title: Antiviral Merosesquiterpenoids Produced by the Antarctic Fungus Aspergillus ochraceopetaliformis SCSIO 05702.
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.
authors.affiliation: 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.
authors.forename: Junfeng
authors.initials: J
authors.lastname: Wang
authors.affiliation: Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences , Guangzhou 510650, People's Republic of China.
authors.forename: Xiaoyi
authors.initials: X
authors.lastname: Wei
authors.affiliation: 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.
authors.forename: Xiaochu
authors.initials: X
authors.lastname: Qin
authors.affiliation: 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.
authors.forename: Xinpeng
authors.initials: X
authors.lastname: Tian
authors.affiliation: SOA Key Laboratory for Polar Science, Polar Research Institute of China , Shanghai 200136, People's Republic of China.
authors.forename: Li
authors.initials: L
authors.lastname: Liao
authors.affiliation: 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.
authors.forename: Kemin
authors.initials: K
authors.lastname: Li
authors.affiliation: 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.
authors.forename: Xuefeng
authors.initials: X
authors.lastname: Zhou
authors.affiliation: 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.
authors.forename: Xianwen
authors.initials: X
authors.lastname: Yang
authors.affiliation: 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.
authors.forename: Fazuo
authors.initials: F
authors.lastname: Wang
authors.affiliation: 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.
authors.forename: Tianyu
authors.initials: T
authors.lastname: Zhang
authors.affiliation: 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.
authors.forename: Zhengchao
authors.initials: Z
authors.lastname: Tu
authors.affiliation: SOA Key Laboratory for Polar Science, Polar Research Institute of China , Shanghai 200136, People's Republic of China.
authors.forename: Bo
authors.initials: B
authors.lastname: Chen
authors.affiliation: 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.
authors.forename: Yonghong
authors.initials: Y
authors.lastname: Liu
mesh_terms: D000864:Antarctic Regions; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D053118:Influenza A Virus, H1N1 Subtype / Q000187:drug effects; D053122:Influenza A Virus, H3N2 Subtype / Q000187:drug effects; D020128:Inhibitory Concentration 50; D008386:Marine Biology; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011753:Pyrones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D012988:Soil Microbiology
chemical_list: D000900:Anti-Bacterial Agents; D000998:Antiviral Agents; D011753:Pyrones; D012717:Sesquiterpenes; C000608582:ochraceopone A; C030923:asteltoxin