2. Academic Validation
  3. Antiviral Merosesquiterpenoids Produced by the Antarctic Fungus Aspergillus ochraceopetaliformis SCSIO 05702

Antiviral Merosesquiterpenoids Produced by the Antarctic Fungus Aspergillus ochraceopetaliformis SCSIO 05702

  • J Nat Prod. 2016 Jan 22;79(1):59-65. doi: 10.1021/acs.jnatprod.5b00650.
Junfeng Wang 1,  Xiaoyi Wei 2,  Xiaochu Qin 3,  Xinpeng Tian 1,  Li Liao 4,  Kemin Li 3,  Xuefeng Zhou 1,  Xianwen Yang 1,  Fazuo Wang 1,  Tianyu Zhang 3,  Zhengchao Tu 3,  Bo Chen 4,  Yonghong Liu 1
Affiliations

Affiliations

  • 1 CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences , Guangzhou 510301, People's Republic of China.
  • 2 Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences , Guangzhou 510650, People's Republic of China.
  • 3 Laboratory of Molecular Engineering and Laboratory of Natural Product Synthesis, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences , Guangzhou 510530, People's Republic of China.
  • 4 SOA Key Laboratory for Polar Science, Polar Research Institute of China , Shanghai 200136, People's Republic of China.
PMID: 26697718 DOI: 10.1021/acs.jnatprod.5b00650
Abstract

Five new highly oxygenated α-pyrone merosesquiterpenoids, ochraceopones A-E (1-5), together with one new double bond isomer of asteltoxin, isoasteltoxin (6), and two known asteltoxin derivatives, asteltoxin (7) and asteltoxin B (8), were isolated from an Antarctic soil-derived fungus, Aspergillus ochraceopetaliformis SCSIO 05702. Their structures were determined through extensive spectroscopic analysis, CD spectra, quantum mechanical calculations, and X-ray single-crystal diffraction. Ochraceopones A-D (1-4) are the first examples of α-pyrone merosesquiterpenoids possessing a linear tetracyclic carbon skeleton, which has not been previously described. All the isolated compounds were tested for their Antiviral, cytotoxic, Antibacterial, and antitubercular activities. Among these compounds, ochraceopone A (1), isoasteltoxin (6), and asteltoxin (7) exhibited Antiviral activities against the H1N1 and H3N2 influenza viruses with IC50 values of >20.0/12.2 ± 4.10, 0.23 ± 0.05/0.66 ± 0.09, and 0.54 ± 0.06/0.84 ± 0.02 μM, respectively. A possible biosynthetic pathway for ochraceopones A-E (1-5) was proposed.

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