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

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. Ascandinin...

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Veröffentlicht in:Journal of organic chemistry 2021-02, Vol.86 (3), p.2431-2436
Hauptverfasser: Zhou, Guoliang, Sun, Chunxiao, Hou, Xuewen, Che, Qian, Zhang, Guojian, Gu, Qianqun, Liu, Chenguang, Zhu, Tianjiao, Li, Dehai
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Sprache:eng
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Zusammenfassung: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 μM, while compound 4 showed cytotoxicity against HL-60 cells with an IC50 value of 7.8 μM.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02575