Pyridovericin and Pyridomacrolidin: Novel Metabolites from Entomopathogenic Fungi, Beauveria bassiana.

Takahashi, Senji; Kakinuma, Norihiro; Uchida, Kenichi; Hashimoto, Ryuju; Yanagisawa, Tadashi; Nakagawa, Akira

doi:10.7164/antibiotics.51.596

Cited by 52 publications

(31 citation statements)

References 11 publications

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“…Kynurenine is then proposed to combine with an isoleucine molecule and cyclized to form a quinolone ring [intermediate (8)], followed by oxidative decarboxylation and lactam formation. Consequently, the consecutive carbons at C-1, C-9a, C-9, and C-8a of 1 originate from different biosynthetic units.…”

Section: Incorporation Of D-[u-13 C]glucose To Quinolactacin Amentioning

confidence: 99%

“…In the course of an HPLC-based, chemical screening program of the metabolites of entomopathogenic fungi, the novel pyridone alkaloids, pyridovericin and pyridomacrolidin, possessing protein kinase inhibitory activity, were isolated from the cultured broth of Beauveria bassiana EPF-5 [8,9]. In addition, novel quinolone alkaloids, quinolactacins A (1), B (2), and C (3) were obtained from the cultured broth of Penicillium sp.…”

Section: Introductionmentioning

confidence: 99%

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Biosynthesis of Quinolactacin A, a TNF Production Inhibitor

et al. 2006

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Quinolactacins, which inhibit tumor necrosis factor production, contain a quinolone skeleton conjugated with a g -lactam. The biosynthesis of quinolactacin was investigated by feeding experiments using 13 Keywords quinolactacin, quinolone, biosynthesis, 13 C labeled precursor, Penicillium sp. IntroductionSince entomopathogenic fungi possess a parasitic function, it was expected that novel biologically active compounds such as insecticides and immunosuppressants would be isolated from them [1ϳ7]. In the course of an HPLC-based, chemical screening program of the metabolites of entomopathogenic fungi, the novel pyridone alkaloids, pyridovericin and pyridomacrolidin, possessing protein kinase inhibitory activity, were isolated from the cultured broth of Beauveria bassiana 9]. In addition, novel quinolone alkaloids, quinolactacins A (1), B (2), and C (3) were obtained from the cultured broth of Penicillium sp. EPF-6, which was isolated from the larvae of the mulberry pyralid (Margaronia pyloalis Welker) [10]. Alkaloid 1, the major constituent, exhibited inhibitory activity against tumor necrosis factor (TNF) production by murine macrophages and macrophage-like J774.1 cells stimulated with lipopolysaccharide (LPS).Quinolactacins have a unique quinolone skeleton conjugated with a g-lactam ring [11], as shown in Figure 1. Subsequently, Kim et al., reported the characterization of stereoisomers of 1 through a screening program for inhibitors of acetylcholinesterase [12], and Tatsuta's group reported the biomimetic synthesis of quinolactacin B (2) using acetic acid, valine, and anthranilic acid [13]. In this paper, the biosynthesis of 1 was studied by feeding experiments using several 13 C single-labeled precursors and D-[U-

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Section: Incorporation Of D-[u-13 C]glucose To Quinolactacin Amentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Biosynthesis of Quinolactacin A, a TNF Production Inhibitor

et al. 2006

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“…6 Species of entomopathogenic fungi have been described as producers of secondary metabolites, including bioactive non-ribosomal peptides and polyketides. 7 B. bassiana produces the cyclooligomer nonribosomal depsipeptides beauvericins and bassianolide, 8,9 beauveriolides, 10 tenellin, bassianin, 11 pyridovericin, pyridomacrolidin, 12 oosporein 13 and bassiacridin. 14 In special, beauvericin is an ionophoric cyclodepsipeptide detected in several fungi, mainly Beauveria, Paecilomyces and Fusarium species.…”

Section: Introductionmentioning

confidence: 99%

Larvicidal Activity of Beauveria bassiana Extracts against Aedes aegypti and Identification of Beauvericins

Daniel

Silva

Nakagawa

et al. 2016

J. Braz. Chem. Soc.

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Beauveria bassiana is an entomopathogenic fungus that has been well known for its capacity to act as biopesticide on various disease vectors. The analysis of organic extracts of strains CG71 and UNI40 led to identification of cyclodepsipeptides beauvericin, beauvericin A or F, beauvericin E and bassianolide by ultra-high pressure liquid chromatography-high resolution mass spectrometry in tandem mode (UHPLC-HRMS/MS). The larvicidal activity on 3 rd instar of Aedes aegypti revealed LC 50 0.9887 and 0.4653 ppm in 24 and 48 hours (CG71 methanolic extract), LC 50 0.7834 ppm in 48 hours (CG71 ethyl acetate), LC 50 0.7834 and 1.8149 ppm (UNI 40 for ethyl acetate and methanolic extracts, respectively) in 48 hours. These findings highlight the potential of B. bassiana metabolites for controlling the vector of Dengue and Zika diseases. Keywords: cyclohexadepsipeptides, Dengue, Zika, beauvericins, UHPLC-HRMS/MS IntroductionThe entomopathogenic Beauveria bassiana has a broad host range naturally attacking insects and variety of arthropod species. [1][2][3] Due to this ability, it is used as a biopesticide agent on diverse disease vectors, including crop pests, ticks and mosquitoes. 4,5 The attack on insect cuticle occurs after hyphae of B. bassiana penetrate the insect integument by enzymatic action. 6 Species of entomopathogenic fungi have been described as producers of secondary metabolites, including bioactive non-ribosomal peptides and polyketides. 7 B. bassiana produces the cyclooligomer nonribosomal depsipeptides beauvericins and bassianolide, 8,9 beauveriolides, 10 D, E and F. 25 Bassianolide is another cyclooctadepsipeptide metabolite produced B. bassiana and Lecanicillium lecanii. 9 It is toxic to insects and probably also acts as an ionophore, such as other cyclodepsipeptides. 15 The structural diversity of metabolites from entomopathogenic fungi, associated with diverse biological activities, stimulates the research by on bioactive fungal extracts for controlling insect pests and disease vectors.Larvicidal Activity of Beauveria bassiana Extracts against Aedes aegypti and Identification of Beauvericins J. Braz. Chem. Soc. 1004 Dengue is a viral infection transmitted to humans by Aedes aegypti mosquitoes that became a major concern of the public health sector. 26 There were 96 million apparent dengue infections globally in 2010, of which the Americas contributed 14% (13 million infections) of worldwide and over half developed in Brazil and Mexico. 27 Due to no effective antiviral agents and licensed vaccine for infection, the decrease in transmission depends only on vector control by elimination of artificial and disposable water inundated larvae breeding sites and application of insecticides. 27,28 Furthermore, studies reveal resistance in the vector population to various substances, in Brazil there is an irregular distribution of insecticide resistance. 28 Furthermore, Aedes mosquitoes also transmit Zika virus; attracting worldwide attention in 2016, when the vector caused widespread epidemic cases in Braz...

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“…Fungos patogênicos a insetos são um grupo de micro-organismos ecologicamente especializados e parecem ser uma interessante fonte de compostos biologicamente ativos como inseticidas (Roberts, 1981) e imunossupressores (Fujita et al, 1994;Iijima et al, 1992), pois todas as ordens de insetos são suscetíveis a infecções por fungos (Takahashi et al, 1998).…”

Section: Beauveria Bassianaunclassified

“…Culturas do fungo entomopatogênico B. bassiana geralmente desenvolvem uma coloração amarela, devido à formação de uma mistura de pigmentos relacionados, entre estes pigmentos tem sido reportados a tenellina, bassianina (Wat et al, 1977), piridovericina e piridomacrolidina (Takahashi et al, 1998).…”

Section: Piridovericina-n-o-(4-o-metil-β-d-glucopiranosídeo) 1-[(2"3unclassified

Otimização das condições de cultivo de Beauveria bassiana e Mycoleptodiscus indicus visando à produção de metabólitos com atividades antimicrobiana, antiparasitária e antitumoral

Andrioli¹

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Versão corrigida da Tese de Doutorado apresentada ao Programa de Pós-Graduação em 16/03/2012. A versão original encontra-se disponível na Faculdade de Ciências Farmacêuticas de Ribeirão Preto/USP Ribeirão Preto 2012 UNIVERSIDADE DE SÃO PAULO FACULDADE DE CIÊNCIAS FARMACÊUTICAS DE RIBEIRÃO PRETO Otimização das condições de cultivo de Beauveria bassiana e Mycoleptodiscus indicus visando à produção de metabólitos com atividades antimicrobiana, antiparasitária e antitumoral DedicatóriaDedico este trabalho à Jaime Andrioli e Lea T. Tedesco Andrioli, meus queridos pais que transmitiram a mim os mais importantes valores da vida, aos meus amados irmãos Gabriela e Ronald e a Deus pelo dom da vida. Agradecimento especialProf. Dr. Jairo Kenupp Bastos "Se eu não fosse imperador, desejaria ser professor. Não conheço missão maior e mais nobre que a de dirigir as inteligências jovens e preparar os homens do futuro." Dom Pedro II AgradecimentosÀ Deus, pelo dom da vida;Aos meus queridos pais, Jaime e Lea Andrioli;Aos meus amados irmãos, Gabriela e Ronald;À toda minha família, repleta de pessoas de bom coração; It is known that microorganisms are considered as promising source of bioactive molecules and endophytic and entomopathogenic fungi are included in this group. Therefore, we selected the entomopathogenic fungus Beauveria bassiana and the endophytic fungus Mycoleptodiscus indicus to initiate the prospection aiming to determine the favorable growing conditions to obtain secondary metabolites with biological activity. This work was guided by biological assays and chromatographic analysis. The fractions obtained in the cultivation in a large scale were subjected to biological tests (leishmanicidal, antimalarial, antimicrobial and cytotoxic). The dichloromethane and ethyl acetate fractions of both fungi showed promising results in antitumor and leishmanicidal assays. Then, these fractions were subjected to chromatographic processes that allowed the isolation of compounds whose chemical structures were elucidated through the use of NMR techniques, mass spectrometry, UV, IR, αD, and X-ray diffraction. From cultures of B. bassiana were obtained compounds from the pyridone class: pyridovericin, pyridovericin-N-O-(4-O-methyl-β-D-glucopyranoside) and pyridovericin-15-deoxy, being the latter two novel compounds; and alloxazine class: 7,8-dimethylalloxazine (lumichrome) and 1-methyl-11-hydroxylumichrome, being this last one unprecedented. From M. indicus cultures were obtained compounds from two classes: azaphilone and chromene. In this thesis we report the derivatives eugenitin, 6-methoxyeugenin and 9-hydroxyeugenin, which have been isolated from a wide variety of plants and fungi. Azaphilones are a class of structurally diverse fungal metabolites, known pigments with pyran-quinone structure and contains a highly oxygenated bicyclic core and a chiral quaternary center. Then, we obtained two known azaphilones: austdiol and austdiol diacetate (product of acetylation), and three unprecedent azaphilones: austdiol dimer, austdiol dihydrois...

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Pyridovericin and Pyridomacrolidin: Novel Metabolites from Entomopathogenic Fungi, Beauveria bassiana.

Cited by 52 publications

References 11 publications

Biosynthesis of Quinolactacin A, a TNF Production Inhibitor

Biosynthesis of Quinolactacin A, a TNF Production Inhibitor

Larvicidal Activity of Beauveria bassiana Extracts against Aedes aegypti and Identification of Beauvericins

Otimização das condições de cultivo de Beauveria bassiana e Mycoleptodiscus indicus visando à produção de metabólitos com atividades antimicrobiana, antiparasitária e antitumoral

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