4.7 Article

Ascandinines A-D, Indole Diterpenoids, from the Sponge-Derived Fungus Aspergillus candidus HDN15-152

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 3, Pages 2431-2436

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02575

Keywords

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Funding

  1. National Key R&D Program of China [2018YFC1406705]
  2. National Natural Science Foundation of China [41876216, 81973234, 81991522]
  3. National Science and Technology Major Project for Significant New Drugs Development [2018ZX09735004]
  4. Marine S&T Fund of Shandong Province for Pilot National Laboratory for Marine Science and Technology (Qingdao) [2018SDKJ0401-2]
  5. China Postdoctoral Science Foundation [2017M622286]
  6. Taishan Scholar Youth Expert Program in Shandong Province [tsqn201812021]

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Four new indole diterpenoids, ascandinines A-D (1-4), were isolated from an Antarctic sponge-derived fungus. One of them exhibited anti-influenza virus activity, and another showed cytotoxicity against HL-60 cells.
Four new indole diterpenoids, ascandinines A-D (1-4), were isolated from an Antarctic sponge-derived fungus Aspergillus candidus HDN15-152. Their structures, including absolute configurations, were established based on NMR data, computational calculations, and biosynthetic considerations. Ascandinine A (1) possesses an unprecedented 2-oxabicyclo[2.2.2]octan-3-ol motif embedded in a pentacyclic ring system, while compounds 2-4 represent a rare type of indole diterpenoid featuring the 6/5/5/6/6/6/6-fused ring system. Compound 3 displayed anti-influenza virus A (H1N1) activity with an IC50 value of 26 mu M, while compound 4 showed cytotoxicity against HL-60 cells with an IC50 value of 7.8 mu M.

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