Abstract
Two novel quinomycins I (1) and J (3) were discovered by UPLC-MS, then the two novel compounds and five known quinomycins A(2), B(4), E(5), C(6) and monosulfoxide quinomycin (7) were isolated from the culture broth of Streptomyces sp. HCCB11876. The structures of these compounds were elucidated through MS and NMR spectroscopic analysis. Compounds 1–7 showed significant antibacterial and cytotoxic activities. The structure-activity relationship indicated that sulfoxide group in N-methylcysteine of quinomycins (1, 3 and 7) would significantly decrease the antibacterial and cytotoxic activities. Moreover, the antibacterial and cytotoxic activities were decreased with the increase of carbon chain in amino-acid residues.
Log in or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
References
Zhang C, Kong LX, Lei X, Deng ZX You DL. Advance in the Research on Quinomycins Biosynthesis. Chin J Org Chem. 2014;34:1240–52.
Foster BJ, Clagett-Carr K,Shoemaker DD, Suffness M, Plowman J,Trissel LA, et al. Echinomycin: the first bifunctional intercalating agent in clinical trials. Invest New Drug. 1986;3:403–10.
Liu HM, Qin S, Wang YX, Li WJ, Zhang J. Insecticidal action of Quinomycin A from Streptomyces sp. KN-0647, isolated from a forest soil. World J Microb & Biot. 2008;24:2243–8.
Fernández J, Marín L, Álvarez-Alonso R, Redondo S, Carvajal J, Villamizar, G, et al. Biosynthetic modularity rules in the bisintercalator family of antitumor compounds. Mar Drugs. 2014;12:2668–99.
Qin XP, Lin BR, Wang ZZ. Research progress of structure-activity relationship of Quinoxaline antibiotics. Chem Bioeng. 2008;25:1–4.
Bentayeb K,Rubio C, Batlle R, Nerín C. Direct determination of carnosic acid in a new active packaging based on natural extract of rosemary. Anal Bioanal Chem. 2007;389:1989–96.
Rao M, Li QS, Feng L, Xia X, Ruan LG, Sheng XF, et al. A new aminopeptidase inhibitor found by UPLC-MS from Streptomyces strain HCCB10043. Anal Bioanal Chem. 2011;401:699–706.
Shi JJ, Qi CJ, Chen WJ. The revision of 1H 13C-NMR assignments of quinomycin A and C. Chin J Antibiot. 1999;24:258–61.
Dell A, Williams DH, Morris HR, Smith GA, Feeney J, Robert GCK. Structure revision of the antibiotic echinomycin. J Am Chem Soc. 1975;97:2497–502.
Shoji J, Konaka R, Kawano K, Higuchi N, Kyogoku Y. Presence of isomers in quinomycin E. J Antibiot. 1976;29:1246–8.
Huang LX, Xu YW, Kuang YW, Zhang QL. Purification and identification of antitumor secondary metabolites from soil Streptomyces sp.2215. Nat Prod Res Dev. 2009;21:235–8.
Acknowledgements
This work was supported in part by grants from the National Natural Science Foundation of China (No. 81773616), and Biopharmaceutical Industry-Education-Research cooperative base construction project of Shanghai Education Commission (No. A2-3201-18-115001).
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Supplementary information
Rights and permissions
About this article
Cite this article
Yang, Z., Shao, L., Wang, M. et al. Two novel quinomycins discovered by UPLC-MS from Stretomyces sp. HCCB11876. J Antibiot 72, 164–168 (2019). https://doi.org/10.1038/s41429-018-0132-1
Received:
Revised:
Accepted:
Published:
Version of record:
Issue date:
DOI: https://doi.org/10.1038/s41429-018-0132-1
This article is cited by
-
Identification of SARS-CoV-2 3CLpro inhibitors from marine actinomycetes through integrated phylogeny-based metabolomics with functional screening and bioinformatic analysis
Scientific Reports (2025)
-
Quinomycins with an unusual N-methyl-3-methylsulfinyl-alanine residue from a Streptomyces sp
The Journal of Antibiotics (2024)
