6-Deoxy-8-O-methylrabelomycin and 8-O-methylrabelomycin from a Streptomyces species.

Abstract

In the course of our screening for new antibiotic, newmembersof benz[a]anthraquinone antibiotics (I and II), which showed antibacterial activity against Gram-positive bacteria were isolated from a culture broth of Streptomyces tsusimaensis MI310-38F7. This strain produced nonactin and a minor yellow compound (III) which was identical with X-14881 E1}. This report describes the isolation, characterization and structure determination of these compounds, named 6-deoxy-8-0-methylrabelomycin (I) and 8-0-methylrabelomycin (II).

Search Method for Inhibitors of Staphyloxanthin Production by Methicillin-Resistant Staphylococcus aureus

“…Five structurally related compounds were isolated from the culture broth and identified as known anthraquinones, 1 to 5. [16][17][18][19] Among them, 4 and 5 were found to show dose-dependent white zones (9, 11 mm for 4 and 18, 26 mm for 5) at 5.0 and 10 μg/disk, respectively (Table 3). Thus, 5 exhibited potent inhibition of yellow pigment production with this assay, but also showed growth inhibition at 10 μg/disk.…”

“…Staphyloxanthin consists of a polyprenyl moiety, a sugar moiety and an acyl moiety; therefore, it seems reasonable that these inhibitors of lipid metabolism were selected as showing a white zone in the paper disk method, since they inhibited the steps of polyprenyl and acyl residue production in the staphyloxanthin structure. Two anthraquinones, originally reported as antibiotics, 18,19) were found to inhibit production of yellow pigment in MRSA. In particular, 4 has high selectivity in the inhibition of yellow pigment production (Table 4).…”

“…Moreover, five anthraquinones, SM-196B (1), 16) 1-deoxo-1-hydroxy-8-O-methylrabelomycin (2), 17) 8-O-methylrabelomycin (3), 18) 6-deoxy-8-O-methylrabelomycin (4) 18) and tetrangomycin (5) 19) (Fig. 1), previously reported as antibiotics, [16][17][18][19] were isolated from the culture broth of actinomycete strain Streptomyces badius 4-6. Among them, 4 and 5 showed inhibitory activity of MRSA staphyloxanthin production in the paper disk assay.…”

Antibiotic and Antimalarial Quinones from Fungus-Growing Ant-Associated Pseudonocardia sp.

“…The known compounds 4 and 5 were identified by 1D and 2D NMR spectroscopy, and their structures were confirmed by comparison of their spectroscopic data with the literature values. 12,13 …”

Elmenols C-H, new angucycline derivatives isolated from a culture of Streptomyces sp. IFM 11490

“…The strain was cultured in Waksman medium 16 at 28°C for 3 days on a reciprocal shaker. Working up of the crude extract resulted in the isolation of five new compounds (1-5; Figure 1) along with the known LS1924A (10) 17 , 6-deoxy-8-methylrabelomycin (11) 18 and tetrangulol methyl ether (12). 19 In addition, previously isolated elmonin (7) and elmenols A (8) and B (9) 14 were detected by the LC-MS analysis.…”