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卤化引导的化学筛选为费氏蓝细菌（Fischerella ambigua）的奇盘唑生物合成提供了见解。

Halogenation-Guided Chemical Screening Provides Insight into Tjipanazole Biosynthesis by the Cyanobacterium Fischerella ambigua.

作者信息

Chilczuk Tomasz, Schäberle Till F, Vahdati Sahel, Mettal Ute, El Omari Mustafa, Enke Heike, Wiese Michael, König Gabriele M, Niedermeyer Timo H J

机构信息

Department of Pharmaceutical Biology/Pharmacognosy Institute of Pharmacy, Martin-Luther-University Halle-Wittenberg, Hoher Weg 8, 06120, Halle (Saale), Germany.

Institute for Insect Biotechnology, Justus-Liebig-University Gießen, Heinrich-Buff-Ring 26-32, 35392, Gießen, Germany.

出版信息

Chembiochem. 2020 Aug 3;21(15):2170-2177. doi: 10.1002/cbic.202000025. Epub 2020 Apr 16.

DOI:10.1002/cbic.202000025
PMID:32182403
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7497240/
Abstract

Halogenated natural products (HNPs) show a wide range of interesting biological activities. Chemistry-guided screening with a software tool dedicated to identifying halogenated compounds in HPLC-MS data indicated the presence of several uncharacterised HNPs in an extract of the cyanobacterium Fischerella ambigua (Näg.) Gomont 108b. Three new natural products, tjipanazoles K, L, and M, were isolated from this strain together with the known tjipanazoles D and I. Taking into account the structures of all tjipanazole derivatives detected in this strain, reanalysis of the tjipanazole biosynthetic gene cluster allowed us to propose a biosynthetic pathway for the tjipanazoles. As the isolated tjipanazoles show structural similarity to arcyriaflavin A, an inhibitor of the clinically relevant multidrug-transporter ABCG2 overexpressed by different cancer cell lines, the isolated compounds were tested for ABCG2 inhibitory activity. Only tjipanazole K showed appreciable transporter inhibition, whereas the compounds lacking the pyrrolo[3,4-c] ring or featuring additional chloro substituents were found to be much less active.

摘要

卤代天然产物（HNPs）具有广泛有趣的生物活性。使用专门用于在HPLC-MS数据中识别卤代化合物的软件工具进行化学引导筛选表明，在蓝藻费氏藻（Näg.）Gomont 108b的提取物中存在几种未表征的HNPs。从该菌株中分离出三种新的天然产物，即替帕纳唑K、L和M，以及已知的替帕纳唑D和I。考虑到在该菌株中检测到的所有替帕纳唑衍生物的结构，对替帕纳唑生物合成基因簇的重新分析使我们能够提出替帕纳唑的生物合成途径。由于分离出的替帕纳唑与阿西瑞黄素A结构相似，阿西瑞黄素A是不同癌细胞系过度表达的临床相关多药转运蛋白ABCG2的抑制剂，因此对分离出的化合物进行了ABCG2抑制活性测试。只有替帕纳唑K表现出明显的转运蛋白抑制作用，而缺乏吡咯并[3,4-c]环或具有额外氯取代基的化合物活性则低得多。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/952c/7497240/690b7da5886e/CBIC-21-2170-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/952c/7497240/8b1914f813c9/CBIC-21-2170-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/952c/7497240/9795e2b8e507/CBIC-21-2170-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/952c/7497240/690b7da5886e/CBIC-21-2170-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/952c/7497240/8b1914f813c9/CBIC-21-2170-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/952c/7497240/9795e2b8e507/CBIC-21-2170-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/952c/7497240/690b7da5886e/CBIC-21-2170-g003.jpg

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