• Title/Summary/Keyword: HMQC

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Isolation and Structure Identification of Antifungal Substance from Aspergillus terreus (Aspergillus terreus로부터 항진균성 물질의 분리 및 구조분석)

  • Kim, Keun-Ki;Park, Ki-Hun;Moon, Suk-Sik;Kang, Kyu-Young
    • Applied Biological Chemistry
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    • v.40 no.6
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    • pp.593-596
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    • 1997
  • In the course of search antagonistic fungi from soil in green house, four kind of fungi (AF1, AF2, AF3, AF4) were isolated, which have activities against Phytophthora capsici, Botrytis cinera, Rhizoctonia solani, Pythium ultimum and Fusarium oxysporum. The AF2 was identified according to the morphological description of Aspergillus terreus. This antagonistic fungus inhibiting various plant pathogens was effective to reduce disease incidence of cucumber seedlings caused by mixed inoculum of Rhizoctonia solani, Pythium ultimum and Fusarium oxysporum. Antifungal compound I was isolated and purified by fresh chromatography from A. terreus. The $^1H$ and $^{13}C$ assignment of compound I was achieved from two-dimensional $^1H-^1H\;COSY$, HMQC, HMBC with the add of homonuclear and heteronuclear double resonance experiment. The compound I was identified butyrolactone I (${\alpha}$-oxo-${\beta}$-(p-hydroxyphenyl)-${\gamma}$-(p-hydroxy-m-3,3-dimethyl-allylbenzyl)-${\gamma}$-methoxycarbonyl-${\gamma}$-butyrolactone, $C_{24}H_{24}O_7$, M.W.=424).

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Toxicity and Characteristics of Antifungal Substances Produced by Bacillus amyloliquefaciens IUB158-03 (Bacillus amyloliquefaciens IUB158-03이 생산하는 항진균물질의 생화학적 특성 및 독성)

  • Kim, Hye-Young;Lee, Tae-Soo
    • Journal of Life Science
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    • v.19 no.11
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    • pp.1672-1678
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    • 2009
  • The purified antifungal substances produced by Bacillus amyloliquefaciens IUB158-03 was positive to ninhydrin but negative to aniline, suggesting that the antifungal substance could be a peptide. FAB-MS, UV adsorption spectrum, and amino acid composition analysis revealed that the molecular weight of the antifungal substance was 1042 and that maximal adsorption was at 220 nm and 277 nm. The antifungal substance was composed of $Asn_3$, $Gln_2$, $Ser_1$, $Gly_1$, and $Tyr_1$. The composition and structural characteristics of antifungal substance were analysed by $^1H$-NMR spectrum, $^1H$-COSY, HMQC, which revealed that the compound belongs to the iturin A family. Temperature and pH had little effect on the stability of the antifungal substance in the ranges of $-70{\sim}121^{\circ}C$ and pH 6.0~10.0, respectively. It showed strong antibiotic activity against fungi. An in vitro cytotoxicity test using NIH3T3 cell showed that the antifungal substance does not have cytotoxicity. The number of circulating leukocytes and the hematobiological analysis of the mice administered with the antifungal substances was similar to those of the control group, indicating no cytotoxicity in vivo. Therefore, the antifungal substances extracted from culture broth of Bacillus amyloliquefaciens IUB158-03 have future potential as biocontrol agents against plant diseases caused by fungi.

Identification of Phenolic Compounds and Quantification of Their Antioxidant Activities in Roasted Wild Ginseng (Panax ginseng C.A. Meyer) Leaves

  • Seog, Ho-Moon;Jung, Chang-Hwa;Choi, In-Wook;Park, Yong-Kon;Cho, Hong-Yon
    • Food Science and Biotechnology
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    • v.16 no.3
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    • pp.349-354
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    • 2007
  • The objectives of this study were to systemically identify phenolic compounds in roasted wild ginseng (Panax ginseng C.A. Meyer) leaves and investigate their radical scavenging activities. Seven phenolic compounds were identified by NMR (H, C, COSY, HMQC, HMBC) and mass (EI-MS, FAB-MS) analyses: 5-caffeoylquinic acid, kaempferol, quercetin, 3,4-dihydroxy-benzoic acid, 4-hydroxy-benzoic acid, 3-(3,4-dihydroxyphenyl)-2-propenoic acid, and 3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid. Their concentrations ranged from 0.4 (3,4-dihydroxy-benzoic acid) to 7.5 mg (kaempferol) per 100 g of roasted leaves. Among these compounds, 5-caffeoylquinic acid, kaempferol, and quercetin were found exclusively in the leaf portions of the ginseng plants. When their antioxidant activities were measured by DPPH and superoxide anion radical scavenging activity, quercetin, and kaempferol were most effective.

Isolation of Dihydrophaseic Acid from Seed Extract of Nelumbo nucifera (연자육으로부터 식물호르몬 Dihydrophaseic Acid의 분리 및 동정)

  • Seo, Jee-Hee;Choi, Yeon-Hee;Yoo, Mi-Young;Hong, Kyung-Sik;Lee, Byung-Hoi;Yon, Gyu-Hwan;Kim, Young-Sup;Kim, Young-Kyoon;Ryu, Shi-Yong
    • Korean Journal of Pharmacognosy
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    • v.37 no.4 s.147
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    • pp.290-293
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    • 2006
  • Phytochemical investigation of the seed extract of Nelumba nucifera Gaerth (Nymphaeaceae) resulted in the isolation of a plant hormon, dihydrophaseic acid (1), a abscisic acid derivative. The chemical structure of 1 was elucidated by 2D-NMR spectroscopic analysis, COSY, DEPT, HMQC and HMBC.

Sesquiterpene Glycosides from the whole Plant Extract of Youngia japonica (뽀리뱅이 전초로부터 분리한 Sesquiterpene 배당체)

  • Kim, Mi-Ri;Cha, Mi-Ran;Choi, Yeon-Hee;Choi, Chun-Whan;Choi, Sang-Un;Kim, Young-Sup;Kim, Young-Kyoon;Kim, Young-Ho;Ryu, Shi-Yong
    • Korean Journal of Pharmacognosy
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    • v.41 no.2
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    • pp.103-107
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    • 2010
  • Extensive phytochemical investigation of the methanol extract from the whole plant of Youngia japonica (Asteraceae) led us to the isolation of a new guaiane-type sesquiterpene (1), together with three related guaianolides, youngiajaponicoside A (2), crepiside H (3) and crepeside E (4). The chemical structure of 1 was elucidated by the aid of spectroscopic analyses including 2D-NMR experiments (COSY, HMBC, HMQC and ROESY). The isolated components (1-4) were evaluated for the inhibitory effect on the proliferation of four cultured human tumor cell lines such as A549, SK-OV-3, SK-MEL-2 and HCT-15, in vitro.

A Sesquiterpene ortho-Naphthoquinone from the Root Bark of Ulmus davidiana Planch

  • Kim, Jong-Pyung;Kim, Won-Gon;Park, Jong-Hee;Jung, Jin;Koshino, Hiroyuki;Yoo, Ick-Dong
    • Korean Journal of Pharmacognosy
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    • v.27 no.1
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    • pp.26-31
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    • 1996
  • A sesquiterpene ortho-naphtpoquinone was isolated from the 80% aqueous methanolic extract of root bark of Ulmus davidiana Planch whose stem and root bark have been used as an oriental medicine for the treatment of edema, mastitis, gastric cancer and inflammation. On the basis of spectral data obtained from UV-vis, IR, HR-EIMS and NMR spectrometry, including the pulse field gradient (PFG) HMQC and HMBC techniques, the structure of this compound was determined as 2,3-dihydro-3-hydroxy-3,6,9-trimethylnaphtho(1,8-b,c)pyran-7,8-dione which has been known as mansonone 1. This compound has been isolated only from the heart-wood of Mansonia altissima Chev, a Sterculiacea from West Africa. Thus, this compound was isolated for the second time from natural source in this study. This is the first report to present the carbon chemical shift assignment of mansonone I.

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MR304-1, A Melanin Synthesis Inhibitor Produced by Trichoderma harzianum (Trichoderma harzianum이 생산하는 melanin 생성 저해물질 MR304-1)

  • Lee, Choong-Hwan;Chung, Myung-Chul;Lee, Ho-Jae;Lee, Ke-Ho;Kho, Yung-Hee
    • Microbiology and Biotechnology Letters
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    • v.23 no.6
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    • pp.641-646
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    • 1995
  • During the screening of inhibitors of melanin biosynthesis from microbial secondary metabolites, a fungal strain MR304 which was capable of producing high level of an inhibitor was selected. Based on taxonomic studies, this fungus could be classified as Trichoderma harzianum. The active compound (MR304-1) was purified from culture broth by Diaion HP-20 column chromatography, ethylacetate extraction, Sephadex LH-20 column chromatographv and HPLC. The inhibitor was identified as 3-(1,5-dihvdroxy-3-isocyanocyclopent-(E)-3-envl)prop-2-enoate by spectroscopic methods of UV, ESIMS, $^{1}$H-NMR, $^{13}$C-NMR, NOE, HMQC and HMBC. MR304-1 showed strong mushroom tyrosinase inhibitory activity with IC$_{50}$ value of 0.25 $\mu $g/ml. It inhibited melanin biosynthesis with 15 mm inhibition zone at 30 $\mu $g/paper disc in Streptomyces bikiniensis, a bacterium used as an indicator organism in this work. It also inhibited melanin biosynthesis in B16 melanoma cells with a niinimum inhibitory concentration of 0.05 $\mu $g/ml.

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Melanin Biosynthesis Inhibitory Activities of Coumarins Isolated from Angelica polymorpha MAXIM (궁궁이(Angelica polymorpha MAXIM)로부터 분리한 Coumarin 계열 화합물의 Melanin 생합성 억제 활성)

  • 이충환;백승화;김진희;김현아;이상명;이찬용;고영희
    • Microbiology and Biotechnology Letters
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    • v.31 no.2
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    • pp.135-139
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    • 2003
  • During the screening for inhibitors of melanin biosynthesis from plant extract, Angelica polymorpha MAXIM which showed a high level of inhibition was selected. The inhibiting substances were purified form methanol extract of Angelica polymorpha MAXIM followed by silica gel column chromatography and HPLC. The inhibitors were identified as heraclenin, isosaxalin and heraclenol 3'-Me ether, by spectrescopic methods of ESI-MS, H-NMR, C-NMR, DEPT, HMQC and HMBC. These compounds did not have mushroom tyrosinase inhibitory activity, but showed a highly potent melanin biosynthesis inhibition zone in the plate culture of Streptomyces bikiniensis, a bacterium used as an indicator organism in this work. These compounds did not show any growth inhibition against S. bikiniensis at the same concentration of melanin biosynthesis test.

Antifungal Effect of Amentoflavone derived from Selaginella tamariscina

  • Jung, Hyun-Jun;Sung, Woo-Sang;Yeo, Soo-Hwan;Kim, Hyun-Soo;Lee, In-Seon;Woo, Eun-Rhan;Lee, Dong-Gun
    • Archives of Pharmacal Research
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    • v.29 no.9
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    • pp.746-751
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    • 2006
  • Amentoflavone is a plant biflavonoid that was isolated from an ethyl acetate extract of the whole plant of Selaginella tamariscina (Beauv.) spring. 1D and 2D NMR spectroscopy including DEPT, HMQC, and HMBC were used to determine its structure. Amentoflavone exhibited potent antifungal activity against several pathogenic fungal strains but had a very low hemolytic effect on human erythrocytes. In particular, amentoflavone induced the accumulation of intracellular trehalose on C. albicans as a stress response to the drug, and disrupted the dimorphic transition that forms pseudo-hyphae during pathogenesis. In conclusion, amentoflavone has great potential to be a lead compound for the development of antifungal agents.

Studies on the Constituents of Ulmus parvifolia (참느릅나무의 성분에 관한 연구)

  • Moon, Young-Hee;Rim, Gi-Ryong
    • Korean Journal of Pharmacognosy
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    • v.26 no.1
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    • pp.1-7
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    • 1995
  • The bark of Ulmus parvifolia Jacq. (Ulmaceae) has been used for the treatment of gonorhea, edema, scabies and eczema marginatum. Previous investigations conducted with the heartwood and leaves have demonstrated it to contain sesquiterpenes as well as fat acids from the heartwood and flavonol glycosides from leaves. However, no phytochemical work has been done on the bark parts of this plant. Investigation of the phytochemical constituents in the barks of U. parvifolia has resulted in the isolation of sterols, sterol glucoside and a catechin glycoside, $(+)-catechin\;7-O-{\alpha}-{_L}-rhamnopyranoside$, all of which were isolated for the first time from this plant. Sterols were consisted of the three components, ${\beta}-sitosterol$, stigmasterol and campesterol in a ratio of 92.1:4.1:3.8, and sterol glucoside was identified as ${\beta}-sitosterol\;3-O-{\beta}-{_D}-glucoside$. The structure of the catechin $7-O-{\alpha}-{_L}-rhamnoside$ was established primarily by analysis of $^1H-and$ COSY-45 NMR, HMQC and HMBC and EI mass spectra of the heptaacetate. Especially, HMBC spectrum provides effective way for the determination of the point of attachment of the rhamnosyl group to catechin moiety.

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