no.5
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    • pp.220-222
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    • 2004
  • A new prenylated pyranoxanthone, inophyllin B (1), was isolated from the roots of Calophyllum inophyllum (Guttiferae). Together with this compound was also isolated the known pyranoxanthone brasilixanthone B (2) and two common triterpenes friedelin (3) and sitosterol (4). Structural elucidations of these compounds were achieved through $^1H,\;^{13}C$, DEPT, COSY, HSQC and HMBC experiments. The molecular mass was determined using MS techniques. The crude extract indicated weak toxicity to the larvae of Aedes aegypti. We report here the isolation, structural elucidation and bioassay data for Inophyllin B and brasilixanthone B.

Antioxidant Activity of Fruits of Ligustrum japonicum (여정실의 항산화 활성)

  • Seo, Youngwan;Kim, Hojun
    • Ocean and Polar Research
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    • v.39 no.2
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    • pp.115-124
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    • 2017
  • The objective of this study is to evaluate the antioxidant activity of the fruits of Ligustrum japonicum. The crude extract was successively fractionated into n-hexane, 85% aqueous methanol (85% aq.MeOH), n-butanol (n-BuOH), and water fractions by means of solvent polarity. The crude extract and its solvent fractions were evaluated for their antioxidant effect by four different assay systems: scavenging power on peroxynitrite and intralcellular ROS produced in HT-1080 cells; DNA oxidation inhibition; ferric reducing antioxidant power (FRAP). The n-BuOH fraction exhibiting potent antioxidant activity was further purified by C18 silica gel column chromatography and RP-HPLC to give tyrosol (1) and salidroside (2). The structure of isolated compounds was determined by extensive 2 D NMR experiments such as $^1H$ COSY, NOESY, HSQC and HMBC as well as by comparison with the published spectral data.

The Structure of Kushenol M from Sophora flavescens

  • Ryu, Shi-Yong;Lee, Seung-Ho;No, Zaesung;Kim, Kye-Young;Lee, Sueg-Geun;Ahn, Jong-Woong
    • Archives of Pharmacal Research
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    • v.18 no.1
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    • pp.41-43
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    • 1995
  • The linkage pattem of two side chains i.e., a isopentenyl and a lavandulyl group in kushenol M(I), a flavonoid from Sophora flavescens was established by the aid of 2-D NMR techniques, especially DEPT, ${13}C-^1H$ COSY and COLOC experiments. Thus, I was unequivocally determined as (2R, 3R)-5, 7, 2', 4'-tetrahydroxy-6-isopentenyl-8-lavandulyflavanonol.

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A New Streptothricin Family Antibiotic Producing Streptomyces Spp. Snus 8810-111 ; Characterization of The Producing Organisms, Fermentation, Isolation, and Structure Elucidation of Antibioitics

  • Goo, Yang-Mo;Kim, Ok-Yun;Joe, Young-Ae;Lee, Young-Bok;Ju, Jeongho;Kim, Beom-Beom-Tae;Lee, Youn-Young
    • Archives of Pharmacal Research
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    • v.19 no.2
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    • pp.153-159
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    • 1996
  • A new streptothricin family antibiotic producing Streptomyces spp. SNUS 8810-111 was isolated from a soil sample. Study of its morphological and physiological characters indicated that the antibiotic producing organism was a Streptomyces spp. Taxonomical studies suggested that the organism might belong to the genus streptomyces gougeroti. The organism produced antibiotics most in calcium carbonate-tryptic soy broth. The active principles were recovered from the broth with a cation exchange resin and eluted from the resin with HCI. Cellulose column chromatography gave two active principles.$^1H-^1H$ Homo-COSY study on the first compound revealed four structural components. Total hydrolysis of the antibiotic with HCI allowed isolation of $\beta-lysine$. From these data the antibiotic was found to be streptothricin D. The other compound showed one additional signal in the .$^1H$NMR and the $^{13}C$ NMR spectra. The signal was from a methyl group attached to a nitrogen atom. Comparison of the NMR signals with those of streptothricin D suggested that the compound was N-methyl-streptothricin D which was a new compound in the family of streptothricin antibiotics.

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Isolation and identification of antifungal compounds from Spatholobus suberectus Dunn (계혈등(Spatholobus suberectus Dunn)으로부터 항균활성 물질의 분리 및 구조결정)

  • Hwang, Joo-Tae;Park, Young-Sik;Kim, Young-Shin;Kim, Jin-Cheol;Lim, Chi-Hwan
    • The Korean Journal of Pesticide Science
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    • v.16 no.3
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    • pp.209-216
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    • 2012
  • In the continued research on natural fungicides for control of plant diseases by using plant-derived products, we found that Spatholobus suberectus Dunn had a strong fungicidal activity against several plant pathogens. S. suberectus (1 kg) was extracted with 80% aqueous MeOH and then the concentrated extract was partitioned with n-hexane, EtOAc, n-BuOH and $H_2O$ successively. The four layers were tested their disease contron efficacies against 6 plant diseases such as rice blast (RCB), rice sheath blight (RSB), tomato grey mold (TGM), tomato late blight (TLB), wheat leaf rust (WLR), and barley powdery mildew (BPM). The EtOAc fraction was highly active showing over 80% control against RCB, TGM, TLB, and BPM. By using silica gel chromatography, preparative TLC and HPLC, six compounds that were expected to have antifungal activity were separated. Their chemical structures were identified as ethanone, hydroxytyrosol, epicatechin, procyanidin B2, dimethoxy daizein and formononetin by ESI-MS, $^1H$-NMR, $^{13}C$-NMR, and 2D-NMR spectroscopic analyses. The chemicals except epicatechin were first reported in S. suberectus. Study on in vitro and in vivo antifungal activities of the isolated compounds is in progress.

Acaricidal Activity and Function of Mite Indicator Using Plumbagin and Its Derivatives Isolated from Diospyros kaki Thunb. Roots (Ebenaceae)

  • Lee, Chi-Hoon;Lee, Hoi-Seon
    • Journal of Microbiology and Biotechnology
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    • v.18 no.2
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    • pp.314-321
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    • 2008
  • Acaricidal effects of materials derived from Diospyros kaki roots against Dermatophagoides farinae and D. pteronyssinus were assessed using impregnated fabric disk bioassay and compared with that of the commercial benzyl benzoate. The observed responses varied according to dosage and mite species. The $LD_{50}$ values of the chloroform extract of Diospyros kaki roots were 1.66 and $0.96{\mu}g/cm^2$ against D. farinae and D. pteronyssinus. The chloroform extract of Diospyros kaki roots was approximately 15.2 more toxic than benzyl benzoate against D. farinae, and 7.6 times more toxic against D. pteronyssinus. Purification of the biologically active constituent from D. kaki roots was done by using silica gel chromatography and high-performance liquid chromatography. The structure of the acaricidal component was analyzed by GC-MS, $^1H-NMR,\;^{13}C-NMR,\;^1H-^{13}C$ COSY-NMR, and DEPT-NMR spectra, and identified as plumbagin. The acaricidal activity of plumbagin and its derivatives (naphthazarin, dichlon, 2,3-dibromo-1,4-naphthoquinone, and 2-bromo-1,4-naphthoquinone) was examined. On the basis of $LD_{50}$ values, the most toxic compound against D. farinae was naphthazarin $(0.011{\mu}g/cm^2)$ followed by plumbagin $(0.019{\mu}g/cm^2),$ 2-bromo-1,4-naphthoquinone $(0.079{\mu}g/cm^2)$, dichlon $(0.422{\mu}g/cm^2)$, and benzyl benzoate $(9.14{\mu}g/cm^2)$. Additionally, the skin color of the dust mites was changed from colorless-transparent to dark brown-black by the treatment of plumbagin. Similar results have been exhibited in its derivatives (naphthazarin, dichlon, and 2-bromo-1,4-naphthoquinone). In contrast, little or no discoloration was observed for benzyl benzoate. From this point of view, plumbagin and its derivatives can be very useful for the potential control agents, lead compounds, and indicator of house dust mites.

A New (E)-4-Hydroxy-dodec-2-enedioic Acid from the Stem Bark of Albizzia julibrissin

  • Jung, Mee-Jung;Kang, Sam-Sik;Choi, Jae-Sue
    • Archives of Pharmacal Research
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    • v.26 no.3
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    • pp.207-209
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    • 2003
  • A new unsaturated hydroxy acid was isolated from the stem bark extract of Albizzia julibrissin through repeated silica gel and Sephadex LH-20 column chromatography. The chemical structure of the new acid was determined as (E)-4-hydroxy-dodec-2-enedioic acid on the basis of several spectral data including 2D-NMR. The stereochemical feature of the double bond was determined to be E on the basis of the coupling pattern of related proton signals in the $^1H-NMR$ and COSY experiments.

Synthesis and DNA-binding Properties of Trehalose-tethered Monomeric and Dimeric Berberines

  • Wang, Yong-Min;Zhou, Chun-Qiong;Chen, Jin-Xiang;Chen, Wen-Hua
    • Bulletin of the Korean Chemical Society
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    • v.34 no.3
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    • pp.749-752
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    • 2013
  • Trehalose-tethered monomeric and dimeric berberines were synthesized in 50% and 30% from the reaction of berberrubine with 6-tosyl-${\alpha}$,${\alpha}^{\prime}$-trehalose and 6,6'-ditosyl-${\alpha}$,${\alpha}^{\prime}$-trehalose, respectively, and fully characterized by MS (HR and ESI) and NMR ($^1H$, $^{13}C$, COSY and HSQC). Spectrophotometric and spectrofluorimetric titrations indicated that compared with berberine, trehalose-tethered monomeric berberine had comparable DNA-binding affinity toward calf-thymus DNA, whereas trehalose-spaced dimeric berberine exhibited higher DNA-binding affinity. The potential application of these conjugates is also briefly discussed.