scholarly journals Biotransformation of Methoxyflavones by Selected Entomopathogenic Filamentous Fungi

2020 ◽  
Vol 21 (17) ◽  
pp. 6121 ◽  
Author(s):  
Mateusz Łużny ◽  
Tomasz Tronina ◽  
Ewa Kozłowska ◽  
Monika Dymarska ◽  
Jarosław Popłoński ◽  
...  
Keyword(s):  
Filamentous Fungi ◽  
Beauveria Bassiana ◽  
Isaria Fumosorosea ◽  
Isaria Farinosa ◽  
Methoxy Groups

The synthesis and biotransformation of five flavones containing methoxy substituents in the B ring: 2′-, 3′-, 4′-methoxyflavones, 2′,5′-dimethoxyflavone and 3′,4′,5′-trimethoxyflavone are described. Strains of entomopathogenic filamentous fungi were used as biocatalysts. Five strains of the species Beauveria bassiana (KCh J1.5, J2.1, J3.2, J1, BBT), two of the species Beauveria caledonica (KCh J3.3, J3.4), one of Isaria fumosorosea (KCh J2) and one of Isaria farinosa (KCh KW 1.1) were investigated. Both the number and the place of attachment of the methoxy groups in the flavonoid structure influenced the biotransformation rate and the amount of nascent products. Based on the structures of products and semi-products, it can be concluded that their formation is the result of a cascading process. As a result of enzymes produced in the cells of the tested strains, the test compounds undergo progressive demethylation and/or hydroxylation and 4-O-methylglucosylation. Thirteen novel flavonoid 4-O-methylglucosides and five hydroxy flavones were isolated and identified.

scholarly journals New Glycosylated Dihydrochalcones Obtained by Biotransformation of 2′-Hydroxy-2-methylchalcone in Cultures of Entomopathogenic Filamentous Fungi

2021 ◽  
Vol 22 (17) ◽  
pp. 9619
Author(s):  
Agnieszka Krawczyk-Łebek ◽  
Monika Dymarska ◽  
Tomasz Janeczko ◽  
Edyta Kostrzewa-Susłow
Keyword(s):  
Nmr Spectroscopy ◽  
Filamentous Fungi ◽  
Beauveria Bassiana ◽  
Bioactive Compounds ◽  
Enzymatic System ◽  
Isaria Fumosorosea ◽  
Isaria Farinosa ◽  
Improved Stability

Flavonoids, including chalcones, are more stable and bioavailable in the form of glycosylated and methylated derivatives. The combined chemical and biotechnological methods can be applied to obtain such compounds. In the present study, 2′-hydroxy-2-methylchalcone was synthesized and biotransformed in the cultures of entomopathogenic filamentous fungi Beauveria bassiana KCH J1.5, Isaria fumosorosea KCH J2 and Isaria farinosa KCH J2.6, which have been known for their extensive enzymatic system and ability to perform glycosylation of flavonoids. As a result, five new glycosylated dihydrochalcones were obtained. Biotransformation of 2′-hydroxy-2-methylchalcone by B. bassiana KCH J1.5 resulted in four glycosylated dihydrochalcones: 2′-hydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside, 2′,3-dihydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside, 2′-hydroxy-2-hydroxymethyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside, and 2′,4-dihydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside. In the culture of I. fumosorosea KCH J2 only one product was formed—3-hydroxy-2-methyldihydrochalcone 2′-O-β-d-(4″-O-methyl)-glucopyranoside. Biotransformation performed by I. farinosa KCH J2.6 resulted in the formation of two products: 2′-hydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside and 2′,3-dihydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside. The structures of all obtained products were established based on the NMR spectroscopy. All products mentioned above may be used in further studies as potentially bioactive compounds with improved stability and bioavailability. These compounds can be considered as flavor enhancers and potential sweeteners.

scholarly journals Entomopathogenic Filamentous Fungi as Biocatalysts in Glycosylation of Methylflavonoids

Catalysts ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 1148
Author(s):  
Agnieszka Krawczyk-Łebek ◽  
Monika Dymarska ◽  
Tomasz Janeczko ◽  
Edyta Kostrzewa-Susłow
Keyword(s):  
Biological Activity ◽  
Filamentous Fungi ◽  
Beauveria Bassiana ◽  
Biological Activities ◽  
Isaria Fumosorosea ◽  
Methyl Group ◽  
Group 2 ◽  
Pharmacological Application

Flavonoids are known for their numerous biological activities; however, their pharmacological application is limited by poor bioavailability. Glycosides are usually more stable and more soluble in water and in this form, flavonoids are present in nature. Likewise, the presence of the methyl group in the flavonoid skeleton results in facilitated absorption and greater bioavailability. Entomopathogenic filamentous fungi are effective in the biotransformation of flavonoids; they are known especially for efficient glycosylation. In the current study we used strains of Beauveria bassiana KCH J1.5 and Isaria fumosorosea KCH J2 to biotransform flavonoids with a single methyl group. 2′-Hydroxy-5′-methylchalcone was biotransformed by both strains into 2′-hydroxy-5′-methylchalcone 3-O-β-D-(4″-O-methyl)-glucopyranoside. In the culture of B. bassiana KCH J1.5 four products were obtained from 6-methylflavanone: 4′-hydroxy-6-methylflavanone 3′-O-β-D-(4″-O-methyl)-glucopyranoside; 4′-hydroxyflavanone 6-methylene-O-β-D-(4″-O-methyl)-glucopyranoside; 6-hydroxymethylflavanone 3′-O-β-D-(4″-O-methyl)-glucopyranoside and 4′-hydroxy-6-hydroxymethylflavanone 3′-O-β-D-(4″-O-methyl)-glucopyranoside. Biotransformation with I. fumosorosea KCH J2 as a biocatalyst resulted in the formation of 6-methylflavanone 4′-O-β-D-(4″-O-methyl)-glucopyranoside and 2-phenyl-6-methylchromane 4-O-β-D-(4″-O-methyl)-glucopyranoside. All of these flavonoids can be used in biological activity tests and can be useful in studies concerning structure—bioactivity relationships.

scholarly journals Culture media selection for mass production of Isaria fumosorosea and Isaria farinosa

2010 ◽  
Vol 53 (4) ◽  
pp. 753-761 ◽  
Author(s):  
Gabriel Moura Mascarin ◽  
Sérgio Batista Alves ◽  
Rogério Biaggioni Lopes
Keyword(s):  
Mass Production ◽  
Culture Media ◽  
Fungal Species ◽  
Complete Medium ◽  
Sugarcane Molasses ◽  
Liquid Media ◽  
Isaria Fumosorosea ◽  
Isaria Farinosa ◽  
Selection For ◽  
Biphasic Fermentation

This work investigated the production of the fungi Isaria fumosorosea and Isaria farinosa in biphasic fermentation using agro-industrial products and residues. Combinations of natural liquid substrates, alternative to the complete medium and potato dextrose medium, were evaluated. The best liquid media were sugarcane molasses + rice broth, rice broth + yeast and sugarcane molasses + yeast + rice broth, which resulted in the highest viable propagule concentration. The molasses + rice broth medium was selected for the next phase of the study in which the production of both fungal isolates was evaluated in solid grain substrates. In solid-state fermentation, the best conidia production was achieved with the soybean meal and broken corn for I. farinosa, and whole rice and broken rice for I. fumosorosea. Results demonstrated that the two fungal species could be rapidly produced with higher yield of conidia on agro-industrial resources by using biphasic fermentation techniques.

Evaluation of the Entomopathogenic Fungi Beauveria bassiana, Metarhizium anisopliae, and Isaria fumosorosea for Control of Sitophilus oryzae

2014 ◽  
Vol 77 (1) ◽  
pp. 87-93 ◽  
Author(s):  
NICKOLAS G. KAVALLIERATOS ◽  
CHRISTOS G. ATHANASSIOU ◽  
MARIA M. AOUNTALA ◽  
DEMETRIUS C. KONTODIMAS
Keyword(s):  
Beauveria Bassiana ◽  
Entomopathogenic Fungi ◽  
Metarhizium Anisopliae ◽  
Galleria Mellonella ◽  
Sitophilus Oryzae ◽  
Exposure Period ◽  
Isaria Fumosorosea ◽  
Stored Grain ◽  
Stored Grain Pest ◽  
Petri Dishes

The entomopathogenic fungi Beauveria bassiana, Metarhizium anisopliae, and Isaria fumosorosea were tested against the stored-grain pest Sitophilus oryzae. The fungi were isolated from the soil (from three locations in Attica, Greece: B. bassiana from Tatoion, M. anisopliae from Marathon, and I. fumosorosea from Aghios Stefanos) using larvae of Galleria mellonella as bait. Suspensions of 2.11 × 107 and 2.11 × 108, 1.77 × 107 and 1.77 × 108, and 1.81 × 107 and 1.81 × 108 conidia per ml of B. bassiana, M. anisopliae, and I. fumosorosea, respectively, were applied by three treatments: (i) sprayed on food and set in petri dishes with adults of S. oryzae, (ii) sprayed on adults of S. oryzae and set in petri dishes without food, and (iii) sprayed on adults of S. oryzae and set in petri dishes with food. The observed mortality of S. oryzae adults during the overall exposure period for the lowest, as well as for the highest, concentrations of B. bassiana, M. anisopliae, and I. fumosorosea ranged from 0 to 100%. Concentration was, in most of the cases tested, a critical parameter that determined the “speed of kill” of the exposed insect species for B. bassiana and M. anisopliae. Conversely, concentration was not that critical for I. fumosorosea, and survival was high in some of the combinations tested, even after 14 days of exposure. Both in the highest and the lowest concentrations of fungi, the mortality of S. oryzae adults was higher when the fungi were applied on adults than when they were applied on food. Higher mortality was observed when food was absent than when food was present, in most of the cases tested. The high efficacy levels recorded in the current study indicate that the tested fungi could be effective biocontrol agents against S. oryzae.

scholarly journals Evaluation of strains of Beauveria bassiana and Isaria fumosorosea to control sugarcane aphids on grain sorghum

age ◽  
2020 ◽  
Vol 3 (1) ◽  
Author(s):  
Karen Harris‐Shultz ◽  
Joseph Knoll ◽  
Somashekhar Punnuri ◽  
Erika Niland ◽  
Xinzhi Ni
Keyword(s):  
Beauveria Bassiana ◽  
Grain Sorghum ◽  
Isaria Fumosorosea

scholarly journals CONSUMO DE APHIS GOSSYPII GLOVER, 1877 E MYZUS PERSICAE (SULZER, 1776) INFECTADOS COM FUNGOS ENTOMOPATOGÊNICOS POR ORIUS INSIDIOSUS (SAY, 1832) (HEMIPTERA, ANTHOCORIDAE)

2008 ◽  
Vol 75 (4) ◽  
pp. 491-498
Author(s):  
E.S. Loureiro ◽  
A. Moino Júnior
Keyword(s):  
Beauveria Bassiana ◽  
Myzus Persicae ◽  
Metarhizium Anisopliae ◽  
Aphis Gossypii ◽  
Orius Insidiosus ◽  
Isaria Fumosorosea ◽  
Lecanicillium Lecanii ◽  
Aphis Gossypii Glover

RESUMO As espécies de pulgões Aphis gossypii e Myzus persicae são cosmopolitas e polífagas, causando prejuízos em plantas cultivadas. Foi avaliado o consumo de A.gossypii e M. persicae, infectados com fungos entomopatogênicos por Orius insidiosus. No centro de placas de Petri foi colocado um disco de 4,5 cm de diâmetro de folha de algodão (para A. gossypii) e um disco de 4,5 cm de diâmetro de folha de pimentão (para M. persicae). A inoculação dos fungos (Beauveria bassiana, Metarhizium anisopliae, Isaria fumosorosea e Lecanicillium lecanii) foi feita através da adição de 1 mL das suspensões fúngicas 1,0 x 105 e 1,0 x 107 conídios/mL sobre a placa de Petri. Os pulgões foram oferecidos a uma fêmea do predador, liberada na placa em diferentes períodos de tempo após a inoculação, além de um tratamento no qual a fêmea do predador foi liberada com os pulgões mortos, já em fase de conidiogênese. As fêmeas do predador foram retiradas após 24 horas da liberação e, em seguida, foi avaliado o consumo de pulgões. O consumo foi significativamente inferior decorridas 24 horas da inoculação, quando comparado com o a testemunha, para as duas espécies de pulgões estudadas. O consumo de pulgões foi menor nas concentrações testadas no período de 24-48 horas que o consumo da testemunha. Após 72 horas da inoculação e após conidiogênese, não foi observado consumo de pulgões pelo predador para as duas concentrações, evidenciando, dessa forma, a capacidade discriminatória do predador, sendo capaz de reconhecer a presa infectada pelo patógeno.

scholarly journals Micobiota de la ZEC Gándaras de Budiño (Pontevedra, N.O. Península Ibérica)

2018 ◽  
pp. 1-216
Author(s):  
Oscar Requejo
Keyword(s):  
Beauveria Bassiana ◽  
Alnus Glutinosa ◽  
Isaria Farinosa ◽  
Península Ibérica

La Zona de Especial Conservación (ZEC) Gándaras de Budiño está situada en el suroeste de la provincia de Pontevedra (Galicia, Península Ibérica). A pesar de las agresiones sufridas a lo largo de la historia, aún se conservan zonas muy representativas de esta con fauna y flora propia de estos lugares y poco frecuente en el resto del N.O. peninsular. Ocupa una extensión de aproximadamente 800 ha, en las que destacan un amplio complejo de humedales, conformados por turberas, brañas, bosques aluviales y lagunas, así como brezales atlánticos, bosques de ribera y amplias extensiones más secas, constituidas básicamente por bosques mixtos de robles y pinos. En este espacio se realiza un estudio micológico con recolecciones periódicas durante 4 años, de las cuales resulta un catálogo con 359 taxa, con una aportación al catálogo gallego de 62 especies. Entre ellas destaca Chaetotyphula actinipes, que se menciona por primera vez para Europa, además de Arnium olerum, Byssosphaeria schiedermayeriana, Conocybe brachypodii, Cordyceps polyarthra, Hemimycena angustispora, Inocybe salicis, Laccaria impolita, Mollisia olivascens, Mycena atrovinosa, Mycena mucor, Oligoporus alni, Russula sphagnophila y Trichoderma piluliferum, no mencionados anteriormente para la Península Ibérica. Desde el punto de vista de la estrategia trófica destacan las especies entomapatógenas: Beauveria bassiana, Cordyceps polyarthra, Gibellula pulchra, Isaria farinosa y Torrubiella arachnophila. De las restantes 125 son micorrícicas, 211 son saprotróficas y 38 necrotróficas, en ambos casos, mayoritariamente lignícolas, justificado porque las ¾ partes del material ha sido recolectado en formaciones arbóreas de Alnus glutinosa y Salix atrocinerea. Además, se analiza la autoecología de las especies, los patrones de fructificación y su aportación corológica, tanto ibérica como mundial.

scholarly journals Synthesis and Antimicrobial Activity of Methoxy- Substituted γ-Oxa-ε-lactones Derived from Flavanones

Molecules ◽  
2019 ◽  
Vol 24 (22) ◽  
pp. 4151 ◽  
Author(s):  
Witold Gładkowski ◽  
Monika Siepka ◽  
Tomasz Janeczko ◽  
Edyta Kostrzewa-Susłow ◽  
Jarosław Popłoński ◽  
...  
Keyword(s):  
Filamentous Fungi ◽  
Nmr Spectra ◽  
Pathogenic Bacteria ◽  
Spectroscopic Analysis ◽  
Inhibitory Effect ◽  
13C Nmr Spectra ◽  
1H And 13C Nmr ◽  
Methoxy Groups ◽  
Alternaria Sp ◽  
And Staphylococcus Aureus

Six γ-oxa-ε-lactones, 4-phenyl-3,4-dihydro-2H-1,5-benzodioxepin-2-one (5a) and its five derivatives with methoxy groups in different positions of A and B rings (5b–f), were synthesized from corresponding flavanones. Three of the obtained lactones (5b,c,f) have not been previously described in the literature. Structures of all synthesized compounds were confirmed by complete spectroscopic analysis with the assignments of signals on 1H and 13C-NMR spectra to the corresponding atoms. In most cases, lactones 5a–f exerted an inhibitory effect on the growth of selected pathogenic bacteria (Escherichia coli, Bacillus subtilis, and Staphylococcus aureus), filamentous fungi (Fusarium graminearum, Aspergillus niger, and Alternaria sp.), and yeast (Candida albicans). The broadest spectrum of activity was observed for unsubstituted lactone 5a, which was particularly active against filamentous fungi and yeast. Lactones with methoxy groups in the 3′ (5c) and 4′ (5d) position of B ring were more active towards bacteria whereas lactone substituted in the 7 position of the A ring (5e) exhibited higher antifungal activity. In most cases, the introduction of lactone function increased the activity of the compound compared to its flavonoid precursors, chalcones 3a–e, and flavanones 4a–f.

scholarly journals Applications of Beauveria bassiana (Hypocreales: Cordycipitaceae) to Control Populations of Spotted Lanternfly (Hemiptera: Fulgoridae), in Semi-Natural Landscapes and on Grapevines

2020 ◽  
Vol 49 (4) ◽  
pp. 854-864
Author(s):  
Eric H Clifton ◽  
Ann E Hajek ◽  
Nina E Jenkins ◽  
Richard T Roush ◽  
John P Rost ◽  
...  
Keyword(s):  
Beauveria Bassiana ◽  
Fourth Instar ◽  
Single Application ◽  
Isaria Fumosorosea ◽  
Public Park ◽  
Fungal Entomopathogens ◽  
Significant Damage ◽  
Lycorma Delicatula ◽  
Natural Landscapes ◽  
Berks County

Abstract Spotted lanternfly, Lycorma delicatula (White), is an invasive Asian insect that was initially found in Berks County, Pennsylvania, in 2014. As of early 2020, this pest had been found in five more eastern states and it is expected to continue to expand its geographical range. Lycorma delicatula is highly polyphagous but seems to prefer tree-of-heaven, Ailanthus altissima. However, grape growers in Pennsylvania have reported significant damage and loss of vines caused by L. delicatula adults. In fall 2018, two fungal entomopathogens (Beauveria bassiana and Batkoa major) drove localized collapses in L. delicatula populations in Berks County, Pennsylvania. In 2019, we tested applications of a commercialized mycoinsecticide based on B. bassiana strain GHA on L. delicatula populations in a public park in southeastern Pennsylvania. A single application of B. bassiana reduced fourth instar nymphs by 48% after 14 d. Applications of B. bassiana to L. delicatula adults in the same park resulted in 43% mortality after 14 d. Beauveria bassiana spores remained viable on foliage for 5–7 d after spraying. We also conducted semi-field bioassays with B. bassiana GHA (formulated as BoteGHA and Aprehend) and another mycoinsecticide containing Isaria fumosorosea Apopka Strain 97 against L. delicatula adults feeding on potted grapes. All the mycoinsecticides killed ≥90% of adults after 9 d using direct applications. Aprehend killed 99% of adults after 9 d with exposure to residues on sprayed grapes. These data show that fungal entomopathogens can help to suppress populations of L. delicatula in agroecosystems and natural areas.

scholarly journals Eficacia de hongos entomopatógenos en el control de Leptopharsa gibbicarina (Hemiptera: Tingidae) en palma de aceite

2016 ◽  
Vol 42 (1) ◽  
pp. 22 ◽  
Author(s):  
Carlos Enrique Barrios T. ◽  
Alex Enrique Bustillo P. ◽  
Kely Lorena Ocampo R. ◽  
Miguel Angel Reina C. ◽  
Hanna Lorena Alvarado M.
Keyword(s):  
Beauveria Bassiana ◽  
Isaria Fumosorosea ◽  
Purpureocillium Lilacinum

Leptopharsa gibbicarina, es una plaga de importancia económica en la palmicultura colombiana. Se evaluó la patogenicidad y virulencia de los hongos Beauveria bassiana (CPBb0404), Isaria fumosorosea (CPIf1001) y Purpureocillium lilacinum (CPPl0601) sobre adultos de L. gibbicarina obtenidos de una cría bajo condiciones controladas. La patogenicidad de los hongos se evaluó en laboratorio, con adultos de L. gibbicarina individualizados en cajas Petri y asperjados con 0,2 ml de una suspensión de 1 x 107 conidias/ml. La virulencia se evaluó en umbráculo en dos etapas, para esto se infestaron hojas de palma con adultos de L. gibbicarina y se asperjaron los hongos en dosis de 1 x 1013 conidias/ha y posteriormente se varió la dosis asperjando el equivalente a 5 x 1012, 1 x 1013 y 1,5 x 1013 conidias/ha. Después los hongos se evaluaron en un lote comercial de palma de aceite. Los esultados del experimento en laboratorio muestra que los tres hongos son patogénicos a L. gibbicarina (> 96% mortalidad). En la evaluacion de la virulencia I. fumosorosea, B. bassiana y P. lilacinum causaron mortalidades del 74,3%, 92,8% y 100%, respectivamente, encontrándose diferencias significativas (P = 0,05). Sin embargo, al evaluar diferentes dosis, no se encontraron diferencias estadísticas entre dosis y hongos evaluados. En la evaluación de los hongos en campo no se encontraron diferencias significativas entre los tratamientos. Este estudio permite recomendar a P. lilacinum para usarlo en programas de manejo integrado para el control de L. gibbicarina debido a que causa altas mortalidades (> 80%) y a los buenos atributos de calidad que presenta en su producción comercial.

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