Rare Carbon-Bridged Citrinin Dimers from the Starfish-Derived Symbiotic Fungus Penicillium sp. GGF16-1-2

被引:23
作者
Fan, Hao [1 ]
Shi, Zhi-Mian [1 ]
Lei, Yan-Hu [1 ]
Si-Tu, Mei-Xia [1 ]
Zhou, Feng-Guo [1 ]
Feng, Chan [1 ]
Wei, Xia [1 ]
Shao, Xue-Hua [2 ]
Chen, Yang [1 ]
Zhang, Cui-Xian [1 ]
机构
[1] Guangzhou Univ Chinese Med, Sch Pharmaceut Sci, Guangzhou 510006, Peoples R China
[2] Guangdong Acad Agr Sci, Inst Fruit Tree Res, Key Lab South Subtrop Fruit Biol & Genet Resource, Guangdong Prov Key Lab Trop & Subtrop Fruit Tree, Guangzhou 510640, Peoples R China
基金
中国国家自然科学基金;
关键词
starfish-derived fungus; Penicillium sp; citrinin dimers; antifungal activities; cytotoxic activities; protein-protein interaction network; IN-VITRO; DERIVATIVES; COMPOUND; GROWTH;
D O I
10.3390/md20070443
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
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 mu g/mL to 16.14 mu g/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).
引用
收藏
页数:12
相关论文
共 41 条
[1]  
BENTRIVEDI A, 1993, J CHEM SOC PERK T 1, P2167
[2]  
Bruhn T., 2017, SpecDis Version 1.71
[3]   The absolute configuration of anti-Vibrio citrinin dimeric derivative by VCD, ECD and NMR methods [J].
Cao, Fei ;
Sun, Tian-Tian ;
Yang, Jian-Kun ;
Zhao, Guo-Zheng ;
Liu, Qing-Ai ;
Hu, Lian-Dong ;
Ma, Zheng-Yue ;
Zhu, Hua-Jie .
NATURAL PRODUCT RESEARCH, 2019, 33 (15) :2192-2199
[4]   Marine natural products [J].
Carroll, Anthony R. ;
Copp, Brent R. ;
Davis, Rohan A. ;
Keyzers, Robert A. ;
Prinsep, Michele R. .
NATURAL PRODUCT REPORTS, 2020, 37 (02) :175-223
[5]   Citrinin revisited: from monomers to dimers and beyond [J].
Clark, BR ;
Capon, RJ ;
Lacey, E ;
Tennant, S ;
Gill, JH .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (08) :1520-1528
[6]   Swiss Target Prediction: updated data and new features for efficient prediction of protein targets of small molecules [J].
Daina, Antoine ;
Michielin, Olivier ;
Zoete, Vincent .
NUCLEIC ACIDS RESEARCH, 2019, 47 (W1) :W357-W364
[7]   Novel systemic treatment approaches for metastatic pancreatic cancer [J].
Dorman, Klara ;
Heinemann, Volker ;
Kobold, Sebastian ;
Von Bergwelt-Baildon, Michael ;
Boeck, Stefan .
EXPERT OPINION ON INVESTIGATIONAL DRUGS, 2022, 31 (03) :249-262
[8]   Unprecedented Citrinin Trimer Tricitinol B Functions as a Novel Topoisomerase IIα Inhibitor [J].
Du, Lin ;
Liu, Hong-Chun ;
Fu, Wei ;
Li, De-Hai ;
Pan, Qiu-Ming ;
Zhu, Tian-Jiao ;
Geng, Mei-Yu ;
Gu, Qan-Qun .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (16) :5796-5810
[9]   Novel carbon-bridged citrinin dimers from a volcano ash-derived fungus Penicillium citrinum and their cytotoxic and cell cycle arrest activities [J].
Du, Lin ;
Li, Dehai ;
Zhang, Guojian ;
Zhu, Tianjiao ;
Ai, Jing ;
Gu, Qianqun .
TETRAHEDRON, 2010, 66 (47) :9286-9290
[10]   Methylene-bridged dimeric natural products involving one-carbon unit in biosynthesis [J].
Fan, Yaqin ;
Shen, Jingjing ;
Liu, Zhi ;
Xia, Kunyu ;
Zhu, Weiming ;
Fu, Peng .
NATURAL PRODUCT REPORTS, 2022, 39 (06) :1305-1324