Three new 12-carbamoylated streptothricins from Streptomyces sp. I08A 1776
- PMID: 22939698
- DOI: 10.1016/j.bmcl.2012.08.003
Three new 12-carbamoylated streptothricins from Streptomyces sp. I08A 1776
Abstract
Two new streptothricins (1 and 2) and a new streptothricin acid derivative (3), all with the carbamoyl group substituted at C-12 of the gulosamine moiety, together with the known N(β)-acetylstreptothricin D acid (4), have been isolated from the culture broth of Streptomyces sp. I08A 1776. The structures of the new compounds were determined by MS, CD, and 1D and 2D NMR spectroscopic data analysis. The isolated compounds were evaluated for antibacterial and antifungal activities. Streptothricin E (6) showed potent activity against the clinically isolated extensively drug-resistant Mycobacterium tuberculosis with MIC values of 0.25-0.5μg/mL.
Copyright © 2012 Elsevier Ltd. All rights reserved.
Similar articles
-
Streptothricin derivatives from Streptomyces sp. I08A 1776.J Nat Prod. 2011 May 27;74(5):1142-7. doi: 10.1021/np2000733. Epub 2011 Apr 21. J Nat Prod. 2011. PMID: 21510638
-
Two streptothricins with a cis-streptolidine lactam moiety from Streptomyces sp. I08A 1776.J Antibiot (Tokyo). 2012 Oct;65(10):513-6. doi: 10.1038/ja.2012.55. Epub 2012 Jul 11. J Antibiot (Tokyo). 2012. PMID: 22781281
-
Two new members of streptothricin class antibiotics from Streptomyces qinlingensis sp. nov.J Antibiot (Tokyo). 2007 Dec;60(12):739-44. doi: 10.1038/ja.2007.96. J Antibiot (Tokyo). 2007. PMID: 18276997
-
[Progress in streptothricin antibiotics - A review].Wei Sheng Wu Xue Bao. 2016 Mar 4;56(3):363-72. Wei Sheng Wu Xue Bao. 2016. PMID: 27382780 Review. Chinese.
-
Bromopyrrole Alkaloids from Okinawan Marine Sponges Agelas spp.Chem Pharm Bull (Tokyo). 2016;64(7):691-4. doi: 10.1248/cpb.c16-00245. Chem Pharm Bull (Tokyo). 2016. PMID: 27373625 Review.
Cited by
-
Streptothricin F is a bactericidal antibiotic effective against highly drug-resistant gram-negative bacteria that interacts with the 30S subunit of the 70S ribosome.PLoS Biol. 2023 May 16;21(5):e3002091. doi: 10.1371/journal.pbio.3002091. eCollection 2023 May. PLoS Biol. 2023. PMID: 37192172 Free PMC article.
-
Glycal Metallanitrenes for 2-Amino Sugar Synthesis: Amidoglycosylation of Gulal-, Allal-, Glucal-, and Galactal 3-Carbamates.J Org Chem. 2018 Aug 3;83(15):8054-8080. doi: 10.1021/acs.joc.8b00893. Epub 2018 Jul 6. J Org Chem. 2018. PMID: 29979042 Free PMC article.
-
Harnessing Actinobacteria secondary metabolites for tuberculosis drug discovery: Historical trends, current status and future outlooks.Nat Prod Bioprospect. 2025 Aug 11;15(1):52. doi: 10.1007/s13659-025-00533-8. Nat Prod Bioprospect. 2025. PMID: 40788464 Free PMC article. Review.
-
The convergent total synthesis and antibacterial profile of the natural product streptothricin F.Chem Sci. 2022 Feb 25;13(12):3447-3453. doi: 10.1039/d1sc06445b. eCollection 2022 Mar 24. Chem Sci. 2022. PMID: 35432870 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Medical