Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2017 Dec 6;15(12):383.
doi: 10.3390/md15120383.

Isolation of Petrocidin A, a New Cytotoxic Cyclic Dipeptide from the Marine Sponge-Derived Bacterium Streptomyces sp. SBT348

Cheng Cheng  1 , Eman M Othman  2   3 , Helga Stopper  4 , RuAngelie Edrada-Ebel  5 , Ute Hentschel  6   7 , Usama Ramadan Abdelmohsen  8   9
Affiliations

Isolation of Petrocidin A, a New Cytotoxic Cyclic Dipeptide from the Marine Sponge-Derived Bacterium Streptomyces sp. SBT348

Cheng Cheng et al. Mar Drugs. .

Abstract

A new cyclic dipeptide, petrocidin A (1), along with three known compounds-2,3-dihydroxybenzoic acid (2), 2,3-dihydroxybenzamide (3), and maltol (4)-were isolated from the solid culture of Streptomyces sp. SBT348. The strain Streptomyces sp. SBT348 had been prioritized in a strain collection of 64 sponge-associated actinomycetes based on its distinct metabolomic profile using liquid chromatography/high-resolution mass spectrometry (LC-HRMS) and nuclear magnetic resonance (NMR). The absolute configuration of all α-amino acids was determined by HPLC analysis after derivatization with Marfey's reagent and comparison with commercially available reference amino acids. Structure elucidation was pursued in the presented study by mass spectrometry and NMR spectral data. Petrocidin A (1) and 2,3-dihydroxybenzamide (3) exhibited significant cytotoxicity towards the human promyelocytic HL-60 and the human colon adenocarcinoma HT-29 cell lines. These results demonstrated the potential of sponge-associated actinomycetes for the discovery of novel and pharmacologically active natural products.

Keywords: actinomycetes; cyclic dipeptide; cytotoxic; sponges; streptomyces.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Compounds isolated from outlying strain Streptomyces sp. SBT348; petrocidin A (1), 2,3-dihydroxybenzoic acid (2), 2,3-dihydroxybenzamide (3), and maltol (4).
Figure 2
Figure 2
Structure of petrocidin A (1) with HMBC key correlations (blue, arrows from H to C in MeOD-d4; Purple, key arrows from H to C in DMSO-d6).
See this image and copyright information in PMC

References

    1. Nouioui I., Ruckert C., Willemse J., van Wezel G.P., Klenk H.P., Busche T., Kalinowski J., Bredholt H., Zotchev S.B. Actinoalloteichus fjordicus sp. nov. isolated from marine sponges: Phenotypic, chemotaxonomic and genomic characterisation. Anton Leeuwenhoek. 2017;110:1705–1717. doi: 10.1007/s10482-017-0920-9. - DOI - PMC - PubMed
    1. De Menezes C.B.A., Afonso R.S., de Souza W.R., Parma M., de Melo I.S., Zucchi T.D., Fantinatti-Garboggini F. Williamsia spongiae sp nov., an actinomycete isolated from the marine sponge Amphimedon viridis. Int. J. Syst. Evol. Microbiol. 2017;67:1260–1265. - PubMed
    1. Hentschel U., Piel J., Degnan S.M., Taylor M.W. Genomic insights into the marine sponge microbiome. Nat. Rev. Microbiol. 2012;10:641–654. doi: 10.1038/nrmicro2839. - DOI - PubMed
    1. Abdelmohsen U.R., Grkovic T., Balasubramanian S., Kamel M.S., Quinn R.J., Hentschel U. Elicitation of secondary metabolism in actinomycetes. Biotechnol. Adv. 2015;33:798–811. doi: 10.1016/j.biotechadv.2015.06.003. - DOI - PubMed
    1. Abdelmohsen U.R., Bayer K., Hentschel U. Diversity, abundance and natural products of marine sponge-associated actinomycetes. Nat. Prod. Rep. 2014;31:381–399. doi: 10.1039/C3NP70111E. - DOI - PubMed

LinkOut - more resources