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Mar Drugs
2022 Jul 06;207:. doi: 10.3390/md20070443.
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Rare Carbon-Bridged Citrinin Dimers from the Starfish-Derived Symbiotic Fungus Penicillium sp. GGF16-1-2.
Fan H
,
Shi ZM
,
Lei YH
,
Si-Tu MX
,
Zhou FG
,
Feng C
,
Wei X
,
Shao XH
,
Chen Y
,
Zhang CX
.
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Four novel, rare carbon-bridged citrinin dimers, namely dicitrinones G-J (1-4), and five known analogs (5-9) were isolated from the starfish-derived fungus Penicillium sp. GGF 16-1-2. Their structures were elucidated by extensive spectroscopic analysis and quantum chemical calculations. Compounds 1-9 exhibited strong antifungal activities against Colletotrichum gloeosporioides with LD50 values from 0.61 μg/mL to 16.14 μg/mL. Meanwhile, all compounds were evaluated for their cytotoxic activities against human pancreatic cancer BXPC-3 and PANC-1 cell lines; as a result, compound 1 showed more significant cytotoxicities than the positive control against both cell lines. In addition, based on the analyses of the protein-protein interaction (PPI) network and Western blot, 1 could induce apoptosis by activating caspase 3 proteins (CASP3).
GDNRC[2021]48 and GDNRC[2020]039 This research was funded by the Special Project for Marine Economic Development of Depart-ment of Natural Resources of Guangdong Province, No. 81741160 the National Natural Science Foundation of China, No. 2017A020217008 and No. 2015A020216017 the Science and Technology Planning Project of Guangdong Province
Figure 1. The structures of compounds 1â9 isolated from Penicillium sp. GGF 16-1-2.
Figure 2. Correlation diagram of main 1H-1H COSY and HMBC of compounds 1â4.
Figure 3. Key NOE correlations of 1â4.
Figure 4. Experimental and calculated ECD spectra of 1â4.
Figure 5. (A) The Venn diagram of 1 and the disease to obtain overlapping genes. (B) The PPI network of 1 and the disease. (C) The effects of 1 on caspase 3 proteins in BXPC-3 cells were determined by western blot analysis. All data are expressed as means ± SD. * p < 0.05 vs. the control group.
Cao,
The absolute configuration of anti-Vibrio citrinin dimeric derivative by VCD, ECD and NMR methods.
2019, Pubmed
Cao,
The absolute configuration of anti-Vibrio citrinin dimeric derivative by VCD, ECD and NMR methods.
2019,
Pubmed
Carroll,
Marine natural products.
2020,
Pubmed
,
Echinobase
Clark,
Citrinin revisited: from monomers to dimers and beyond.
2006,
Pubmed
de Oliveira Filho,
A comprehensive review on biological properties of citrinin.
2017,
Pubmed
Dorman,
Novel systemic treatment approaches for metastatic pancreatic cancer.
2022,
Pubmed
Du,
Unprecedented citrinin trimer tricitinol B functions as a novel topoisomerase IIα inhibitor.
2011,
Pubmed
Fan,
Methylene-bridged dimeric natural products involving one-carbon unit in biosynthesis.
2022,
Pubmed
Fujita,
In vitro and in vivo cytotoxicity of troglitazone in pancreatic cancer.
2017,
Pubmed
Gfeller,
SwissTargetPrediction: a web server for target prediction of bioactive small molecules.
2014,
Pubmed
Li,
Cordycepin inhibits pancreatic cancer cell growth in vitro and in vivo via targeting FGFR2 and blocking ERK signaling.
2020,
Pubmed
Li,
Dimeric and Oligomeric Steroids.
1997,
Pubmed
Liu,
Sodium cantharidinate, a novel anti-pancreatic cancer agent that activates functional p53.
2021,
Pubmed
Mosmann,
Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.
1983,
Pubmed
Ni,
A novel citrinin derivative from the marine-source fungus Penicillium citrinum.
2015,
Pubmed
Pan,
Stelleranoids A-M, guaiane-type sesquiterpenoids based on [5,7] bicyclic system from Stellera chamaejasme and their cytotoxic activity.
2021,
Pubmed
Sadhasivam,
Rapid Detection and Quantification of Patulin and Citrinin Contamination in Fruits.
2021,
Pubmed
Shannon,
Cytoscape: a software environment for integrated models of biomolecular interaction networks.
2003,
Pubmed
Song,
Cleistocaltones A and B, Antiviral Phloroglucinol-Terpenoid Adducts from Cleistocalyx operculatus.
2019,
Pubmed
Su,
Phloroglucinol Derivatives with Unusual Skeletons from Cleistocalyx operculatus and Their in Vitro Antiviral Activity.
2018,
Pubmed
Szklarczyk,
STRING v11: protein-protein association networks with increased coverage, supporting functional discovery in genome-wide experimental datasets.
2019,
Pubmed
Wang,
CgSCD1 Is Essential for Melanin Biosynthesis and Pathogenicity of Colletotrichum gloeosporioides.
2020,
Pubmed
Wang,
Citrinin Monomer and Dimer Derivatives with Antibacterial and Cytotoxic Activities Isolated from the Deep Sea-Derived Fungus Penicillium citrinum NLG-S01-P1.
2019,
Pubmed
Wei,
Pyranodipyran Derivatives with Tyrosyl DNA Phosphodiesterase 1 Inhibitory Activities and Fluorescent Properties from Aspergillus sp. EGF 15-0-3.
2022,
Pubmed
Wei,
Probing Indole Diketopiperazine-Based Hybrids as Environmental-Induced Products from Aspergillus sp. EGF 15-0-3.
2022,
Pubmed
Wei,
Enantiomeric Polyketides from the Starfish-Derived Symbiotic Fungus Penicillium sp. GGF16-1-2.
2019,
Pubmed
,
Echinobase
Wezeman,
Xanthone dimers: a compound family which is both common and privileged.
2015,
Pubmed
Wu,
Activation of the silent secondary metabolite production by introducing neomycin-resistance in a marine-derived Penicillium purpurogenum G59.
2015,
Pubmed
Xin,
Isocoumarin Derivatives from the Sea Squirt-derived Fungus Penicillium stoloniferum QY2-10 and the Halotolerant Fungus Penicillium notatum B-52.
2007,
Pubmed
