Aspertaichunol A, an Immunomodulatory Polyketide with an Uncommon Scaffold from the Insect-Derived Endophytic Aspergillus taichungensis SMU01,Organic Letters

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Aspertaichunol A, an Immunomodulatory Polyketide with an Uncommon Scaffold from the Insect-Derived Endophytic Aspergillus taichungensis SMU01
Organic Letters ( IF 4.9 ) Pub Date : 2022-09-25 , DOI: 10.1021/acs.orglett.2c02978
Xia Cheng ₁ , Fo-Pei Ma ₂ , Yong-Ming Yan ₃ , Wen-Li Zhao ₄ , Jin Shi ₅ , Wei Xiao ₁ , En-Guang Bi ₄ , Qi Luo _{1,

2}

Affiliation

Aspertaichunol A (1), a polyketide with a novel scaffold, was isolated from the medicinal insect (Periplaneta americana)-derived endophytic Aspergillus taichungensis SMU01. Its structure was assigned on the basis of spectroscopic data and quantum chemical computational methods. Notably, 1 possesses an uncommon tricyclo[6.2.0.0^2,6]decane motif and an unusual bridgehead double bond (anti-Bredt system). A plausible biosynthetic pathway, involving a key intramolecular [2+2] cycloaddition and a reductive cyclization, is postulated. Finally, the immunomodulatory activity of 1 at 20 nM was evaluated by promoting Th9 cell differentiation from naive CD4⁺CD62L⁺ T cells.

中文翻译：

Aspertaichunol A，一种免疫调节聚酮化合物，具有来自昆虫衍生的内生曲霉 taichungensis SMU01 的罕见支架

Aspertaichunol A ( 1 ) 是一种具有新型支架的聚酮化合物，是从药用昆虫 ( Periplaneta americana ) 衍生的内生性Aspergillus taichungensis SMU01 中分离出来的。它的结构是根据光谱数据和量子化学计算方法分配的。值得注意的是，1拥有一个不常见的三环 [6.2.0.0 ^2,6 ]decane 基序和一个不寻常的桥头双键（反 Bredt 系统）。假设了一个合理的生物合成途径，涉及关键的分子内 [2+2] 环加成和还原环化。最后，通过促进 Th9 细胞从幼稚 CD4 ⁺ CD62L分化来评估1在 20 nM 时的免疫调节活性⁺ T 细胞。

更新日期：2022-09-25

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