• Title/Summary/Keyword: Antifungal compounds

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Biotransformation of natural polyacetylene in red ginseng by Chaetomium globosum

  • Wang, Bang-Yan;Yang, Xue-Qiong;Hu, Ming;Shi, Li-Jiao;Yin, Hai-Yue;Wu, Ya-Mei;Yang, Ya-Bin;Zhou, Hao;Ding, Zhong-Tao
    • Journal of Ginseng Research
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    • v.44 no.6
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    • pp.770-774
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    • 2020
  • Background: Fermentation has been shown to improve the biological properties of plants and herbs. Specifically, fermentation causes decomposition and/or biotransformation of active metabolites into high-value products. Polyacetylenes are a class of polyketides with a pleiotropic profile of bioactivity. Methods: Column chromatography was used to isolate compounds, and extensive NMR experiments were used to determine their structures. The transformation of polyacetylene in red ginseng (RG) and the production of cazaldehyde B induced by the extract of RG were identified by TLC and HPLC analyses. Results: A new metabolite was isolated from RG fermented by Chaetomium globosum, and this new metabolite can be obtained by the biotransformation of polyacetylene in RG. Panaxytriol was found to exhibit the highest antifungal activity against C. globosum compared with other major ingredients in RG. The fungus C. globosum cultured in RG extract can metabolize panaxytriol to Metabolite A to survive, with no antifungal activity against itself. Metabolites A and B showed obvious inhibition against NO production, with ratios of 42.75 ± 1.60 and 63.95 ± 1.45% at 50 µM, respectively. A higher inhibitory rate on NO production was observed for Metabolite B than for a positive drug. Conclusion: Metabolite A is a rare example of natural polyacetylene biotransformation by microbial fermentation. This biotransformation only occurred in fermented RG. The extract of RG also stimulated the production of a new natural product, cazaldehyde B, from C. globosum. The lactone in Metabolite A can decrease the cytotoxicity, which was deemed to be the intrinsic activity of polyacetylene in ginseng.

Biological Activities and Bioactive Compounds in the Extract of Acer tegmentosum Maxim. Stem (산겨릅나무 줄기추출물의 생리활성 및 유효성분 분리)

  • Hong, Bo-Kyong;Eom, Seok-Hyun;Lee, Chan-Ok;Lee, Ji-Won;Jeong, Jong-Hyun;Kim, Jae-Kwang;Cho, Dong-Ha;Yu, Chang-Yeon;Kwon, Yong-Soo;Kim, Myong-Jo
    • Korean Journal of Medicinal Crop Science
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    • v.15 no.4
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    • pp.296-303
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    • 2007
  • Acer tegmentosum (Acereaceae) has been used a source of traditional medicines for the treatment of hepatic disorders in Korea. This research was conducted to determine biofunctional activities of A. tegmentosum stem extract and to identify its bioactive components. Methanolic extract from A. tegmentosum stem was partitioned by using organic solvents, including n-hexane, ethyl acetate, n-butanol, and water. Two compounds were isolated by using an ODS column chromatography from ethyl acetate soluble fraction shown to the strongest antioxidant activity ($RC_{50}=3.15\;{\mu}g/m{\ell}$) among the fractions. The isolated compounds were analyzed by $^1H$ and $^{13}C$ NMR, IR, UV/VIS, MS spectrum data and identified as catechin, ${\rho}-Hydroxyphenethyl$ alcohol $1-O-{\beta}-_D-(6'-O-galloyl)-glucopyranoside$. The compounds have shown strong antioxidant activity, with similar activity to BHA ($RC_{50}=2\;{\mu}g/m{\ell}$). Especially, ${\rho}-Hydroxyphenethyl$ alcohol 1-O-{\beta}-_D-(6'-O-galloyl)-glucopyranoside$ was shown strong anti-lipid peroxidative activity. However, the compounds were not shown antimicrobial activities. In antimicrobial activity assays, ethyl acetate soluble fraction was effective to bacterial inhibition, such as Escherichia coli and Klebsiella pneumonia, with minimum inhibitory concentrations in $125\;{\mu}g/m{\ell}$. Otherwise, antifungal activity against Candida albicans was shown in n-hexane soluble fraction exhibiting $63\;{\mu}g/m{\ell}$ of minimum inhibitory concentration. In anticomplementary activity assays, water soluble fraction was the most effective exhibiting 24% inhibitory activity.

A two-component sensor kinase (GacS) mediated signal transduction pathway involved in production of antifungal compounds in Pseudomonas chlororaphis O6.

  • Kang, Beom-Ryong;Lee, Jung-Hoon;Kim, Hyun-Jung;Cho, Baik-Ho;Kim, Young-Cheol
    • Proceedings of the Korean Society of Plant Pathology Conference
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    • 2003.10a
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    • pp.99.1-100
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    • 2003
  • E. intermedium Blocontrol activity of a P. chlororaphis rhizobacteium O6, depends to the synthesis of extracellular secondary metabolites and exoenzymes, thought to antagonize the pathogenicity of a variety of phytopathogenic fungi. The production of secondary metabolites and exoenzymes in O6, depends essentially on the GacS-mediated signal transduction pathway, which activates largely unknown signal transduction pathway. To exploit the GacS-mediated signal transdcution pathway involved in activation of ph genes that are necessary for biosynthesis of phenazine from P. chlororaphis O6, we cloned and sequenced the phz operon, rpoS gene encoding stationary specific sigma factor, ppx gene encoding polyphosphatase, and lon gene encoding ion protease. Expression of each gene in wild type and GacS mutant were analyzed by RT-PCR. Transcripts from rpoS, phzI enconing acylhomoserine lactone (AHL) synthase, and ph structural genes in the GacS mutant were reduced in each of these growth phases compared to the wild type. The GacS or Lon mutant was found to be deficient in the production of phenzines, exoenzymes, and the acylhomoserine lactone. These mutants were not complemented by ph operon and addition of exogenous AHL. These results indicate that the GacS global regulatory systems controls phenazine production at multiple levels. Future research will focus to identifying the GacS-mediated regulatory cascade involving in production of phenazine in P. chlororaphis.

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In Vivo Antifungal Effects of Coptis japonica Root-Derived Isoquinoline Alkaloids Against Phytopathogenic Fungi

  • LEE CHI-HOON;LEE HOI-JOUNG;JEON JU-HYUN;LEE HOI-SEON
    • Journal of Microbiology and Biotechnology
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    • v.15 no.6
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    • pp.1402-1407
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    • 2005
  • The fungicidal activities of Coptis japonica (Makino) extracts and their active principles were determined against Botrytis cineria, Erysiphe graminis, Phytophthora infestans, Puccinia recondita, Pyricularia grisea, and Rhizoctonia solani using a whole plant method in vivo, and compared with natural fungicides. The responses varied according to the plant pathogen tested. At 2,000 mg/l, the chloroform and butanol fractions obtained from methanolic extracts of C. japonica exhibited strong/moderate fungicidal activities against B. cinerea, E. graminis, P. recondita, and Py. grisea. Two active constituents from the chloroform fractions and one active constituent from the butanol fractions were characterized as isoquinoline alkaloids, berberine chloride, palmatine iodide, and coptisine chloride, respectively, using spectral analysis. Berberine chloride had an apparent $LC_{50}$ value of approximately 190, 80, and 50 mg/l against B. cinerea, E. graminis, and P. recondita, respectively; coptisine chloride had an $LC_{50}$ value of 210,20, 180, and 290 mg/l against B. cinerea, E. graminis, P. recondita, and Py. grisea, respectively; and palmatine iodide had an $LC_{50}$ value of 160 mg/l against Py. grisea. The isoquinoline alkaloids were also found to be more potent than the natural fungicides, curcumin and emodin. Therefore, these compounds isolated from C. japonica may be useful leads for the development of new types of natural fungicides for controlling B. cinerea, E. graminis, P. recondita, and Py. grisea in crops.

Purification and Chemical Identification of the Inhibitor on Bleb Formation of K562 Cell Induced by Phorbol Ester from Actinornycetes Isolate No. 1882-5 (방선균 분리주 No. 1882-5로부터 Phorbol Ester에 의해 유도되는 K562 Cell의 소포형성을 억제하는 물질의 분리와 동정)

  • 안종석;안순철;박문수;김보연;민태익;이현선;오원근
    • Microbiology and Biotechnology Letters
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    • v.20 no.5
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    • pp.565-573
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    • 1992
  • We isolated Actinomycetes strain No. 1882-5, which produces the inhibitor on the bleb formation of K562 cell induced by phorbol ester, from soil sample. Through solvent extraction, Amberlite XAD-4, silica and Lobar low pressure LC, antifungal antibiotic MT 1882-1 and bleb forming inhibitor MT 1882-II were purified from strain No. 1882-5. MT 1882-1 was identified as piericidin $A_{1}$($C_{25}H_{37}0_4N$, M.W. 415) and MT 1882-11 as glucopiericidin A($C_{31}H_{47}0_9N$, M.W. 577) from the analysis of physico-chemical properties and UV, $^1H-NMR$, $^13C-NMR$, and mass spectra of these compounds.

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Application of Rhizobacteria for Plant Growth Promotion Effect and Biocontrol of Anthracnose Caused by Colletotrichum acutatum on Pepper

  • Lamsal, Kabir;Kim, Sang Woo;Kim, Yun Seok;Lee, Youn Su
    • Mycobiology
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    • v.40 no.4
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    • pp.244-251
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    • 2012
  • In vitro and greenhouse screening of seven rhizobacterial isolates, AB05, AB10, AB11, AB12, AB14, AB15 and AB17, was conducted to investigate the plant growth promoting activities and inhibition against anthracnose caused by Colletotrichum acutatum in pepper. According to identification based on 16S rDNA sequencing, the majority of the isolates are members of Bacillus and a single isolate belongs to the genus Paenibacillus. All seven bacterial isolates were capable of inhibiting C. acutatum to various degrees. The results primarily showed that antibiotic substances produced by the selected bacteria were effective and resulted in strong antifungal activity against the fungi. However, isolate AB15 was the most effective bacterial strain, with the potential to suppress more than 50% mycelial growth of C. acutatum in vitro. Moreover, antibiotics from Paenibacillus polymyxa (AB15) and volatile compounds from Bacillus subtilis (AB14) exerted efficient antagonistic activity against the pathogens in a dual culture assay. In vivo suppression activity of selected bacteria was also analyzed in a greenhouse with the reference to their prominent in vitro antagonism efficacy. Induced systemic resistance in pepper against C. acutatum was also observed under greenhouse conditions. Where, isolate AB15 was found to be the most effective bacterial strain at suppressing pepper anthracnose under greenhouse conditions. Moreover, four isolates, AB10, AB12, AB15, and AB17, were identified as the most effective growth promoting bacteria under greenhouse conditions, with AB17 inducing the greatest enhancement of pepper growth.

Physiological and Pharmacological Activites of Nutraceutical Tea by Leaves and Flowers of Domestic Camellia(Camellia japonica)

  • Lee, Sook-Young;Cha, Young-Ju;Lee, Jang-Won;Hwang, Eun-Ju;Kwon, Su-Jung;Cho, Su-In
    • Proceedings of the Plant Resources Society of Korea Conference
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    • 2003.10b
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    • pp.48-49
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    • 2003
  • This project was conducted to development several camellia tea mixed herb teas having any physiological effects. Leaves of tea tree contain many compounds, such as polysaccharides, volatile oils, vitamins, minerals, purines, alkaloids(eg. caffeine) and polyphenols(catechins and flavonoids). Although all three tea types(green, oolonr and black) have antibacterial and free radical capturing(antioxidizing) activities, the efficacy decreases substantially the darker the variety of tea is. This is due to lower contents of anti-oxidizing polyphenols remaining in the leaves. Unlike tea tree(Camellia sinensis), the biochemical features and effects of camellia(Camellia japonica) are not well known. Fresh mature leaf of sasanqua camellia(C. sasanqua), roasted young leaf tea(C. japonica) and fresh mature leaf and bark of camellia had high antibacterial activity against P. vulgaris and B. subtilis. In antifungal activity bioassay, young leaf roasted teas of camellia and sasanqua camellia had high activity against C. albicans and T. beigelil. Plant extracts from Camelia japonica had higher inhibitory activity against fungi than against bacteria. In cytotoxic effect against human acute myelogenous leukaemia cell extracts including fresh leaf(200$\mu\textrm{g}$/m1), bark(230$\mu\textrm{g}$/ml) and flower tea (320$\mu\textrm{g}$/m1)inhibited growth of AML cells.(중략)

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Production of HCN, Weed Control Substance, by Pseudomonas koreensis and its Plant Growth-Promoting and Termiticidal Activities (Pseudomonas koreensis에 의한 잡초제어활성물질인 HCN 생성과 이 균주의 식물성장 촉진 및 흰개미 살충 활성)

  • Yoo, Ji-Yeon;Jang, Eun-Jin;Park, Soo-Yeun;Son, Hong-Joo
    • Journal of Environmental Science International
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    • v.27 no.9
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    • pp.771-780
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    • 2018
  • To develope a microbial weed control agent, HCN-producing bacteria were isolated, and their characteristics were investigated. A selected strain of WA15 was identified as Pseudomonas koreensis by morphological, cultural, biochemical and 16S rRNA gene analyses. The conditions for HCN production was investigated by a One-Variable-at-a-Time (OVT) method. The optimal HCN production conditions were tryptone 1%, glycine 0.06%, NaCl 1%, and an initial pH and temperature of 5.0 and $30^{\circ}C$, respectively. The major component for HCN production was glycine. Under optimal conditions, HCN production was about 3 times higher than that of the basal medium. The WA15 strain had physiological activities, such as indoleacetic acid that was associated with the elongation of plant roots and siderophore and ammonification inhibiting fungal growth, and produced hydrolytic enzymes, such as cellulase, pectinase and lipase. The strain was able to inhibit the growth of phytopathogenic fungi, such as Rhizoctonia solani, Botrytis cinerea and Fusarium oxysporum, by the synergistic action of volatile HCN and diffusible antimicrobial compounds. A microscopic observation of R. solani that was teated with the WA15 strain showed morphological abnormalities of fungal mycelia, which could explain the role of the antimicrobial metabolites that were produced by the WA15 strain. The volatile HCN produced by the WA15 strain was also found to have insecticidal activity against termites. Our results indicate that Pseudomonas koreensis WA15 can be applied as a microbial agent for weed control and also as a termite repellent. Furthermore, it could be applied as a microbial termiticidal agent to replace synthetic insecticides.

Synthesis of Tetrazolo[1,5-a]quinoxalines with Antimicrobial Activity (항균성을 가진 Tetrazolo[1,5-a]quinoxaline류의 합성)

  • Kim, Ho Sik;Kim, Dong Eun;Yoshihisa Kurasawa
    • Journal of the Korean Chemical Society
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    • v.45 no.4
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    • pp.325-333
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    • 2001
  • The 4-substituted tetrazolo[1,5-a]quinoxalines were synthesized from 4-chlorotetrazolo-[1,5-a]quinoxaline(8) or 4-hydrazinotetrazolo[1,5-a]quinoxaline(9). Refluxing of the tetrazolo[1,5-a]quinoxaline(12) in N,N-dimethylformamide gave the 1,2,4-triazolo[3,4-c]tetrazolo[1,5-a]quinoxaline(13), which was also obtained by the reaction of compound 9 with ethyl chloroformate in N,N-dimethylformamide. The reaction of compound 9 with isothiocyanates in ethanol provided the tetrazolo[1,5-a]quinoxalines(14), whose reaction with dimethyl acetylenedicarboxylate afforded the tetrazolo[1,5-a]quinoxalines(15). The tetrazolo [1,5-a]quinoxalines(18) were obtained by the reaction of compound 9 with alkyl (ethoxymethylene)cyanoacetates. Some of the compounds showed antibacterial, antifungal or algicidal activities against some strains.

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Isolation of Antimicrobial Active Substance from Aristolochia tagala Champ. against Sclerotial Rot (Sclerotinia sclerotiorum) (이엽마두령(Aristolochia tagala Champ.)추출물로부터 균핵병 병원균(Sclerotinia sclerotiorum)에 대한 항균 활성물질 탐색)

  • Kim, Hyun-Sang;Shon, Jinhan;Choi, Yong-Hwa
    • Korean Journal of Organic Agriculture
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    • v.23 no.4
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    • pp.951-962
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    • 2015
  • To develop environment-friendly agricultural products with anti-microbial activity against Sclerotinia sclerotiorum as a pathogen of sclerotium disease, Aristolochia tagala Champ. was extracted by methanol and its extract was fractionated into several solvent fractions. The chloroform fraction, which showed the highest antimicrobial activity, was separated by column chromatography and obtained forty three subfractions. The forty three fractions were searched the anti-fungal activities by bioassay. The most active No. 26 subfraction was analyzed by GC-MS. Each mass spectra, corresponding to each peak of chromatogram, was compared to MS database of Wiley library. As a result, 2,4-di-tetra-butyl-phenol, 2-mono-palmitin, 1-mono-stearin were profiled as maine compounds in No. 26 subfraction. Bioassay using commercial 1-mono-stearin to test for the anti-microbial activity conformed the antimicrobial active compound. In conclusion, 1-mono-stearin identified from Aristolochia tagala Champ. was antimicrobial chemical against Sclerotinia sclerotiorum.