5'-Methoxyarmillane, a Bioactive Sesquiterpenoid Aryl Ester from the Fungus Armillaria ostoyae.

IF 2.6 4区 生物学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY
ChemBioChem Pub Date : 2024-05-13 DOI:10.1002/cbic.202400168
Axel M. Orban, Johanna Eichberg, Michael Marner, Sandra Breuer, Maria A. Patras, Ute Mettal, Till F. Schäberle, Martin Rühl
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引用次数: 0

摘要

属于担子菌门的高等真菌Armillaria属会产生具有生物活性的倍半萜芳基酯类,这种酯类被称为melleolides。通过生物活性引导的发现过程,我们从奥托耶氏菌(Armillaria ostoyae)菌丝体的有机提取物中鉴定出了新的三叶醇内酯 5'-methoxyarmillane (1)。值得注意的是,在培养基马铃薯葡萄糖肉汤中添加菜籽油后,在 35 天的发酵过程中,1 的产量增加了 6 倍。通过超高效液相色谱-QTOF-HR-MS/MS 和核磁共振光谱,分离并阐明了化合物 1 的结构。它对 Madin-Darby 犬肾 II(MDCK II,IC50 19.2 毫克/毫升,44.1 毫摩尔)和人肺癌 Calu-3 细胞(IC50 15.2 毫克/毫升,34.9 毫摩尔)具有毒性,对结核分枝杆菌(MIC 8 毫克/毫升,18.4 毫摩尔)和烟曲霉分枝杆菌(MIC 16 毫克/毫升,36.8 毫摩尔),但对金黄色葡萄球菌、大肠杆菌、白色念珠菌和三尖杉球菌没有抑制作用。没有观察到 1 对 H3N2、H1N1pdm、B/马来西亚和 B/马萨诸塞州流感病毒的抑制作用。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

5’-Methoxyarmillane, a Bioactive Sesquiterpenoid Aryl Ester from the Fungus Armillaria ostoyae

5’-Methoxyarmillane, a Bioactive Sesquiterpenoid Aryl Ester from the Fungus Armillaria ostoyae

Higher fungi of the genus Armillaria belonging to the phylum Basidiomycota produce bioactive sesquiterpenoid aryl esters called melleolides. A bioactivity-guided discovery process led to the identification of the new melleolide 5’-methoxyarmillane (1) in organic extracts from the mycelium of Armillaria ostoyae. Remarkably, supplementation of rapeseed oil to the culture medium potato dextrose broth increased the production of 1 by a factor of six during the course of the 35 days fermentation. Compound 1 was isolated and its structure elucidated by UHPLC-QTOF-HR-MS/MS and NMR spectroscopy. It showed toxicity against Madin-Darby canine kidney II (MDCK II, IC50 19.2 μg/mL, 44.1 μM) and human lung cancer Calu-3 cells (IC50 15.2 μg/mL, 34.9 μM) as well as moderate bioactivity against Mycobacterium tuberculosis (MIC 8 mg/mL, 18.4 μM) and Mycobacterium smegmatis (MIC 16 mg/mL, 36.8 μM), but not against Staphylococcus aureus, Escherichia coli, Candida albicans, and Septoria tritici. No inhibitory effects of 1 against the influenza viruses H3N2, H1N1pdm, B/Malaysia, and B/Massachusetts were observed.

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来源期刊
ChemBioChem
ChemBioChem 生物-生化与分子生物学
CiteScore
6.10
自引率
3.10%
发文量
407
审稿时长
1 months
期刊介绍: ChemBioChem (Impact Factor 2018: 2.641) publishes important breakthroughs across all areas at the interface of chemistry and biology, including the fields of chemical biology, bioorganic chemistry, bioinorganic chemistry, synthetic biology, biocatalysis, bionanotechnology, and biomaterials. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies, and supported by the Asian Chemical Editorial Society (ACES).
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