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Journal articles on the topic 'Antifungal metabolites'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Lemriss, S., F. Laurent, A. Couble, E. Casoli, J. M. Lancelin, D. Saintpierre-Bonaccio, S. Rifai, A. Fassouane, and P. Boiron. "Screening of nonpolyenic antifungal metabolites produced by clinical isolates of actinomycetes." Canadian Journal of Microbiology 49, no. 11 (November 1, 2003): 669–74. http://dx.doi.org/10.1139/w03-088.

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The purpose of this work was to screen clinical isolates of actinomycetes producing nonpolyenic antifungals. This choice was made to limit the problem of rediscovery of well-known antifungal families, especially polyenic antifungals. One hundred and ten strains were tested, using two diffusion methods and two test media, against three yeast species and three filamentous fungi. Among 54 strains (49%) showing antifungal activity, five strains belonging to the genus Streptomyces were active against all test organisms and appeared promising. These results indicate that clinical and environmental isolates of actinomycetes could be an interesting source of antifungal bioactive substances. The production of nonpolyenic antifungal substances by these five active isolates was investigated using several criteria: antibacterial activity, ergosterol inhibition, and UV-visible spectra of active extracts. One active strain responded to all three selection criteria and produced potentially nonpolyenic antifungal metabolites. This strain was retained for further investigation, in particular, purification, structure elucidation, and mechanism of action of the active product.Key words: actinomycetes, Streptomyces, clinical isolates, antifungal, non-polyene.

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2

Kokil, Sachin, and Manish Bhatia. "Antifungal Azole Metabolites: Significance in Pharmaceutical and Biomedical Analysis." Journal of Medical Biochemistry 28, no. 1 (January 1, 2009): 1–10. http://dx.doi.org/10.2478/v10011-008-0040-1.

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Antifungal Azole Metabolites: Significance in Pharmaceutical and Biomedical Analysis Individualised therapy and factors determining such variability among patients are confusing to both physicians and their patients because of the observed therapeutic, metabolic and toxic response. The same is true about antifungal azoles. They are under the influence and become targets of metabolic drug-drug interactions where more than one active form of the drug may be involved. The clinical relevance of these interactions may vary upon the azole involved and upon the intention of drug administration. The pharmacodynamics and pharmacokinetics of azole drugs as indicated by the reviewed data make the need for characterization of all their metabolites even more evident. The health care systems also emphasize the identification and quantitation of the metabolites for a comprehensive understanding of the biological safety of individual metabolites, thus, revealing the need and scope of bioanalytical research in metabolite and toxicity profiling of drugs. Availability of protocols for qualitative and quantitative characterization of all metabolites will have many applications for therapeutic drug monitoring, bioequivalence, toxicological and all related studies. Identification of metabolites may be done by a variety of chromatographic and spectroscopic techniques, either alone or in combination with other techniques. Conventional liquid chromatography has been exploited widely in the field of metabolite profiling. The arrival of hyphenated techniques has revolutionized metabolite profiling, by not only separating but also generating data for the structural identification of metabolites as well. Among all techniques, the most exploited are Liquid Chromatography-Mass Spectroscopy, Nuclear Magnetic Resonance spectroscopy, Liquid Chromatography-Nuclear Magnetic Resonance spectroscopy, Liquid Chromatography-Nuclear Magnetic Resonance spectroscopy-Mass Spectroscopy and Extraction-Nuclear Magnetic Resonance spectroscopy. This compilation provides a tool for the metabolic, bioanalytical and biomedical understanding of antifungal azole metabolites.

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3

Whyte, Authrine C., Katherine B. Gloer, James B. Gloer, Brenda Koster, and David Malloch. "New antifungal metabolites from the coprophilous fungus Cercophorasordarioides." Canadian Journal of Chemistry 75, no. 6 (June 1, 1997): 768–72. http://dx.doi.org/10.1139/v97-093.

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A chemical investigation of the coprophilous fungus Cercophorasordarioides has led to the isolation of arthrinone (1), a known fungal metabolite, and three new related compounds: 1-dehydroxyarthrinone (2), 3a,9a-deoxy-3a-hydroxy-1-dehydroxyarthrinone (3), and cerdarin (4). These metabolites were obtained from antifungal ethyl acetate extracts of liquid cultures of C. sordarioides through bioassay-guided fractionation, and their structures were assigned on the basis of 1D-NMR, HMQC, and HMBC results. Compounds 2 and 4 exhibited anti-Candida activity. Key words: antifungal, fungal metabolite, natural product, Cercophorasordarioides.

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4

Ghisalberti, Emilio L., and Catherine Y. Rowland. "Antifungal Metabolites from Trichoderma harzianum." Journal of Natural Products 56, no. 10 (October 1993): 1799–804. http://dx.doi.org/10.1021/np50100a020.

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5

Pacciaroni, Adriana del V., María de los Angeles Gette, Marcos Derita, Luis Ariza-Espinar, Roberto R. Gil, Susana A. Zacchino, and Gloria L. Silva. "Antifungal activity ofHeterothalamus alienus metabolites." Phytotherapy Research 22, no. 4 (2008): 524–28. http://dx.doi.org/10.1002/ptr.2380.

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6

Ragasa, Consolacion Y., Angel Lyn Kristin C. Co, and John A. Rideout. "Antifungal metabolites from Blumea balsamifera." Natural Product Research 19, no. 3 (April 1, 2005): 231–37. http://dx.doi.org/10.1080/14786410410001709773.

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7

Buatong, Jirayu, Vatcharin Rukachaisirikul, Suthinee Sangkanu, Frank Surup, and Souwalak Phongpaichit. "Antifungal Metabolites from Marine-Derived Streptomyces sp. AMA49 against Pyricularia oryzae." Journal of Pure and Applied Microbiology 13, no. 2 (June 30, 2019): 653–65. http://dx.doi.org/10.22207/jpam.13.2.02.

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8

Broberg, Anders, Karin Jacobsson, Katrin Ström, and Johan Schnürer. "Metabolite Profiles of Lactic Acid Bacteria in Grass Silage." Applied and Environmental Microbiology 73, no. 17 (July 6, 2007): 5547–52. http://dx.doi.org/10.1128/aem.02939-06.

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ABSTRACT The metabolite production of lactic acid bacteria (LAB) on silage was investigated. The aim was to compare the production of antifungal metabolites in silage with the production in liquid cultures previously studied in our laboratory. The following metabolites were found to be present at elevated concentrations in silos inoculated with LAB strains: 3-hydroxydecanoic acid, 2-hydroxy-4-methylpentanoic acid, benzoic acid, catechol, hydrocinnamic acid, salicylic acid, 3-phenyllactic acid, 4-hydroxybenzoic acid, (trans, trans)-3,4-dihydroxycyclohexane-1-carboxylic acid, p-hydrocoumaric acid, vanillic acid, azelaic acid, hydroferulic acid, p-coumaric acid, hydrocaffeic acid, ferulic acid, and caffeic acid. Among these metabolites, the antifungal compounds 3-phenyllactic acid and 3-hydroxydecanoic acid were previously isolated in our laboratory from liquid cultures of the same LAB strains by bioassay-guided fractionation. It was concluded that other metabolites, e.g., p-hydrocoumaric acid, hydroferulic acid, and p-coumaric acid, were released from the grass by the added LAB strains. The antifungal activities of the identified metabolites in 100 mM lactic acid were investigated. The MICs against Pichia anomala, Penicillium roqueforti, and Aspergillus fumigatus were determined, and 3-hydroxydecanoic acid showed the lowest MIC (0.1 mg ml−1 for two of the three test organisms).

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9

Koval, Daniel, Milada Plocková, Jan Kyselka, Pavel Skřivan, Marcela Sluková, and Šárka Horáčková. "Buckwheat Secondary Metabolites: Potential Antifungal Agents." Journal of Agricultural and Food Chemistry 68, no. 42 (September 28, 2020): 11631–43. http://dx.doi.org/10.1021/acs.jafc.0c04538.

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10

Coleman, Jeffrey J., Suman Ghosh, Ikechukwu Okoli, and Eleftherios Mylonakis. "Antifungal Activity of Microbial Secondary Metabolites." PLoS ONE 6, no. 9 (September 22, 2011): e25321. http://dx.doi.org/10.1371/journal.pone.0025321.

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11

TAHARA, Satoshi, Shiro NAKAHARA, John L. INGHAM, and Junya MIZUTANI. "Fungal metabolites of antifungal isoflavone wighteone." Journal of the agricultural chemical society of Japan 59, no. 10 (1985): 1039–44. http://dx.doi.org/10.1271/nogeikagaku1924.59.1039.

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12

Widiantini, Fitri, Mia Rahmah Qadryani, Fuji Hartati, and Endah Yulia. "Antifungal Potency of Secondary Metabolites Produced by Endophytic Bacteria against Pathogenic Fungi Pyricularia oryzae Cav." Jurnal Perlindungan Tanaman Indonesia 23, no. 2 (December 3, 2019): 185. http://dx.doi.org/10.22146/jpti.48392.

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Blast disease caused by Pyricularia oryzae Cav. is one of the most important diseases on rice. One of the alternative controlling methods in P. oryzae is biological control through the utilization of secondary metabolites produced by endophytic bacteria. The study aimed to determine the antifungal potency of secondary metabolites produced by rice endophytic bacteria against P. oryzae. The experiment was conducted using 9 endophytic bacteria isolated rice (Os1, Os2, Os3, Os4, Os5, Os6, Os7, Os8, and Os10). Each isolates were grown in ISP2 liquid media and the secondary metabolites compounds were extracted using two different solvents; methanol and ethyl acetate : methanol (4:1) (v/v). The effect of secondary metabolites was tested using agar well diffusion method. The results demonstrated that the secondary metabolites extracted by both solvents have antifungal effect on the growth of P. oryzae. The highest growth inhibition was shown by secondary metabolites extracted by ethyl acetate : methanol (4:1) from Os1 (42%) and Os3 (39%). Antifungal activity of the secondary metabolites was indicated by the formation of clear zone. HPLC (High Performance Liquid Chromatography) analysis showed the differences of peaks and retention time between secondary metabolites produced by Os1 and Os3 which has antifungal activity and secondary metabolites produced by Os10 that did not show the antifungal activity.

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13

Dubey, Olga, Sylvain Dubey, Sylvain Schnee, Gaëtan Glauser, Christiane Nawrath, Katia Gindro, and Edward E. Farmer. "Plant surface metabolites as potent antifungal agents." Plant Physiology and Biochemistry 150 (May 2020): 39–48. http://dx.doi.org/10.1016/j.plaphy.2020.02.026.

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14

You, Fei, Ting Han, Jing-zhong Wu, Bao-kang Huang, and Lu-ping Qin. "Antifungal secondary metabolites from endophytic Verticillium sp." Biochemical Systematics and Ecology 37, no. 3 (July 2009): 162–65. http://dx.doi.org/10.1016/j.bse.2009.03.008.

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15

Sidorova, T. M., A. M. Asaturova, and V. V. Allakhverdyan. "Chromatographic profiles of antifungal exo- and endometabolites of Bacillus velezensis." TAURIDA HERALD OF THE AGRARIAN SCIENCES 2(26) (August 3, 2021): 191–99. http://dx.doi.org/10.33952/2542-0720-2021-2-26-191-199.

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The antifungal activity of the Bacillus bacteria is based on their ability to produce metabolites. Therefore, when selecting a strain that produces an effective biofungicide, it is necessary to assess the metabolism of bacteria. The aim of this work is to isolate exo- and endometabolites of the promising B. velezensis BZR 336g and B. velezensis BZR 517 strains and assess their antifungal activity. Studies were carried out in 2020–2021. The object of the study is a liquid culture of the B. velezensis BZR 336g and B. velezensis BZR 517 strains. Methods of liquid extraction, ascending thin layer chromatography (TLC), bioautography with a test-culture of Fusarium oxysporum var. orthoceras and Alternaria sp. fungi were used to analyze metabolites. The ability of the strains to accumulate a complex of active metabolites showing antifungal effect from fungistatic to fungicidal action was revealed. On the bioautogram of exometabolites, we found two most pronounced zones (Rf 0.18 and 0.29) of Fusarium oxysporum var. orthoceras BZR P1 growth inhibition (fungicide). Zones with Rf 0.58 for B. velezensis BZR 336g and Rf 0.70 for B. velezensis BZR 517 correspond to the test fungus growth retardation (fungistatic). Significant suppression of Alternaria sp. BZR P8 growth was also observed in two zones (Rf 0.18 and 0.29). The use of surfactin, iturin A, fengycin (Sigma-Aldrich®) in the TLC analysis made it possible to detect similar lipopeptides in the composition of metabolite complexes produced by the studied bacteria. It should be noted that the studied strains differed both in their ability to produce metabolites of different structure (can be found when analyzing chromatograms under ultraviolet light) and in their effect on phytopathogenic fungi in vitro. This may indicate possible differences in the mechanism of antagonistic activity of bacteria against phytopathogenic fungi. Thus, B. velezensis BZR 336g and B. velezensis BZR 517 produce a significant set of antifungal metabolites and can be used as strains to produce effective biofungicides.

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16

DALIE, D. K. D., A. M. DESCHAMPS, V. ATANASOVA-PENICHON, and F. RICHARD-FORGET. "Potential of Pediococcus pentosaceus (L006) Isolated from Maize Leaf To Suppress Fumonisin-Producing Fungal Growth." Journal of Food Protection 73, no. 6 (June 1, 2010): 1129–37. http://dx.doi.org/10.4315/0362-028x-73.6.1129.

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The present study was aimed at characterizing the ability of lactic acid bacteria isolated from maize to repress the growth of fumonisin-producing fungi. A total of 67 isolates were screened for their antifungal activity against Fusarium proliferatum and Fusarium verticillioides by using the overlay method. The most efficient antifungal isolate was identified as Pediococcus pentosaceus (L006), on the basis of physiological and biochemical characterization and 16S rRNA gene sequencing. Production of the antifungal metabolite by this isolate commenced at the end of the growth exponential phase (8 h) and reached a maximum level after a long period of incubation (120 h). The antifungal metabolites produced were shown to be heat stable, resistant to proteolytic enzyme treatments, and pH dependent. The exact chemical nature of these substances remains to be clarified.

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17

Silva, Eliane O., Antonio Ruano-González, Raquel A. Dos Santos, Rosario Sánchez-Maestre, Niege A. J. C. Furtado, Isidro G. Collado, and Josefina Aleu. "Antifungal and Cytotoxic Assessment of Lapachol Derivatives Produced by Fungal Biotransformation." Natural Product Communications 11, no. 1 (January 2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100128.

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In the screening for biological active compounds, the biotransformation processes catalyzed by filamentous fungi are useful because they can provide information about the possible appearance of toxic metabolites after oral administration and also generate new leads. In this paper, biotransformation of lapachol (1) by three fungal strains, Mucor circinelloides NRRL3631, Botrytis cinerea UCA992 and Botrytis cinerea 2100, has been investigated for the first time. Lapachol (1) was biotransformed into avicequinone-A (2) by M. circinelloides, 3′-hydroxylapachol (3) by B. cinerea, and into dehydro-α-lapachone (4) by both fungi. All these compounds were evaluated for their cytotoxic activities. The metabolite 2 displayed non-selective cytotoxicity against tumor and normal cell lines, 3 did not show cytotoxicity against the same cells, while 4 showed higher cytotoxicity against cancer cell lines than lapachol (1). The transformation of 1 into harmless and reactive metabolites evidences the importance of the evaluation of drug metabolism in the drug discovery process. Antifungal potential of lapachol (1) and its metabolites 2 and 4 against B. cinerea has also been evaluated. Dehydro-α-lapachone (4) has been shown to be less toxic to fungal growth than lapachol (1), which indicates a detoxification mechanism of the phytopathogen.

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18

Karioti, Anastasia, Helen Skaltsa, Diamanto Lazari, Marina Sokovic, Begoña Garcia, and Catherine Harvala. "Secondary Metabolites from Centaurea deusta with Antimicrobial Activity." Zeitschrift für Naturforschung C 57, no. 1-2 (February 1, 2002): 75–80. http://dx.doi.org/10.1515/znc-2002-1-213.

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The aerial parts of Centaurea deusta Ten. afforded in addition to several known compounds, mainly sesquiterpene lactones, one new eudesmanolide and one new elemane derivative. Structures of the new compounds were elucidated by spectroscopic methods. The in vitro antifungal and antibacterial activities of the isolated compounds was tested, using the microdilution method. All compounds tested showed high antifungal activity.

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19

Farooq, Afgan, Iqbal Choudhary, Atta-ur Rahman, Satoshi Tahara, K. Hüsnü Can Başer, and Fatih Demirci. "Detoxification of Terpinolene by Plant Pathogenic Fungus Botrytis cinerea." Zeitschrift für Naturforschung C 57, no. 9-10 (October 1, 2002): 863–66. http://dx.doi.org/10.1515/znc-2002-9-1018.

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Detoxification of an antifungal monoterpene terpinolene (1) by the plant pathogenic fungus Botrytis cinerea afforded hydroxlyated metabolites 2,3-dihydro-3β,6β-dihydroxy-terpinolene (2) (39%) and 2,3-dihydro-1α,3α-dihydroxy-terpinolene (3) (20%), respectively. Terpinolene showed good levels of antifungal activity while both the metabolites were inactive against another plant pathogenic fungus Cladosporium herbarum.

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20

Henkels, Marcella D., Teresa A. Kidarsa, Brenda T. Shaffer, Neal C. Goebel, Peter Burlinson, Dmitri V. Mavrodi, Michael A. Bentley, et al. "Pseudomonas protegens Pf-5 Causes Discoloration and Pitting of Mushroom Caps Due to the Production of Antifungal Metabolites." Molecular Plant-Microbe Interactions® 27, no. 7 (July 2014): 733–46. http://dx.doi.org/10.1094/mpmi-10-13-0311-r.

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Bacteria in the diverse Pseudomonas fluorescens group include rhizosphere inhabitants known for their antifungal metabolite production and biological control of plant disease, such as Pseudomonas protegens Pf-5, and mushroom pathogens, such as Pseudomonas tolaasii. Here, we report that strain Pf-5 causes brown, sunken lesions on peeled caps of the button mushroom (Agaricus bisporus) that resemble brown blotch symptoms caused by P. tolaasii. Strain Pf-5 produces six known antifungal metabolites under the control of the GacS/GacA signal transduction system. A gacA mutant produces none of these metabolites and did not cause lesions on mushroom caps. Mutants deficient in the biosynthesis of the antifungal metabolites 2,4-diacetylphloroglucinol and pyoluteorin caused less-severe symptoms than wild-type Pf-5 on peeled mushroom caps, whereas mutants deficient in the production of lipopeptide orfamide A caused similar symptoms to wild-type Pf-5. Purified pyoluteorin and 2,4-diacetylphloroglucinol mimicked the symptoms caused by Pf-5. Both compounds were isolated from mushroom tissue inoculated with Pf-5, providing direct evidence for their in situ production by the bacterium. Although the lipopeptide tolaasin is responsible for brown blotch of mushroom caused by P. tolaasii, P. protegens Pf-5 caused brown blotch–like symptoms on peeled mushroom caps through a lipopeptide-independent mechanism involving the production of 2,4-diacetylphloroglucinol and pyoluteorin.

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21

Mitrović, I., J. Grahovac, J. Dodić, A. Jokić, Z. Rončević, and M. Grahovac. "Production of plant protection agents in medium containing waste glycerol by Streptomyces hygroscopicus: Bioprocess analysis." Acta Alimentaria 49, no. 3 (September 27, 2020): 270–77. http://dx.doi.org/10.1556/066.2020.49.3.5.

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The surplus of waste glycerol, by-product of the biodiesel production process, is available at the global market. Some species of the genera Streptomyces have the ability to assimilate glycerol and convert it into valuable metabolic products. In the present study, the ability of Streptomyces hygroscopicus to assimilate waste glycerol and convert it into metabolic compounds with antifungal activity against four phytopathogenic fungi obtained from apple fruit samples expressing rot symptoms, was investigated. Production of antifungal metabolites by S. hygroscopicus was carried out in 3 l stirred tank bioreactor through 7 days. Fermentation was carried out at 27 °C with aeration rate of 1.5 vvm and agitation rate of 100 r.p.m. The aim of this work was to analyse bioprocess parameters and to determine at which stage of bioprocess the production of antifungal metabolites occurs. Activity of the cultivation liquid on two isolates of Alternaria alternata and two isolates of Fusarium avenaceum were determined every 12 h using in vitro well diffusion method. It was found that the maximum production of antifungal metabolites occurred at 108 hour of cultivation. Formed inhibition zones have shown that the produced antifungal metabolites have high efficacy on tested phytopathogenic fungi (inhibition zone diameter higher than 35 mm for all test organisms).

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Ayer, William A., and Luis Diego Jimenez. "Phomalone, an antifungal metabolite of Phoma etheridgei." Canadian Journal of Chemistry 72, no. 11 (November 1, 1994): 2326–32. http://dx.doi.org/10.1139/v94-296.

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The metabolites produced by liquid cultures of Phoma etheridgei, a new fungus isolated from black galls of aspen, have been examined. This fungus is antagonistic to the aspen decay fungus Phellinus tremulae. The compound responsible for this antagonism has been isolated and its structure elucidated. Phomalone (1) is a previously undescribed natural product that possesses the same carbon skeleton as the Phoma pigmentivora metabolite LL-D253α. The structure was determined by physical methods, mainly 1H and 13C NMR. INAPT experiments played an important role. Some chemical transformations of phomalone (1) are described and it is shown by 13C-labelling experiments to be derived from six acetate units. Phomalone is active against Phellinus tremulae. Compounds 4, 6, 7, and 8 are also new natural products produced by P. etheridgei.

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23

Scano, Paola, M. Barbara Pisano, Antonio Murgia, Sofia Cosentino, and Pierluigi Caboni. "GC-MS Metabolomics and Antifungal Characteristics of Autochthonous Lactobacillus Strains." Dairy 2, no. 3 (June 23, 2021): 326–35. http://dx.doi.org/10.3390/dairy2030026.

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Lactobacillus strains with the potential of protecting fresh dairy products from spoilage were studied. Metabolism and antifungal activity of different L. plantarum, L. brevis, and L. sakei strains, isolated from Sardinian dairy and meat products, were assessed. The metabolite fingerprint of each strain was obtained by GC-MS and data submitted to multivariate statistical analysis. The discriminant analysis correctly classified samples to the Lactobacillus species and indicated that, with respect to the other species, L. plantarum had higher levels of organic acids, while L. brevis and L. sakei showed higher levels of sugars than L. plantarum. Partial Least Square (PLS) regression correlated the GC-MS metabolites to the antifungal activity (p < 0.05) of Lactobacillus strains and indicated that organic acids and oleamide are positively related with this ability. Some of the metabolites identified in this study have been reported to possess health promoting proprieties. These overall results suggest that the GC-MS-based metabolomic approach is a useful tool for the characterization of Lactobacillus strains as biopreservatives.

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Jovicic-Petrovic, Jelena, Sanja Jeremic, Ivan Vuckovic, Sandra Vojnovic, Aleksandra Bulajic, Vera Raicevic, and Jasmina Nikodinovic-Runic. "Aspergillus piperis A/5 from plum-distilling waste compost produces a complex of antifungal metabolites active against the phytopathogen Pythium aphanidermatum." Archives of Biological Sciences 68, no. 2 (2016): 279–89. http://dx.doi.org/10.2298/abs150602016j.

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Adding compost to soil can result in plant disease suppression through the mechanisms of antagonistic action of compost microflora against plant pathogens. The aim of the study was to select effective antagonists of Pythium aphanidermatum from compost, to assess the effect of its extracellular metabolites on the plant pathogen, and to characterize antifungal metabolites. The fungal isolate selected by a confrontation test was identified as Aspergillus piperis A/5 on the basis of morphological features and the internal transcribed spacer (ITS) region, ?-tubulin and calmodulin partial sequences. Liquid chromatography-mass spectroscopy (LC-MS) analysis showed that gluconic and citric acid were the most abundant in the organic culture extract. However, the main antifungal activity was contained in the aqueous phase remaining after the organic solvent extraction. The presence of considerable amounts of proteins in both the crude culture extract as well as the aqueous phase remaining after solvent extraction was confirmed by SDS-PAGE. Isolated Aspergillus piperis A/5 exhibits strong antifungal activity against the phytopathogen Pythium aphanidermatum. It secretes a complex mixture of metabolites consisting of small molecules, including gluconic acid, citric acid and itaconic acid derivatives, but the most potent antifungal activity was associated with proteins resistant to heat and organic solvents. Our findings about the activity and characterization of antagonistic strain metabolites contribute to the understanding of the mechanism of interaction of antifungal metabolites as well as fungal-fungal interaction. The obtained results provide a basis for further application development in agriculture and food processing.

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Mohamed, Cissé, N’guessan Elise Amoin, and Assoi Sylvie. "Identification of Antifungal Metabolites of Lactic Acid Bacteria." International Journal of Current Microbiology and Applied Sciences 8, no. 1 (January 10, 2019): 109–20. http://dx.doi.org/10.20546/ijcmas.2019.801.014.

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M., Fathalla, Samy Abd El-Azeem, Metwaly Baraka, and Elshahat Ramadan. "Characterization of Antifungal Metabolites from Antagonistic Fluorescent Pseudomonads." Journal of Applied Plant Protection 4, no. 1 (December 31, 2015): 13–21. http://dx.doi.org/10.21608/japp.2015.7593.

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27

Sumarah, Mark W., Julie R. Kesting, Dan Sørensen, and J. David Miller. "Antifungal metabolites from fungal endophytes of Pinus strobus." Phytochemistry 72, no. 14-15 (October 2011): 1833–37. http://dx.doi.org/10.1016/j.phytochem.2011.05.003.

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Li, He, Jing Wei, Shi-Yin Pan, Jin-Ming Gao, and Jun-Mian Tian. "Antifungal, phytotoxic and toxic metabolites produced byPenicillium purpurogenum." Natural Product Research 28, no. 24 (August 7, 2014): 2358–61. http://dx.doi.org/10.1080/14786419.2014.940586.

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Ding, Gang, Shuchun Liu, Liangdong Guo, Yuguang Zhou, and Yongsheng Che. "Antifungal Metabolites from the Plant Endophytic FungusPestalotiopsis foedan." Journal of Natural Products 71, no. 4 (April 2008): 615–18. http://dx.doi.org/10.1021/np070590f.

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Nguyen, Xuan Hoa, Kyaw Wai Naing, Young Seong Lee, Yong Hwan Kim, Jae Hak Moon, and Kil Yong Kim. "Antagonism of antifungal metabolites fromStreptomyces griseusH7602 againstPhytophthora capsici." Journal of Basic Microbiology 55, no. 1 (February 19, 2014): 45–53. http://dx.doi.org/10.1002/jobm.201300820.

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Chetverikov, S. P., and O. N. Loginov. "New metabolites of Azotobacter vinelandii exhibiting antifungal activity." Microbiology 78, no. 4 (August 2009): 428–32. http://dx.doi.org/10.1134/s0026261709040055.

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Hajlaou, M. R., J. A. Traquair, W. R. Jarvis, and R. R. Belanger. "Antifungal activity of extracellular metabolites produced bySporothrix flocculosa." Biocontrol Science and Technology 4, no. 2 (January 1994): 229–37. http://dx.doi.org/10.1080/09583159409355331.

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Aparna, K., and D. L. N. Rao. "Split-agar assay of antifungal soil microbial metabolites." Biocatalysis and Agricultural Biotechnology 6 (April 2016): 184–88. http://dx.doi.org/10.1016/j.bcab.2016.04.002.

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Álvarez-Caballero, Juan Manuel, and Ericsson Coy-Barrera. "Chemical and Antifungal Variability of Several Accessions of Azadirachta indica A. Juss. from Six Locations Across the Colombian Caribbean Coast: Identification of Antifungal Azadirone Limonoids." Plants 8, no. 12 (November 29, 2019): 555. http://dx.doi.org/10.3390/plants8120555.

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Plant materials (i.e., leaves, fruits, and seeds) from 40 trees of Azadirachta indica A. Juss. were collected from six different locations across the Colombian Caribbean coast. Eighty-four ethanolic extracts were prepared and the total limonoid contents (TLiC) and the antifungal activity against Fusarium oxysporum conidia were measured. Their chemical profiles were also recorded via liquid chromatography-electrospray ionization interface-mass spectrometry (LC-ESI-MS) analysis and the top-ranked features were then annotated after supervised multivariate statistics. Inter-location chemical variability within sample set was assessed by sparse partial least squares discriminant analysis (sPLS-DA) and the chemical profiles and biological activity datasets were integrated through single-Y orthogonal partial least squares (OPLS) to identify antifungal bioactives in test extracts. The TLiC and antifungal activity (IC50 values) of the A. indica-derived extracts were found to be ranging from 4.5 to 48.5 mg limonin equivalent per g dry extract and 0.08–44.8 μg/mL, respectively. The presence/abundance of particular limonoids between collected samples influenced the variability among locations. In addition, the integration of chemical and antifungal activity datasets showed five features as markers probably contributing to the bioactivity, annotated as compounds with an azadirone-like moiety. To validate the information provided by the single-Y OPLS model, a high performance liquid chromatography (HPLC)-based microfractionation was then carried out on an active extract. The combined plot of chromatographic profile and microfraction bioactivity also evidenced five signals possessing the highest antifungal activity. The most active limonoid was identified as nimonol 1. Hence, this untargeted metabolite profiling was considered as a convenient tool for identifying metabolites as inter-location markers as well as antifungals against Fusarium oxysporum.

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Mitrovic, Ivana, Jovana Grahovac, Jelena Dodic, Mila Grahovac, Sinisa Dodic, Damjan Vucurovic, and Vanja Vlajkov. "Effect of agitation rate on the production of antifungal metabolites by Streptomyces hygroscopicus in a lab-scale bioreactor." Acta Periodica Technologica, no. 48 (2017): 231–44. http://dx.doi.org/10.2298/apt1748231m.

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The application of antifungal compounds produced by microorganisms in the control of plant diseases caused by phytopathogenic fungi is a promising alternative to synthetic pesticides. Among phytopathogenic fungi, Alternaria alternata and Fusarium avenaceum are significant pathogens responsible for the storage rot of apple fruits. During storage, transport and marketing A. alternata and F. avenaceum can cause significant losses of apple fruits and their control is of great importance for the producers and consumers. In the present study, the effects of agitation rate on the production of antifungal methabolite( s) by Streptomyces hygroscopicus in a 3-L lab-scale bioreactor (Biostat? Aplus, Sartorius AG, Germany) against two isolates of A. alternata and two isolates of F. avenaceum were investigated. The cultivation of S. hygroscopicus was carried out at 27?C with agitation rates of 100 rpm and 200 rpm during 7 days. The aim was to analyze the bioprocess parameters of biofungicide production in a medium containing glycerol as a carbon source, and examine the effect of agitation rate on the production of antifungal metabolite(s). The in vitro antifungal activity of the produced metabolites against fungi from the genera Alternaria and Fusarium grown on potato dextrose agar medium was determined every 24 h using wells technique. In the experiments conducted in the bioreactor at different stirring speeds, it was found that the maximum production of antifungal metabolites occurred after 96 hours of cultivation. A higher consumption of nutrients and a larger inhibition zone diameter was registered in the experiment with an agitation rate of 200 rpm.

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Sonkar, Preeti. "Identification and Characterization of Antagonism Band of Secondary Metabolite from T. asperellum MK045610 against F. oxysporum f. sp. ciceri and F. oxysporum f. sp. lycopersici based on HPTLC and GC-MS." INTERNATIONAL JOURNAL OF PLANT AND ENVIRONMENT 5, no. 03 (July 31, 2019): 219–22. http://dx.doi.org/10.18811/ijpen.v5i03.12.

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The present investigation was carried out on identification and characterization of an antagonism band of extract secondary metabolites from Trichoderma asperellum MK045610 against Fusarium oxysporum f. sp. ciceri and Fusarium oxysporum f. sp. lycopersici. In this experiment, analysis was performed by High Performance Thin Layer Chromatography (HPTLC), paper disc assay, gas chromatography-Mass spectrometry (GC-MS). Firstly, extract crude secondary metabolites were used for partial purification based on HPTLC. Secondly, the paper disc assay method was used for the determination of antifungal property on PDA plate from the partial purified compound. Thirdly, GC-MS was used for identification of partial purified compound based on peaks. Identified compounds are named as Phenol, 3, 5-bis (1,1-dimethylethyl), Pentadecanoic Acid, 14-methyl, methyl ester, Benzenepropanoic acid, 3,5,-bis (1,1-dimethyl ethyl)-4-hydroxy-methyl ester and represented to antifungal property. Conclusively, Secondary metabolite of Trichoderma asperellum MK045610 has a significant role in radial growth inhibition of Fusarium oxysporum f. sp. ciceri and Fusarium oxysporum f. sp. lycopersici.

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Plocková, M., J. Stiles, J. Chumchalová, and R. Halfarová. "Control of mould growth by Lactobacillus rhamnosus VT1 and Lactobacillus reuteri CCM 3625 on milk agar plates." Czech Journal of Food Sciences 19, No. 2 (February 7, 2013): 46–50. http://dx.doi.org/10.17221/6574-cjfs.

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The possibility to control mould growth by Lactobacillus rhamnosus VT1 and Lactobacillus reuteri CCM 3625 in a milk environment was assessed using the milk agar plate method. Higher antifungal activity was exhibited by actively growing cells of both lactobacilli strains compared with the MRS broth supernatants of both bacterial strains containing metabolites with antifungal activity. The control of mould growth by Lactobacillus reuteri CCM 3625 was proved to be associated with the production of the mixture of lactic (0.9% w/w), acetic (0.2% w/w), and succinic (0.2% w/w) acids. The mechanism of mould growth control by Lactobacillus rhamnosus VT1 probably consists in the production of lactic acid (1.2% w/w) together with some other metabolite(s) of non-proteinaceous and non-saccharidic nature with antifungal activity

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Vieira, Natália Carolina, Patrícia Cardoso Cortelo, and Ian Castro-Gamboa. "Rapid qualitative profiling of metabolites present in Fusarium solani, a rhizospheric fungus derived from Senna spectabilis, using GC/MS and UPLC-QTOF/MSE techniques assisted by UNIFI information system." European Journal of Mass Spectrometry 26, no. 4 (May 3, 2020): 281–91. http://dx.doi.org/10.1177/1469066720922424.

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Fungi are an important source of natural products found in a variety of plant species. A wide range of methods for the detection of metabolites present in fungi have been reported in the literature. The search for methodologies that allow the rapid detection of compounds present in crude extracts is crucial to enable the metabolite annotation doing a qualitative analysis of the complex matrix. Mass spectrometry is an important ally when it comes to in silico detection of previously reported metabolites. In this work, the ethyl acetate extract of Fusarium solani was analyzed by gas chromatography coupled to mass spectrometry (GC/MS) after derivatization process. The ethyl acetate extract was also investigated by liquid chromatography coupled with high-resolution tandem mass spectrometry assisted by the UNIFI software system. A library containing previously reported metabolites from the Fusarium genus was added to the UNIFI platform. Simultaneously, the extract was analyzed through anticholinesterase and antifungal assays. The analysis of the derivatized extract by GC/MS led to the putative identification of five metabolites, and the investigation using Ultra-High Performance Liquid Chromatography - Quadrupole Time-of-Flight Mass Spectrometry (UPLC-QTOF) analysis in data-independent acquisition mode (mass spectrometry) led to the annotation of 15 compounds present in the built-in Fusarium library added to the UNIFI system. The Fusarium solani extract showed potential anticholinesterase and in vitro antifungal activity supported by the detection of bioactive metabolites.

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Engler, Michaela, Timm Anke, and Olov Sterner. "Production of Antibiotics by Collybia nivalis, Omphalotus olearius, a Favolaschia and a Pterula Species on Natural Substrates." Zeitschrift für Naturforschung C 53, no. 5-6 (June 1, 1998): 318–24. http://dx.doi.org/10.1515/znc-1998-5-604.

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Abstract Collybia nivalis, Favolaschia sp. 87129, Pterula sp. 82168 and Omphalotus olearius were cultivated on natural substrates. The antibiotic metabolites oudemansin A, strobilurins A, D. illudin S and pterulone were isolated and identified. A new antifungal metabolite, pterulone B, was described from cultures of Pterula sp. 82168 on wood. Collybia nivalis was found to be the first species of this genus to produce strobilurins and oudemansin A. As compared to rich media the cultivation on natural substrates resulted in the production of fewer metabolites. The concentrations of the antibiotics, however, were sufficient to inhibit other saprophytic fungi.

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Xue, Huanhuan, Yifan Jiang, Hongwei Zhao, Tobias G. Köllner, Sumei Chen, Fadi Chen, and Feng Chen. "Characterization of Composition and Antifungal Properties of Leaf Secondary Metabolites from Thirteen Cultivars of Chrysanthemum morifolium Ramat." Molecules 24, no. 23 (November 20, 2019): 4202. http://dx.doi.org/10.3390/molecules24234202.

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Chrysanthemum morifolium Ramat is an ornamental plant of worldwide cultivation. Like many other species in the family Asteraceae, C. morifolium is a rich producer of secondary metabolites. There are two objectives in this study: (I) to determine and compare the diversity of apolar secondary metabolites among different cultivars of C. morifolium and (II) to compare their properties as antifungal agents. To attain these objectives, we selected 13 cultivars of C. morifolium that are commonly used for making chrysanthemum tea as experimental materials. Leaves at the same developmental stage were collected from respective mature plants and subjected to organic extraction. The extracts were analyzed using gas chromatography–mass spectrometry. A total of 37 apolar secondary metabolites including 26 terpenoids were detected from the 13 cultivars. These 13 cultivars can be largely divided into three chemotypes based on chemical principal components analysis. Next, the extracts from the 13 cultivars were examined in in vitro assays for their antifungal properties against three species of pathogenic fungi: Fusarium oxysporum, Magnaporthe oryzae, and Verticillium dahliae. Significant variability in antifungal activity of the leaf extracts among different cultivars was observed. The 13 cultivars can be divided into four groups based on their antifungal activities, which could be partly correlated to the contents of terpenoids. In short, this study reveals large variations in chemical composition, particularly of terpenoids, of leaf secondary metabolites among different cultivars of C. morifolium and their different abilities in functioning as antifungal agents.

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Dewi, Tirta Kumala, Dwi Agustiani, and Sarjiya Antonius. "Secondary Metabolites Production by Actinomycetes and their Antifungal Activity." KnE Life Sciences 3, no. 4 (March 27, 2017): 256. http://dx.doi.org/10.18502/kls.v3i4.713.

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<p class="Els-Abstract-text">Wilt desease of banana caused by <em>Fusarium oxysporum</em> f.sp. <em>cubense</em> (FOC) is one of the most destructive deseases of banana in the tropics. Actinomycetes are the most economically and biotechnologically valuable prokaryotes able to produce wide range of bioactive secondary metabolites. The aims of the present study are to isolate and screen the actinomycetes with high potential ability to produce secondary metabolites that have inhibitory activity against plant pathogenic fungi, <em>Fusarium oxysporum</em> f. sp. <em>cubense</em>. Two isolates from Lampung and Cianjur showed activity against fungi. The isolates designed as L.3.1 and CiIA5b. The metabolites from potent stain was produced by extraction of culture filtrate with ethyl acetate : methanol (4:1), it was tested for their antifungal activity by well diffusion method. Evidence for in vitro antibiosis of L.3.1 and CiIA5b isolates was demonstrated by the zone of fungal-growth inhibition. Production of secondary metabolites was analysis by thin layer chromatography (TLC) and bioautography assays. In this study, the metabolites from L.3.1 and CiIA5b have showed good antifungal activity.</p><div><p class="Els-keywords"><em> </em></p><p class="Els-keywords"><strong>Keywords:</strong> Actinomycetes; antifungal activity; bioautography; secondary metabolites; thin layer chromatography.</p></div>

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Escher, Silvia Katrine Silva, José Jeosafá Vieira de Sousa Júnior, Adrielle Leal Dias, Elba Lúcia Cavalcanti de Amorim, and Janete Magalí de Araújo. "Influence of glucose and stirring in the fermentation process in order to produce anti- Candida metabolites produced by Streptomyces sp." Brazilian Journal of Pharmaceutical Sciences 52, no. 2 (June 2016): 265–72. http://dx.doi.org/10.1590/s1984-82502016000200004.

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ABSTRACT This study evaluated the influence of glucose and stirring in the fermentation process in order to produce anti-Candida metabolites produced by Streptomyces sp. MPO4 isolated from Amazon soil. The anti-Candida metabolites production was registered after 24 h of fermentation in stirred ISP2 medium, having antifungal inhibition halos between 12.3 mm and 25.3 mm, yielding higher production of anti-Candida agents after 96 h. Stirring was a determining factor for the production of anti-Candida secondary metabolites, since the absence of glucose reflected in the late production of the antifungal starting from Streptomyces sp.

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Castañeda-Novoa, Carlos Daniel, Diana Marcela Vinchira-Villarraga, Ibonne Aydee García Romero, and Nubia Moreno-Sarmiento. "Evaluation of the production of antifungal metabolites against Colletotrichum gloeosporioides in Streptomyces 5.1 by random mutagenesis." Acta Scientiarum. Biological Sciences 43 (March 24, 2021): e54709. http://dx.doi.org/10.4025/actascibiolsci.v43i1.54709.

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Streptomyces 5.1 is a bacterium isolated from rice soils in the south of the Tolima department (Colombia). This microorganism is characterized by its antagonistic activity against rubber tree phytopathogens like Colletotrichum gloeosporioides, the causal agent of leaf anthracnose. The antifungal activity of this Streptomyces isolate has been associated with secondary metabolites production. However, the identity of those metabolites is unknown because its purification and identification have not been possible through classic chemical studies. Therefore, aiming to contribute in the study of the secondary metabolites produced by 5.1 from a molecular approach, this research seeks to identify -preliminarily- the genomic fingerprint changes associated with the production of antifungal secondary metabolites produced by Streptomyces 5.1 through the evaluation of a mutant library of 5.1 obtained by random mutagenesis using controlled ultraviolet light exposure. The antifungal activity of obtained mutants was evaluated using Colletotrichum gloeosporioides (C1) fungus as a biosensor, isolated by the Biotechnology Institute of Universidad Nacional de Colombia. In this way, the library of mutants of 5.1, initially formed by 300 isolations, was classified into two phenotypic groups of interest: enhanced mutants (1 isolate) and null mutants (11 isolates) of secondary metabolites. The genomic changes in both groups were analyzed by obtaining the genomic profile of the isolates using Repetitive Extragenic Palindromic (Rep-PCR). The obtained profiles evidenced the presence of one additional band in the enhanced mutant, and the absence of a specific band in the non-producing mutants, both in comparison with the original strain. These bands are proposed for a future sequencing study which will define their role in the production process of metabolites with antifungal activity in Streptomyces 5.1.

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Kusumawati, Pipin, Yosi Bayu Murti, and Nastiti Wijayanti. "Screening of anti-Candida albicans metabolites produced by marine sponge-associated bacteria." Marine Research in Indonesia 45, no. 2 (December 31, 2020): 47–58. http://dx.doi.org/10.14203/mri.v45i2.575.

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This study selected bacteria with high anti-Candida albicans (CA) activity among ten bacteria isolated from marine sponges. Bacteria were cultivated using the basal medium to produce the extract. Minimum Inhibitory Concentration (MIC) microdilution broth was used as an anti-CA assay followed by TLC-direct bioautography to characterize their active compound with spray reagents. The bacteria determination was done by molecular approaches using Repetitive-Element Sequences-based-PCR (rep-PCR) and amplification of 16S rDNA partial gene sequences, continued with BLAST analysis. The four out of ten tested bacteria had high anti-CA compounds and were potentially to be produced on a larger scale using the basal medium, which was BYT5C4, BYT5C5, BYT1A, and BYT7, with MIC of 1 mg/mL against 7.5×106 CFU/mL CA. TLC-bioautography test results showed that all metabolites from each isolate had different Rf and types of metabolites. Rep-PCR test showed that four bacteria had a low similarity index, indicating that they were different species. Based on molecular identification results, the BYT5C4, BYT5C5, BYT1A, and BYT7 isolates are strictly related to Brevibacterium casei, Exiguobacterium profundum, Micrococcus lylae, and Bacillus firmus, respectively. The active metabolites identified in this study can be isolated to determine the active molecules and their inhibitory routes to fungal growth. It is worth noting that additional research might be conducted to compare the activity of each antifungal metabolite to the synergistic activity of numerous antifungal metabolites detected in plant extracts.

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Sarker, Ashish Kumar, Md Anwarul Haque, Urmi Saha, Md Ajijur Rahman, and Md Anwar Ul Islam. "Evaluation of Antibacterial, Antifunfgal and Cytotoxic Potentials of Crude Metabolite of ANAM-39, a Marine Bacterium Isolated from Sundarbans, Bangladesh." Bangladesh Pharmaceutical Journal 18, no. 2 (July 26, 2015): 103–9. http://dx.doi.org/10.3329/bpj.v18i2.24306.

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The present study was undertaken to screen the antimicrobial, antifungal and cytotoxic potentials of crude metabolite of a marine bacterium isolated from a soil sample collected from Sundarbans, Bangladesh. Primary and secondary screenings for antimicrobial activity were conducted by cross streak and agar well diffusion method, respectively. The antifungal potency of the crude extract was also tested by agar well-diffusion method. The brine shrimp lethality test was conducted to determine the cytotoxic nature of crude metabolites, which showed that the degree of lethality of metabolite was directly proportional to the concentration (LC50 30.19 ?g/ml). Further studies are needed to isolate and characterize the active principles present in the crude metabolite and determine their biological activity. The results of this investigation suggested that the soils of Sundarbans are rich sources of microorganisms with potent biological activities and systematic screening programs need to be conducted to explore the presence of pharmacologically active marine bacterial metabolites.Bangladesh Pharmaceutical Journal 18(2): 103-109, 2015

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Saryanah, Nur Alfi, Suryo Wiyono, and Dadang Dadang. "Aktivitas Metabolit Sekunder Cendawan Endofit terhadap Colletotrichum acutatum pada Cabai Merah." Jurnal Fitopatologi Indonesia 15, no. 1 (November 14, 2019): 36. http://dx.doi.org/10.14692/jfi.15.1.36.

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Activity of Fungal Endophyte Secondary Metabolites against Colletotrichum acutatum on Chili PepperColletotrichum acutatum is one of anthracnose causal agents on chili pepper that has been reported to be predominant species in a some regions of Java Island. Secondary metabolites of endophytic fungi have been reported to have a potency as antifungal agents against plant pathogen. However, its antifungal activity against C. acutatum has not been reported yet. This study was aimed to evaluate the antifungal activity of fungal endophyte secondary metabolite against C. acutatum at in vitro and in vivo assay. In vitro assay was conducted to evaluate antifungal activity of fungal endophyte CBR1D14 isolate culture filtrate (FCBR) and mycelia extract (MCBR) in inhibiting conidial germination of C. acutatum. The results of in vitro assay showed that ethyl acetate extract of FCBR (EA FCBR) had the highest activity in inhibiting C. acutatum conidial germination. Methanol fraction from the partition of EA FCBR (FM FCBR) and from the partition of MCBR ethyl acetate extract (FM MCBR) showed the ability in inhibiting C. acutatum conidial germination. In vivo assay to chili pepper fruit showed that the treatment of FM FCBR (IC95 609.9 µg mL-1) and FM MCBR (IC95 1178.27 µg mL-1) decreased anthracnose disease incidence and lesion diameter. The efficacy rate of FM FCBR and FM MCBR treatments against anthracnose was 36.72 and 48.68%, respectively. Bioautography test was done on silica gel thin layer chromatogram. Methanol fraction of FCBR and MCBR were separated into 3 bioautographic spots respectively (Rf 0.04, 0.07, 0.7 for FM FCBR and Rf 0.06, 0.52, 0.7 for FM MCBR).

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Ahn, Il-Pyung, Soon-Ok Kim, and Yong-Hwan Lee. "High Throughput Screening of Antifungal Metabolites Against Colletotrichum gloeosporioides." Plant Pathology Journal 24, no. 1 (March 31, 2008): 24–30. http://dx.doi.org/10.5423/ppj.2008.24.1.024.

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Liu, Qiu, Jicheng Yu, Jianfang Yan, Xiaohui Qi, Changjian Liu, and Hua Jin. "Antagonism and Action Mechanism of Antifungal Metabolites fromStreptomyces rimosusMY02." Journal of Phytopathology 157, no. 5 (May 2009): 306–10. http://dx.doi.org/10.1111/j.1439-0434.2008.01494.x.

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Ebrahim, Weaam, Ferhat C. Özkaya, and Sherif S. Ebada. "Antifungal metabolites from endophytic fungus Fusarium verticillioides strain WF18." South African Journal of Botany 133 (September 2020): 40–44. http://dx.doi.org/10.1016/j.sajb.2020.06.029.

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Yue, Qun, Li Chen, Xiaoling Zhang, Kuan Li, Jingzu Sun, Xingzhong Liu, Zhiqiang An, and Gerald F. Bills. "Evolution of Chemical Diversity in Echinocandin Lipopeptide Antifungal Metabolites." Eukaryotic Cell 14, no. 7 (May 29, 2015): 698–718. http://dx.doi.org/10.1128/ec.00076-15.

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ABSTRACTThe echinocandins are a class of antifungal drugs that includes caspofungin, micafungin, and anidulafungin. Gene clusters encoding most of the structural complexity of the echinocandins provided a framework for hypotheses about the evolutionary history and chemical logic of echinocandin biosynthesis. Gene orthologs among echinocandin-producing fungi were identified. Pathway genes, including the nonribosomal peptide synthetases (NRPSs), were analyzed phylogenetically to address the hypothesis that these pathways represent descent from a common ancestor. The clusters share cooperative gene contents and linkages among the different strains. Individual pathway genes analyzed in the context of similar genes formed unique echinocandin-exclusive phylogenetic lineages. The echinocandin NRPSs, along with the NRPS from theinpgene cluster inAspergillus nidulansand its orthologs, comprise a novel lineage among fungal NRPSs. NRPS adenylation domains from different species exhibited a one-to-one correspondence between modules and amino acid specificity that is consistent with models of tandem duplication and subfunctionalization. Pathway gene trees and Ascomycota phylogenies are congruent and consistent with the hypothesis that the echinocandin gene clusters have a common origin. The disjunct Eurotiomycete-Leotiomycete distribution appears to be consistent with a scenario of vertical descent accompanied by incomplete lineage sorting and loss of the clusters from most lineages of theAscomycota. We present evidence for a single evolutionary origin of the echinocandin family of gene clusters and a progression of structural diversification in two fungal classes that diverged approximately 290 to 390 million years ago. Lineage-specific gene cluster evolution driven by selection of new chemotypes contributed to diversification of the molecular functionalities.

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