WF11899A, B and C, novel antifungal lipopeptides. I. Taxonomy, fermentation, isolation and physico-chemical properties.

Iwamoto, Toshiro; Fujie, Akihiko; Sakamoto, Kazutoshi; Tsurumi, Yasuhisa; Shigematsu, Nobuharu; Yamashita, Michio; Hashimoto, Seiji; Okuhara, Masakuni; Kohsaka, Masanobu

doi:10.7164/antibiotics.47.1084

Cited by 89 publications

(37 citation statements)

References 17 publications

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“…The original anidulafungin, caspofungin and micafungin compounds were echinocandin B from Aspergillus nidulans var. echinulatus, 6 pneumocandin B0 from Glarea lozoyensis 7 and FR901379 from Coleophoma empetri, 8 respectively.…”

Section: Introductionmentioning

confidence: 99%

Micafungin: a sulfated echinocandin

Hashimoto

2009

J Antibiot

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Micafungin is the second approved antifungal agent in the echinocandin series and is now used worldwide in chemotherapy for life-threatening fungal infections. It is water-soluble and is semi-synthesized from the acylated cyclic hexapeptide FR901379, a natural product from the fungus Coleophoma empetri F-11899, through enzymatic deacylation of FR901379, followed by chemical reacylation with the optimized N-acyl side chain. The water solubility of micafungin is ascribed to a sulfate moiety in the molecule. This feature differentiates micafungin from other echinocandin members. Micafungin is a potent inhibitor of 1,3-b-glucan synthase, an enzyme necessary for cell-wall synthesis of several fungal pathogens. The Journal of Antibiotics (2009) and Cryptococcus neoformans are a threat to human health. Incidences of these systemic fungal infections have increased significantly over the past few years. The major reasons for this dramatic increase are the extensive use of broad-spectrum antibiotics and the growing number of immunocompromised patients with acquired immunodeficiency syndrome (AIDS), cancer and transplants. 1,2 In the mid 1900s, few compounds, such as polyenes (for example, nystatin and amphotericin B) and flucytosine, were available for antifungal chemotherapy. Although the development of azole drugs started in the early 1970s, only a limited number of antifungal agents were available for treatment of life-threatening fungal infections. Moreover, the existing agents had disadvantages, such as the significant nephrotoxicity of amphotericin B 3 and the emergence of resistance to the azoles. 4 To overcome these defects, lipid formulations of polyenes were developed to reduce toxicity, and new triazoles (for example, voriconazole, ravuconazole and posaconazole) were developed to improve the antifungal spectra or susceptibility to azoleresistant isolates. 5 Despite a number of therapeutic advancements, there was a need to develop a new class of antifungal agents with novel mechanisms of action.

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Section: Introductionmentioning

confidence: 99%

Micafungin: a sulfated echinocandin

Hashimoto

2009

J Antibiot

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“…These compounds belong to the echinocandin family, a class of antifungal agents that act on the fungal cell wall by inhibiting glucan synthesis. The members of the echinocandin family of fungal origin are FR901379 [14,15], echinocandin B [16], aclueacins [17], mulundocandin [18] and pneumocandins [19], which are produced by C. empetri No. 11899, Aspergillus nidulans, A. aculeatus, A. sydowi and Glarea lozoyensis, respectively.…”

Section: Discussionmentioning

confidence: 99%

“…At first, the structure of FR209602 was elucidated by comparison of the 1 H and 13 C NMR data with those of FR901379 [13,14] and it was finally established by application of a series of 2-D NMR techniques. In the 1 H NMR spectrum of Fig.…”

Section: Structure Elucidation Of Fr209602mentioning

confidence: 99%

FR209602 and Related Compounds, Novel Antifungal Lipopeptides from Coleophoma crateriformis No. 738

Kanasaki¹,

Sakamoto²,

Hashimoto³

et al. 2006

J Antibiot

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Novel antifungal lipopeptides, FR209602, FR209603 and FR209604, were isolated from the fermentation broth of a fungal strain No. 738 which was identified as Coleophoma crateriformis from morphological and physiological characteristics. The antibiotics were purified by solvent extraction, HP-20, YMC-ODS and silica gel column chromatography and lyophilization. These compounds were structurally similar to FR901379 previously reported by ourselves which had a sulfate residue in the cyclic peptide portion.

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“…FR901379 and echinocandin B were prepared from the fermentation broth of C. empetri F-11899 1 and Aspergillus nidulans var. echinulatus A-32204, NRRL 3860, 6 respectively.…”

Section: Reagents and Microorganismsmentioning

confidence: 99%

Screening and characterization of microorganisms with FR901379 acylase activity

et al. 2009

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A simple and rapid screen was performed for microorganisms producing cyclic lipopeptide acylase, an enzyme that deacylates the acyl side chain of FR901379 to yield a cyclic peptide, FR179642, which is an important intermediate in producing micafungin. Among B3800 newly isolated strains from soil samples, 5 microorganisms expressing high acylase activity were selected and classified, 3 as Streptomyces spp. and 2 as filamentous fungi. This is the first time that these strains have been identified as cyclic lipopeptide acylase producers. Both fungi and streptomycetes showed differing optimum pH and temperature profiles for acylase activity.

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WF11899A, B and C, novel antifungal lipopeptides. I. Taxonomy, fermentation, isolation and physico-chemical properties.

Cited by 89 publications

References 17 publications

Micafungin: a sulfated echinocandin

Micafungin: a sulfated echinocandin

FR209602 and Related Compounds, Novel Antifungal Lipopeptides from Coleophoma crateriformis No. 738

Screening and characterization of microorganisms with FR901379 acylase activity

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