Dereplication strategies for targeted isolation of new antitrypanosomal actinosporins A and B from a marine sponge associated-Actinokineospora sp. EG49

Usama Ramadan Abdelmohsen, Cheng Cheng, Christina Viegelmann, Tong Zhang, Tanja Grkovic, Safwat Ahmed, Ronald J Quinn, Ute Hentschel, RuAngelie Edrada-Ebel

Research output: Contribution to journalArticle

51 Citations (Scopus)

Abstract

High resolution Fourier transform mass spectrometry (HRFTMS) and nuclear magnetic resonance (NMR) spectroscopy were employed as complementary metabolomic tools to dereplicate the chemical profile of the new and antitrypanosomally active sponge-associated bacterium Actinokineospora sp. EG49 extract. Principal Component (PCA), hierarchical clustering (HCA), and orthogonal partial least square-discriminant analysis (OPLS-DA) were used to evaluate the HRFTMS and NMR data of crude extracts from four different fermentation approaches. Statistical analysis identified the best culture one-strain-many-compounds (OSMAC) condition and extraction procedure, which was used for the isolation of novel bioactive metabolites. As a result, two new O-glycosylated angucyclines, named actinosporins A (1) and B (2), were isolated from the broth culture of Actinokineospora sp. strain EG49, which was cultivated from the Red Sea sponge Spheciospongia vagabunda. The structures of actinosporins A and B were determined by 1D- and 2D-NMR techniques, as well as high resolution tandem mass spectrometry. Testing for antiparasitic properties showed that actinosporin A exhibited activity against Trypanosoma brucei brucei with an IC₅₀ value of 15 µM; however no activity was detected against Leishmania major and Plasmodium falciparum, therefore suggesting its selectivity against the parasite Trypanosoma brucei brucei; the causative agent of sleeping sickness.

LanguageEnglish
Pages1220-1244
Number of pages25
JournalMarine Drugs
Volume12
Issue number3
DOIs
Publication statusPublished - 6 Mar 2014

Fingerprint

Porifera
Trypanosoma brucei brucei
Magnetic Resonance Spectroscopy
Fourier Analysis
Mass Spectrometry
Leishmania major
Antiparasitic Agents
Indian Ocean
Metabolomics
Discriminant Analysis
Plasmodium falciparum
Tandem Mass Spectrometry
Least-Squares Analysis
Complex Mixtures
Fermentation
Cluster Analysis
Parasites
Bacteria
actinosporin A

Keywords

  • actinosporins
  • spheciospongia vagabunda
  • actinokineospora
  • anti-trypanosomal
  • dereplication
  • secondary metabolomics

Cite this

Abdelmohsen, Usama Ramadan ; Cheng, Cheng ; Viegelmann, Christina ; Zhang, Tong ; Grkovic, Tanja ; Ahmed, Safwat ; Quinn, Ronald J ; Hentschel, Ute ; Edrada-Ebel, RuAngelie. / Dereplication strategies for targeted isolation of new antitrypanosomal actinosporins A and B from a marine sponge associated-Actinokineospora sp. EG49. In: Marine Drugs. 2014 ; Vol. 12, No. 3. pp. 1220-1244.
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abstract = "High resolution Fourier transform mass spectrometry (HRFTMS) and nuclear magnetic resonance (NMR) spectroscopy were employed as complementary metabolomic tools to dereplicate the chemical profile of the new and antitrypanosomally active sponge-associated bacterium Actinokineospora sp. EG49 extract. Principal Component (PCA), hierarchical clustering (HCA), and orthogonal partial least square-discriminant analysis (OPLS-DA) were used to evaluate the HRFTMS and NMR data of crude extracts from four different fermentation approaches. Statistical analysis identified the best culture one-strain-many-compounds (OSMAC) condition and extraction procedure, which was used for the isolation of novel bioactive metabolites. As a result, two new O-glycosylated angucyclines, named actinosporins A (1) and B (2), were isolated from the broth culture of Actinokineospora sp. strain EG49, which was cultivated from the Red Sea sponge Spheciospongia vagabunda. The structures of actinosporins A and B were determined by 1D- and 2D-NMR techniques, as well as high resolution tandem mass spectrometry. Testing for antiparasitic properties showed that actinosporin A exhibited activity against Trypanosoma brucei brucei with an IC₅₀ value of 15 µM; however no activity was detected against Leishmania major and Plasmodium falciparum, therefore suggesting its selectivity against the parasite Trypanosoma brucei brucei; the causative agent of sleeping sickness.",
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Dereplication strategies for targeted isolation of new antitrypanosomal actinosporins A and B from a marine sponge associated-Actinokineospora sp. EG49. / Abdelmohsen, Usama Ramadan; Cheng, Cheng; Viegelmann, Christina; Zhang, Tong; Grkovic, Tanja; Ahmed, Safwat; Quinn, Ronald J; Hentschel, Ute; Edrada-Ebel, RuAngelie.

In: Marine Drugs, Vol. 12, No. 3, 06.03.2014, p. 1220-1244.

Research output: Contribution to journalArticle

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T1 - Dereplication strategies for targeted isolation of new antitrypanosomal actinosporins A and B from a marine sponge associated-Actinokineospora sp. EG49

AU - Abdelmohsen, Usama Ramadan

AU - Cheng, Cheng

AU - Viegelmann, Christina

AU - Zhang, Tong

AU - Grkovic, Tanja

AU - Ahmed, Safwat

AU - Quinn, Ronald J

AU - Hentschel, Ute

AU - Edrada-Ebel, RuAngelie

PY - 2014/3/6

Y1 - 2014/3/6

N2 - High resolution Fourier transform mass spectrometry (HRFTMS) and nuclear magnetic resonance (NMR) spectroscopy were employed as complementary metabolomic tools to dereplicate the chemical profile of the new and antitrypanosomally active sponge-associated bacterium Actinokineospora sp. EG49 extract. Principal Component (PCA), hierarchical clustering (HCA), and orthogonal partial least square-discriminant analysis (OPLS-DA) were used to evaluate the HRFTMS and NMR data of crude extracts from four different fermentation approaches. Statistical analysis identified the best culture one-strain-many-compounds (OSMAC) condition and extraction procedure, which was used for the isolation of novel bioactive metabolites. As a result, two new O-glycosylated angucyclines, named actinosporins A (1) and B (2), were isolated from the broth culture of Actinokineospora sp. strain EG49, which was cultivated from the Red Sea sponge Spheciospongia vagabunda. The structures of actinosporins A and B were determined by 1D- and 2D-NMR techniques, as well as high resolution tandem mass spectrometry. Testing for antiparasitic properties showed that actinosporin A exhibited activity against Trypanosoma brucei brucei with an IC₅₀ value of 15 µM; however no activity was detected against Leishmania major and Plasmodium falciparum, therefore suggesting its selectivity against the parasite Trypanosoma brucei brucei; the causative agent of sleeping sickness.

AB - High resolution Fourier transform mass spectrometry (HRFTMS) and nuclear magnetic resonance (NMR) spectroscopy were employed as complementary metabolomic tools to dereplicate the chemical profile of the new and antitrypanosomally active sponge-associated bacterium Actinokineospora sp. EG49 extract. Principal Component (PCA), hierarchical clustering (HCA), and orthogonal partial least square-discriminant analysis (OPLS-DA) were used to evaluate the HRFTMS and NMR data of crude extracts from four different fermentation approaches. Statistical analysis identified the best culture one-strain-many-compounds (OSMAC) condition and extraction procedure, which was used for the isolation of novel bioactive metabolites. As a result, two new O-glycosylated angucyclines, named actinosporins A (1) and B (2), were isolated from the broth culture of Actinokineospora sp. strain EG49, which was cultivated from the Red Sea sponge Spheciospongia vagabunda. The structures of actinosporins A and B were determined by 1D- and 2D-NMR techniques, as well as high resolution tandem mass spectrometry. Testing for antiparasitic properties showed that actinosporin A exhibited activity against Trypanosoma brucei brucei with an IC₅₀ value of 15 µM; however no activity was detected against Leishmania major and Plasmodium falciparum, therefore suggesting its selectivity against the parasite Trypanosoma brucei brucei; the causative agent of sleeping sickness.

KW - actinosporins

KW - spheciospongia vagabunda

KW - actinokineospora

KW - anti-trypanosomal

KW - dereplication

KW - secondary metabolomics

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DO - 10.3390/md12031220

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