Structure revision of tricholomenyn B, an antimitotic geranylcyclohexenone rediscovered as a bitter and antibacterial substance, from a basidiomycete Tricholoma japonicum (Shiro-shimeji)

IF 2.1 4区医学 Q3 BIOTECHNOLOGY & APPLIED MICROBIOLOGY

Journal of Antibiotics Pub Date : 2024-05-31 DOI:10.1038/s41429-024-00746-y

Md. Julkar Nime, Yuna Oguri, Naoya Oku, Yasuhiro Igarashi

引用次数: 0

Abstract

Tricholomenyn B, an antimitotic geranylcyclohexenone originally discovered from a basidiomycete Tricholoma acerbum, was isolated as a bitter and antibacterial constituent from fruiting bodies of T. japonicum. Careful comparison of NMR, MS, and other physicochemical properties of the isolated substance with the literature values revised a previously proposed macrolide structure 1 to a macrodiolide 2. Compound 2 was perceived bitter at a minimum dose of 37.5 μg, showed weak antimicrobial activity against Kocuria rhizophila and Staphylococcus aureus, and was marginally cytotoxic (IC50 2.6 µM) against P388 murine leukemia cells.

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重新发现的一种苦味和抗菌物质--日本毛孢子菌（Shiro-shimeji）中的抗炎药香叶环己烯酮 tricholomenyn B 的结构修订。

Tricholomenyn B 最初是从一种基枝菌 Tricholoma acerbum 中发现的一种抗硝化甘油环己烯酮，它是从日本蓟马的子实体中分离出的一种苦味抗菌成分。将分离物质的核磁共振、质谱和其他理化性质与文献值进行仔细比较后，将之前提出的大环内酯结构 1 修正为大环内酯 2。化合物 2 在最低剂量为 37.5 μg 时有苦味，对 Kocuria rhizophila 和金黄色葡萄球菌有微弱的抗菌活性，对 P388 小鼠白血病细胞有微弱的细胞毒性（IC50 2.6 µM）。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Antibiotics 医学-免疫学

CiteScore

6.60

自引率

3.00%

发文量

审稿时长

1 months

期刊介绍： The Journal of Antibiotics seeks to promote research on antibiotics and related types of biologically active substances and publishes Articles, Review Articles, Brief Communication, Correspondence and other specially commissioned reports. The Journal of Antibiotics accepts papers on biochemical, chemical, microbiological and pharmacological studies. However, studies regarding human therapy do not fall under the journal’s scope. Contributions regarding recently discovered antibiotics and biologically active microbial products are particularly encouraged. Topics of particular interest within the journal''s scope include, but are not limited to, those listed below: Discovery of new antibiotics and related types of biologically active substances Production, isolation, characterization, structural elucidation, chemical synthesis and derivatization, biological activities, mechanisms of action, and structure-activity relationships of antibiotics and related types of biologically active substances Biosynthesis, bioconversion, taxonomy and genetic studies on producing microorganisms, as well as improvement of production of antibiotics and related types of biologically active substances Novel physical, chemical, biochemical, microbiological or pharmacological methods for detection, assay, determination, structural elucidation and evaluation of antibiotics and related types of biologically active substances Newly found properties, mechanisms of action and resistance-development of antibiotics and related types of biologically active substances.