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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 1–9 isolated from Penicillium sp. GGF 16-1-2.
Figure 2. Correlation diagram of main 1H-1H COSY and HMBC of compounds 1–4.
Figure 3. Key NOE correlations of 1–4.
Figure 4. Experimental and calculated ECD spectra of 1–4.
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.
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