Isolation of petrocidin A, a new cytotoxic cyclic dipeptide from the marine sponge-derived bacterium Streptomyces sp. SBT348

Cheng Cheng, Eman M. Othman, Helga Stopper, RuAngelie Edrada-Ebel, Ute Hentschel, Usama Ramadan Abdelmohsen

Research output: Contribution to journalArticle

  • 3 Citations

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.
LanguageEnglish
Number of pages9
JournalMarine Drugs
Volume15
Issue number12
DOIs
StatePublished - 6 Dec 2017

Fingerprint

Actinobacteria
Dipeptides
Streptomyces
Porifera
Mass Spectrometry
Magnetic Resonance Spectroscopy
Bacteria
Amino Acids
HT29 Cells
Metabolomics
Biological Products
Liquid Chromatography
Colon
Adenocarcinoma
High Pressure Liquid Chromatography
Cell Line
2,3-dihydroxybenzoic acid
Marfey's reagent
maltol

Keywords

  • sponges
  • actinomycetes
  • streptomyces
  • cyclic dipeptide
  • cytotoxic

Cite this

Cheng, Cheng ; Othman, Eman M. ; Stopper, Helga ; Edrada-Ebel, RuAngelie ; Hentschel, Ute ; Abdelmohsen, Usama Ramadan. / Isolation of petrocidin A, a new cytotoxic cyclic dipeptide from the marine sponge-derived bacterium Streptomyces sp. SBT348. In: Marine Drugs. 2017 ; Vol. 15, No. 12.
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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.",
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Isolation of petrocidin A, a new cytotoxic cyclic dipeptide from the marine sponge-derived bacterium Streptomyces sp. SBT348. / Cheng, Cheng; Othman, Eman M.; Stopper, Helga ; Edrada-Ebel, RuAngelie; Hentschel, Ute; Abdelmohsen, Usama Ramadan.

In: Marine Drugs, Vol. 15, No. 12, 06.12.2017.

Research output: Contribution to journalArticle

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T1 - Isolation of petrocidin A, a new cytotoxic cyclic dipeptide from the marine sponge-derived bacterium Streptomyces sp. SBT348

AU - Cheng,Cheng

AU - Othman,Eman M.

AU - Stopper,Helga

AU - Edrada-Ebel,RuAngelie

AU - Hentschel,Ute

AU - Abdelmohsen,Usama Ramadan

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N2 - 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.

AB - 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.

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