Genus Smenospongia: Untapped Treasure of Biometabolites—Biosynthesis, Synthesis, and Bioactivities
Abstract
:1. Introduction
2. Methodology
3. Smenospongia Metabolites and Their Bioactivities
3.1. Indole Derivatives
3.2. Aplysinopsin Derivatives
3.3. Bisspiroimidazolidinone Alkaloids
3.4. Polyketides
3.5. Terpenoids
3.5.1. Hydroquinone and Quinone Sesquiterpenoids
3.5.2. Tetronic Acid and Cyclopentenone Sesquiterpenoids
3.5.3. Diterpenoids
3.5.4. Sesterterpenoids
3.6. Chromene Derivatives
3.7. γ-Pyrone Derivatives
3.8. Phenyl Alkenes
3.9. Naphthoquinones
3.10. Fatty Acids, Sterols, and Phthalates
4. Biological Activity of Extracts
4.1. Antimicrobial Activity
4.2. Cytotoxic Activity
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Abbreviations
A549 | Human lung adenocarcinoma epithelial cell line |
A2780 | Human ovarian cancer cells line |
AMPK | AMP-Activated protein kinase |
ARPE-19 | Retinal pigment epithelial cell line |
ATR | Adenosine triphosphate |
BV2 | Microglia cells |
BxPC-3 | Human pancreas adenocarcinoma cell line |
Calu-1 | Human nonsmall-cell lung cancer cell line |
CD | Circular dichroism |
CH2Cl2 | Dichloromethane |
CHCl3 | Chloroform |
CHOP, CCAAT | Enhancer-binding protein homologous protein |
CNV | Choroidal neovascularization |
CRT | β-catenin response transcription |
DLD-1 | Human colorectal cancer cell line |
DR4 | Death receptor 4 |
DR5 | Death receptor 5 |
DPPH | 1,1-Diphenyl-2-picrylhydrazyl |
EC50 | Half-maximal effective concentration |
ERK | Extracellular signal-regulated kinase |
EtOH | Ethanol |
EtOAc | Ethyl acetate |
FST | Porsolt forced swim test |
FRET | Fluorescence resonance energy transfer |
FP | Fluorescence polarization |
GCMS | Gas chromatography mass spectrometry |
GIAO | Gauge-invariant atomic orbital |
GI50 | The concentration for 50% of maximal inhibition of cell |
HCT-116 | Human colon cancer cell line |
HEK293 | Human embryonic kidney cell |
HepG2 | Human liver cancer cell line |
Hepa59T/VGH | Human liver carcinoma cell line |
HeLa | Human cervical epitheloid carcinoma cell line |
HL-60 | Human promyelocytic leukemia cell line |
HPLC | High-performance liquid chromatography |
HT-29 | Human colon cancer cell line |
hTERT-RPE1 | Retinal pigment epithelial cell lines |
HuCCA-1 | Human cholangiocarcinoma cell line |
HUVECs | Human umbilical vein endothelial cell line |
HUVSMCs | Human umbilical vein smooth muscle cells line |
IC50 | Half-maximal inhibitory concentration |
ICL | Microbial enzyme isocitrate lyase |
K562 | Human immortalized myelogenous leukemia cell line |
KB | Human oral epidermoid carcinoma cell line |
L1210 | Mouse lymphocytic leukemia cell line |
LC31 | Human lung squamous adenocarcinoma cell line |
LC50 | Lethal concentration 50 |
LC–MS–NMR | Liquid chromatography–mass spectrometry–nuclear magnetic resonance |
LD50 | Half maximal lethal concentration |
LPS | Lipopolysaccharide |
LLC | Murine Lewis lung carcinoma |
L-NMMA | Nitric oxide synthase inhibitor NG-monomethyl-L-arginine |
LU-1 | Human lung carcinoma cell line |
MCF-7 | Human breast cancer cell line |
MDA-MB-231 | Human breast cancer cell line |
MeOH | Methanol |
MG-63 | Human osteosarcoma cell line |
MIC | Minimum inhibitory concentration |
MOLT-3 | Human T lymphoblast cell line |
MTS | (3-(4,5-Dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazoliuminner salt) |
MTT | 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide |
nAMD | Neovascular age-related macular degeneration |
n-BuOH | n-Butanol |
NMR | Nuclear magnetic resonance |
NO | Nitric oxide |
p38 MAPK | p38 Mitogen-activated protein kinase |
P 388 | Human leukemia cell line |
PANC-1 | Human pancreas ductal carcinoma cell line |
PARP | Poly-AD Pribose polymerase |
PDK1 | Pyruvate dehydrogenase kinase 1 |
PDHA1 | Phosphorylation of its E1α subunit |
RKO | Human colon cancer cell line |
ROS | Reactive oxygen species |
RTCA | xCELLigence system real-time cell analyzer |
RP-18 | Reversed phase-18 |
SRB | Sulforhodamine B |
SiO2 CC | Silica gel column chromatography |
SK-MEL-2 | Human melanoma cell line |
SRB | Sulforhodamine B |
SW480 | Human colorectal cancer cell line |
TLC | Thin layer chromatography |
TRAIL | Tumor necrosis factor-related apoptosis-inducing ligand |
UPLC–MS | Ultra performance liquid chromatography–tandem mass spectrometer |
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Ibrahim, S.R.M.; Fadil, S.A.; Fadil, H.A.; Hareeri, R.H.; Abdallah, H.M.; Mohamed, G.A. Genus Smenospongia: Untapped Treasure of Biometabolites—Biosynthesis, Synthesis, and Bioactivities. Molecules 2022, 27, 5969. https://doi.org/10.3390/molecules27185969
Ibrahim SRM, Fadil SA, Fadil HA, Hareeri RH, Abdallah HM, Mohamed GA. Genus Smenospongia: Untapped Treasure of Biometabolites—Biosynthesis, Synthesis, and Bioactivities. Molecules. 2022; 27(18):5969. https://doi.org/10.3390/molecules27185969
Chicago/Turabian StyleIbrahim, Sabrin R. M., Sana A. Fadil, Haifa A. Fadil, Rawan H. Hareeri, Hossam M. Abdallah, and Gamal A. Mohamed. 2022. "Genus Smenospongia: Untapped Treasure of Biometabolites—Biosynthesis, Synthesis, and Bioactivities" Molecules 27, no. 18: 5969. https://doi.org/10.3390/molecules27185969