Structure determination of oligomycins A and C

Carter, Guy T.

doi:10.1021/jo00372a030

Cited by 48 publications

(20 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the 1 H-and 13 C-NMR spectra, similar signal patterns were observed between compound I and oligomycin A, or compound II and oligomycin C (Carter 1986;Kim et al 1999;Kobayashi et al 1987;Masamune et al 1958;Morris et al 1985;Szilágyi and Fehér 1998;von Gelehn et al 1972;Wagenaar et al 2007). The comparison of the 13 C-NMR data of compound I (column 1) and oligomycin A (3), or compound II (2) and oligomycin C (4) ( Table II) showed the identity of compound I with oligomycin A and of II with oligomycin C (Fig.…”

Section: Resultssupporting

confidence: 56%

Oligomycins A and C, major secondary metabolites isolated from the newly isolated strain Streptomyces diastaticus

Zhao

Zhu

et al. 2010

Folia Microbiol

View full text Add to dashboard Cite

During the screening program for fungicides, one actinomycete strain ECO 00047 was isolated with the potential activity against fungus. According to the morphology and analysis of the nucleotide sequence of the 16S rRNA gene (1500 bp) this isolate was identified as Streptomyces diastaticus. The active compounds were separated by silica gel column chromatography, Sephadex LH-20 gel filtration and then purified by flash chromatography on C18 (20-45 microm). The chemical structure of the bioactive compounds I and II were elucidated, based on the spectroscopic data of MS, IR, UV, 1H-NMR, 13C-NMR and X-ray single crystal diffraction analysis. Compounds I and II were identical with oligomycins A and C, the macrolide antibiotics which have been known to be produced by Streptomyces diastatochromogenes, S. libani and S. avermitilis. The two compounds exhibited a strong activity against Aspergillus niger, Alternaria alternata, Botrytis cinerea and Phytophthora capsici but no activity toward bacteria. Although the two above antibiotics were known, their isolation has so far not been reported from S. diastaticus.

show abstract

Section: Resultssupporting

confidence: 56%

Oligomycins A and C, major secondary metabolites isolated from the newly isolated strain Streptomyces diastaticus

Zhao

Zhu

et al. 2010

Folia Microbiol

View full text Add to dashboard Cite

show abstract

“…12 The structures for 2 and 4 inclusive of relative configurations were subsequently assigned by single-crystal X-ray analysis in 1972 13 and 1978, 14 with absolute configurations confirmed by enantiospecific synthesis in 1993 15 and 1990, 16 respectively. Structures were assigned to 1 and 3 in 1986 based on spectroscopic analysis and correlation of base degradation products with 2 , 17 with ab initio 1 H and 13 C NMR assignments reported in 1985 for 1 , 18 and in 1998 for 2 and 3 , 19 and X-Ray analyses (inclusive of absolute configurations) reported for 2 in 2008 20 and 3 in 2010. 21 Oligomycin E ( 5 ) was reported in 1987 from Streptomyces sp.…”

Section: Introductionmentioning

confidence: 99%

Oligomycins as inhibitors of K-Ras plasma membrane localisation

et al. 2016

View full text Add to dashboard Cite

Frequently present in pancreatic, colorectal and non-small cell lung carcinomas, oncogenic mutant K-Ras must be localised to the plasma membrane (PM) to be functional. Inhibitors of K-Ras PM localisation are therefore putative cancer chemotherapeutics. By screening a microbial extract library in a high content cell-based assay we detected the rare oligomycin class of Streptomyces polyketides as inhibitors of K-Ras PM localisation. Cultivation and fractionation of three unique oligomycin producing Streptomyces strains yielded oligomycins A–E (1–5) and 21-hydroxy-oligomycin A (6), together with the new 21-hydroxy-oligomycin C (7) and 40-hydroxy-oligomycin B (8). Structures for 1–8 were assigned by detailed spectroscopic analysis. Cancer cell viability screening confirmed 1–8 were cytotoxic to human colorectal carcinoma cells (IC50 >3 μM), and were inhibitors of the ABC transporter efflux pump P-glycoprotein (P-gp), with 5 being comparable in potency to the positive control verapamil. Significantly, oligomycins 1–8 proved to be exceptionally potent inhibitors of K-Ras PM localisation (Emax 0.67–0.75 with an IC50 ~1.5–14 nM).

show abstract

“…Spectral parameters of these compounds were compared with those of oligomycin A obtained in this study and with literature data (Table 1). 8,13,14 To elucidate the structures of novel derivatives, their 15 N-labeled analogs 15 N-2 and 15 N-3 were synthesized with the use of 15 N-hydroxyl amine or 1-15 N-aminopyridine, respectively. For the 15 N-labeled compounds, 1-D ( 1 H and 13 C) spectra were measured and the coupling constants J 15N,1H and J 15N,13C were determined (Table 2).…”

Section: Resultsmentioning

confidence: 99%

The first examples of chemical modification of oligomycin A

et al. 2009

View full text Add to dashboard Cite

The first examples of chemical modification of antibiotic oligomycin A are described. The interaction of oligomycin A with hydroxylamine yielded six-membered nitrone annelated with the antibiotic at the positions 3,4,5,6,7. The reaction with 1-aminopyridinium iodide in pyridine led to pyrazolo[1,5-a]pyridine conjugated with the antibiotic at the positions 2 and 3 (product of addition to the C 2 -C 3 double bond followed by spontaneous oxidation). The structures of the compounds obtained were supported by NMR and mass spectrometry methods including the 15 N-labeling of compounds.

show abstract

Structure determination of oligomycins A and C

Cited by 48 publications

References 3 publications

Oligomycins A and C, major secondary metabolites isolated from the newly isolated strain Streptomyces diastaticus

Oligomycins A and C, major secondary metabolites isolated from the newly isolated strain Streptomyces diastaticus

Oligomycins as inhibitors of K-Ras plasma membrane localisation

The first examples of chemical modification of oligomycin A

Contact Info

Product

Resources

About