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化学表观遗传修饰剂 5-氮杂胞苷调控内生真菌 sp. KMU18029 中次生代谢产物的合成。

Regulation of secondary metabolites in the endophytic fungus sp. KMU18029 by the chemical epigenetic modifier 5-azacitidine.

机构信息

School of Pharmaceutical Science & Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming, China.

Faculty of Bioengineering, Zhuhai Campus of Zunyi Medical University, Zhuhai, China.

出版信息

Nat Prod Res. 2024 Feb-Mar;38(4):581-588. doi: 10.1080/14786419.2023.2183199. Epub 2023 Feb 28.

Abstract

The chemical epigenetic modifier 5-azacitidine (5-Aza C), a DNA methyltransferase inhibitor, was used to manipulate the endophytic fungus sp. KMU18029. From its rice fermentation extract, a new polyketone compound (3,4)-3,4,8-trihydroxy-6-methyl-3,4-dihydronaphthalen-1(2)-one (), along with 13 known compounds, 3,4,8-trihydroxy-6-(hydroxymethyl)-3,4-dihydronaphthalen-1(2)-one (), decaturin B (), 15-hydroxydecaturin A (), oxalicine A (), pileotin A (), pyrandecarurin A (), decaturenol A (), decaturenoid (), penisarins A (), oxaline (), (4,8)-N-D-2'-hydroxyocta-decanoyl-1-O--D-glycopy-ranosyl-9-methyl-4,8-sphingadienine (), ergosterol () and stigma-5-en-3-O--glucoside (), were separated. Among the known compounds, , , and were not found in our previous research on this strain. The structure of the new compound was identified by spectroscopic techniques such as HR-ESIMS, 1D NMR, 2D NMR and CD. Furthermore, all the isolated compounds were tested for their antimicrobial activities, and only compounds , and showed weak activities against , with MICs of 128 μg/mL.

摘要

化学表观遗传修饰剂 5-氮杂胞苷(5-Aza C),一种 DNA 甲基转移酶抑制剂,被用于操纵内生真菌 sp. KMU18029。从其大米发酵提取物中,分离得到一种新的聚酮化合物(3,4)-3,4,8-三羟基-6-甲基-3,4-二氢萘-1(2)-酮(),以及 13 种已知化合物,3,4,8-三羟基-6-(羟甲基)-3,4-二氢萘-1(2)-酮(),decaturin B(),15-羟基 decaturin A(),oxalicine A(),pileotin A(),pyrandecarurin A(),decaturenol A(),decaturenoid(),penisarins A(),oxaline(),(4,8)-N-D-2'-羟基辛酰基-1-O--D-吡喃葡萄糖基-9-甲基-4,8-麦角二烯胺(),麦角甾醇()和麦角甾-5-烯-3-O--葡萄糖苷()。在已知化合物中,、、和在我们之前对该菌株的研究中未发现。新化合物的结构通过高分辨电喷雾电离质谱(HR-ESIMS)、1D NMR、2D NMR 和 CD 等光谱技术进行鉴定。此外,所有分离得到的化合物都进行了抗微生物活性测试,只有化合物、和表现出对的微弱活性,MIC 值为 128μg/mL。

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