Sassafrins A–D, new antimicrobial azaphilones from the fungus Creosphaeria sassafras

Quang, Đặng Ngọc; Hashimoto, Toshihiro; Fournier, Jacques; Stadler, Marc; Radulović, Niko S.; Asakawa, Yoshinori

doi:10.1016/j.tet.2004.12.031

Cited by 49 publications

(52 citation statements)

References 13 publications

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“…All azaphilones showed weak to very weak antioxidant activities (Table 1) compared to the known standard, ascorbic acid. In particular, compounds (8)(9)(10) in group C were void of any activity, so the inhibition of NO production in RAW cells was not due to their free-radical scavenging activities.…”

Section: Discussionmentioning

confidence: 96%

“…Fifteen azaphilones, specifically daldinins C, E and F (1-3) from Hypoxylon fuscum, 20,21) multiformin D (4) from H. multiforme, 11) sassafrins A-C (5-7) from Creospharia sassafras, 10) entonaemin A (8) and rubiginosins A-C (9-11) from H. rubiginosin, 22) cohaerins A and B (12, 13) from H. cohaerens, 23) rutilins A and B (14, 15) from H. rutilin, 24) were isolated from xylariaceous fungi and their structures characterized by a combination of NMR spectrometry and X-ray crystallographic analysis.…”

Section: Isolation Of Azaphilonesmentioning

confidence: 99%

“…2,3) Although previous publications showed that azaphilones exhibit broad activities in many biological systems, such as cholesteryl ester transfer protein, 4) monoamine oxidase inhibition, 5) endothelin receptor binding, 6) the inhibition of gp120-CD4 binding, 7) telomerase inhibition, 8) the induction of Epstein-Barr virus, 9) and antimicrobial activities, 3,10,11) there is no report about the inhibition of nitric oxide (NO) production by azaphilones.…”

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Inhibition of Nitric Oxide Production in RAW 264.7 Cells by Azaphilones from Xylariaceous Fungi

Quang

Harinantenaina

Nishizawa

et al. 2006

Biological & Pharmaceutical Bulletin

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The Xylariaceae (Ascomycete) is a large family and currently comprises more than 36 genera. So far, at least one third of these genera have been chemically investigated. 1)One of these specific metabolites repeatedly isolated from this family is azaphilone, with various substitution groups linked to the main skeleton.2,3) Although previous publications showed that azaphilones exhibit broad activities in many biological systems, such as cholesteryl ester transfer protein, 4) monoamine oxidase inhibition, 5) endothelin receptor binding, 6) the inhibition of gp120-CD4 binding, 7) telomerase inhibition, 8) the induction of Epstein-Barr virus, 9) and antimicrobial activities, 3,10,11) there is no report about the inhibition of nitric oxide (NO) production by azaphilones.NO is synthesized from L-arginine by nitric oxide synthase (NOS). Currently, three distinct isoforms of NOS have been identified: Neuronal NOS (nNOS), inducible NOS (iNOS), and endothelial NOS (eNOS).12) Of these, iNOS is an important enzyme involved in the regulation of inflammation 13) and in the generation of a large amount of NO.14) Overproduction of NO by iNOS has been implicated in various pathological processes including septic shock, tissue damage following inflammation, and rheumatoid arthritis. [15][16][17][18][19] Therefore, suppression of nitric oxide (NO) production in macrophages could be a target for potential anti-inflammatory drugs.In the present study, we screened the inhibitory activity of fifteen azaphilones, which were isolated from mushrooms belonging to the Xylariaceae family, and also elucidated the mechanism of inhibition of NO production stimulated by lipopolysaccharide (LPS) in RAW 264.7 cells. MATERIALS AND METHODS Isolation of AzaphilonesFifteen azaphilones, specifically daldinins C, E and F (1-3) from Hypoxylon fuscum, 20,21) multiformin D (4) from H. multiforme, 11) sassafrins A-C (5-7) from Creospharia sassafras, 10) entonaemin A (8) and rubiginosins A-C (9-11) from H. rubiginosin, 22) cohaerins A and B (12, 13) from H. cohaerens, 23) rutilins A and B (14, 15) from H. rutilin, 24) were isolated from xylariaceous fungi and their structures characterized by a combination of NMR spectrometry and X-ray crystallographic analysis.Cell Culture RAW 264.7 cells, a mouse macrophage cell line, were grown in RPMI 1640 supplemented with 10% fetal bovine serum, kanamycin (50 mg/ml), and ampicillin (60 mg/ml) at 37°C in an atmosphere of 5% CO 2 and 95% air.Inhibition of NO Production of Fifteen Azaphilones One hundred microliters of RAW 264.7 cells (8ϫ10 5 cells/ ml) was pipetted into the wells of 96-well culture plates and then cultured. After 24 h incubation, 50 ml of medium containing various concentrations of each azaphilone derivative diluted in DMSO was added to each well. The final DMSO concentration was less than 0.1%. At this concentration, DMSO did not show any NO-induction without stimulation with LPS. Then, 50 ml of vehicle or LPS purified from Pantoea agglomerans (4 mg/ml) was added to each well. The cells were further in...

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Section: Discussionmentioning

confidence: 96%

Section: Isolation Of Azaphilonesmentioning

confidence: 99%

mentioning

confidence: 99%

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Inhibition of Nitric Oxide Production in RAW 264.7 Cells by Azaphilones from Xylariaceous Fungi

Quang

Harinantenaina

Nishizawa

et al. 2006

Biological & Pharmaceutical Bulletin

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“…ramulosin, 4) and sassafrins A-D. 5) During our ongoing search for biologically active metabolites from the endophytic fungi, the broth extract of the xylariaceous fungus PSU-A80, isolated from the leaves of Garcinia atroviridis, showed the antioxidant activity in 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical assay. To search for antioxidant metabolites, the ethyl acetate extracts from the culture broth and cell of the xylariaceous fungus PSU-A80 were subjected to various chromatographic separation.…”

mentioning

confidence: 99%

Metabolites from the Xylariaceous Fungus PSU-A80

Rukachaisirikul

Sommart

Phongpaichit

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Vias biossintéticas são sugeridas para as seguintes azafilonas: monascorubrina e monascoflavina (Kurono et al, 1963); mitorubrina e rubropunctatina (Turner, 1971); ascochitina (Turner e Aldridge, 1983); ochrefilona (Turner e Aldridge, 1983); citrinina (Turner e Aldridge, 1983;Hajjaj et al, 1999); monascusonas A e B, monascina (Jongrungruangchok et al, 2004) e sassafina D (Quang et al, 2005). No entanto, alguns pesquisadores são da opinião de que um compreensivo conhecimento sobre a via de biossíntese dos pigmentos policetídeos (incluindo os extensivamente pesquisados pigmentos de Monascus) ainda não está disponível (Mapari et al, 2009).…”

Section: Azafilonasunclassified

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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Sassafrins A–D, new antimicrobial azaphilones from the fungus Creosphaeria sassafras

Cited by 49 publications

References 13 publications

Inhibition of Nitric Oxide Production in RAW 264.7 Cells by Azaphilones from Xylariaceous Fungi

Inhibition of Nitric Oxide Production in RAW 264.7 Cells by Azaphilones from Xylariaceous Fungi

Metabolites from the Xylariaceous Fungus PSU-A80

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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