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Taichunins A–D, Norditerpenes from Aspergillus taichungensis (IBT 19404)
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    Taichunins A–D, Norditerpenes from Aspergillus taichungensis (IBT 19404)
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    • Hikaru Kato
      Hikaru Kato
      Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan
      More by Hikaru Kato
    • Momona Sebe
      Momona Sebe
      Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan
      More by Momona Sebe
    • Mika Nagaki
      Mika Nagaki
      Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan
      More by Mika Nagaki
    • Keisuke Eguchi
      Keisuke Eguchi
      Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan
    • Ippei Kagiyama
      Ippei Kagiyama
      Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan
    • Yuki Hitora
      Yuki Hitora
      Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan
      More by Yuki Hitora
    • Jens C. Frisvad
      Jens C. Frisvad
      Section for Eukaryotic Biotechnology, Departments of System Biology, Technical University of Denmark, Building 221, 2800 Kongens Lyngby, Denmark
    • Robert M. Williams
      Robert M. Williams
      Department of Chemistry, Colorado State University, 301 West Pitkin Street, Fort Collins, Colorado 80523, United States
      University of Colorado Cancer Center, Aurora, Colorado 80045, United States
    • Sachiko Tsukamoto*
      Sachiko Tsukamoto
      Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan
      *E-mail: [email protected]
    Other Access OptionsSupporting Information (1)

    Journal of Natural Products

    Cite this: J. Nat. Prod. 2019, 82, 5, 1377–1381
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    https://doi.org/10.1021/acs.jnatprod.8b01032
    Published April 17, 2019
    Copyright © 2019 American Chemical Society and American Society of Pharmacognosy

    Abstract

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    Four new norditerpenes, taichunins A–D (14), were isolated from the fungus Aspergillus taichungensis (IBT 19404). Compound 1 has a new carbon framework. The absolute configurations were determined by the calculated ECD spectral method. Compound 1 was cytotoxic against HeLa cells with an IC50 value of 4.5 μM, whereas 24 were nontoxic at 50 μM.

    Copyright © 2019 American Chemical Society and American Society of Pharmacognosy

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jnatprod.8b01032.

    • 1D and 2D NMR spectra of 14; experimental and calculated 13C NMR data based on ωB97X-D/6-31G for 1 (PDF)

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    This article is cited by 8 publications.

    1. Ahmed H. H. El-Desoky, Natsumi Inada, Yuka Maeyama, Hikaru Kato, Yuki Hitora, Momona Sebe, Mika Nagaki, Aika Kai, Keisuke Eguchi, Tomoaki Inazumi, Yukihiko Sugimoto, Jens C. Frisvad, Robert M. Williams, Sachiko Tsukamoto. Taichunins E–T, Isopimarane Diterpenes and a 20-nor-Isopimarane, from Aspergillus taichungensis (IBT 19404): Structures and Inhibitory Effects on RANKL-Induced Formation of Multinuclear Osteoclasts. Journal of Natural Products 2021, 84 (9) , 2475-2485. https://doi.org/10.1021/acs.jnatprod.1c00486
    2. Antonio Evidente. The incredible story of ophiobolin A and sphaeropsidin A: two fungal terpenes from wilt-inducing phytotoxins to promising anticancer compounds. Natural Product Reports 2024, 41 (3) , 434-468. https://doi.org/10.1039/D3NP00035D
    3. Ni Zeng, Qiongdan Zhang, Qingying Yao, Gang Fu, Wei Su, Wei Wang, Bin Li. A Comprehensive Review of the Classification, Sources, Phytochemistry, and Pharmacology of Norditerpenes. Molecules 2024, 29 (1) , 60. https://doi.org/10.3390/molecules29010060
    4. Ke Ye, Hong-lian Ai. Pimarane Diterpenes from Fungi. Pharmaceuticals 2022, 15 (10) , 1291. https://doi.org/10.3390/ph15101291
    5. K. Glässnerová, F. Sklenář, Ž Jurjević, J. Houbraken, T. Yaguchi, C.M. Visagie, J. Gené, J.P.Z. Siqueira, A. Kubátová, M. Kolařík, V. Hubka. A monograph of Aspergillus section Candidi. Studies in Mycology 2022, 102 (1) , 1-51. https://doi.org/10.3114/sim.2022.102.01
    6. Wen-Yu Zhao, Jing Yi, Yi-Bo Chang, Cheng-Peng Sun, Xiao-Chi Ma. Recent studies on terpenoids in Aspergillus fungi: Chemical diversity, biosynthesis, and bioactivity. Phytochemistry 2022, 193 , 113011. https://doi.org/10.1016/j.phytochem.2021.113011
    7. Zhushuang Bai, Cairong Zhang, Yongyi Chen, Aiqin Liu, Xinyu Wang, Chuna Yan, Xuechao Liu, Xiaoru Zhang, Ying Li, Ye Yuan, Zemei Ge, Jingxiang Pang, Yongshuai Chai, Xin Wang, Runtao Li. A vinylogous Michael reaction of 2-furanone dimers with α,β-unsaturated nitroolefins for constructing chiral γ,γ-disubstituted butenolides. Organic Chemistry Frontiers 2020, 7 (19) , 2910-2915. https://doi.org/10.1039/D0QO00376J
    8. Jens Christian Frisvad, Thomas Isbrandt, Thomas Ostenfeld Larsen. Fungal Partially Reducing Polyketides and Related Natural Products From Aspergillus, Penicillium, and Talaromyces. 2020, 313-332. https://doi.org/10.1016/B978-0-12-409547-2.14731-6

    Journal of Natural Products

    Cite this: J. Nat. Prod. 2019, 82, 5, 1377–1381
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jnatprod.8b01032
    Published April 17, 2019
    Copyright © 2019 American Chemical Society and American Society of Pharmacognosy

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