Conglobatin, a novel macrolide dilactone from Streptomyces conglobatus ATCC 31005.

Abstract

Fermentationof deposited cultures of Streptomyces conglobatus, known to produce the polyether antibiotic, ionomycin has resulted in the isolation and characterization of a second metabolite, conglobatin (C28H33N2O6). X-Ray analysis revealed a dimeric macrolide dilactone structure for conglobatin, similar to the structures of the mold metabolites vermiculin and pyrenophorin, from which the absolute configuration of conglobatin has been inferred. The dimer consists of two molecules of 7-hydroxy-8-oxazoyl-2,4,6-trimethyl-2-octenoic acid joined by two ester linkages.

FW-04-806 inhibits proliferation and induces apoptosis in human breast cancer cells by binding to N-terminus of Hsp90 and disrupting Hsp90-Cdc37 complex formation

“…FW-04-806, extracted from the China-native Streptomyces FIM-04-806 [14], is identical in structure to Conglobatin [15] according to ultraviolet spectra, infrared spectra, and NMR ( 1 H and 13 C) data and single-crystal X-ray diffraction data [16]. Cell proliferation assays have shown that FW-04-806 inhibits the growth of a human chronic myelocytic leukemia K562 cell line with an IC 50 of 6.66 μg/mL (almost 10 μM) [16].…”

“…Cell proliferation assays have shown that FW-04-806 inhibits the growth of a human chronic myelocytic leukemia K562 cell line with an IC 50 of 6.66 μg/mL (almost 10 μM) [16]. Conglobatin has been reported to be non-toxic at doses up to 1 g/kg when administered to mice either orally or interperitoneally [15]. In addition, our acute toxicity test showed that mice survived after oral administration of 900 mg/kg of FW-04-806.…”

Panowamycins A and B, new antitrypanosomal isochromans produced by Streptomyces sp. K07-0010

“…[3][4][5] Our ongoing studies have led to the discovery of two novel NFAT-133 analogs, panowamycins A (1) and B (2) isolated from a culture broth of Streptomyces sp. K07-0010, along with NFAT-133 (3), 6 conglobatin (4), 7 piericidins C 1 -C 4 (5-8) 8 and dinactin (11) 9 ( Figure 1). In this paper, the taxonomy of the producing strain, fermentation, isolation, physicochemical properties and structure elucidation of 1 and 2, and antitrypanosomal activities of isolated compounds are described.…”

Secondary Metabolites by Chemical Screening. 30. Helmidiol, a New Macrodiolide from Alternaria alternata

“…Whereas vermiculin exhibits an exocyclic ketopropyl side chain, an oxazole side chain is to be found in conglobatin, 11 isolated from Streptomyces conglobatus. However, 16-membered dilactones of the helmidiol type are found in pyrenophorin 9 isolated from the phytopathogen fungus Pyrenophora avenae and vermiculin 10 from Penicillium vermiculatum, which bears a keto group at C-4 (1: OH-4).…”