BE-24566B, a New Antibiotic Produced by Streptomyces violaceusniger.

Abstract

In the course of our screening program for new antibacterial compounds, a strain A24566 isolated from a lichen collected at Jyogasaki, Shizuoka prefecture, Japan, was found to produce a potent antibiotic. This compound, BE-24566B (1), was isolated from the mycelial cake of cultural broth, and was shown to have the unique structure in Fig. 1 Characterization of the strain followed the method adopted by the International Streptomyces Project (ISP)1}. The strain A24566 formed well developed and branching substrate mycelia and aerial mycelia, but fragmentation of the substrate mycelia was not observed. The whole cell hydrolysate contained L,L-diaminopimelic acid. The spore chains of the strain were spirals and the spore surface was rugose. The spore mass was gray, becoming black and moist with maturity.Melanoid pigments and soluble pigments were absent. Utilization of carbon sources was examined according to the method of Pridham and Gottlieb2) on the agar medium culture at 28°C for 14 days. D-glucose, D-xylose, L-arabinose, L-rhamnose, D-fructose, raffinose, sucrose and D-galactose were utilized for growth. Utilization of inositol was doutful and salicin was not utilized by the The strain A24566, cultured on a slant agar medium, was inoculated into four 500-ml volume Erlenmeyer flasks which contained 110ml of a culture medium comprising 0.2% glucose, 2.0% dextrin, 0.5% meat meal, 0.5% degreased rice bran, 0.2% degreased meat bone powder, 0.1% dry yeast, 0.05% magnesium sulfate, 0.05% sodium bromide, 0.5% sodium chloride, 0.1% potassium hydrogen phosphate, 0.002% calcium chlo- hours. Twoml each of the culture broth was inoculated into 100 of 500-ml volume Erlenmeyer flasks containing 110ml of the foregoing culture medium and placed on a rotary shaker (180rpm) at 28°C for 120hours. The broth (ca. 1 1 liters) so obtained was filtered to give mycelium. Methanol (8 liters) was added to the resulting mycelium and stirred at room temperature for 30 minutes, then the mycelium was filtered yielding the methanol extract. The methanol extract was concentrated to about 1 liter under reduced pressure and then 1.5 liters of ethyl acetate was added for extraction. Fresh ethyl acetate (0.7liter) was added to the resulting aqueous layer to perform second extraction and the ethyl acetate extracts were combined. The extract was washed twice with water (1 literx2) and then concentrated under reduced pressure. To the resulting residue 240ml of methanol and 400ml of n-hexane were added and the methanol layer was separated. To the n-hexane layer 50ml of methanol was added and methanol layer was separated. The two methanol layers were combinedand evaporated under reduced pressure. The resulting residue was dissolved with 200ml of chloroform and applied to a column of silica gel (3x38cm) and the column was developed with solvent mixture (chloroform -meth-

Antibacterial, Antifungal and Anticancer Activities of Compounds Produced by Newly Isolated Streptomyces Strains from the Szczelina Chochołowska Cave (Tatra Mountains, Poland)

“…It seems that anthrabenzoxocinone compounds might be of special interest among substances isolated from Streptomyces strains. Early studies on Streptomyces violaceusniger, isolated in Japan, led to discovery of a potent anthrabenzoxocinone derivative, named BE-24566B, which might be used against MRSA [28]. Two such compounds were then isolated from Streptomyces sp.…”

Development of a Cross‐Conjugated Vinylogous [4+2] Anionic Annulation and Application to the Total Synthesis of Natural Antibiotic (±)‐ABX

“…Without purification, the mixture was further deprotected through hydrogenolysis under catalysis with Pd/C to accomplish the desired target, in racemic form, in 65 % yield over 2 steps. The 1 H NMR, 13 C NMR, and mass spectral data obtained for the synthetic (±)‐ABX, whose structure is further unambiguously confirmed by an X‐ray crystallographic analysis, are in good agreement with those reported for the naturally occurring product …”

Toxicity and antiviral activity of cinnabarin obtained from Pycnoporus sanguineus (Fr.) Murr

“…The results found in the literature for LD 50% in animal models are extremely varied. Kojiri et al (1995) obtained a LD 50% for substance BE-24566B, isolated from Streptomyces violaceusniger, of 100 mg/ml. However, Nakagawa et al (1987) observed that the compound BO-1236, in doses of 2.201 mg/ml, was lethal in 50% of the inoculated animals.…”