Antifungal and Antibacterial Metabolites from a Sclerotium-Colonizing Isolate of Mortierella vinacea

Soman, Ashish G.; Gloer, James B.; Wicklow, Donald T.

doi:10.1021/np980411h

Cited by 44 publications

(44 citation statements)

References 9 publications

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“…These data from the NOE experiment confirmed the relationship between the methine group (C-10, δ C 31.6) and the two methyls (C-11, δ C 20.7; C-12, δ C 20.7) and the attachment overall of the isopropyl group at C-6 ( δ C 139.9). The 1 H and 13 C chemical shifts for the thiomethyl group of 1 were comparable to those reported for 3 [12] and 4 [13]. …”

Section: Resultssupporting

confidence: 78%

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The Isolation of a NewS-Methyl Benzothioate Compound from a Marine-DerivedStreptomycessp.

Mahyudin

Blunt

Cole

et al. 2012

Journal of Biomedicine and Biotechnology

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The application of an HPLC bioactivity profiling/microtiter plate technique in conjunction with microprobe NMR instrumentation and access to the AntiMarin database has led to the isolation of a new 1. In this example, 1 was isolated from a cytotoxic fraction of an extract obtained from marine-derived Streptomyces sp. cultured on Starch Casein Agar (SCA) medium. The 1D and 2D 1H NMR and ESIMS data obtained from 20 μg of compound 1 fully defined the structure. The known 2 was also isolated and readily dereplicated using this approach.

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Section: Resultssupporting

confidence: 78%

“…S. collinus remained the only reported producer of this unusual structural type until a comparable structure, 4 , was identified from a sclerotium-colonizing isolate of the fungus, Mortierella vinacea [13]. The production of 5 was also reported from a marine Streptomyces sp.…”

Section: Introductionmentioning

confidence: 99%

The Isolation of a NewS-Methyl Benzothioate Compound from a Marine-DerivedStreptomycessp.

Mahyudin

Blunt

Cole

et al. 2012

Journal of Biomedicine and Biotechnology

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“…The phenolic hydroxyl 4-OH was placed ortho to the carbonyl substituent C-4′ on the basis of its 1 H NMR chemical shift ( δ H 11.83), as well as the HMBC correlations of its proton to C-3a, C-4, and C-5. Lastly, the presence of a methyl thioester was revealed by HMBC correlations of the S -CH 3 methyl protons ( δ H 2.47) to the carbonyl carbon C-4′ ( δ C 197.7), and the 1 H and 13 C NMR chemical shifts for S -CH 3 ( δ H / δ C 2.47/13.0) which are characteristic of a methyl thiolester group [31,32]. Moreover, the base peak in the EIMS spectrum corresponds to loss of 47 mass units, which is consistent with the expected [M − SCH 3 ] + fragmentation peak [32].…”

Section: Resultsmentioning

confidence: 99%

“…To the best of our knowledge, the presence of a methyl thiolester group is quite rare among secondary metabolites. Two examples resembling compounds 1 and 2 are mortivinacin [31] and resorthiomycin [40,41], which were isolated from Mortierella vinacea and Streptomyces collinus , respectively. The isolated compounds were evaluated for their α-glucosidase inhibitory effects.…”

Section: Discussionmentioning

confidence: 99%

Eurothiocin A and B, Sulfur-Containing Benzofurans from a Soft Coral-Derived Fungus Eurotium rubrum SH-823

et al. 2014

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Two new sulfur-containing benzofuran derivatives, eurothiocin A and B (1 and 2), along with five known compounds, zinniol (3), butyrolactone I (4), aspernolide D (5), vermistatin (6), and methoxyvermistatin (7), were isolated from the cultures of Eurotium rubrum SH-823, a fungus obtained from a Sarcophyton sp. soft coral collected from the South China Sea. The new compounds (1 and 2) share a methyl thiolester moiety, which is quite rare among natural secondary metabolites. The structures of these metabolites were assigned on the basis of detailed spectroscopic analysis. The absolute configurations of 1 and 2 were determined by comparison of the experimental and calculated electronic circular dichroism (ECD) data. Compounds 1 and 2 exhibited more potent inhibitory effects against α-glucosidase activity than the clinical α-glucosidase inhibitor acarbose. Further mechanistic analysis showed that both of them exhibited competitive inhibition characteristics.

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“…This leaves only one oxygen atom which must connect to both C-2 and C-9 to form the remaining ring. Although no HMBC correlations between H 2 -2 and C-9 or between H-9 and C-2 were observed using acetone-d 6 as the solvent, a weak correlation was observed between H-2α and C-9 when the data were recorded using CD 3 OD. Four-bond correlations of H-5 and H-6 to C-2 and C-9, respectively, were also observed, and are most likely if C-2 and C-9 are connected to C-3 and C-8, respectively.…”

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confidence: 80%

Phaeofurans and Sorbicillin Analogues from a FungicolousPhaeoacremoniumSpecies (NRRL 32148)

2006

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Two new benzofuran-derived metabolites of polyketide origin called phaeofurans A and B (1-2), along with three sorbicillin analogs (3-5) have been obtained from a fungicolous isolate of the genus Phaeoacremonium (NRRL 32148). The structures were determined by analysis of MS and 2D NMR data. The antifungal effects of the extract were ascribed to the sorbicillin analogs.Previous chemical studies of mycoparasites and fungicolous fungi that attack the nutrient-rich stromata of wood-decay fungi have yielded novel metabolites with antifungal effects and other biological activities. 1-6 As part of our ongoing studies of these types of fungi, chemical investigations of a culture identified as Phaeoacremonium sp. (Incertae sedis; NRRL 32148) isolated from field-collected stromata of Hypoxylon truncatum (Xylariaceae) produced two new polyketides named phaeofurans A and B (1-2) and three sorbicillin analogs (3-5), two of which have not been previously reported. Details of the isolation and structure determination of these compounds are presented here. Results and discussionSolid-substrate fermentation cultures of a Phaeoacremonium species grown on rice were extracted with ethyl acetate. The resulting extract showed antifungal activity against Aspergillus flavus and Fusarium verticillioides, and was partitioned between acetonitrile and hexane to yield an acetonitrile-soluble mixture that was subsequently fractionated over Sephadex LH-20. Active fractions were subjected to silica gel flash chromatography and/or reversed phase HPLC to yield compounds 1-5.Phaeofuran A (1) was isolated as a white film that formed fine needles upon evaporation of an acetone solution. The formula of 1 was tentatively assigned as CgHgCX based on analysis of EIMS (apparent M + at m/z 168) and NMR data ( Table 1). The intensities of the EIMS M + ion and the ESIMS M+H ion proved to be insufficient for obtaining high resolution MS data, but the NMR data suggested the presence of two exchangeable protons in the molecule, so a diacetate derivative of 1 was prepared. With five unsaturations, four olefinic or aromatic sp 2 carbon atoms (two of them protonated), four oxygenated sp 3 methines, and no carbonyl carbons, phaeofuran A (1) must contain three rings, two double bonds, and two OH groups. In addition, observation of four pairs of signals with very similar 13 C NMR chemical shifts (Table 1) suggested a pseudo-symmetrical structure. The NMR shifts for two of the oxymethine units (δ C 55.9 and 55.5/δ H 3.40 and 3.38) were diagnostic for the presence of a 1,2-disubstituted epoxide. Each of the epoxide protons was coupled to one of the other two oxymethines with a small J-value, enabling construction of a substructure corresponding to the C4-C7 unit in 1. The same unit was evident in the 1 H NMR spectrum of the diacetate, except that the signals for the oxymethine protons at C-4 and C-7 were downfield shifted from δ 5.05/5.06 to δ 6.12/6.18. The remaining two 1 H NMR signals in the spectrum of 1 corresponded to olefinic/aromatic protons that show...

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Antifungal and Antibacterial Metabolites from a Sclerotium-Colonizing Isolate of Mortierella vinacea

Cited by 44 publications

References 9 publications

The Isolation of a NewS-Methyl Benzothioate Compound from a Marine-DerivedStreptomycessp.

The Isolation of a NewS-Methyl Benzothioate Compound from a Marine-DerivedStreptomycessp.

Eurothiocin A and B, Sulfur-Containing Benzofurans from a Soft Coral-Derived Fungus Eurotium rubrum SH-823

Phaeofurans and Sorbicillin Analogues from a FungicolousPhaeoacremoniumSpecies (NRRL 32148)

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