Dactylfungins, novel antifungal antibiotics produced by Dactylaria parvispora.

Xaio, Jin-Zhong; Kumazawa, Shigenori; Yoshikawa, Nobuji; Matsukawa, Takashi; Sato, Yoshikazu

doi:10.7164/antibiotics.46.48

Cited by 17 publications

(38 citation statements)

References 8 publications

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“…100 ppm were observed. These NMR data are characteristic of an a-pyrone [5,6]; this finding was also supported by the IR spectrum [5,6].…”

Section: Introductionsupporting

confidence: 62%

“…The signals due to an olefinic methine at d H 5.81 and d C 108.1 and due to quaternary carbon atoms at d C 182.2, 170.0, 168.9, and 97.6 indicated the presence of a g-pyrone system (C-1 to C-5). The presence of the g-pyrone moiety was also confirmed by the comparison of NMR and IR data of reported g-pyrone-type compounds [5,6]. Unambiguous signals in the 1 H-and 13 C-NMR spectra of 2 were assigned based on HMBC experiments (Table 2).…”

Section: Introductionmentioning

confidence: 82%

“…Over the past 20 years, some structurally similar fungal metabolites containing a pyrone moiety, long chain, and polyalcohol moiety have been reported. Dactylfungins A and B and YM-202204 were isolated from Dactylaria parvispora and the marine-derived fungus Phoma sp., respectively [6,7]. It is interesting to note that these pyrone derivatives exhibited antifungal activity.…”

Section: Introductionmentioning

confidence: 99%

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Isolation and Structure Elucidation of Neofusapyrone from a Marine-derived Fusarium species, and Structural Revision of Fusapyrone and Deoxyfusapyrone

et al. 2006

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Three polyketides containing a pyrone ring, neofusapyrone, fusapyrone, and deoxyfusapyrone, were isolated from the marine-derived fungus Fusarium sp. FH-146. Their structures were determined by extensive 1D-and 2D-NMR and MS spectral analyses. Fusapyrone and deoxyfusapyrone were originally reported as a -pyrone derivatives; however, the revised structures indicate that they are g -pyrone derivatives. These three compounds exhibited antimicrobial activities.

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“…100 ppm were observed. These NMR data are characteristic of an a-pyrone [5,6]; this finding was also supported by the IR spectrum [5,6].…”

Section: Introductionsupporting

confidence: 62%

Section: Introductionmentioning

confidence: 82%

Section: Introductionmentioning

confidence: 99%

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Isolation and Structure Elucidation of Neofusapyrone from a Marine-derived Fusarium species, and Structural Revision of Fusapyrone and Deoxyfusapyrone

et al. 2006

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“…Dactylarin and dactylariol have been isolated from D. lu tea [12,13] and the dactylfungins were obtained from D. parvispora [14]. In both cases, the produc ing strains were isolated from soil and have not been shown to be nematode-trapping.…”

Section: Resultsmentioning

confidence: 99%

New Biologically Active Compounds from the Nematode-Trappmg Fungus Arthrobotrys oligospora Fresen

Stadler¹,

Sterner²,

Anke³

1993

Zeitschrift Für Naturforschung C

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Dedicated to Professor D r. W olfgang Steglich on the occasion o f his 60 th birthdayArthrobotrys oligospora, Nematode-Trapping Fungi, Oligosporon, Oligosporols A and B, Cytotoxic ActivitiesThe isolation, structural elucidation and biological activities of oligosporon (1), oligosporol A (2) and oligosporol B (3), three new antibiotics from cultures of the predacious deuteromycete, Arthrobotrys oligospora, are reported. The structures were elucidated by means of high resolution mass and high field N M R spectroscopy. The compounds exhibited weak antimicro bial, cytotoxic and hemolytic effects, but were not active towards the nematode Caenorhabditis elegans. Other Arthrobotrys species were also found to produce these or similar compounds.

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“…Aureothin, isolated from S. spectabilis , features a α-pyrone with a tetrahydrofuran-containing aryl polyene side chain and has displayed significant anti-fungal and anti-proliferative activity (Werneberg et al, 2010). The neofusapyrones and dactylfungins are pyrone-containing polyketides isolated from fungi with antifungal activity (Honma et al, 2010; Xaio et al, 1993). The structures of the yoshipyrones, kalkipyrone analogs from a field-collected Leptolyngbya sp., have recently been characterized and yoshipyrone A was shown to inhibit adipogenic differentiation in 3T3-L1 cells (Inuzuka et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

Kalkipyrone B, a marine cyanobacterial γ-pyrone possessing cytotoxic and anti-fungal activities

et al. 2016

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Bioassay-guided fractionation of two marine cyanobacterial extracts using the H-460 human lung cancer cell line and the OVC-5 human ovarian cancer cell line led to the isolation of three related α-methoxy-β, β’-dimethyl-γ-pyrones each containing a modified alkyl chain, one of which was identified as the previously reported kalkipyrone and designated kalkipyrone A. The second compound was an analog designated kalkipyrone B. The third was identified as the recently reported yoshipyrone A, also isolated from a marine cyanobacterium. Kalkipyrone A and B were obtained from a field-collection of the cyanobacterium Leptolyngbya sp. from Fagasa Bay, American Samoa, while yoshipyrone A was isolated from a field-collection of cyanobacteria (cf. Schizothrix sp.) from Panama. One-dimensional and two-dimensional NMR experiments were used to determine the overall structures and relative configurations of the kalkipyrones, and the absolute configuration of kalkipyrone B was determined by 1H NMR analysis of diastereomeric Mosher’s esters. Kalkipyrone A showed good cytotoxicity to H-460 human lung cancer cells (EC50 = 0.9 µM), w M), while kalkipyrone B and yoshipyrone A were less active (EC50 = 9.0 µM and > 10 µM, respectively). Both kalkipyrone A and B showed moderate toxicity to Saccharomyces cerevisiae ABC16-Monster strain (IC50 = 14.6 and 13.4 µM, respectively), whereas yoshipyrone A was of low toxicity to this yeast strain (IC50 = 63.8 µM).

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Dactylfungins, novel antifungal antibiotics produced by Dactylaria parvispora.

Cited by 17 publications

References 8 publications

Isolation and Structure Elucidation of Neofusapyrone from a Marine-derived Fusarium species, and Structural Revision of Fusapyrone and Deoxyfusapyrone

Isolation and Structure Elucidation of Neofusapyrone from a Marine-derived Fusarium species, and Structural Revision of Fusapyrone and Deoxyfusapyrone

New Biologically Active Compounds from the Nematode-Trappmg Fungus Arthrobotrys oligospora Fresen

Kalkipyrone B, a marine cyanobacterial γ-pyrone possessing cytotoxic and anti-fungal activities

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