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Mar. Drugs 2017, 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

1
Department of Botany II, Julius-von-Sachs Institute for Biological Sciences, University of Würzburg, Julius-von-Sachs-Platz 3, D-97082 Würzburg, Germany
2
Department of Toxicology, University of Würzburg, Versbacher Str. 9, D-97078 Würzburg, Germany
3
Department of Analytical Chemistry, Faculty of Pharmacy, Minia University, Minia 61519, Egypt
4
Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, The John Arbuthnott Building, 27 Taylor Street, Glasgow G4 0NR, UK
5
GEOMAR Helmholtz Centre for Ocean Research, RD3 Marine Microbiology, and Christian-Albrechts University of Kiel, Düsternbrooker Weg 20, D-24105 Kiel, Germany
6
Department of Pharmacognosy, Faculty of Pharmacy, Minia University, Minia 61519, Egypt
*
Author to whom correspondence should be addressed.
Received: 25 October 2017 / Revised: 6 November 2017 / Accepted: 16 November 2017 / Published: 6 December 2017
(This article belongs to the Special Issue Bioprospecting of Marine Microorganisms)
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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. View Full-Text
Keywords: sponges; actinomycetes; streptomyces; cyclic dipeptide; cytotoxic sponges; actinomycetes; streptomyces; cyclic dipeptide; cytotoxic
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MDPI and ACS Style

Cheng, C.; Othman, E.M.; Stopper, H.; Edrada-Ebel, R.; Hentschel, U.; Abdelmohsen, U.R. Isolation of Petrocidin A, a New Cytotoxic Cyclic Dipeptide from the Marine Sponge-Derived Bacterium Streptomyces sp. SBT348. Mar. Drugs 2017, 15, 383.

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