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
  • 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.