Galbonolides A and B - Two non-glycosidic antifungal macrolides.

Fauth, U.; Zähner, Hans; Mühlenfeld, Andreas; Achenbach, Hans

doi:10.7164/antibiotics.39.1760

Cited by 37 publications

(28 citation statements)

References 4 publications

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“…S. galbus and C. neoformans were maintained on GYM plates (0.4% glucose, 0.4% yeast extract, 1% malt extract, 0.2% calcium carbonate, and 2% Bacto agar) at 30°C. For GAL production, the preculture of S. galbus was grown at 28°C with vigorous shaking in GAL production medium, which contained 0.8% glucose, 0.4% yeast extract, 1% malt extract, and 1 mM L-isoleucine (13). After 3 days, the production culture was initiated in GAL production medium, with 1 ⁄ 10 volume of inoculum from the preculture, and maintained for 48 h at the same condition.…”

Section: Methodsmentioning

confidence: 99%

“…In proton-decoupled 13 C NMR measurements, 13 C-13 C coupling is represented by doublet splitting surrounding the cognate natural abundance 13 C signal. Intact incorporation of [U- 13 C]propionate was evident in GAL-A and -B as judged by 13 C-13 C coupling, especially at the position originating from C-1 and C-3 of [U- 13 C]propionate. The positions originating from C-2 of [U- 13 C]propionate formed multiple splits due to tandem coupling.…”

Section: Gene Inactivation Of Galb -C and -D And The Identificationmentioning

confidence: 99%

“…[U- 13 C]Propionate Feeding Experiment and 13 C Incorporation in GAL-A and -B-To determine whether GalA-E are involved in the biosynthesis of a special, yet unidentified, precursor unit [U- 13 C]propionate was fed to WT cultures, and the propionate incorporation in GAL-A and GAL-B was examined by NMR analysis (Fig. 5 and Table 3).…”

Section: Gene Inactivation Of Galb -C and -D And The Identificationmentioning

confidence: 99%

“…The preparation of 13 C-enriched GAL-A and -B was performed by feeding 80 mg of [U- 13 C 3 ] sodium propionate ( 13 C 3 , 99%; Cambridge Isotope Laboratories) to the 1.6-liter culture of the wild-type S. galbus (WT). The methanol cell extract and the ethyl acetate supernatant extract were combined, dried under the reduced pressure, and dissolved in methanol for the HPLC preparation as described for the isolation of GAL-C. One-and two-dimensional NMR analysis of GAL-A and -B was conducted in CD 3 OD with the 600-MHz Bruker AVANCE 600 NMR, as previously described for GAL-C. Heteronuclear single quantum coherence and heteronuclear multiple bond correlation data were used to identify 13 C chemical shifts for each carbon atom in GAL-A and -B.…”

Section: Isolation Of Gals and Nuclear Magnetic Resonance (Nmr) Measumentioning

confidence: 99%

“…The methanol cell extract and the ethyl acetate supernatant extract were combined, dried under the reduced pressure, and dissolved in methanol for the HPLC preparation as described for the isolation of GAL-C. One-and two-dimensional NMR analysis of GAL-A and -B was conducted in CD 3 OD with the 600-MHz Bruker AVANCE 600 NMR, as previously described for GAL-C. Heteronuclear single quantum coherence and heteronuclear multiple bond correlation data were used to identify 13 C chemical shifts for each carbon atom in GAL-A and -B. 13 C-13 C coupling was determined to deduce the intact incorporation of [ 13 C 3 ]propionate in GAL-A and -B.…”

Section: Isolation Of Gals and Nuclear Magnetic Resonance (Nmr) Measumentioning

confidence: 99%

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A Single Module Type I Polyketide Synthase Directs de Novo Macrolactone Biogenesis during Galbonolide Biosynthesis in Streptomyces galbus

Kim

Karki

Kwon

et al. 2014

Journal of Biological Chemistry

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Section: Methodsmentioning

confidence: 99%

Section: Gene Inactivation Of Galb -C and -D And The Identificationmentioning

confidence: 99%

Section: Gene Inactivation Of Galb -C and -D And The Identificationmentioning

confidence: 99%

Section: Isolation Of Gals and Nuclear Magnetic Resonance (Nmr) Measumentioning

confidence: 99%

Section: Isolation Of Gals and Nuclear Magnetic Resonance (Nmr) Measumentioning

confidence: 99%

See 3 more Smart Citations

A Single Module Type I Polyketide Synthase Directs de Novo Macrolactone Biogenesis during Galbonolide Biosynthesis in Streptomyces galbus

Kim

Karki

Kwon

et al. 2014

Journal of Biological Chemistry

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Stoffwechselprodukte von Mikroorganismen, 35. Mitt. Asperdurin, ein neues antimykotisches Phthalid aus Aspergillus duricaulis

Mühlenfeld

Achenbach

1988

Archiv der Pharmazie

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Aus Fermentationsextrakten von Aspergillus duricaulis wurde das neue Phthalid Asperdurin (4) isoliert und in seiner Struktur aufgeklart, 4 zeigt ausgepragte antifungische Wirksamkeit. Metabolites of Microorganisms, XXXV'): Asperdurin, a Novel Antimycotic Phthalide from ApergiZZus dru&auZisFrom fermentation extracts of Aspergillus duricaulis the novel phthalide asperdurin (4) was isolated and its structure elucidated. 4 exhibits significant antifungal activity.Kulturen von Aspergillus duricaulis (Tu 679) zeichnen sich durch signifikante antibakterielle Wirkung aus, als deren Trager Cyclopaldsaure (1)2,3) und ihr 5-0-Prenylether (2)49 5 ) erkannt wurden.

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In Vitro Reconstitution of a PKS Pathway for the Biosynthesis of Galbonolides in Streptomyces sp. LZ35

Liu

Zhu

et al. 2015

ChemBioChem

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The galbonolides are 14-membered macrolide antibiotics with a macrocyclic backbone similar to that of erythromycins. Galbonolides exhibit broad-spectrum antifungal activities. Retro-biosynthetic analysis suggests that the backbone of galbonolides is assembled by a type I modular polyketide synthase (PKS). Unexpectedly, the galbonolide biosynthetic gene cluster, gbn, in Streptomyces sp. LZ35 encodes a hybrid fatty acid synthase (FAS)-PKS pathway. In vitro reconstitution revealed the functions of GbnA (an AT-ACP didomain protein), GbnC (a FabH-like enzyme), and GbnB (a novel multidomain PKS module without AT and ACP domains) responsible for assembling the backbone of galbonolides, respectively. To our knowledge, this study is the first biochemical characterization of a hybrid FAS-PKS pathway for the biosynthesis of 14-membered macrolides. The identification of this pathway provides insights into the evolution of PKSs and could facilitate the design of modular pools for synthetic biology.

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Galbonolides A and B - Two non-glycosidic antifungal macrolides.

Cited by 37 publications

References 4 publications

A Single Module Type I Polyketide Synthase Directs de Novo Macrolactone Biogenesis during Galbonolide Biosynthesis in Streptomyces galbus

A Single Module Type I Polyketide Synthase Directs de Novo Macrolactone Biogenesis during Galbonolide Biosynthesis in Streptomyces galbus

Stoffwechselprodukte von Mikroorganismen, 35. Mitt. Asperdurin, ein neues antimykotisches Phthalid aus Aspergillus duricaulis

In Vitro Reconstitution of a PKS Pathway for the Biosynthesis of Galbonolides in Streptomyces sp. LZ35

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