Ascandinines A–D, Indole Diterpenoids, from the Sponge-Derived Fungus Aspergillus candidus HDN15-152,The Journal of Organic Chemistry

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Ascandinines A–D, Indole Diterpenoids, from the Sponge-Derived Fungus Aspergillus candidus HDN15-152
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-01-20 , DOI: 10.1021/acs.joc.0c02575
Guoliang Zhou ₁ , Chunxiao Sun ₁ , Xuewen Hou ₁ , Qian Che ₁ , Guojian Zhang _{1,

2} , Qianqun Gu ₁ , Chenguang Liu ₃ , Tianjiao Zhu ₁ , Dehai Li _{1,

2,

4}

Affiliation

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.

中文翻译：

Ascandinines A-d，吲哚二萜，从海绵源性真菌白色曲霉HDN15-152

四个新的吲哚二萜类化合物，ascandinines A-d（1 - 4），是从南极海绵衍生的真菌分离白色曲霉HDN15-152。它们的结构（包括绝对构型）是基于NMR数据，计算计算和生物合成考虑因素而建立的。Ascandinine A（1）具有前所未有的2-氧杂二环[2.2.2]辛-3-醇基序嵌入在五环的环系统，而化合物2 - 4表示为特色的6/5/5/6一种罕见的吲哚二萜的/ 6/6/6融合环系统。化合物3表现出抗流感病毒A（H1N1）活性，IC ₅₀值为26μM，而化合物4对HL-60细胞具有细胞毒性，IC ₅₀值为7.8μM。

更新日期：2021-02-05

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