Bioactive brominated oxindole alkaloids from the Red Sea sponge Callyspongia siphonella

Seham S. El-Hawary, Ahmed M. Sayed, Rabab Mohammed, Hossam M. Hassan, Mostafa E. Rateb, Elham Amin, Tarek A. Mohammed, Mohamed El-Mesery, Abdullatif Bin Muhsinah, Abdulrhman Alsayari, Harald Wajant, Mohamed A. Anany*, Usama Ramadan Abdelmohsen

*Corresponding author for this work

Research output: Contribution to journalArticle

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Abstract

In the present study, LC-HRESIMS-assisted dereplication along with bioactivity-guided isolation led to targeting two brominated oxindole alkaloids (compounds 1 and 2) which probably play a key role in the previously reported antibacterial, antibiofilm, and cytotoxicity of Callyspongia siphonella crude extracts. Both metabolites showed potent antibacterial activity against Gram-positive bacteria, Staphylococcus aureus (minimum inhibitory concentration (MIC) = 8 and 4 µg/mL) and Bacillus subtilis (MIC = 16 and 4 µg/mL), respectively. Furthermore, they displayed moderate biofilm inhibitory activity in Pseudomonasaeruginosa (49.32% and 41.76% inhibition, respectively), and moderate in vitro antitrypanosomal activity (13.47 and 10.27 µM, respectively). In addition, they revealed a strong cytotoxic effect toward different human cancer cell lines, supposedly through induction of necrosis. This study sheds light on the possible role of these metabolites (compounds 1 and 2) in keeping fouling organisms away from the sponge outer surface, and the possible applications of these defensive molecules in the development of new anti-infective agents.

Original languageEnglish
Article number465
Number of pages13
JournalMarine Drugs
Volume17
Issue number8
DOIs
Publication statusPublished - 9 Aug 2019

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Callyspongia
Indian Ocean
Porifera
Microbial Sensitivity Tests
Alkaloids
Gram-Positive Bacteria
Biofilms
Anti-Infective Agents
Bacillus subtilis
Complex Mixtures
Staphylococcus aureus
Necrosis
Cell Line
Neoplasms
oxindole

Keywords

  • Callyspongia siphonella
  • LC-HRESIMS
  • Metabolomic profiling
  • Oxindole alkaloids
  • Tisindoline
  • Antibacterial
  • Antibiofilm
  • Antitrypanosomal
  • Anticancer

Cite this

El-Hawary, S. S., Sayed, A. M., Mohammed, R., Hassan, H. M., Rateb, M. E., Amin, E., ... Abdelmohsen, U. R. (2019). Bioactive brominated oxindole alkaloids from the Red Sea sponge Callyspongia siphonella. Marine Drugs, 17(8), [465]. https://doi.org/10.3390/md17080465
El-Hawary, Seham S. ; Sayed, Ahmed M. ; Mohammed, Rabab ; Hassan, Hossam M. ; Rateb, Mostafa E. ; Amin, Elham ; Mohammed, Tarek A. ; El-Mesery, Mohamed ; Bin Muhsinah, Abdullatif ; Alsayari, Abdulrhman ; Wajant, Harald ; Anany, Mohamed A. ; Abdelmohsen, Usama Ramadan. / Bioactive brominated oxindole alkaloids from the Red Sea sponge Callyspongia siphonella. In: Marine Drugs. 2019 ; Vol. 17, No. 8.
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abstract = "In the present study, LC-HRESIMS-assisted dereplication along with bioactivity-guided isolation led to targeting two brominated oxindole alkaloids (compounds 1 and 2) which probably play a key role in the previously reported antibacterial, antibiofilm, and cytotoxicity of Callyspongia siphonella crude extracts. Both metabolites showed potent antibacterial activity against Gram-positive bacteria, Staphylococcus aureus (minimum inhibitory concentration (MIC) = 8 and 4 µg/mL) and Bacillus subtilis (MIC = 16 and 4 µg/mL), respectively. Furthermore, they displayed moderate biofilm inhibitory activity in Pseudomonasaeruginosa (49.32{\%} and 41.76{\%} inhibition, respectively), and moderate in vitro antitrypanosomal activity (13.47 and 10.27 µM, respectively). In addition, they revealed a strong cytotoxic effect toward different human cancer cell lines, supposedly through induction of necrosis. This study sheds light on the possible role of these metabolites (compounds 1 and 2) in keeping fouling organisms away from the sponge outer surface, and the possible applications of these defensive molecules in the development of new anti-infective agents.",
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El-Hawary, SS, Sayed, AM, Mohammed, R, Hassan, HM, Rateb, ME, Amin, E, Mohammed, TA, El-Mesery, M, Bin Muhsinah, A, Alsayari, A, Wajant, H, Anany, MA & Abdelmohsen, UR 2019, 'Bioactive brominated oxindole alkaloids from the Red Sea sponge Callyspongia siphonella', Marine Drugs, vol. 17, no. 8, 465. https://doi.org/10.3390/md17080465

Bioactive brominated oxindole alkaloids from the Red Sea sponge Callyspongia siphonella. / El-Hawary, Seham S.; Sayed, Ahmed M.; Mohammed, Rabab; Hassan, Hossam M.; Rateb, Mostafa E.; Amin, Elham; Mohammed, Tarek A.; El-Mesery, Mohamed; Bin Muhsinah, Abdullatif; Alsayari, Abdulrhman; Wajant, Harald; Anany, Mohamed A.; Abdelmohsen, Usama Ramadan.

In: Marine Drugs, Vol. 17, No. 8, 465, 09.08.2019.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Bioactive brominated oxindole alkaloids from the Red Sea sponge Callyspongia siphonella

AU - El-Hawary, Seham S.

AU - Sayed, Ahmed M.

AU - Mohammed, Rabab

AU - Hassan, Hossam M.

AU - Rateb, Mostafa E.

AU - Amin, Elham

AU - Mohammed, Tarek A.

AU - El-Mesery, Mohamed

AU - Bin Muhsinah, Abdullatif

AU - Alsayari, Abdulrhman

AU - Wajant, Harald

AU - Anany, Mohamed A.

AU - Abdelmohsen, Usama Ramadan

PY - 2019/8/9

Y1 - 2019/8/9

N2 - In the present study, LC-HRESIMS-assisted dereplication along with bioactivity-guided isolation led to targeting two brominated oxindole alkaloids (compounds 1 and 2) which probably play a key role in the previously reported antibacterial, antibiofilm, and cytotoxicity of Callyspongia siphonella crude extracts. Both metabolites showed potent antibacterial activity against Gram-positive bacteria, Staphylococcus aureus (minimum inhibitory concentration (MIC) = 8 and 4 µg/mL) and Bacillus subtilis (MIC = 16 and 4 µg/mL), respectively. Furthermore, they displayed moderate biofilm inhibitory activity in Pseudomonasaeruginosa (49.32% and 41.76% inhibition, respectively), and moderate in vitro antitrypanosomal activity (13.47 and 10.27 µM, respectively). In addition, they revealed a strong cytotoxic effect toward different human cancer cell lines, supposedly through induction of necrosis. This study sheds light on the possible role of these metabolites (compounds 1 and 2) in keeping fouling organisms away from the sponge outer surface, and the possible applications of these defensive molecules in the development of new anti-infective agents.

AB - In the present study, LC-HRESIMS-assisted dereplication along with bioactivity-guided isolation led to targeting two brominated oxindole alkaloids (compounds 1 and 2) which probably play a key role in the previously reported antibacterial, antibiofilm, and cytotoxicity of Callyspongia siphonella crude extracts. Both metabolites showed potent antibacterial activity against Gram-positive bacteria, Staphylococcus aureus (minimum inhibitory concentration (MIC) = 8 and 4 µg/mL) and Bacillus subtilis (MIC = 16 and 4 µg/mL), respectively. Furthermore, they displayed moderate biofilm inhibitory activity in Pseudomonasaeruginosa (49.32% and 41.76% inhibition, respectively), and moderate in vitro antitrypanosomal activity (13.47 and 10.27 µM, respectively). In addition, they revealed a strong cytotoxic effect toward different human cancer cell lines, supposedly through induction of necrosis. This study sheds light on the possible role of these metabolites (compounds 1 and 2) in keeping fouling organisms away from the sponge outer surface, and the possible applications of these defensive molecules in the development of new anti-infective agents.

KW - Callyspongia siphonella

KW - LC-HRESIMS

KW - Metabolomic profiling

KW - Oxindole alkaloids

KW - Tisindoline

KW - Antibacterial

KW - Antibiofilm

KW - Antitrypanosomal

KW - Anticancer

U2 - 10.3390/md17080465

DO - 10.3390/md17080465

M3 - Article

VL - 17

JO - Marine Drugs

JF - Marine Drugs

SN - 1660-3397

IS - 8

M1 - 465

ER -