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

doi:10.3390/md17080465

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 journal › Article › peer-review

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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 language	English
Article number	465
Number of pages	13
Journal	Marine Drugs
Volume	17
Issue number	8
DOIs	https://doi.org/10.3390/md17080465
Publication status	Published - 9 Aug 2019

Keywords

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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3390/md17080465Licence: CC BY

2019 07 23 El-Hawary et al Oxindole final versionFinal published version, 2.39 MBLicence: CC BY

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title = "Bioactive brominated oxindole alkaloids from the Red Sea sponge Callyspongia siphonella",

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.",

keywords = "Callyspongia siphonella, LC-HRESIMS, Metabolomic profiling, Oxindole alkaloids, Tisindoline, Antibacterial, Antibiofilm, Antitrypanosomal, Anticancer",

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

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doi = "10.3390/md17080465",

language = "English",

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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

C2 - 31395834

SN - 1660-3397

VL - 17

JO - Marine Drugs

JF - Marine Drugs

IS - 8

M1 - 465

ER -

Bioactive brominated oxindole alkaloids from the Red Sea sponge Callyspongia siphonella

Abstract

Keywords

UN SDGs

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