Metacytofilin, a novel immunomodulator produced by Metarhizium sp. TA2759.

Iijima, Masatomi; Masuda, Tohru; Nakamura, Hikaru; Naganawa, Hiroshi; Kurasawa, Shogo; Okami, Yoshirō; Ishizuka, Masaaki; Takeuchi, Tomio; Iitaka, Yōichi

doi:10.7164/antibiotics.45.1553

Cited by 36 publications

(20 citation statements)

References 2 publications

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“…The 13 C NMR spectra were obtained with the pulse width of 6.0 mseconds (30°pulse) and 1.44 seconds reputation cycle under full proton decoupling. All the samples of isotopically labeled 1 were dissolved in DMSO-d 6 . The chemical shift values of 1 H and 13 C NMR signals were measured using DMSO signals by the conversion factors as 2.54 ppm for the 1 H NMR signals and 39.50 ppm for the 13 C NMR signals, respectively.…”

Section: Nmr Measurementsmentioning

confidence: 99%

“…Consequently, by feeding a mixture of nonlabeled and D-[U-13 C]glucoses, the C 4 unit of erythrose 4-phosphate either must have all carbons labeled (7a) or nonlabeled (7d). On the other hand, glucose is also metabolized into glyceraldehydes 3-phosphate (5) and dihydroxyacetone phosphate (6). Thus, if non-labeled glucose and D-[U-13 C]glucose are metabolized according to this scheme, two kinds of C 3 units described above are produced: i.e.…”

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

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: Nmr Measurementsmentioning

confidence: 99%

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

confidence: 99%

Biosynthesis of Quinolactacin A, a TNF Production Inhibitor

et al. 2006

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“…produce secondary metabolites in other chemical classes. These include the cytochalasins (1,24), helvolic acid (19), swainsonine (33,59), 12-hydroxyovalicin (47), viridoxins (29), fungerins (78), and metacytofilin (37). Although most of the known metabolites of Metarhizium exhibit biological activities in vitro against mammalian, insect, microbial, or plant cells, none has yet been demonstrated conclusively by genetic means to play an essential role in invertebrate disease.…”

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confidence: 99%

Agrobacterium -Mediated Disruption of a Nonribosomal Peptide Synthetase Gene in the Invertebrate Pathogen Metarhizium anisopliae Reveals a Peptide Spore Factor

Moon

Donzelli

Krasnoff

et al. 2008

Appl Environ Microbiol

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Numerous secondary metabolites have been isolated from the insect pathogenic fungus Metarhizium anisopliae, but the roles of these compounds as virulence factors in disease development are poorly understood. We targeted for disruption by Agrobacterium tumefaciens-mediated transformation a putative nonribosomal peptide synthetase (NPS) gene, MaNPS1. Four of six gene disruption mutants identified were examined further. Chemical analyses showed the presence of serinocyclins, cyclic heptapeptides, in the extracts of conidia of control strains, whereas the compounds were undetectable in ⌬Manps1 mutants treated identically or in other developmental stages, suggesting that MaNPS1 encodes a serinocyclin synthetase. Production of the cyclic depsipeptide destruxins, M. anisopliae metabolites also predicted to be synthesized by an NPS, was similar in ⌬Manps1 mutant and control strains, indicating that MaNPS1 does not contribute to destruxin biosynthesis. Surprisingly, a MaNPS1 fragment detected DNA polymorphisms that correlated with relative destruxin levels produced in vitro, and MaNPS1 was expressed concurrently with in vitro destruxin production. ⌬Manps1 mutants exhibited in vitro development and responses to external stresses comparable to control strains. No detectable differences in pathogenicity of the ⌬Manps1 mutants were observed in bioassays against beet armyworm and Colorado potato beetle in comparison to control strains. This is the first report of targeted disruption of a secondary metabolite gene in M. anisopliae, which revealed a novel cyclic peptide spore factor.

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“…Entomopathogenic fungi seem to be interesting as a source of biologically active compounds such as an insecticides1) and immunosuppressants2, 3), because all insect orders are susceptible to fungal diseases. With the goal of finding novel bioactive compounds from fungi, we investigated metabolite diversity using an HPLC screening program.…”

mentioning

confidence: 99%

The Structures of Pyridovericin and Pyridomacrolidin, New Metabolites from the Entomopathogenic Fungus, Beauveria bassiana.

et al. 1998

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Entomopathogenic fungi seem to be interesting as a source of biologically active compounds such as an insecticides1) and immunosuppressants2,3), because all insect orders are susceptible to fungal diseases. With the goal of finding novel bioactive compounds from fungi, we investigated metabolite diversity using an HPLC screening program. During the screening process, we isolated two novel metabolites named pyridovericin (1) and pyridomacrolidin (2) (Fig.

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Metacytofilin, a novel immunomodulator produced by Metarhizium sp. TA2759.

Cited by 36 publications

References 2 publications

Biosynthesis of Quinolactacin A, a TNF Production Inhibitor

Biosynthesis of Quinolactacin A, a TNF Production Inhibitor

Agrobacterium -Mediated Disruption of a Nonribosomal Peptide Synthetase Gene in the Invertebrate Pathogen Metarhizium anisopliae Reveals a Peptide Spore Factor

The Structures of Pyridovericin and Pyridomacrolidin, New Metabolites from the Entomopathogenic Fungus, Beauveria bassiana.

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