Diversified Polyketides and Nitrogenous Compounds from the Mangrove Endophytic Fungus Penicillium steckii SCSIO 41025

被引:20
作者
Chen, Chun-Mei [1 ,4 ]
Chen, Wei-Hao [1 ,4 ]
Tao, Hua-Ming [5 ]
Yang, Bin [1 ,3 ]
Zhou, Xue-Feng [1 ,3 ]
Luo, Xiao-Wei [2 ]
Liu, Yong-Hong [1 ,2 ,3 ,4 ]
机构
[1] Chinese Acad Sci, South China Sea Inst Oceanol, Guangdong Key Lab Marine Mat Med, CAS Key Lab Trop Marine Bioresources & Ecol, Guangzhou 510301, Guangdong, Peoples R China
[2] Guangxi Univ Chinese Med, Inst Marine Drugs, Nanning 530200, Guangxi, Peoples R China
[3] Southern Marine Sci & Engn Guangdong Lab Guangzho, Guangzhou 511458, Guangdong, Peoples R China
[4] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[5] Southern Med Univ, Sch Tradit Chinese Med, Guangzhou 510515, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
Mangrove endophytic fungus; Penicillium steckii; Polyketides; Alkaloids; Biological activity; MARINE-DERIVED FUNGUS; METABOLITES; DERIVATIVES; BIOSYNTHESIS; CYTOTOXICITY; LOVASTATIN; ALKALOIDS;
D O I
10.1002/cjoc.202100226
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Main observation and conclusion Four new polyketide decalin derivatives, penicisteck acids A-D (1-4), and three new nitrogenous compounds (7-9), together with eight previously reported compounds, were isolated from the mangrove endophytic fungus Penicillium steckii SCSIO 41025. Their structures and absolute configurations were characterized by analysis of comprehensive spectroscopic data combined with ECD calculations and modified Marfey's method. Structurally, compounds 1-3 were highly oxygenated decalin derivatives harboring an unusual propanoic acid unit at C-1. Compound 8 was identified as a rare natural alkaloid-N-oxide confirmed by single crystal X-ray diffraction analysis. A plausible biogenetic pathway of compounds 1-6 is proposed. Compounds 13 and 15 showed significant anti-bacterial activity against Staphylococcus aureus with the MIC values of 3.9 and 7.8 mu g/mL, respectively. Compounds 10 and 12 exhibited potent alpha-glucosidase inhibitory activity with the IC50 values of 64.1 and 191.4 mu mol/L, respectively.
引用
收藏
页码:2132 / 2140
页数:9
相关论文
共 42 条
[1]   Tanzawaic acid derivatives from freshwater sediment-derived fungus Penicillium sp. [J].
Abdelwahab, Miada F. ;
Fouad, Mostafa A. ;
Kamel, Mohamed S. ;
Oezkaya, Ferhat Can ;
Kalscheuer, Rainer ;
Mueller, Werner E. G. ;
Lin, Wenhan ;
Liu, Zhen ;
Ebrahim, Weaam ;
Daletos, Georgios ;
Proksch, Peter .
FITOTERAPIA, 2018, 128 :258-264
[2]   Biosynthesis of Lovastatin and Related Metabolites Formed by Fungal Iterative PKS Enzymes [J].
Campbell, Chantel D. ;
Vederas, John C. .
BIOPOLYMERS, 2010, 93 (09) :755-763
[3]   Tanzawaic acids isolated from a marine-derived fungus of the genus Penicillium with cytotoxic activities [J].
Cardoso-Martinez, Faviola ;
de la Rosa, Jose M. ;
Diaz-Marrero, Ana R. ;
Darias, Jose ;
Cerella, Claudia ;
Diederichc, Marc ;
Cueto, Mercedes .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (26) :7248-7256
[4]   Marine natural products [J].
Carroll, Anthony R. ;
Copp, Brent R. ;
Davis, Rohan A. ;
Keyzers, Robert A. ;
Prinsep, Michele R. .
NATURAL PRODUCT REPORTS, 2021, 38 (02) :362-413
[5]   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
[6]   Copper-Catalyzed Selective N-Vinylation of 3-(Hydroxyimino)indolin-2-ones with Alkenyl Boronic Acids: Synthesis of N-Vinyl Nitrones and Spirooxindoles [J].
Chen, Chun-Hua ;
Liu, Qing-Qing ;
Ma, Xiao-Pan ;
Feng, Yu ;
Liang, Cui ;
Pan, Cheng-Xue ;
Su, Gui-Fa ;
Mo, Dong-Liang .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (12) :6417-6425
[7]   Pyrrolyl 4-quinolone alkaloids from the mangrove endophytic fungus Penicillium steckii SCSIO 41025: Chiral resolution, configurational assignment, and enzyme inhibitory activities [J].
Chen, Chun-Mei ;
Chen, Wei-Hao ;
Pang, Xiao-Yan ;
Liao, Sheng-Rong ;
Wang, Jun-Feng ;
Lin, Xiu-Ping ;
Yang, Bin ;
Zhou, Xue-Feng ;
Luo, Xiao-Wei ;
Liu, Yong-Hong .
PHYTOCHEMISTRY, 2021, 186
[8]   Bioactive secondary metabolites from the deep-sea derived fungus Aspergillus sp. SCSIO 41029 [J].
Chen, Weihao ;
Chen, Chunmei ;
Long, Jieyi ;
Lan, Sujuan ;
Lin, Xiuping ;
Liao, Shengrong ;
Yang, Bin ;
Zhou, Xuefeng ;
Wang, Junfeng ;
Liu, Yonghong .
JOURNAL OF ANTIBIOTICS, 2021, 74 (02) :156-159
[9]   Peptides from the Soft Coral-associated Fungus Simplicillium sp SCSIO41209 [J].
Dai, Yu ;
Lin, Yun ;
Pang, Xiaoyan ;
Luo, Xiaowei ;
Salendra, Limbadri ;
Wang, Junfeng ;
Zhou, Xuefeng ;
Lu, Yongjun ;
Yang, Bin ;
Liu, Yonghong .
PHYTOCHEMISTRY, 2018, 154 :56-62
[10]   The isolation, structure determination and cytotoxicity of the new fungal metabolite, trichodermamide C [J].
Davis, Rohan A. ;
Longden, James ;
Avery, Vicky M. ;
Healy, Peter C. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (09) :2836-2839