Abstract
Two new glycosylated piericidins, glucopiericidinol A3 (1) and 7-demethyl-glucopiericidin A (2), along with four known analogs were isolated from the culture broth of Streptomyces sp. KIB-H1083. The chemical structures of new compounds were elucidated by spectroscopic analyses. Their cytotoxicity on HL-60, SMMC-772, A-549, MCF-7, and SW480 cell lines, as well as antimicrobial activities was evaluated. The results showed that glucopiericidin A (4) has potent cytotoxicity against HL-60, SMMC-772, A-549, and MCF-7 cell lines with IC50 values of 0.34, 0.65, 0.60, and 0.50 μm, respectively. For the antimicrobial activity, piericidin A (6) showed most powerful inhibitory activities against Xanthomonas oryzae pv. oryzicola, and Penicillium decumbens.
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
Solecka J, Zajko J, Postek M, Rajnisz A. Biologically active secondary metabolites from Actinomycetes. Open Life Sci. 2012;7:373–90.
Demain AL, Sanchez S. Microbial drug discovery: 80 years of progress. J Antibiot. 2009;62:5–16.
Demain AL. Importance of microbial natural products and the need to revitalize their discovery. J Ind Microbiol Biot. 2014;41:185–201.
D’Costa VanessaM, et al. Antibiotic resistance is ancient. Nature. 2011;477:457–61.
Cao P, et al. New duclauxamide from Penicillium manginii YIM PH30375 and structure revision of the duclauxin family. Org Lett. 2015;17:1146–9.
Yan Y, et al. Tropolone ring construction in the biosynthesis of rubrolone B, a cationic tropolone alkaloid from endophytic Streptomyces. Org Lett. 2016;18:1254–7.
Yang R, et al. Lorneic acid analogues from an endophytic actinomycete. J Nat Prod. 2017;80:2615–9.
Oka, H et al. Antitumor glycosides BE-14324 and their manufacture with Streptomyces. JP 03081283 (1991).
Matsumoto M, et al. New piericidin glucosides, glucopiericidins A and B. J Antibiot. 1987;40:149–56.
Funayama S, et al. Novel cytocidal antibiotics, glucopiericidinols A1 and A2. J Antibiot. 1989;42:1734–40.
Yoshida S, Yoneyama K, Shiraishi S, Watanabe A, Takahashi N. Chemical structures of new piericidins produced by Streptomyces pactum. Agric Biol Chem. 1977;41:855–62.
Wu J, Zhang S, Li Q, Huang J, Xiao Z, Long L. Two new cyclolignan glycosides from Acanthus ilicifolius. Z. Naturforsch B. 2004;59:341–4.
Luo JG, Ma L, Kong LY. New triterpenoid saponins with strong α-glucosidase inhibitory activity from the roots of Gypsophila oldhamiana. Bioorg Med Chem. 2008;16:2912–20.
Kimura KI, Takahashi H, Miyata N, Yoshihama M, Uramoto M. New piericidin antibiotics, 7-demethylpiericidin A1 and 7-demethyl-3’-rhamnopiericidin A1. J Antibiot. 1996;49:697–9.
Monks A, et al. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J Natl Cancer I. 1991;83:757–66.
Hamid AA, et al. Chemical composition, antimicrobial and free radical scavenging activities of Grewia pubescens. Chem Int. 2016;2:254–61.
Zhou X, Fenical W. The unique chemistry and biology of the piericidins. J Antibiot. 2016;69:582–93.
Helmke E, Kelter G, Laatsch H, Fiebig HH, Shaaban KA. Glucopiericidin C: a cytotoxic piericidin glucoside antibiotic produced by a marine Streptomyces isolate. J Antibiot. 2011;64:205–9.
Acknowledgements
This work was financially supported by the National Natural Science Foundation of China to S-XH. (Nos. 81522044 and U1702285), Applied Basic Research Foundation of Yunnan Province to Y-TM and S-XH (Nos. 2016FB021 and 2013HA022), and foundation from Chinese Academy of Sciences to S-XH (QYZDB-SSW-SMC051).
Author Contribution
S-XH designed the research, and ZZ and J-PH wrote the paper. NNS and ZZ performed experiments. JYL, JY, YY, and TP analyzed the NMR data and performed the structures determination of isolated compounds. LW and S-XH corrected the manuscript.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Electronic supplementary material
Rights and permissions
About this article
Cite this article
Shang, NN., Zhang, Z., Huang, JP. et al. Glycosylated piericidins from an endophytic streptomyces with cytotoxicity and antimicrobial activity. J Antibiot 71, 672–676 (2018). https://doi.org/10.1038/s41429-018-0051-1
Received:
Revised:
Accepted:
Published:
Issue date:
DOI: https://doi.org/10.1038/s41429-018-0051-1
This article is cited by
-
Identification and genomic analyses of a novel actinobacterium Streptomyces shaowuensis sp. nov. with biocontrol potential for rice bacterial blight
Phytopathology Research (2025)
-
Endophytic Streptomyces: an underexplored source with potential for novel natural drug discovery and development
Archives of Microbiology (2024)
-
New phenoxazinone-related alkaloids from strain Streptomyces sp. KIB-H1318
The Journal of Antibiotics (2018)
