Anti-IAV indole-diterpenoids from the marine-derived fungus Penicillium citrinum

Abstract A new indole-diterpenoid, penijanthine E (1), and a known analogue (2), were obtained from the PDB culture of the marine-derived fungus Penicillium citrinum ZSS-9. The absolute configuration of 1 was elucidated by calculated TDDFT ECD and DP4plus calculations. The absolute configuration of 2 was confirmed by single-crystal X-ray diffraction analysis and TDDFT ECD calculations. Compounds 1 and 2 showed antiviral activity against influenza A virus (IAV) of A/WSN/33(H1N1) and A/PR/8/34(H1N1) strains with IC50 values ranging from 12.6 to 46.8 μM. Graphical Abstract

[1]  Hung Kay Lee,et al.  Anti-influenza mechanism of phenolic phytochemicals from Canarium album (Lour.) DC. leaf extract. , 2022, Journal of ethnopharmacology.

[2]  Fei Cao,et al.  Marine Natural Products as A Source of Drug Leads against Respiratory Viruses: Structural and Bioactive Diversity. , 2020, Current medicinal chemistry.

[3]  Fei Cao,et al.  Dipleosporalones A and B, Dimeric Azaphilones from a Marine-Derived Pleosporales sp. Fungus. , 2020, Journal of natural products.

[4]  Bin Yang,et al.  Cytotoxicity of polyketides and steroids isolated from the sponge-associated fungus Penicillium citrinum SCSIO 41017 , 2019, Natural product research.

[5]  Chang-Yun Wang,et al.  Two new benzophenones and one new natural amide alkaloid isolated from a mangrove-derived Fungus Penicillium citrinum , 2019, Natural product research.

[6]  Fei Cao,et al.  Anti-Vibrio Indole-Diterpenoids and C-25 Epimeric Steroids From the Marine-Derived Fungus Penicillium janthinellum , 2019, Front. Chem..

[7]  Fei Cao,et al.  Absolute Configuration of Bioactive Azaphilones from the Marine-Derived Fungus Pleosporales sp. CF09-1. , 2019, Journal of natural products.

[8]  Hui Liu,et al.  A new benzopyrans derivatives from a mangrove-derived fungus Penicillium citrinum from the South China Sea , 2016, Natural product research.

[9]  Ariel M. Sarotti,et al.  Beyond DP4: an Improved Probability for the Stereochemical Assignment of Isomeric Compounds using Quantum Chemical Calculations of NMR Shifts. , 2015, The Journal of organic chemistry.

[10]  R. Schinazi,et al.  Role of Marine Natural Products in the Genesis of Antiviral Agents. , 2015, Chemical reviews.

[11]  Zhihui Zheng,et al.  Three new polyketides from marine-derived fungus Penicillium citrinum SCSGAF 0167 , 2014, Natural product research.

[12]  Haifeng Wang,et al.  Two new indole-diterpenoids from the fungus Penicilliumcrustosum YN-HT-15 , 2014, Journal of Asian natural products research.

[13]  Tonghan Zhu,et al.  Indole-diterpenoids with anti-H1N1 activity from the aciduric fungus Penicillium camemberti OUCMDZ-1492. , 2013, Journal of natural products.

[14]  G. Bringmann,et al.  SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. , 2013, Chirality.

[15]  M. Ison Antivirals and resistance: influenza virus. , 2011, Current opinion in virology.

[16]  Galba Maria Campos Takaki,et al.  A new indoloditerpene derivative, penijanthine A, isolated from Penicillium janthinellum , 2009, Journal of Natural Medicines.

[17]  C. Viboud,et al.  Explorer The genomic and epidemiological dynamics of human influenza A virus , 2016 .

[18]  A. Perelson,et al.  Kinetics of Influenza A Virus Infection in Humans , 2006, Journal of Virology.