Production, purification, and antifungal activity of the antibiotic nucleoside, tubercidin, produced by Streptomyces violaceoniger

1994 ◽  
Vol 72 (4) ◽  
pp. 480-485 ◽  
Author(s):  
Byung Kook Hwang ◽  
Sang Joon Ahn ◽  
Surk Sik Moon

Three antibiotic substances strongly inhibitory to Phytophthora capsici or Magnaporthe grisea were isolated from the broth culture of Streptomyces violaceoniger strain A50. A butanol-soluble mixture of antibiotics from the broth were partially purified by XAD-2 column chromatography. The XAD-2 eluates inhibited the mycelial growth of P. capsici and M. grisea and the development of Phytophthora blight on pepper (Capsicum annuum L.) plants. The antibiotics were separated by silica gel column chromatography and then purified on a Sephadex LH-20 column to yield three peaks of antifungal activity: SF1A, SF1B, and SF2A. The pure antibiotic SF2A was further purified by preparative HPLC and identified as the pyrrolo[2,3-d]-pyrimidine nucleoside tubercidin based on the UV, 1H, and 13C NMR spectral data and other chemical evidence. The antibiotic SF2A and authentic tubercidin showed a high antifungal activity against the plant pathogenic fungi P. capsici, Botryosphaeria dothidea, and Rhizoctonia solani. Key words: Streptomyces violaceoniger, tubercidin, antifungal activity.

2002 ◽  
Vol 48 (5) ◽  
pp. 407-417 ◽  
Author(s):  
Jung Yeop Lee ◽  
Byung Kook Hwang

Diversity of actinomycetes and their antifungal activities against some plant pathogenic fungi were examined in various vegetative soils from 14 different sites in the western part of Korea. Actinomycete counts ranged from 1.17 × 106to 4.20 × 106cfu·g-1dried soil. A total of 1510 actinomycetes were isolated from the soil samples. Streptomyces was predominant in soils with a pH range of 5.1-6.5, 9.1-13.0% moisture, and 9.1-11.0% organic matter. Most Micromonospora, Dactylosporangium, and Streptosporangium were distributed in soils with pH 4.0-5.0, 2.0-9.0% moisture, and 4.0-7.0% organic matter. Actinomadura and nocardioform actinomycetes were abundant in soils with pH 4.0-5.0 and 13.1-20.0% moisture and with 9.1-11.0 and 4.0-7.0% organic matter, respectively. Populations of Streptomyces were predominant in all the soils, but were highest in grassland and lowest in mountain-forest soils. Micromonospora was most abundant in pepper-field soil and nocardioform actinomycetes were highest in rice paddy field soil. Dactylosporangium was predominant in lake-mud sediments and pepper-field soil, Streptosporangium in lake-mud sediments, and Actinomadura in mountain-forest soil. Antifungal actinomycetes were abundant in orchard soil and lake mud. More than 50% of antifungal isolates from most soils were classified as genus Streptomyces. Actinomycete isolates that showed strong antifungal activity against Alternaria mali, Colletotrichum gloeosporioides, Fusarium oxysporum f.sp. cucumerinum, and Rhizoctonia solani were predominant in pepper-field soils, whereas those against Magnaporthe grisea and Phytophthora capsici were abundant in radish-field soils.Key words: actinomycetes, antifungal activity, plant pathogenic fungi, vegetative soils.


Plant Disease ◽  
2009 ◽  
Vol 93 (10) ◽  
pp. 1037-1043 ◽  
Author(s):  
Young-Ki Jo ◽  
Byung H. Kim ◽  
Geunhwa Jung

Silver in ionic or nanoparticle forms has a high antimicrobial activity and is therefore widely used for various sterilization purposes including materials of medical devices and water sanitization. There have been relatively few studies on the applicability of silver to control plant diseases. Various forms of silver ions and nanoparticles were tested in the current study to examine the antifungal activity on two plant-pathogenic fungi, Bipolaris sorokiniana and Magnaporthe grisea. In vitro petri dish assays indicated that silver ions and nanoparticles had a significant effect on the colony formation of these two pathogens. Effective concentrations of the silver compounds inhibiting colony formation by 50% (EC50) were higher for B. sorokiniana than for M. grisea. The inhibitory effect on colony formation significantly diminished after silver cations were neutralized with chloride ions. Growth chamber inoculation assays further confirmed that both ionic and nanoparticle silver significantly reduced these two fungal diseases on perennial ryegrass (Lolium perenne). Particularly, silver ions and nanoparticles effectively reduced disease severity with an application at 3 h before spore inoculation, but their efficacy significantly diminished when applied at 24 h after inoculation. The in vitro and in planta evaluations of silver indicated that both silver ions and nanoparticles influence colony formation of spores and disease progress of plant-pathogenic fungi. In planta efficacy of silver ions and nanoparticles is much greater with preventative application, which may promote the direct contact of silver with spores and germ tubes, and inhibit their viability.


2011 ◽  
Vol 343-344 ◽  
pp. 1070-1073 ◽  
Author(s):  
Yan Jun Shen ◽  
Hua Sun ◽  
Yu Wan Fu ◽  
Chu Yang Xu ◽  
Min Wang

The biotransformation of progesterone by Colletotrichum lini AS3. 4486 was studied. The formation of the product was monitored by HPLC. Product was purified from broth culture supernatants by silica gel column chromatography and identified as 7β,12β-dihydoxylprogesterone with MS, 1H NMR, 13C NMR and NOE.


1999 ◽  
Vol 77 (6) ◽  
pp. 850-858 ◽  
Author(s):  
Beom Seok Kim ◽  
Surk Sik Moon ◽  
Byung Kook Hwang

The antibiotic As1A, strongly inhibitory to Phytophthora capsici Leonian in vitro and in vivo, was isolated from the broth culture of Streptomyces libani Baldacci & Grein using various chromatographic procedures. The molecular formula of the antibiotic As1A was deduced to be C45H74O11 (M+H, m/z 791.5307) by high resolution fast atom bombardment - mass spectroscopy. The analysis of 1H-NMR (nuclear magnetic resonance) and 13C-NMR spectroscopy, DEPT experiment, and two-dimensional NMR spectral data revealed that the antibiotic is a macrolide antibiotic having a 26-membered alpha, beta-unsaturated macrolactone ring with a conjugated diene fused to a bicyclic spiroketal. Based on the comparison of NMR data and other chemical properties, the antibiotic As1A turned out to have the same structure as oligomycin A. The antibiotic As1A showed a high level of inhibitory activity against Botrytis cinerea Pers.: Pers., Cladosporium cucumerinum Ellis & Arthur, Colletotrichum lagenarium (C.P. Robin) Berkhout, Magnaporthe grisea (Herb.) Barr, and P. capsici, ranging from 3 to 5 µg·mL-1 of MICs. However, no antimicrobial activity was found against yeasts and bacteria. In further evaluation under greenhouse conditions, developments of the Phytophthora disease, anthracnose, and leaf blast were markedly inhibited on pepper (Capsicum annuum L. cv. Hanbyul), cucumber (Cucumis sativus L. cv. Baekrokdadaki), and rice (Oryza sativa L. cv. Nakdong) plants by treatments with the antibiotic As1A, respectively. Control efficacies of the antibiotic As1A against these plant diseases were in general similar to those of metalaxyl, chlorothalonil, and tricyclazole. The antibiotic As1A did not show any phytotoxicity on pepper, cucumber, and rice plants even at 500 µg·mL-1.Key words: Streptomyces libani, oligomycin A, antifungal activity, plant disease control.


Holzforschung ◽  
1999 ◽  
Vol 53 (5) ◽  
pp. 487-490 ◽  
Author(s):  
Shang-Tzen Chang ◽  
Sheng-Yang Wang ◽  
Chi-Lin Wu ◽  
Yu-Chang Su ◽  
Yueh-Hsiung Kuo

Summary This study was to isolate and identify the antifungal compounds in the ethyl acetate soluble fraction of the methanol extractives of Taiwania (Taiwania cryptomerioides Hayata) heartwood and to examine their antifungal activity. Five compounds were obtained by open column chromatography and HPLC and based upon the results from Mass, 1H-NMR, and 13C-NMR analyses. Their structures were identified, namely ferruginol, helioxanthin, savinin, taiwanin C, and hinokiol. According to the results of antifungal test, the order of antifungal index of these compounds for Coriolus versicolor (L. ex Fr.) Quel. was ferruginol > taiwanin C > savinin > hinokiol. For Laetiporus sulphureus (B. ex Fr.) Bond. it was taiwanin C > savinin > ferruginol > hinokiol.


2019 ◽  
Vol 19 (11) ◽  
pp. 1399-1404 ◽  
Author(s):  
Yangcheng Liu ◽  
Wei Liu ◽  
Changlan Chen ◽  
Zheng Xiang ◽  
Hongwei Liu

Background and Purpose:: Patrinia villosa Juss is an important Chinese herbal medicine widely used for thousands of years, but few reports on the ingredients of the herb have been presented. In this study, we aim to isolate the bioactive compound from the plant. Material and Methods:: The air-dried leaves of P. villosa (15kg) were extracted three times with 70% EtOH under reflux. The condensed extract was suspended in H2O and partitioned with light petroleum, dichloromethane and n-BuOH. The dichloromethane portion was then subjected to normal-phase silica gel column chromatography, ODS silica gel column chromatography and semi-preparative HPLC to yield compound 1. Cytotoxicities of 1 were assayed on HepG2, A549 and A2780 cell lines. The mechanism of apoptosis and cell cycle on A549 was confirmed subsequently. Results: A new impecylone (Impecylone A) was isolated from the leaves of Patrinia villosa Juss, and its structures were established using 1D, 2D-NMR spectra and HR-ESI-MS. Impecylone A could selectivity inhibit HepG2 and A549 cell lines. The compound could induce apoptosis of A549 and arrest the cell cycle at G2/M phase in a dose-dependent manner. Conclusion: Impecylone A is a novel compound from Patrinia villosa Juss and could be a potential antitumor agent especially in the cell lines of A549.


Author(s):  
Anna Biernasiuk ◽  
Anna Berecka-Rycerz ◽  
Anna Gumieniczek ◽  
Maria Malm ◽  
Krzysztof Z. Łączkowski ◽  
...  

Abstract Recently, the occurrence of candidiasis has increased dramatically, especially in immunocompromised patients. Additionally, their treatment is often ineffective due to the resistance of yeasts to antimycotics. Therefore, there is a need to search for new antifungals. A series of nine newly synthesized thiazole derivatives containing the cyclopropane system, showing promising activity against Candida spp., has been further investigated. We decided to verify their antifungal activity towards clinical Candida albicans isolated from the oral cavity of patients with hematological malignancies and investigate the mode of action on fungal cell, the effect of combination with the selected antimycotics, toxicity to erythrocytes, and lipophilicity. These studies were performed by the broth microdilution method, test with sorbitol and ergosterol, checkerboard technique, erythrocyte lysis assay, and reversed phase thin-layer chromatography, respectively. All derivatives showed very strong activity (similar and even higher than nystatin) against all C. albicans isolates with minimal inhibitory concentration (MIC) = 0.008–7.81 µg/mL Their mechanism of action may be related to action within the fungal cell wall structure and/or within the cell membrane. The interactions between the derivatives and the selected antimycotics (nystatin, chlorhexidine, and thymol) showed additive effect only in the case of combination some of them and thymol. The erythrocyte lysis assay confirmed the low cytotoxicity of these compounds as compared to nystatin. The high lipophilicity of the derivatives was related with their high antifungal activity. The present studies confirm that the studied thiazole derivatives containing the cyclopropane system appear to be a very promising group of compounds in treatment of infections caused by C. albicans. However, this requires further studies in vivo. Key points • The newly thiazoles showed high antifungal activity and some of them — additive effect in combination with thymol. • Their mode of action may be related with the influence on the structure of the fungal cell wall and/or the cell membrane. • The low cytotoxicity against erythrocytes and high lipophilicity of these derivatives are their additional good properties. Graphical abstract


Polymers ◽  
2021 ◽  
Vol 13 (6) ◽  
pp. 888
Author(s):  
Nguyen Thi Thanh Hai ◽  
Nguyen Duc Cuong ◽  
Nguyen Tran Quyen ◽  
Nguyen Quoc Hien ◽  
Tran Thi Dieu Hien ◽  
...  

Cu nanoparticles are a potential material for creating novel alternative antimicrobial products due to their unique antibacterial/antifungal properties, stability, dispersion, low cost and abundance as well as being economical and ecofriendly. In this work, carboxymethyl cellulose coated core/shell SiO2@Cu nanoparticles (NPs) were synthesized by a simple and effective chemical reduction process. The initial SiO2 NPs, which were prepared from rice husk ash, were coated by a copper ultrathin film using hydrazine and carboxymethyl cellulose (CMC) as reducing agent and stable agent, respectively. The core/shell SiO2@Cu nanoparticles with an average size of ~19 nm were surrounded by CMC. The results indicated that the SiO2@Cu@CMC suspension was a homogenous morphology with a spherical shape, regular dispersion and good stability. Furthermore, the multicomponent SiO2@Cu@CMC NPs showed good antifungal activity against Phytophthora capsici (P. capsici). The novel Cu NPs-based multicomponent suspension is a key compound in the development of new fungicides for the control of the Phytophthora disease.


Author(s):  
Cong You ◽  
Jun Yu ◽  
Guangjiong Qin ◽  
JinPeng Yang ◽  
Chunlei Yang ◽  
...  

Abstract Background Artemisia hedinii is a well-known traditional Chinese medicine. It can be used to extract dihydroartemisinin (DHA). Objective The purpose of this study was to explore the optimal conditions for the homogenate extraction of DHA from A. hedinii and the antifungal activity of DHA. Methods In this study, single factor experiments and response surface method were used to determine the optimal extraction conditions of crude extract and DHA, the method of spore germination was used to study the antifungal activity of DHA to Alternaria alternata. Result The optimal conditions were found as fellow: ratio of liquid to material 22 mL/g; Extraction time 60 s; soaking time 34 min. Under these conditions, extraction yield of DHA was (1.76 ± 0.04%). When the concentration of crude extract were 0.5 and 8 mg/mL, the spore germination inhibition rates of Alternaria alternata were (17.00 ± 2.05%) and (92.56 ± 2.01%), which were 3.34 and 1.15 times that of DHA standard, respectively. Conclusion Homogenate extraction technology is a fast and efficient method to extract DHA from A. hedinii. The crude extract has significant antifungal activity against A. alternata with low cost, which provides a possibility for the use of DHA in the prevention and treatment of plant pathogenic fungi. Highlights The optimum conditions of the extraction of DHA from A. hedinii by homogenate extraction were obtained. DHA has antifungal activity against A. alternata. Compared with pure DHA, the crude extract has stronger antifungal activity against A. alternata.


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