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基于 Mizoroki-Heck 反应的微生物筛选有助于探索土壤中产生羟基己基衣康酸的真菌。

Microbial Screening Based on the Mizoroki-Heck Reaction Permits Exploration of Hydroxyhexylitaconic-Acid-Producing Fungi in Soils.

作者信息

Sano Mei, Yada Ryoki, Nomura Yusuke, Kusukawa Takahiro, Ando Hiroshi, Matsumoto Keiji, Wada Kazuhito, Tanaka Tomonari, Ohara Hitomi, Aso Yuji

机构信息

Department of Biobased Materials Science, Kyoto Institute of Technology, Kyoto 606-8585, Japan.

Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Kyoto 606-8585, Japan.

出版信息

Microorganisms. 2020 Apr 29;8(5):648. doi: 10.3390/microorganisms8050648.

DOI:10.3390/microorganisms8050648
PMID:32365722
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7284703/
Abstract

Recently, we developed a unique microbial screening method based on the Mizoroki-Heck reaction for itaconic acid (IA)-producing fungi. This method revealed that 37 out of 240 fungal strains isolated from soils produce vinyl compounds, including IA. In this study, we further characterized these compounds in order to verify that the screening method permits the isolation of fungi that produce other vinyl compounds, excluding IA. HPLC analysis showed that 11 out of 37 isolated strains produced IA, similar to Aspergillus terreus S12-1. Surprisingly, the other 8 isolated strains produced two vinyl compounds with HPLC retention times different from that of IA. From these strains, the vinyl compounds of Aspergillus niger S17-5 were characterized. Mass spectrometric and NMR analyses showed that they were identical to 8-hydroxyhexylitaconic acid (8-HHIA) and 9-HHIA. This finding showed that 8-HHIA- and 9-HHIA-producing fungi, as well as IA-producing fungi, are ubiquitously found in soils. Neither 8-HHIA nor 9-HHIA showed antibacterial or anti-inflammatory activities. Interestingly, 8-HHIA and 9-HHIA showed cytotoxicity against the human cervical cancer cell line (HeLa) and human diploid cell line (MRC-5), and MRC-5 only, respectively, compared to IA at the same concentration. This study indicates that the screening method could easily discover fungi producing 8-HHIA and 9-HHIA in soils.

摘要

最近，我们开发了一种基于Mizoroki-Heck反应的独特微生物筛选方法，用于筛选产衣康酸（IA）的真菌。该方法显示，从土壤中分离出的240株真菌中有37株能产生包括IA在内的乙烯基化合物。在本研究中，我们进一步对这些化合物进行了表征，以验证该筛选方法是否能够分离出除IA之外还能产生其他乙烯基化合物的真菌。高效液相色谱（HPLC）分析表明，37株分离菌株中有11株产生IA，与土曲霉S12-1相似。令人惊讶的是，其他8株分离菌株产生了两种乙烯基化合物，其HPLC保留时间与IA不同。从这些菌株中，对黑曲霉S17-5的乙烯基化合物进行了表征。质谱和核磁共振分析表明，它们与8-羟基己基衣康酸（8-HHIA）和9-HHIA相同。这一发现表明，产8-HHIA和9-HHIA的真菌以及产IA的真菌在土壤中普遍存在。8-HHIA和9-HHIA均未表现出抗菌或抗炎活性。有趣的是，在相同浓度下，与IA相比，8-HHIA和9-HHIA分别仅对人宫颈癌细胞系（HeLa）和人二倍体细胞系（MRC-5）表现出细胞毒性。本研究表明，该筛选方法可以轻松发现土壤中产8-HHIA和9-HHIA的真菌。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cda3/7284703/940b310f3445/microorganisms-08-00648-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cda3/7284703/8874f6762036/microorganisms-08-00648-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cda3/7284703/241498bae1e3/microorganisms-08-00648-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cda3/7284703/2c5738f796f2/microorganisms-08-00648-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cda3/7284703/c955808e8e4d/microorganisms-08-00648-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cda3/7284703/940b310f3445/microorganisms-08-00648-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cda3/7284703/8874f6762036/microorganisms-08-00648-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cda3/7284703/241498bae1e3/microorganisms-08-00648-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cda3/7284703/2c5738f796f2/microorganisms-08-00648-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cda3/7284703/c955808e8e4d/microorganisms-08-00648-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cda3/7284703/940b310f3445/microorganisms-08-00648-g005.jpg

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