Abstract
Roseophilin (2) is a unique prodigiosin-related compound produced by Streptomyces griseoviridis 2464-S5, and is characterized by a central furan ring and a bicyclic alkyl chain. During a search for biosynthetic intermediates of 2, a new metabolite designated prodigiosin R2 (1) was isolated from the culture of the roseophilin producer. The molecular formula of 1 was established as C27H35N3O by high-resolution FAB-MS. The structure of 1 was determined by NMR spectroscopic analyses as a prodigiosin derivative with the same bicyclic alkyl chain as 2. Prodigiosin R2 (1) showed potent cytotoxicity against HeLa human cervical carcinoma cells and HT1080 human fibrosarcoma cells with IC50s of 0.41 and 0.82 μM, respectively.
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
Stankovic N, Senerovic L, Ilic-Tomic T, Vasiljevic B, Nikodinovic-Runic J. Properties and applications of undecylprodigiosin and other bacterial prodigiosins. J Appl Microbiol Biotechnol. 2014;98:3841–58.
Hayakawa Y, Kawakami K, Seto H. Structure of a new antibiotic, roseophilin. Tetrahedron Lett. 1992;33:2701–4.
Hayakawa Y, Nagatsuka S, Kawasaki T. Dechlororoseophilin: a new cytotoxic metabolite from Streptomyces griseoviridis. J Antibiot. 2009;62:531–2.
Kawasaki T, Sakurai F, Hayakawa Y. A prodigiosin from the roseophilin producer Streptomyces griseoviridis. J Nat Prod. 2008;71:1265–7.
Kawasaki T, Sakurai F, Nagatsuka S, Hayakawa Y. Prodigiosin biosynthesis gene cluster in the roseophilin producer Streptomyces griseoviridis. J Antibiot. 2009;62:271–6.
Summers MF, Marzilli LG, Bax A. Complete 1H and 13C assignments of coenzyme B12 through the use of new two-dimensional NMR experiments. J Am Chem Soc. 1986;108:4285–94.
Bax A, Summers MF. 1H and 13C assignments from sensitivity enhanced detection of heteronuclear multiple-bond connectivity by multiple quantum NMR. J Am Chem Soc. 1986;108:2093–4.
Pandey R, Chander R, Sainis KB. Prodigiosins as anti cancer agents: living upto their name. Curr Pharm Des. 2009;15:732–41.
Ohkuma S, et al. Prodigiosins uncouple lysosomal vacuolar-type ATPase through promotion of H+/Cl− symport. Biochem J. 1998;334:731–41.
Kimata S, Izawa M, Kawasaki T, Hayakawa Y. Identification of a prodigiosin cyclization gene in the roseophilin producer and production of a new cyclized prodigiosin in a heterologous host. J Antibiot. 2017;70:196–9.
Acknowledgements
We thank F. Hasegawa, Tokyo University of Science, for assistance with mass spectrometry.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Additional information
Publisher's note: Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Rights and permissions
About this article
Cite this article
Kimata, S., Matsuda, T., Suizu, Y. et al. Prodigiosin R2, a new prodigiosin from the roseophilin producer Streptomyces griseoviridis 2464-S5. J Antibiot 71, 393–396 (2018). https://doi.org/10.1038/s41429-017-0011-1
Received:
Revised:
Accepted:
Published:
Version of record:
Issue date:
DOI: https://doi.org/10.1038/s41429-017-0011-1
This article is cited by
-
Prodigiosin R3, a new multicyclic prodigiosin formed by prodigiosin cyclization genes in the roseophilin producer
The Journal of Antibiotics (2023)
-
Structures, biosynthesis, and bioactivities of prodiginine natural products
Applied Microbiology and Biotechnology (2022)
-
A comprehensive review on recent trends in production, purification, and applications of prodigiosin
Biomass Conversion and Biorefinery (2022)
