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昆虫病原真菌来源的具有 2,2'-和 4,4'-轴向连接的生物活性二聚四氢蒽酮

Bioactive Dimeric Tetrahydroxanthones with 2,2'- and 4,4'-Axial Linkages from the Entomopathogenic Fungus .

机构信息

Integrated Applied Chemistry Research Unit, Faculty of Science, King Mongkut's Institute of Technology Ladkrabang, Chalongkrung Road, Ladkrabang, Bangkok 10520, Thailand.

Department of Chemistry, Faculty of Science, King Mongkut's Institute of Technology Ladkrabang, Chalongkrung Road, Ladkrabang, Bangkok 10520, Thailand.

出版信息

J Nat Prod. 2021 Apr 23;84(4):1149-1162. doi: 10.1021/acs.jnatprod.0c01212. Epub 2021 Apr 14.

DOI:10.1021/acs.jnatprod.0c01212
PMID:33852304
Abstract

Thirteen tetrahydroxanthone dimers, -ascherxanthone A (), ascherxanthones C-G (-), and confluxanthones A-G (-), were isolated from the entomopathogenic fungus BCC53152. The chemical structures were determined based on analysis of NMR spectroscopic and mass spectrometric data. The absolute configurations of compounds and were confirmed by single-crystal X-ray diffraction experiments, while the configurations of other compounds were assigned based upon evidence from NOESY and NOEDIFF experiments, modified Mosher's method, and ECD spectroscopic data together with biogenetic considerations. Compounds , -, -, and showed antimalarial activity against (K1, multidrug-resistant strain) (IC 0.6-6.1 μM), antitubercular activity against H37Ra (MIC 6.3-25.0 μg/mL), and cytotoxicity against NCI-H187 (IC 0.5-3.5 μM) and Vero (IC 0.9-6.1 μM) cells. All tested compounds except for compound exhibited cytotoxicity against KB cells (IC 1.3-9.7 μM).

摘要

从昆虫病原真菌 BCC53152 中分离得到了 13 种四羟基蒽酮二聚体,包括 -ascherxanthone A()、ascherxanthones C-G(-)和 confluxanthones A-G(-)。根据 NMR 光谱和质谱数据分析确定了这些化合物的化学结构。通过单晶 X 射线衍射实验确定了化合物和的绝对构型,而其他化合物的构型则是根据 NOESY 和 NOEDIFF 实验、改进的 Mosher 法、ECD 光谱数据以及生物发生学考虑来确定的。化合物、、、和表现出抗疟活性,对(K1,多药耐药株)的抑制活性为 0.6-6.1 μM;对结核分枝杆菌 H37Ra 的抗结核活性为 6.3-25.0 μg/mL;对 NCI-H187(IC 0.5-3.5 μM)和 Vero(IC 0.9-6.1 μM)细胞的细胞毒性;除了化合物外,所有测试的化合物对 KB 细胞均具有细胞毒性(IC 1.3-9.7 μM)。

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