A new antimicrobial polyketide glycoside (1) and three known compounds, gilvocarcins H (2), V (3) and M (4) were isolated from the ethyl acetate extract of Streptomyces sp. QD01-2. The structure of (1) was established by spectroscopic analysis, X-ray single crystal diffraction and CD spectra. The new compound (1) showed potent antimicrobial activities against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Candida albicans, with MIC values of 0.5-5.0 mM. Compound (1) also showed weak cytotoxicity against the MCF-7, K562 and P388 cell lines, with IC 50 values of 36, 39 and 45 mM, respectively. The results showed that the vinyl side chain helps to increase the cytotoxicity and antimicrobial activities of gilvocarcin-type glycosides. In addition, the NMR data of gilvocarcin H (2) were also reported for the first time. Keywords: antimicrobial activity; cytotoxicity; gilvocarcin HE; polyketide glycoside; Streptomyces INTRODUCTION Producing 13 000 bioactive metabolites described, cultured bacteria have been a prolific resource for drug discovery. 1 About 70% of these bioactive compounds have been isolated from cultured actinomycetes. 2 Among them, polyketide metabolites represent a major source for novel chemotherapeutics. 3 A particularly promising lead structure is gilvocarcin V (3), the prototype of a family of benzo[d]naphtha[1,2-b]pyran-6-one glycosides from Streptomyces spp. [4][5][6][7][8] Members of this family generally exhibit high antimicrobial and antitumor activities. 9 Structurally these gilvocarcintype polyketide glycosides differ in the nature of the sugar moiety and the side chain at C-8. [10][11][12][13][14] As part of our ongoing search for bioactive secondary metabolites from actinomycetes, 15-17 strain Streptomyces sp. QD01-2 was isolated from the 3-m-deep soil collected at Huiquan Square near Qingdao First Beach, China. Its secondary metabolites showed antibacterial activity against Staphylococcus aureus at a concentration of 100 mg ml -1 . And a series of peaks with the similar UV absorptions to those of gilvocarcin-type polyketide glycosides [4][5][6][7][8] were observed at l max 242, 274, 314 and 386 nm in the HPLC-UV profile (Supplementary Figure S7). Chemical investigation resulted in the isolation of a new gilvocarcin, gilvocarcin HE (1), along with the known gilvocarcins H (2), 18 V (3), 5 and M (4) (Figure 1). 5 New compound (1) displayed significant antimicrobial activities against S. aureus, Escherichia coli, Bacillus subtilis and Candida albicans, with MIC values of 0.5, 2.8, 5.0 and 3.6 mM, respectively. It also showed cytotoxicity against the MCF-7, K562 and P388 cell lines, with IC 50 values of 36, 39 and 45 mM, respectively.
Two new pyran-2-ones, nocardiopyrones A and B (1 and 2, resp.), along with four known compounds, pyridinols 3-5, and 1-acetyl-β-carboline (6) were isolated from the alkalophilic actinomycete Nocardiopsis alkaliphila sp. nov. YIM-80379. Their structures were established on the basis of spectroscopic analysis, CD spectra, and the quantum-chemical ECD calculation. Pyridinols 3-5 were isolated from a natural source for the first time. Compounds 1 and 2 showed weak antibacterial activities against Pseudomonas aeruginosa, Enterobacter aerogenes, and Escherichia coli with MIC values of 20-48 μM. Compound 2 showed weak antimicrobial activities against Candida albicans and Staphylococcus aureus with MIC values of 24 and 48 μM, respectively.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
hi@scite.ai
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.