Fermentation, Isolation and Characterization of Isonitrile Antibiotics

Fujiwara, Akiko; Okuda, Tôru; Masuda, Setsuko; Shiomi, Yoshihiko; Miyamoto, Chikara; Sekine, Yuzuru; Tazoe, Masaaki; Fujiwara, Mitsuhiko

doi:10.1080/00021369.1982.10865344

Cited by 14 publications

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“…Although a nitrile or isonitrile functional group is rarely found in natural products (2,6), recently a group of isonitrile-containing compounds was isolated from several species of the soil-inhabiting fungus Trichoderma (3). In addition, an inhibitor (A32390A) of dopamine P-hydroxylase, which is also an antimicrobial compound, was isolated and characterized (5).…”

Section: Discussionmentioning

confidence: 99%

“…In addition, an inhibitor (A32390A) of dopamine P-hydroxylase, which is also an antimicrobial compound, was isolated and characterized (5). The chemical, physical, and biological properties of these compounds appear to be different from those of treponemycin (2,3,5,6). Assignment of a diene function in the molecule was also made on the basis of PMR and 'IC-magnetic resonance spectra of treponemycin; the spectra further indicate that the molecule may contain three olefinic protons and four unsaturated carbons in addition to nitrile carbon.…”

Section: Discussionmentioning

confidence: 99%

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Treponemycin, a nitrile antibiotic active against Treponema hyodysenteriae

Singh¹,

Gurusiddaiah²,

Whalen³

1985

Antimicrob Agents Chemother

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Two strains of Streptomyces sp. (isolates 275 and 124) were isolated from soil samples collected from the fields around Lewiston, Idaho. Based on their cellular morphology and physiology, the two isolates were identified as Streptomyces albovinaceous. Both isolates produced an antibiotic when grown in liquid culture medium containing homogenized oats. The antibiotic (treponemycin) was isolated from the culture broth by solvent extraction and purified by silica gel column and preparative thin-layer chromatographies. Treponemycin is a crystalline light-yellow compound with an mp of 93 to 95C, levorotatory, and soluble in most organic solvents. It is sparingly soluble in water but insoluble in petroleum ether. On the basis of elemental analysis and mass spectral data, the molecular formula of the antibiotic was deduced to be C28H43O0N. The infrared spectrum of the antibiotic indicated the presence of unsaturation, nitrile, lactone, or ester or all three functions, and carbonyl functions in the molecule. A sharp infrared absorption band for nitrile at 2,220 cm-and the presence of an unsaturated group indicated that the nitrile function may be attached to an unsaturated carbon atom. The presence of dienenitrile functions was further supported by the UV absorption spectrum of the antibiotic, which gave a UVmax at 257 nm. The proton magnetic resonance spectrum of the antibiotic did not give any peak which could be exchanged with deuterated water, which is an indication of the absence of carboxylic and hydroxyl functions in the molecule. All of the functional groupings indicated by the infrared and UV spectra of the molecule were further confirmed by the "C-magnetic resonance spectrum of the compound. A brief hydrogenation of the antibiotic yielded a biologically active tetrahydro derivative, whereas extended hydrogenation produced an inactive primary amine. Mild alkaline hydrolysis and subsequent esterification of the antibiotic with diazomethane produced an inactive dimethyl ester. Apparently both the nitrile and the lactone functions are essential for the treponomycin molecule to show antimicrobial activity. The antibiotic showed inhibitory activity against several species of bacteria, especially Treponema hyodysenteriae, the causative agent of swine dysentery. In view of the oral 50% lethal dose of 400 mg/kg and its low MIC against four strains of T. hyodysenteriae, the antibiotic may have value as a swine dysentery therapeutic.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Treponemycin, a nitrile antibiotic active against Treponema hyodysenteriae

Singh¹,

Gurusiddaiah²,

Whalen³

1985

Antimicrob Agents Chemother

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“…Subsequently, an increasing number of the antimicrobial metabolites produced by Trichoderma spp. have been the subject of intensive studies and consequently several compounds with antimicrobial properties have been elucidated (Moffatt et al 1969;Collins and Halim 1972;Fujiwara et al 1982;Almassi et al 1991). Compounds produced by Trichoderma spp.…”

Section: Introductionmentioning

confidence: 99%

Detection of viridiofungin A and other antifungal metabolites excreted by Trichoderma harzianum active against different plant pathogens

et al. 2009

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Antibiosis is assumed to be an essential mechanism exerted by potential biocontrol agents (BCAs) of Trichoderma spp. Therefore, in the present study, we report for the first time on the elucidation and production of viridiofungin A (VFA) from T. harzianum isolate T23 cultures and investigate the antifungal potential of VFA and some other secondary metabolites purified from T. harzianum cultures against Fusarium moniliforme. The bioautography assay revealed that T. harzianum isolates T16 and T23 excreted several secondary metabolites with antifungal activity. Following isolation and purification of the antifungal zones, three fractions (F223, F323 and F423) from extracts of isolate T23 and two fractions (F416 and F516) from extracts of isolate T16 exhibited pronounced fungitoxic activity in the bioautography and antibiotic disk assays against Cladosporium spp. and F. moniliforme, respectively. The structure of the antifungal metabolite in fraction F323 was identified as viridiofungin A (VFA), the first report of production of VFA by isolate T23 of T. harzianum. Following cultivation of isolate T23 in PDB medium for 9 days, 94.6 mg l −1 of VFA were determined. VFA and fraction F516 retarded the mycelial growth of F. moniliforme in the nonvolatile phase assay by >90% for each 250 μg ml −1 7 days post-inoculation (dpi). While VFA and fraction F416 showed both volatile and non-volatile effects, fraction F516 seemed to exhibit mainly non-volatile activity. Microscopic examination revealed that hyphae of F. moniliforme grown on VFA-amended medium were less branched and appeared thicker than untreated hyphae. Furthermore, in the presence of VFA, formation of chlamydospores by F. moniliforme was increased. Finally, the antifungal spectrum of VFA towards various important plant pathogens was evaluated. Germination of propagules of a variety of fungal pathogens in vitro was differentially inhibited by VFA. While in the presence of 100 μg ml −1 VFA conidial germination of V. dahliae was completely inhibited, a slightly higher concentration (150 μg ml −1 ) of the inhibitor was required to suppress germination of Phytophthora infestans sporangia or sclerotia of Sclerotinia sclerotiorum. Contrary to several reports in the literature, VFA proved to be fungistatic rather than fungicidal. However, neither VFA nor the other Trichoderma metabolites, such as 6PAP, F416 and F516, exhibited any antibacterial activity against Gram-positive and Gram-negative bacteria.

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“…The fungus also is known to produce CWDEs including chitinases, b-1,3-glucanases, proteases and b-1,4-glucanases (Baek et al 1999, Cruz et al 1995, Flores et al 1997, Elad and Kapat 1999, antibiotics (Dennis and Webster 1971;Claydon et al 1987;Fujiwara et al 1982;Vinale et al 2006Vinale et al , 2009 and antibiotic peptides, such as peptaibols (Iida et al 1994).…”

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confidence: 97%

Scanning electron microscopy observations of the interaction betweenTrichoderma harzianumand perithecia ofGibberella zeae

Inch¹,

Gilbert

2011

Mycologia

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Chronological events associated with the interaction between a strain of Trichoderma harzianum, T472, with known biological control activity against perithecial production of G. zeae, were studied with scanning electron microscopy to investigate the mechanisms of control. Large clusters of perithecia consisting of 5-15 perithecia formed on the autoclaved, mulched wheat straw inoculated with G. zeae alone (control) with an average of 157 perithecia per plate. Small clusters consisting of 3-6 and an average of 15 perithecia per plate perithecia formed on straw that was treated with T. harzianum. The mature perithecia from straw treated with T. harzianum produced less pigment and were lighter in color than those from the control plates. Furthermore the cells of the outer wall of these perithecia were abnormal in appearance and unevenly distributed across the surface. Immature perithecia were colonized by T. harzianum approximately 15 d after inoculation (dai) with the biocontrol agent and pathogen. Few perithecia were colonized at later stages. The affected perithecia collapsed 21 dai, compared to the perithecia in the control samples that began to collapse 28 dai. Abundant mycelium of T. harzianum was seen on the perithecia of treated samples. Perithecial structures may be resistant to penetration by the mycelium because direct penetration was not observed. Trichoderma harzianum colonized the substrate quickly and out-competed the pathogen, G. zeae.

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Fermentation, Isolation and Characterization of Isonitrile Antibiotics

Cited by 14 publications

References 0 publications

Treponemycin, a nitrile antibiotic active against Treponema hyodysenteriae

Treponemycin, a nitrile antibiotic active against Treponema hyodysenteriae

Detection of viridiofungin A and other antifungal metabolites excreted by Trichoderma harzianum active against different plant pathogens

Scanning electron microscopy observations of the interaction betweenTrichoderma harzianumand perithecia ofGibberella zeae

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